data1000_v2.json

[
  {
    "input_text": "A mixture of N-butyltrifluoromethanesulfonamide (62.0 g, 0.302 mole), potassium carbonate (45.54 g, 0.330 mole) and methanol (250 ml) was refluxed with stirring for two hours. Allyl bromide (39.93 g, 0.330 mole) was then added and this mixture stirred under reflux for 24 hours, cooled, filtered, and the solvent evaporated in vacuo. The residue was fractionally distilled yielding 37.0 g (b.p. of 53\u00b0-58\u00b0 C. at 0.07 torr) of the desired compound, N-allyl-N-butyltrifluoromethanesulfonamide.",
    "output_reaction_inputs": {
      "m2_m3_m5": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "N-butyltrifluoromethanesulfonamide"
              }
            ],
            "amount": {
              "mass": {
                "value": 62.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "potassium carbonate"
              }
            ],
            "amount": {
              "mass": {
                "value": 45.54,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "methanol"
              }
            ],
            "amount": {
              "volume": {
                "value": 250.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      },
      "m4": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "Allyl bromide"
              }
            ],
            "amount": {
              "mass": {
                "value": 39.93,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "stirring": {
        "type": "CUSTOM",
        "details": "with stirring for two hours"
      },
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-a47dfcdbc77f4442a03410e327d1f0ff"
  },
  {
    "input_text": "n-dodecanoyl chloride (8.74 g.; 40 mmoles) is added dropwise to a solution of dissolved p-aminobenzoic acid (5.5 g.; 40 mmoles) dissolved in pyridine (100 ml.). The mixture is stirred for 3 hours and poured into water (3 l.). The precipitate which forms is filtered and dried in vacuo to give N-(n-dodecanoyl)-p-aminobenzoic acid (11.01 g.).",
    "output_reaction_inputs": {
      "m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "water"
              }
            ],
            "amount": {
              "volume": {
                "value": 3.0,
                "units": "LITER"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      },
      "m1_m2": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "n-dodecanoyl chloride"
              }
            ],
            "amount": {
              "mass": {
                "value": 8.74,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "p-aminobenzoic acid"
              }
            ],
            "amount": {
              "mass": {
                "value": 5.5,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      },
      "m4": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "pyridine"
              }
            ],
            "amount": {
              "volume": {
                "value": 100.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "stirring": {
        "type": "CUSTOM",
        "details": "The mixture is stirred for 3 hours"
      },
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-8e49992621f3467d83ab1a0ce880ae41"
  },
  {
    "input_text": "n-Dodecanoyl chloride (8.74 g.; 40 mmoles) is added dropwise to a solution of p-aminobenzoic acid (40 mmoles) dissolved in pyridine (100 ml.). The mixture is stirred for 3 hours and poured into water (3 l.). The precipitate which forms is filtered and dried in vacuo to give N-(n-dodecanoyl)-p-aminobenzoic acid (11.01 g.).",
    "output_reaction_inputs": {
      "m4": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "pyridine"
              }
            ],
            "amount": {
              "volume": {
                "value": 100.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      },
      "m1_m2": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "n-Dodecanoyl chloride"
              }
            ],
            "amount": {
              "mass": {
                "value": 8.74,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "p-aminobenzoic acid"
              }
            ],
            "amount": {
              "moles": {
                "value": 40.0,
                "units": "MILLIMOLE"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      },
      "m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "water"
              }
            ],
            "amount": {
              "volume": {
                "value": 3.0,
                "units": "LITER"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "stirring": {
        "type": "CUSTOM",
        "details": "The mixture is stirred for 3 hours"
      },
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-e8acb047d24c456bbe80bf55f1c0ae04"
  },
  {
    "input_text": "A solution of p-hydroxybenzoic acid (19.2 g., 150 mmole) in 10% aqueous sodium hydroxide (120 ml.) is added to DMSO (480 ml.) previously heated to 80\u00b0 C. n-Octyl bromide (28.95 g., 150 mmole) is added dropwise to the solution. The reaction mixture is stirred for 4 hours at room temperature after which it is poured into ice water (1200 ml.). Conc. hydrochloric acid (30 ml.) is added, and the mixture is allowed to stand until precipitation is complete. The precipitate is collected, dried, and crystallized from acetonitrile-water. m.p. 97\u00b0-99\u00b0 C.",
    "output_reaction_inputs": {
      "m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "n-Octyl bromide"
              }
            ],
            "amount": {
              "mass": {
                "value": 28.95,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      },
      "m1_m6_m2": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "p-hydroxybenzoic acid"
              }
            ],
            "amount": {
              "mass": {
                "value": 19.2,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "DMSO"
              }
            ],
            "amount": {
              "volume": {
                "value": 480.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "sodium hydroxide"
              }
            ],
            "amount": {
              "volume": {
                "value": 120.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      },
      "m5": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "hydrochloric acid"
              }
            ],
            "amount": {
              "volume": {
                "value": 30.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      },
      "m4": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "ice water"
              }
            ],
            "amount": {
              "volume": {
                "value": 1200.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "temperature": {
        "control": {
          "type": "AMBIENT"
        }
      },
      "stirring": {
        "type": "CUSTOM",
        "details": "The reaction mixture is stirred for 4 hours at room temperature after which it"
      },
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-d8515af103cd4a659c88c27401778821"
  },
  {
    "input_text": "A solution of n-tridecanoic acid (Sigma Chemical Co, 12.5 g), 2,4,5-trichlorophenol (11.5 g), and N,N'-dicyclohexylcarbodiimide (12.0 g) in methylene chloride (650 ml) is stirred at room temperature for 16 hours. The reaction mixture is then filtered and dried in vacuo to give 2,4,5-trichlorophenyl tridecanoate (22 g). The material is purified by column chromatography over silica gel (Woelm) using toluene as the eluent. Fractions are monitored by TLC using a shortwave UV light for detection. Fractions containing the purified product are pooled and concentrated in vacuo to dryness.",
    "output_reaction_inputs": {
      "m1_m2_m3_m4": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "n-tridecanoic acid"
              }
            ],
            "amount": {
              "mass": {
                "value": 12.5,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "2,4,5-trichlorophenol"
              }
            ],
            "amount": {
              "mass": {
                "value": 11.5,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "N,N'-dicyclohexylcarbodiimide"
              }
            ],
            "amount": {
              "mass": {
                "value": 12.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "methylene chloride"
              }
            ],
            "amount": {
              "volume": {
                "value": 650.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-3dc684b374ab44179724569d62cddcdc"
  },
  {
    "input_text": "n-Dodecanoyl chloride (8.74 g; 40 mmoles) is added dropwise to a solution of p-aminobenzoic acid (5.5 g; 40 mmoles) dissolved in pyridine (100 ml). The mixture is stirred for 3 hours and poured into water (3 L). The precipitate which forms is filtered and dried in vacuo to give N-(n-dodecanoyl)-p-aminobenzoic acid (11.01 g).",
    "output_reaction_inputs": {
      "m1_m2": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "n-Dodecanoyl chloride"
              }
            ],
            "amount": {
              "mass": {
                "value": 8.74,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "p-aminobenzoic acid"
              }
            ],
            "amount": {
              "mass": {
                "value": 5.5,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      },
      "m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "water"
              }
            ],
            "amount": {
              "volume": {
                "value": 3.0,
                "units": "LITER"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      },
      "m4": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "pyridine"
              }
            ],
            "amount": {
              "volume": {
                "value": 100.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "stirring": {
        "type": "CUSTOM",
        "details": "The mixture is stirred for 3 hours"
      },
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-91ea9e30b3b74fd0a8df91a40e7d9ef6"
  },
  {
    "input_text": "A solution of p-hydroxybenzoic acid (19.2 g, 150 mmoles) in 10% aqueous sodium hydroxide (120 ml) is added to dimethyl sulfoxide (DMSO) (480 ml) previously heated to 80\u00b0 C. n-Octyl bromide (28.95 g, 150 mmoles) is added dropwise to the solution. The reaction mixture is stirred for 4 hours at room temperature after which it is poured into ice water (1200 ml). Conc. hydrochloric acid (30 ml) is added, and the mixture is allowed to stand until precipitation is complete. The precipitate is collected, dried, and crystallized from acetonitrile-water. mp 97\u00b0-99\u00b0 C.",
    "output_reaction_inputs": {
      "m1_m6_m2": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "p-hydroxybenzoic acid"
              }
            ],
            "amount": {
              "mass": {
                "value": 19.2,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "dimethyl sulfoxide"
              }
            ],
            "amount": {
              "volume": {
                "value": 480.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "sodium hydroxide"
              }
            ],
            "amount": {
              "volume": {
                "value": 120.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      },
      "m5": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "hydrochloric acid"
              }
            ],
            "amount": {
              "volume": {
                "value": 30.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      },
      "m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "n-Octyl bromide"
              }
            ],
            "amount": {
              "mass": {
                "value": 28.95,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      },
      "m4": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "ice water"
              }
            ],
            "amount": {
              "volume": {
                "value": 1200.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "temperature": {
        "control": {
          "type": "AMBIENT"
        }
      },
      "stirring": {
        "type": "CUSTOM",
        "details": "The reaction mixture is stirred for 4 hours at room temperature after which it"
      },
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-2588e2a6d913424fae2b64d02b5ce5fd"
  },
  {
    "input_text": "A solution of p-hydroxybenzoic acid (19.2 g., 150 mmole) in 10% aqueous sodium hydroxide (120 ml.) is added to DMSO (480 ml.) previously heated to 80\u00b0 C. n-Octyl bromide (28.95 g., 150 mmole) is added dropwise to the solution. The reaction mixture is stirred for 4 hours at room temperature after which it is poured into ice water (1200 ml.). Conc. hydrochloric acid (30 ml.) is added, and the mixture is allowed to stand until precipitation is complete. The precipitate is collected, dried, and crystallized from acetonitrile-water. m.p. 97\u00b0-99\u00b0 C.",
    "output_reaction_inputs": {
      "m1_m6_m2": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "p-hydroxybenzoic acid"
              }
            ],
            "amount": {
              "mass": {
                "value": 19.2,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "DMSO"
              }
            ],
            "amount": {
              "volume": {
                "value": 480.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "sodium hydroxide"
              }
            ],
            "amount": {
              "volume": {
                "value": 120.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      },
      "m4": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "ice water"
              }
            ],
            "amount": {
              "volume": {
                "value": 1200.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      },
      "m5": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "hydrochloric acid"
              }
            ],
            "amount": {
              "volume": {
                "value": 30.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      },
      "m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "n-Octyl bromide"
              }
            ],
            "amount": {
              "mass": {
                "value": 28.95,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "temperature": {
        "control": {
          "type": "AMBIENT"
        }
      },
      "stirring": {
        "type": "CUSTOM",
        "details": "The reaction mixture is stirred for 4 hours at room temperature after which it"
      },
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-216d950bb4254212bfa67eef21490697"
  },
  {
    "input_text": "n-Dodecanoyl chloride (8.74 g.; 40 mmoles) is added dropwise to a solution of p-aminobenzoic acid (40 mmoles) dissolved in pyridine (100 ml.). The mixture is stirred for 3 hours and poured into water (3 l.). The precipitate which forms is filtered and dried in vacuo to give N-(n-dodecanoyl)-p-aminobenzoic acid (11.01 g.).",
    "output_reaction_inputs": {
      "m1_m2": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "n-Dodecanoyl chloride"
              }
            ],
            "amount": {
              "mass": {
                "value": 8.74,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "p-aminobenzoic acid"
              }
            ],
            "amount": {
              "moles": {
                "value": 40.0,
                "units": "MILLIMOLE"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      },
      "m4": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "pyridine"
              }
            ],
            "amount": {
              "volume": {
                "value": 100.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      },
      "m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "water"
              }
            ],
            "amount": {
              "volume": {
                "value": 3.0,
                "units": "LITER"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "stirring": {
        "type": "CUSTOM",
        "details": "The mixture is stirred for 3 hours"
      },
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-629ca66586a841b6a4dcaee95203c2f0"
  },
  {
    "input_text": "A solution of n-tridecanoic acid (Sigma Chemical Co.) (12.5 g), 2,4,5-trichlorophenol (11.5 g), and N,N'-dicyclohexylcarbodiimide (12.0 g) in methylene chloride (650 ml) is stirred at room temperature for 16 hours. The reaction mixture is then filtered and dried in vacuo to give 2,4,5-trichlorophenyl n-tridecanoate (22 g). The material is purified by column chromatography over silica gel (Woelm) using toluene as the eluent. Fractions are monitored by TLC using a shortwave UV light for detection. Fractions containing the purified product are pooled and concentrated in vacuo to dryness.",
    "output_reaction_inputs": {
      "m1_m2_m3_m4": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "n-tridecanoic acid"
              }
            ],
            "amount": {
              "mass": {
                "value": 12.5,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "2,4,5-trichlorophenol"
              }
            ],
            "amount": {
              "mass": {
                "value": 11.5,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "N,N'-dicyclohexylcarbodiimide"
              }
            ],
            "amount": {
              "mass": {
                "value": 12.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "methylene chloride"
              }
            ],
            "amount": {
              "volume": {
                "value": 650.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-de0950a1f61c464dbb9fadb1de26cc8b"
  },
  {
    "input_text": "n-Dodecanoyl chloride (8.74 g; 40 mmoles) is added dropwise to a solution of p-aminobenzoic acid (40 mmoles) dissolved in pyridine (100 ml). The mixture is stirred for 3 hours and poured into water (3 L). The precipitate which forms is filtered and dried in vacuo to give N-(n-dodecanoyl)-p-aminobenzoic acid (11.01 g).",
    "output_reaction_inputs": {
      "m4": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "pyridine"
              }
            ],
            "amount": {
              "volume": {
                "value": 100.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      },
      "m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "water"
              }
            ],
            "amount": {
              "volume": {
                "value": 3.0,
                "units": "LITER"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      },
      "m1_m2": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "n-Dodecanoyl chloride"
              }
            ],
            "amount": {
              "mass": {
                "value": 8.74,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "p-aminobenzoic acid"
              }
            ],
            "amount": {
              "moles": {
                "value": 40.0,
                "units": "MILLIMOLE"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "stirring": {
        "type": "CUSTOM",
        "details": "The mixture is stirred for 3 hours"
      },
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-2b233c995cc74008b4dc9ca65702cb36"
  },
  {
    "input_text": "A solution of p-hydroxybenzoic acid (19.2 g, 150 moles) in 10% aqueous sodium hydroxide (120 ml) is added to dimethyl sulfoxide (DMSO) (480 ml) previously heated to 80\u00b0 C. n-Octyl bromide (28.95 g, 150 moles) is added dropwise to the solution. The reaction mixture is stirred for 4 hours at room temperature after which it is poured into ice water (1200 ml). Conc. hydrochloric acid (30 ml) is added, and the mixture is allowed to stand until precipitation is complete. The precipitate is collected, dried, and crystallized from acetonitrile-water. mp 97\u00b0-99\u00b0 C.",
    "output_reaction_inputs": {
      "m5": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "hydrochloric acid"
              }
            ],
            "amount": {
              "volume": {
                "value": 30.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      },
      "m4": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "ice water"
              }
            ],
            "amount": {
              "volume": {
                "value": 1200.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      },
      "m1_m6_m2": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "p-hydroxybenzoic acid"
              }
            ],
            "amount": {
              "mass": {
                "value": 19.2,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "dimethyl sulfoxide"
              }
            ],
            "amount": {
              "volume": {
                "value": 480.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "sodium hydroxide"
              }
            ],
            "amount": {
              "volume": {
                "value": 120.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      },
      "m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "n-Octyl bromide"
              }
            ],
            "amount": {
              "mass": {
                "value": 28.95,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "temperature": {
        "control": {
          "type": "AMBIENT"
        }
      },
      "stirring": {
        "type": "CUSTOM",
        "details": "The reaction mixture is stirred for 4 hours at room temperature after which it"
      },
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-05023bc7b75c458d91805355bc24d015"
  },
  {
    "input_text": "A solution of p-hydroxybenzoic acid (19.2 g., 150 mmole) in 10% aqueous sodium hydroxide (120 ml.) is added to DMSO (480 ml.) previously heated to 80\u00b0 C. n-Octyl bromide (28.95 g., 150 mmole) is added dropwise to the solution. The reaction mixture is stirred for 4 hours at room temperature after which it is poured into ice water (1200 ml.). Conc. hydrochloric acid (30 ml.) is added, and the mixture is allowed to stand until precipitation is complete. The precipitate is collected, dried, and crystallized from acetonitrile-water. m.p. 97\u00b0-99\u00b0 C.",
    "output_reaction_inputs": {
      "m5": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "hydrochloric acid"
              }
            ],
            "amount": {
              "volume": {
                "value": 30.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      },
      "m1_m6_m2": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "p-hydroxybenzoic acid"
              }
            ],
            "amount": {
              "mass": {
                "value": 19.2,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "DMSO"
              }
            ],
            "amount": {
              "volume": {
                "value": 480.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "sodium hydroxide"
              }
            ],
            "amount": {
              "volume": {
                "value": 120.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      },
      "m4": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "ice water"
              }
            ],
            "amount": {
              "volume": {
                "value": 1200.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      },
      "m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "n-Octyl bromide"
              }
            ],
            "amount": {
              "mass": {
                "value": 28.95,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "temperature": {
        "control": {
          "type": "AMBIENT"
        }
      },
      "stirring": {
        "type": "CUSTOM",
        "details": "The reaction mixture is stirred for 4 hours at room temperature after which it"
      },
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-f7b5093a46f84f4ba3aff75e79642c5b"
  },
  {
    "input_text": "4,6-Dioxo-10-propyl-4H,6H-benzo[1,2-b:5,4-b']dipyran-2,8-dicarboxylic acid (1.0 g) was added to a stirred solution of guanidinium carbonate (0.52 g) in water (20 ml) and the mixture was stirred at room temperature until effervescence had ceased. The precipitated solid was collected using a centrifuge, washed with water and acetone and dried in vacuo at 70\u00b0 C. to give the title compound (0.83 g; 62%).",
    "output_reaction_inputs": {
      "m1_m2_m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "4,6-Dioxo-10-propyl-4H,6H-benzo[1,2-b:5,4-b']dipyran-2,8-dicarboxylic acid"
              }
            ],
            "amount": {
              "mass": {
                "value": 1.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "guanidinium carbonate"
              }
            ],
            "amount": {
              "mass": {
                "value": 0.52,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "water"
              }
            ],
            "amount": {
              "volume": {
                "value": 20.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "temperature": {
        "control": {
          "type": "AMBIENT"
        }
      },
      "stirring": {
        "type": "CUSTOM",
        "details": "the mixture was stirred at room temperature until effervescence"
      },
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-9bd503af679c4e8098bc16607c14d1cd"
  },
  {
    "input_text": "(ci) 1.58 g (1.2 equivalents) of silver p-toluenesulphinate are added in portions, in the course of 10 minutes, to a solution of 3.25 g (5.0 mmols) of 2-[4-(benzthiazol-2-yldithio)-3-phenoxyacetamido-2-oxoazetidin-1-yl]-3-methylenebutyric acid p-nitrobenzyl ester in 200 ml of acetone/water, 9:1 (v/v). The suspension is stirred for one hour at room temperature, filtered and further processed as described in Example 1(c). 2-[4-(p]Toluenesulphonylthio)-3-phenoxyacetamido-2-oxoazetidin-1-yl]-3-methylenebutyric acid p-nitrobenzyl ester is obtained in quantitative yield.",
    "output_reaction_inputs": {
      "m3_m1_m2": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "2-[4-(benzthiazol-2-yldithio)-3-phenoxyacetamido-2-oxoazetidin-1-yl]-3-methylenebutyric acid p-nitrobenzyl ester"
              }
            ],
            "amount": {
              "mass": {
                "value": 3.25,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "acetone water"
              }
            ],
            "amount": {
              "volume": {
                "value": 200.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "silver p-toluenesulphinate"
              }
            ],
            "amount": {
              "mass": {
                "value": 1.58,
                "units": "GRAM"
              }
            },
            "reactionRole": "CATALYST"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "temperature": {
        "control": {
          "type": "AMBIENT"
        }
      },
      "stirring": {
        "type": "CUSTOM",
        "details": "The suspension is stirred for one hour at room temperature"
      },
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-1f92a1a88e7a41a19cd9e267689582e5"
  },
  {
    "input_text": "3 ml of an ethereal diazomethane solution (0.5 molar, 1.5 equivalents) are added in the course of about 10 minutes to a solution, cooled to 0\u00b0 C., of 485 mg of 7\u03b2-phenoxyacetamido-3-hydroxy-3-cephem-4-carboxylic acid p-nitrobenzyl ester in 10 ml of dry chloroform. The pale yellow solution is stirred for 1 hour at 0\u00b0 C., flushed with nitrogen in order to remove excess diazomethane and concentrated in vacuo. The residue is recrystallised from methylene chloride and gives 7\u03b2-phenoxyacetamido-3-methoxy-3-cephem-4-carboxylic acid p-nitrobenzyl ester of melting point 140.5\u00b0-142\u00b0 C.",
    "output_reaction_inputs": {
      "m1": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "diazomethane"
              }
            ],
            "amount": {
              "volume": {
                "value": 3.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      },
      "m2_m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "7\u03b2-phenoxyacetamido-3-hydroxy-3-cephem-4-carboxylic acid p-nitrobenzyl ester"
              }
            ],
            "amount": {
              "mass": {
                "value": 485.0,
                "units": "MILLIGRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "chloroform"
              }
            ],
            "amount": {
              "volume": {
                "value": 10.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "temperature": {
        "setpoint": {
          "value": 0.0,
          "units": "CELSIUS"
        }
      },
      "stirring": {
        "type": "CUSTOM",
        "details": "The pale yellow solution is stirred for 1 hour at 0\u00b0 C."
      },
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-d455ec8cf33f4f68a9421487d3eed8ec"
  },
  {
    "input_text": "(ai) A suspension of 4.85 g of 7\u03b2-phenoxyacetamido-3-hydroxy-3-cephem-4-carboxylic acid p-nitrobenzyl ester in 25 ml of carbon tetrachloride and 27 ml of water is treated, at 20\u00b0, whilst stirring vigorously, successively with 3.0 g of potassium bicarbonate, 3.8 ml of dimethyl sulphate and 1.93 g of tetrabutylammonium bromide. The mixture is stirred vigorously for 4 hours at 20\u00b0. After diluting with 50 ml of water, the mixture is extracted with twice 50 ml of methylene chloride. 7\u03b2-Phenoxyacetamido-3-methoxy-3-cephem-4-carboxylic acid p-nitrobenzyl ester is obtained by evaporating the extracts, previously dried over sulphate, and crystallising the residue from methylene chloride/diethyl ether.",
    "output_reaction_inputs": {
      "m1_m4_m5": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "7\u03b2-phenoxyacetamido-3-hydroxy-3-cephem-4-carboxylic acid p-nitrobenzyl ester"
              }
            ],
            "amount": {
              "mass": {
                "value": 4.85,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "carbon tetrachloride"
              }
            ],
            "amount": {
              "volume": {
                "value": 25.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "water"
              }
            ],
            "amount": {
              "volume": {
                "value": 27.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      },
      "m7": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "water"
              }
            ],
            "amount": {
              "volume": {
                "value": 50.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      },
      "m2_m3_m6": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "potassium bicarbonate"
              }
            ],
            "amount": {
              "mass": {
                "value": 3.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "dimethyl sulphate"
              }
            ],
            "amount": {
              "volume": {
                "value": 3.8,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "tetrabutylammonium bromide"
              }
            ],
            "amount": {
              "mass": {
                "value": 1.93,
                "units": "GRAM"
              }
            },
            "reactionRole": "CATALYST"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "stirring": {
        "type": "CUSTOM",
        "details": "The mixture is stirred vigorously for 4 hours at 20\u00b0"
      },
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-b8d748b1a0b946b59b8969672193faf0"
  },
  {
    "input_text": "A solution of 1.26 g 1-[3-hydroxy-3-(2-naphthyl)-n-propyl]imidazole in 20 ml pyridine is treated dropwise with stirring with 0.72 ml of benzoyl chloride and the mixture stirred overnight. The resulting solution is poured into 100 ml water, extracted with ethyl acetate and the extracts washed, dried (MgSO4) and evaporated in vacuo to remove residual pyridine and afford 1-[3-benzoyloxy-3-(2-naphthyl)-n-propyl]imidazole. The residue is dissolved in ether, treated with ethereal hydrogen chloride and the resulting precipitate recrystallized from acetone/methanol to give the hydrochloride salt.",
    "output_reaction_inputs": {
      "m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "water"
              }
            ],
            "amount": {
              "volume": {
                "value": 100.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      },
      "m2": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "benzoyl chloride"
              }
            ],
            "amount": {
              "volume": {
                "value": 0.72,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      },
      "m1_m4": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "1-[3-hydroxy-3-(2-naphthyl)-n-propyl]imidazole"
              }
            ],
            "amount": {
              "mass": {
                "value": 1.26,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "pyridine"
              }
            ],
            "amount": {
              "volume": {
                "value": 20.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "stirring": {
        "type": "CUSTOM",
        "details": "the mixture stirred overnight"
      },
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-fe28f0008a0e4f5ba4e752f6eb3040b8"
  },
  {
    "input_text": "A mixture of 2,4,5-trimethoxybenzaldehyde (9.8 g; 0.05 mole), 3-n-butylhydantoin (7.8 g; 0.05 mole) and ethanolamine (4.6 g; 0.075 mole) in water/ethanol (50 ml/30 ml) was stirred and boiled under reflux for 3 hours. The cloudy solution was cooled in the refrigerator and the resultant yellow solid filtered off, washed with water, sucked dry and recrystallised from ethanol to give the title compound (14.5 g; 87%) m.p. 170\u00b0 C.",
    "output_reaction_inputs": {
      "m1_m2_m3_m4": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "2,4,5-trimethoxybenzaldehyde"
              }
            ],
            "amount": {
              "mass": {
                "value": 9.8,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "3-n-butylhydantoin"
              }
            ],
            "amount": {
              "mass": {
                "value": 7.8,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "ethanolamine"
              }
            ],
            "amount": {
              "mass": {
                "value": 4.6,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "water ethanol"
              }
            ],
            "amount": {
              "volume": {
                "value": 50.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "stirring": {
        "type": "CUSTOM",
        "details": "was stirred"
      },
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-46f6399e00fb448299f70f27a8338801"
  },
  {
    "input_text": "3-n-Butyl-5-[4-(1,3-dioxol-2-yl)benzylidene] hydantoin (2.7 g; 0.0085 mole) was dissolved in acetone (100 ml.) and stirred overnight at room temperature with p-toluene sulphonic acid (0.5 g.). The hazy solution was evaporated in vacuo and the resultant solid suspended in water (100 ml) and neutralised to pH 7 using dilute sodium bicarbonate solution. The residual solid was filtered off, washed with water and dried to give the title compound m.p. 180\u00b0 C.",
    "output_reaction_inputs": {
      "m1_m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "3-n-Butyl-5-[4-(1,3-dioxol-2-yl)benzylidene] hydantoin"
              }
            ],
            "amount": {
              "mass": {
                "value": 2.7,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "acetone"
              }
            ],
            "amount": {
              "volume": {
                "value": 100.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      },
      "m2": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "p-toluene sulphonic acid"
              }
            ],
            "amount": {
              "mass": {
                "value": 0.5,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-4ff5eea0dfb64dcfa512b571882168fd"
  },
  {
    "input_text": "3-n-Butyl-5-(2,4,5-trimethoxybenzylidene) hydantoin (10.0 g; 0.03 mole) was mixed with glacial acetic acid (150 ml.) and hydrogenated in a Parr apparatus in the presence of 5% Pd/C (2 g). After 2 hours the catalyst was filtered off, washed with warm acetic acid and the colourless filtrate evaporated in vacuo to give a white crystalline solid. Recrystallisation from ethyl acetate gave the title compound, yield 9.2 g (91% ), m.p. 122\u00b0 C.",
    "output_reaction_inputs": {
      "m1_m3_m2": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "3-n-Butyl-5-(2,4,5-trimethoxybenzylidene) hydantoin"
              }
            ],
            "amount": {
              "mass": {
                "value": 10.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "Pd/C"
              }
            ],
            "amount": {
              "mass": {
                "value": 2.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "CATALYST"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "acetic acid"
              }
            ],
            "amount": {
              "volume": {
                "value": 150.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-ce3a288b229b4defa7c5dbe1380b8974"
  },
  {
    "input_text": "3-n-Butyl-5-[4-(1,3-dioxol-2-yl)benzyl] hydantoin (5.5 g., 0.017 mole) was dissolved in acetone (150 ml.) and stirred overnight at room temperature with p-toluene sulphonic acid (0.5 g). The acetone was evaporated off in vacuo and the residual oily solid partitioned between water and chloroform. The chloroform phase was washed with sodium carbonate solution (2% W/V), then evaporated in vacuo to give a yellow oil which slowly crystallised and was recrystallised from petroleum ether 60/80\u00b0 C./ethyl acetate (3/1 V/V) to give 3-n-butyl-5-(4-formylbenzyl) hydantoin, 4.5 g (95%), m.p. 160\u00b0 C.",
    "output_reaction_inputs": {
      "m1_m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "3-n-Butyl-5-[4-(1,3-dioxol-2-yl)benzyl] hydantoin"
              }
            ],
            "amount": {
              "mass": {
                "value": 5.5,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "acetone"
              }
            ],
            "amount": {
              "volume": {
                "value": 150.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      },
      "m2": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "p-toluene sulphonic acid"
              }
            ],
            "amount": {
              "mass": {
                "value": 0.5,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-e32c4f91ca864252b4e3c0180e96718b"
  },
  {
    "input_text": "3-n-Butyl-5-(4-carboxybenzyl) hydantoin (7.2 g., 0.025 mole) was added to a stirred solution of thionyl chloride (1.8 ml., 0.025 mole) in methanol (100 ml) prepared at -5\u00b0 to -10\u00b0 C. The mixture was allowed to come to room temperature and finally heated under reflux for 1 hour. After cooling, the clear solution was evaporated in vacuo to dryness and the resultant white crystalline solid was recrystallised from ethyl acetate to give the title compound. Yield 7.1 g (94%) m.p. 144\u00b0 C.",
    "output_reaction_inputs": {
      "m1_m2_m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "3-n-Butyl-5-(4-carboxybenzyl) hydantoin"
              }
            ],
            "amount": {
              "mass": {
                "value": 7.2,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "thionyl chloride"
              }
            ],
            "amount": {
              "volume": {
                "value": 1.8,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "methanol"
              }
            ],
            "amount": {
              "volume": {
                "value": 100.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-f5dcc54f17b44cd0839af2ac1f114022"
  },
  {
    "input_text": "5-Benzyl-3-n-butyl hydantoin (7.38 g, 0.03 mole) was dissolved in dimethylformamide (50 ml.) and added dropwise with stirring to a suspension of sodium hydride (1.44 g. 50% oil dispersion) in dimethylformamide (20 ml). When gassing ceased, iodomethane (2 ml) was added and the mixture warmed to 50\u00b0 C. and maintained at 50\u00b0 C. for 5 hours. The mixture was poured into ice/water (500 ml) and extracted with ether. The ether extract was evaporated in vacuo to give a colourless oil which failed to crystallise and was distilled in a Kugelrohr apparatus to give the title compound (6.6 g; 85%) b.p. 145\u00b0 C./0.02 mm.",
    "output_reaction_inputs": {
      "m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "iodomethane"
              }
            ],
            "amount": {
              "volume": {
                "value": 2.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      },
      "m2_m6": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "sodium hydride"
              }
            ],
            "amount": {
              "mass": {
                "value": 1.44,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "dimethylformamide"
              }
            ],
            "amount": {
              "volume": {
                "value": 20.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      },
      "m4": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "ice water"
              }
            ],
            "amount": {
              "volume": {
                "value": 500.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      },
      "m1_m5": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "5-Benzyl-3-n-butyl hydantoin"
              }
            ],
            "amount": {
              "mass": {
                "value": 7.38,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "dimethylformamide"
              }
            ],
            "amount": {
              "volume": {
                "value": 50.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "temperature": {
        "setpoint": {
          "value": 50.0,
          "units": "CELSIUS"
        }
      },
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-40f1712659d04956a0f03cbd49efcbe5"
  },
  {
    "input_text": "A mixture of thiophene-2-carboxaldehyde (5.6 g; 0.05 mole), 3-n-butylhydantoin (7.8 g; 0.05 mole) and ethanolamine (4.6 g; 0.075 mole) in water/ethanol (50 ml/30 ml) was stirred and boiled under reflux for 4 hours. The mixture was cooled in the refrigerator and the resultant brownish yellow crystals filtered off, washed with water, sucked dry and recrystallised from ethyl acetate (with carbon treatment) to give the title compound (6.4 g; 51%) having m.p. 140\u00b0 C.",
    "output_reaction_inputs": {
      "m1_m2_m3_m4": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "thiophene-2-carboxaldehyde"
              }
            ],
            "amount": {
              "mass": {
                "value": 5.6,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "3-n-butylhydantoin"
              }
            ],
            "amount": {
              "mass": {
                "value": 7.8,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "ethanolamine"
              }
            ],
            "amount": {
              "mass": {
                "value": 4.6,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "water ethanol"
              }
            ],
            "amount": {
              "volume": {
                "value": 50.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "stirring": {
        "type": "CUSTOM",
        "details": "was stirred"
      },
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-6702625bc23d4655ae427b9f26a2a1c2"
  },
  {
    "input_text": "DL-\u03b2-(5-Methylthiophen-2-yl)alanine (4.1 g; 0.022 mole) was dissolved in 2 N sodium hydroxide solution (11 ml; 0.022 mole), cooled to 0\u00b0 C. and n-butylisocyanate (3.75 ml; 0.033 mole) added gradually maintaining the temperature at 0\u00b0 C. for 2 hours. The mixture was allowed to come to room temperature and stirred overnight. The mixture was filtered (solid discarded) and the filtrate washed with ether. The washed filtrate was acidified with concentrated hydrochloric acid (11 ml) and heated on a steam bath for 1 hour. After cooling to room temperature the resultant solid was separated by filtration, water washed and dried. Recrystallisation from ethyl acetate gave the title compound. Yield 4.2 g (72%), m.p. 107\u00b0 C.",
    "output_reaction_inputs": {
      "m1_m2": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "\u03b2-(5-Methylthiophen-2-yl)alanine"
              }
            ],
            "amount": {
              "mass": {
                "value": 4.1,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "sodium hydroxide"
              }
            ],
            "amount": {
              "volume": {
                "value": 11.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      },
      "m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "n-butylisocyanate"
              }
            ],
            "amount": {
              "volume": {
                "value": 3.75,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "temperature": {
        "setpoint": {
          "value": 0.0,
          "units": "CELSIUS"
        }
      },
      "stirring": {
        "type": "CUSTOM",
        "details": "stirred overnight"
      },
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-149bd1c2cb344d889102f006cfa99188"
  },
  {
    "input_text": "A suspension of 12.7 g (60 mmols) of 3-chloro-4-trifluoromethoxyaniline and 15.15 g (60 mmols) of 1-chloro-2,4-dinitronaphthalene in 150 ml of water was heated to the boil. 5.6 g (67 mmols) of sodium bicarbonate were introduced in the course of 30 minutes and heating was continued for 2 hours under reflux. After the mixture had cooled to 20\u00b0 C., the product was filtered off. 24 g of 1-(3-chloro-4-trifluoromethoxyphenylamino)-2,4-dinitronaphthalene of melting point 140\u00b0 C. were obtained; after recrystallization from ethanol, 17.4 g of melting point 159\u00b0 C. were obtained.",
    "output_reaction_inputs": {
      "m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "sodium bicarbonate"
              }
            ],
            "amount": {
              "mass": {
                "value": 5.6,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      },
      "m1_m2_m4": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "3-chloro-4-trifluoromethoxyaniline"
              }
            ],
            "amount": {
              "mass": {
                "value": 12.7,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "1-chloro-2,4-dinitronaphthalene"
              }
            ],
            "amount": {
              "mass": {
                "value": 15.15,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "water"
              }
            ],
            "amount": {
              "volume": {
                "value": 150.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "temperature": {
        "setpoint": {
          "value": 20.0,
          "units": "CELSIUS"
        }
      },
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-a4fc12bdc2634e4d877d5cc71d7347ca"
  },
  {
    "input_text": "A mixture of 1 g of 3-[3-(1-piperidinylmethyl)phenoxy]propylamine, 1 g of sodium formate and 3 ml of formic acid was refluxed for 1 hour, and a greater portion of the solvent was distilled off under reduced pressure, and water was added to the residue. The mixture was alkalized with 4% sodium hydroxide solution. The product was extracted with chloroform. The extract was dried over anhydrous magnesium sulfate. The solvent was distilled off, and the residue was separated and purified by thin-layer chromatography (TLC) (developing solvent: chloroform/methanol=9/l) to afford 436 mg of N-[3-[3-(1-piperidinylmethyl)phenoxy]propyl]formamide as an oil.",
    "output_reaction_inputs": {
      "m1_m2_m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "3-[3-(1-piperidinylmethyl)phenoxy]propylamine"
              }
            ],
            "amount": {
              "mass": {
                "value": 1.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "sodium formate"
              }
            ],
            "amount": {
              "mass": {
                "value": 1.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "formic acid"
              }
            ],
            "amount": {
              "volume": {
                "value": 3.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-c58f9afa3f03429b9333be6c16f591b8"
  },
  {
    "input_text": "240 mg of 3-[3-[1-(1-pyrrolidinyl)ethyl]phenoxy]propylamine was dissolved in 4.5 ml of chloroform, and a solution of 144 mg of 3-hydroxypropionic acid in 0.5 ml of ethanol was added, followed by further addition of 300 mg of dicyclohexylcarbodiimide. The mixture was stirred at room temperature for 6 hours, and the solvent was distilled off under reduced pressure. The residue was purified by TLC (developing solvent: chloroform/methanol=9/l) to afford 180 mg of N-[3-[3-[1-(1-pyrrolidinyl)ethyl]phenoxy]propyl]hydroxypropionamide as an oil.",
    "output_reaction_inputs": {
      "m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "dicyclohexylcarbodiimide"
              }
            ],
            "amount": {
              "mass": {
                "value": 300.0,
                "units": "MILLIGRAM"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      },
      "m2_m4": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "3-hydroxypropionic acid"
              }
            ],
            "amount": {
              "mass": {
                "value": 144.0,
                "units": "MILLIGRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "ethanol"
              }
            ],
            "amount": {
              "volume": {
                "value": 0.5,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      },
      "m1_m5": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "3-[3-[1-(1-pyrrolidinyl)ethyl]phenoxy]propylamine"
              }
            ],
            "amount": {
              "mass": {
                "value": 240.0,
                "units": "MILLIGRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "chloroform"
              }
            ],
            "amount": {
              "volume": {
                "value": 4.5,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "temperature": {
        "control": {
          "type": "AMBIENT"
        }
      },
      "stirring": {
        "type": "CUSTOM",
        "details": "The mixture was stirred at room temperature for 6 hours"
      },
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-32daf5430fc74b4da6d79cd4688df297"
  },
  {
    "input_text": "150 mg of N-[3-[3-(1-piperidinylmethyl)phenoxy]propyl]hydroxyacetamide was dissolved in 0.5 ml of pyridine, and 150 mg of benzoyl chloride was added dropwise to the solution under ice cooling. After the addition, the mixture was stirred at room temperature for 2 hours. The solvent was distilled off and water was added. The mixture was alkalized with aqueous ammonia, and extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate, and the solvent was distilled off. The residue was separated and purified by TLC (developing solvent: chloroform/methanol=19/l) to afford 165 mg of N-[3-[3-(1-piperidinylmethyl)phenoxy]propyl]benzoyloxyacetamide.",
    "output_reaction_inputs": {
      "m1_m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "N-[3-[3-(1-piperidinylmethyl)phenoxy]propyl]hydroxyacetamide"
              }
            ],
            "amount": {
              "mass": {
                "value": 150.0,
                "units": "MILLIGRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "pyridine"
              }
            ],
            "amount": {
              "volume": {
                "value": 0.5,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      },
      "m2": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "benzoyl chloride"
              }
            ],
            "amount": {
              "mass": {
                "value": 150.0,
                "units": "MILLIGRAM"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "temperature": {
        "control": {
          "type": "AMBIENT"
        }
      },
      "stirring": {
        "type": "CUSTOM",
        "details": "the mixture was stirred at room temperature for 2 hours"
      },
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-b6eef20fd2ef43d0b3017faef5ebed17"
  },
  {
    "input_text": "500 mg of the amide compound obtained in step (A) was heated under reflux for 2 hours in 1 ml of ethanolamine and 1 ml of ethanol. The solvent was distilled off under reduced pressure, and potassium carbonate was added. The mixture was extracted with chloroform. The solvent was distilled off, and the residue was purified by TLC (developing solvent: chloroform/diethylamine=10:1) to afford 355 mg of N-[3-(2-hydroxyethylamino)propionyl]-3-[3-[1-(1-pyrrolidinyl)ethyl]phenoxy]propylamine.",
    "output_reaction_inputs": {
      "m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "ethanol"
              }
            ],
            "amount": {
              "volume": {
                "value": 1.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      },
      "m2": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "ethanolamine"
              }
            ],
            "amount": {
              "volume": {
                "value": 1.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      },
      "m1": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "amide"
              }
            ],
            "amount": {
              "mass": {
                "value": 500.0,
                "units": "MILLIGRAM"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-87a3e3b29a9d4fe6835ac1ee6c6f1d93"
  },
  {
    "input_text": "191 mg of 3-(1-piperidinylmethyl)phenol was dissolved in 10 ml of ethanol, and 116 mg of potassium hydroxide was added. The mixture was heated under reflux, and a solution of 360 mg of 3-acetamino-1-bromopropane in 3 ml of ethanol. The reaction mixture was heated under reflux for 8 hours, and the solvent was distilled off under reduced pressure. Water was added, and the mixture was extracted with chloroform. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by TLC (developing solvent: chloroform/methanol=9/l) to afford 205 mg of N-[3-[3-(1-piperidinylmethyl)phenoxy]propyl]acetamide as an oil. The resulting product coincided with the product obtained in Example 2.",
    "output_reaction_inputs": {
      "m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "3-acetamino-1-bromopropane"
              }
            ],
            "amount": {
              "mass": {
                "value": 360.0,
                "units": "MILLIGRAM"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      },
      "m2": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "potassium hydroxide"
              }
            ],
            "amount": {
              "mass": {
                "value": 116.0,
                "units": "MILLIGRAM"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      },
      "m1_m4": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "3-(1-piperidinylmethyl)phenol"
              }
            ],
            "amount": {
              "mass": {
                "value": 191.0,
                "units": "MILLIGRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "ethanol"
              }
            ],
            "amount": {
              "volume": {
                "value": 10.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      },
      "m5": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "ethanol"
              }
            ],
            "amount": {
              "volume": {
                "value": 3.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-4d72ee2b4fe04a1684558eed2b18c234"
  },
  {
    "input_text": "2.5 g of N-[3-[3-(hydroxymethyl)phenoxy]propyl]phthalimide was dissolved in 12 ml of benzene, and 3 ml of thionyl chloride was added. The mixture was refluxed for 1 hour. The solvent was distilled off under reduced pressure, and the residue was dissolved in ether. The solution was washed twice with a 5% aqueous solution of potassium carbonate, and then rinsed with water. The product was dried over anhydrous sodium sulfate, and the solvent was distilled off to afford 2.8 g of N-[3-[3-(chloromethyl)phenoxy]propyl]phthalimide as an oil.",
    "output_reaction_inputs": {
      "m2": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "thionyl chloride"
              }
            ],
            "amount": {
              "volume": {
                "value": 3.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      },
      "m1_m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "N-[3-[3-(hydroxymethyl)phenoxy]propyl]phthalimide"
              }
            ],
            "amount": {
              "mass": {
                "value": 2.5,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "benzene"
              }
            ],
            "amount": {
              "volume": {
                "value": 12.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-4acc6f6d34994a98ae1d20f68d245aad"
  },
  {
    "input_text": "30 g of the 3-(imidazo[4,5-b]pyridine-2-ylthio)-3-(4-chlorobenzoyl)propionic acid hydrobromide obtained above are dissolved in a dilute NaHCO3 solution (25 g NaHCO3 in 800 ml water), and the solution is filtered and the filtrate acidified with acetic acid. The solid is collected, washed well with water and air dried, yielding 20 g of material. The solid is recrystallized from hot acetonitrile. The title compound decomposes at about 140\u00b0 C.",
    "output_reaction_inputs": {
      "m1": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "3-(imidazo[4,5-b]pyridine-2-ylthio)-3-(4-chlorobenzoyl)propionic acid hydrobromide"
              }
            ],
            "amount": {
              "mass": {
                "value": 30.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      },
      "m2": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "NaHCO3"
              }
            ],
            "amount": {
              "volume": {
                "value": 800.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-72a653a017d34596906a2c6964b0f4a6"
  },
  {
    "input_text": "17 g (0.047 m) of 3-(imidazo[4,5-b]pyridine-2-ylthio)-3-(4-chlorobenzoyl)propionic acid, prepared according to Example 2, is dissolved in 200 ml trifluoroacetic acid, and the solution is heated to gentle reflux overnight. The solution is cooled and filtered, the solvent is removed in vacuo and the residual solid triturated with ether and the solid collected. The resulting trifluoroacetate is disproportionated in hot acetonitrile to give 9.3 g of title compound, m.p. 250\u00b0-252\u00b0 C.",
    "output_reaction_inputs": {
      "m1": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "3-(imidazo[4,5-b]pyridine-2-ylthio)-3-(4-chlorobenzoyl)propionic acid"
              }
            ],
            "amount": {
              "mass": {
                "value": 17.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      },
      "m2": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "trifluoroacetic acid"
              }
            ],
            "amount": {
              "volume": {
                "value": 200.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-ed3f2308d1124396a094389c0bef8e52"
  },
  {
    "input_text": "18.2 g of the nitro compound obtained above was suspended in 300 ml of ethanol, which was reduced over 2 g of 5% palladium black under atmospheric pressure. After reaction, the catalyst was filtered off and the solvent was evaporated in vacuo. The residue was crystallized from benzene to obtain 13.8 g of 3-ethoxy-2-methyl-6-aminopyridine (Compound IV where R2 =C2H5), m.p. 98\u00b0-99\u00b0 C.",
    "output_reaction_inputs": {
      "m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "palladium black"
              }
            ],
            "amount": {
              "mass": {
                "value": 2.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "CATALYST"
          }
        ]
      },
      "m1": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "nitro"
              }
            ],
            "amount": {
              "mass": {
                "value": 18.2,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      },
      "m2": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "ethanol"
              }
            ],
            "amount": {
              "volume": {
                "value": 300.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-7546caff650d435fac3441641d4fbc59"
  },
  {
    "input_text": "16.1 g of the Compound VI obtained as above was added to 160 ml of boiling Dowtherm (produced by Dow Chemical Co.) and refluxed for 1 hour. After cooling, the precipitated crystals were collected by filtration to obtain 11.8 g of crude crystals which were then recrystallized from dimethylformamide to yield ethyl 6-ethoxy-4-hydroxy-7-methyl-1,8-naphthyridine-3-carboxylate (Compound VII where R2 =R3 =C2H5), m.p. 279\u00b0-282\u00b0 C. (with decomposition).",
    "output_reaction_inputs": {
      "m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "Dowtherm"
              }
            ],
            "amount": {
              "volume": {
                "value": 160.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      },
      "m2": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "Compound VI"
              }
            ],
            "amount": {
              "mass": {
                "value": 16.1,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-06ed29e55c7f4346a522b66aacd0fc10"
  },
  {
    "input_text": "A mixture of 9.5 g of 5,8-dihydro-5-ethyl-8-oxofuro-[3,2-b]-1,8-naphthyridine-2,7-dicarboxylic acid (Compound X where R1 =C2H5), 0.8 g of copper powder and 250 ml of diethyl phthalate was heated at 250\u00b0 to 260\u00b0 C. for 25 minutes. After cooling, the reaction mixture was separated by partitioning between chloroform and aqueous potassium carbonate solution. The aqueous layer which separated out was acidified with hydrochloric acid and extracted with chloroform. The extract was treated with charcoal, and washed with water, dried and concentrated. The crystals precipitated by adding ethanol were collected by filtration to obtain 4.2 g of 5,8-dihydro-5-ethyl-8-oxofuro[3,2-b]-1,8-naphthyridine-7-carboxylic acid (Compound Ia where R1 =C2H5).",
    "output_reaction_inputs": {
      "m1_m2_m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "5,8-dihydro-5-ethyl-8-oxofuro-[3,2-b]-1,8-naphthyridine-2,7-dicarboxylic acid"
              }
            ],
            "amount": {
              "mass": {
                "value": 9.5,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "copper"
              }
            ],
            "amount": {
              "mass": {
                "value": 0.8,
                "units": "GRAM"
              }
            },
            "reactionRole": "CATALYST"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "diethyl phthalate"
              }
            ],
            "amount": {
              "volume": {
                "value": 250.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-4e5eec42a8134bec9b82deb1793f41ad"
  },
  {
    "input_text": "6 g of 7a,8,9,10,11,11a-hexahydro-4-oxo-4H-pyrido[3,2,1-jk]carbazol-5-carboxylic acid was dissolved in 35 ml of concentrated sulfuric acid and stirred while cooling with ice, followed by dropwise addition of a mixture of 4.3 ml of concentrated nitric acid having a specific gravity and 15 ml of the concentrated sulfuric acid. After completion of the addition, the resulting mixture was stirred for one hour at room temperature and poured into 200 g of ice to precipitate yellow crystals. Recrystallization from dimethylformamide-water gave 7 g of 3-nitro-7a,8,9,10,11,11a-hexahydro-4-oxo-4H-pyrido[3,2,1-jk]carbazol-5-carboxylic acid having a melting point of 251\u00b0-253\u00b0 C.",
    "output_reaction_inputs": {
      "m2_m5": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "nitric acid"
              }
            ],
            "amount": {
              "volume": {
                "value": 4.3,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "sulfuric acid"
              }
            ],
            "amount": {
              "volume": {
                "value": 15.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      },
      "m1_m4": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "7a,8,9,10,11,11a-hexahydro-4-oxo-4H-pyrido[3,2,1-jk]carbazol-5-carboxylic acid"
              }
            ],
            "amount": {
              "mass": {
                "value": 6.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "sulfuric acid"
              }
            ],
            "amount": {
              "volume": {
                "value": 35.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      },
      "m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "ice"
              }
            ],
            "amount": {
              "mass": {
                "value": 200.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "stirring": {
        "type": "CUSTOM",
        "details": "stirred"
      },
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-84f1f75dc0f441f2b9ff27d25c28ed6e"
  },
  {
    "input_text": "2 g of ethyl 2-fluoro-7a,8,9,10,11,11a-hexahydro-4-oxo-4H-pyrido[3,2,1-jk]carbazol-5-carboxylate was dissolved in 80 ml of methanol, and 5 ml of hydrazine hydrate was added thereto. The mixture was then heated while refluxing. The precipitated yellow needle crystals were separated by filtration, and recrystallized from ethanol to obtain 1.7 g of 2-fluoro-7a,8,9,10,11,11a-hexahydro-4-oxo-4H-pyrido[3,2,1-jk]carbazol-5-carbohydrazide monohydrate.",
    "output_reaction_inputs": {
      "m1_m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "ethyl 2-fluoro-7a,8,9,10,11,11a-hexahydro-4-oxo-4H-pyrido[3,2,1-jk]carbazol-5-carboxylate"
              }
            ],
            "amount": {
              "mass": {
                "value": 2.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "methanol"
              }
            ],
            "amount": {
              "volume": {
                "value": 80.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      },
      "m2": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "hydrazine hydrate"
              }
            ],
            "amount": {
              "volume": {
                "value": 5.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-fe13b9eb967e43fdbad07113c54f1046"
  },
  {
    "input_text": "27.2 G. (0.139 moles) of 2-methanesulfonyl benzimidazole and 26.5 g. (0.3 moles) of N,N-dimethylethylene diamine are combined and heated at 170\u00b0-175\u00b0 C. for 5 hours. The mixture is then cooled and concentrated in vacuo. The residue is dissolved in methylene chloride washed with saturated sodium chloride, dried over sodium sulfate and evaporated to dryness affording 22 g. of N,N-dimethyl-N'-(2-benzimidazolyl)-1,2-ethane diamine compound which is recrystallized from benzene yielding 20.3 g. with a m.p. of 143.5-145.5.",
    "output_reaction_inputs": {
      "m1": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "2-methanesulfonyl benzimidazole"
              }
            ],
            "amount": {
              "moles": {
                "value": 0.139,
                "units": "MOLE"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      },
      "m2": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "N,N-dimethylethylene diamine"
              }
            ],
            "amount": {
              "moles": {
                "value": 0.3,
                "units": "MOLE"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-f831274c0fe7442d9d96f3f47f5cd32a"
  },
  {
    "input_text": "4-Chlorobenzothiazolone (9.28 g, 0.05 mole) was dissolved in a solution of sodium hydroxide (3.19 g, 0.075 mole) in water (220 ml), and tetra-n-butylammonium bromide (0.48 g, 0.0015 mole) and toluene (80 ml) were added thereto. Methyl iodide (11.21 g, 0.075 mole) was added dropwise thereto at room temperature, and the mixture was stirred at room temperature for 30 minutes and then at 50\u00b0 to 60\u00b0 C. for 1 hour, followed by cooling and phase-separation. The toluene layer was washed once with water, and the solvent was removed under reduced pressure to obtain 9.58 g of 4-chloro-N-methylbenzothiazolone as pale yellow crystals. Yield 96.0%, purity 99.3%, m.p. 130\u00b0-132\u00b0 C.",
    "output_reaction_inputs": {
      "m4": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "Methyl iodide"
              }
            ],
            "amount": {
              "mass": {
                "value": 11.21,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      },
      "m1_m2_m5_m6_m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "4-Chlorobenzothiazolone"
              }
            ],
            "amount": {
              "mass": {
                "value": 9.28,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "sodium hydroxide"
              }
            ],
            "amount": {
              "mass": {
                "value": 3.19,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "toluene"
              }
            ],
            "amount": {
              "volume": {
                "value": 80.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "water"
              }
            ],
            "amount": {
              "volume": {
                "value": 220.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "tetra-n-butylammonium bromide"
              }
            ],
            "amount": {
              "mass": {
                "value": 0.48,
                "units": "GRAM"
              }
            },
            "reactionRole": "CATALYST"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "temperature": {
        "control": {
          "type": "AMBIENT"
        }
      },
      "stirring": {
        "type": "CUSTOM",
        "details": "at room temperature, and the mixture was stirred at room temperature for 30 minutes"
      },
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-b81c8edefd514e0a93afb0a4c8545220"
  },
  {
    "input_text": "4-Chlorobenzothiazolone (9.28 g, 0.05 mole) was dissolved in a solution of sodium hydroxide (3.19 g, 0.075 mole) in water (220 ml), and tetra-n-butylammonium bromide (0.48 g, 0.0015 mole) and toluene (80 ml) were added thereto. Dimethyl sulfate (9.40 g, 0.075 mole) was added dropwise thereto at room temperature, and the mixture was stirred at room temperature for 1 hour, followed by phase-separation. The toluene layer was washed once with water, and the solvent was removed under reduced pressure to obtain 9.80 g of 4-chloro-N-methylbenzothiazolone as pale yellow crystals. Yield 98.2%, purity 98.2%, m.p. 130\u00b0-132\u00b0 C.",
    "output_reaction_inputs": {
      "m1_m2_m5_m6_m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "4-Chlorobenzothiazolone"
              }
            ],
            "amount": {
              "mass": {
                "value": 9.28,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "sodium hydroxide"
              }
            ],
            "amount": {
              "mass": {
                "value": 3.19,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "toluene"
              }
            ],
            "amount": {
              "volume": {
                "value": 80.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "water"
              }
            ],
            "amount": {
              "volume": {
                "value": 220.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "tetra-n-butylammonium bromide"
              }
            ],
            "amount": {
              "mass": {
                "value": 0.48,
                "units": "GRAM"
              }
            },
            "reactionRole": "CATALYST"
          }
        ]
      },
      "m4": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "Dimethyl sulfate"
              }
            ],
            "amount": {
              "mass": {
                "value": 9.4,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "temperature": {
        "control": {
          "type": "AMBIENT"
        }
      },
      "stirring": {
        "type": "CUSTOM",
        "details": "at room temperature, and the mixture was stirred at room temperature for 1 hour"
      },
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-a244a87ea35445fa86cd33d441bf9140"
  },
  {
    "input_text": "4-chlorobenzothiazolone (9.28 g, 0.05 mole) was dissolved in a solution of sodium hydroxide (3.19 g, 0.075 mole) in water (220 ml), and benzyltriethylammonium chloride (0.34 g, 0.0015 mole) and toluene (80 ml) were added thereto. Dimethyl sulfate (9.40 g, 0.075 mole) was added dropwise thereto at room temperature, and the mixture was stirred at room temperature for 4 hours, followed by phase-separation. The toluene layer was washed once with water, and the solvent was removed under reduced pressure to obtain 8.97 g of 4-chloro-N-methylbenzothiazolone as pale yellow crystals. Yield 90.3%, purity 96.7%, m.p. 129\u00b0-131\u00b0 C.",
    "output_reaction_inputs": {
      "m4": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "Dimethyl sulfate"
              }
            ],
            "amount": {
              "mass": {
                "value": 9.4,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      },
      "m1_m2_m5_m6_m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "4-chlorobenzothiazolone"
              }
            ],
            "amount": {
              "mass": {
                "value": 9.28,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "sodium hydroxide"
              }
            ],
            "amount": {
              "mass": {
                "value": 3.19,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "toluene"
              }
            ],
            "amount": {
              "volume": {
                "value": 80.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "water"
              }
            ],
            "amount": {
              "volume": {
                "value": 220.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "benzyltriethylammonium chloride"
              }
            ],
            "amount": {
              "mass": {
                "value": 0.34,
                "units": "GRAM"
              }
            },
            "reactionRole": "CATALYST"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "temperature": {
        "control": {
          "type": "AMBIENT"
        }
      },
      "stirring": {
        "type": "CUSTOM",
        "details": "at room temperature, and the mixture was stirred at room temperature for 4 hours"
      },
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-d646ea01e9074c4ab6ceb304c2449f60"
  },
  {
    "input_text": "4-Chlorobenzothiazolone (9.28 g, 0.05 mole) was dissolved in a solution of sodium hydroxide (3.19 g, 0.075 mole) in water (500 ml), and tetra-n-butylammonium bromide (0.48 g, 0.0015 mole) and ethylene dichloride (300 ml) were added thereto. Dimethyl sulfate (9.40 g, 0.075 mole) was added dropwise thereto at room temperature, and the mixture was stirred at room temperature for 1 hour, followed by phase-separation. The ethylene dichloride layer was washed once with water, and the solvent was removed under reduced pressure to obtain 9.37 g of 4-chloro-N-methylbenzothiazolone as pale yellow crystals. Yield 93.9%, purity 98.7%, m.p. 130\u00b0-132\u00b0 C.",
    "output_reaction_inputs": {
      "m4": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "Dimethyl sulfate"
              }
            ],
            "amount": {
              "mass": {
                "value": 9.4,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      },
      "m1_m2_m5_m6_m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "4-Chlorobenzothiazolone"
              }
            ],
            "amount": {
              "mass": {
                "value": 9.28,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "sodium hydroxide"
              }
            ],
            "amount": {
              "mass": {
                "value": 3.19,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "ethylene dichloride"
              }
            ],
            "amount": {
              "volume": {
                "value": 300.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "water"
              }
            ],
            "amount": {
              "volume": {
                "value": 500.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "tetra-n-butylammonium bromide"
              }
            ],
            "amount": {
              "mass": {
                "value": 0.48,
                "units": "GRAM"
              }
            },
            "reactionRole": "CATALYST"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "temperature": {
        "control": {
          "type": "AMBIENT"
        }
      },
      "stirring": {
        "type": "CUSTOM",
        "details": "at room temperature, and the mixture was stirred at room temperature for 1 hour"
      },
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-5d1e1d871b804ddda12daf9877af0ddf"
  },
  {
    "input_text": "(i)(a) A solution of 4-hydroxymethyl-5-methylimidazole hydrochloride (30.0 g.) and cysteamine hydrochloride (23.0 g.) in acetic acid (200 ml.) was heated under reflux for 10 hours. Following cooling to 15\u00b0-20\u00b0, the solid which crystallised was collected and washed with isopropyl alcohol to give 4-methyl-5-[(2-aminoethyl)thiomethyl]imidazole dihydrochloride (45.5 g.), m.p. 189\u00b0-192\u00b0.",
    "output_reaction_inputs": {
      "m1_m2_m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "4-hydroxymethyl-5-methylimidazole hydrochloride"
              }
            ],
            "amount": {
              "mass": {
                "value": 30.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "cysteamine hydrochloride"
              }
            ],
            "amount": {
              "mass": {
                "value": 23.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "acetic acid"
              }
            ],
            "amount": {
              "volume": {
                "value": 200.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-4577d7101905425ca8e4157812423f2f"
  },
  {
    "input_text": "Sulphuryl chloride (286 g.) was added dropwise to a solution of ethyl 3-oxopentanoate (300 g.) in chloroform (250 ml.) at 10\u00b0-15\u00b0. Following addition the mixture was stirred overnight at room temperature, heated under reflux for 0.5 hours and cooled. After washing with water, sodium bicarbonate and water, the solution was dried (sodium sulphate), concentrated, and fractionated to yield ethyl 2-chloro-3-oxopentanoate, b.p. 94\u00b0-96\u00b0/14 mm.",
    "output_reaction_inputs": {
      "m1_m2_m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "Sulphuryl chloride"
              }
            ],
            "amount": {
              "mass": {
                "value": 286.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "ethyl 3-oxopentanoate"
              }
            ],
            "amount": {
              "mass": {
                "value": 300.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "chloroform"
              }
            ],
            "amount": {
              "volume": {
                "value": 250.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "temperature": {
        "control": {
          "type": "AMBIENT"
        }
      },
      "stirring": {
        "type": "CUSTOM",
        "details": "was stirred overnight at room temperature"
      },
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-98895f2780bf48829c5337a85be9394e"
  },
  {
    "input_text": "A solution of sodium nitrite (43.8 g.) in water (92 ml.) was added dropwise, with stirring, to a solution of ethyl isobutyrylacetate (100.3 g.) in acetic acid (80 ml.) at 0\u00b0. After stirring at 0\u00b0 for 30 minutes then at room temperature for 3 hours, water (100 ml.) was added and the mixture extracted with ether. The extracts were washed with water, saturated sodium bicarbonate solution and water. After drying (CaSO4), the solution was evaporated to give ethyl 2-oximino-4-methyl-3-oxopentanoate (112 g.) as a crude oil.",
    "output_reaction_inputs": {
      "m5": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "water"
              }
            ],
            "amount": {
              "volume": {
                "value": 100.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      },
      "m1_m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "sodium nitrite"
              }
            ],
            "amount": {
              "mass": {
                "value": 43.8,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "water"
              }
            ],
            "amount": {
              "volume": {
                "value": 92.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      },
      "m2_m4": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "ethyl isobutyrylacetate"
              }
            ],
            "amount": {
              "mass": {
                "value": 100.3,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "acetic acid"
              }
            ],
            "amount": {
              "volume": {
                "value": 80.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "stirring": {
        "type": "CUSTOM",
        "details": "After stirring at 0\u00b0 for 30 minutes"
      },
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-bf68e4c717244f0c9c3a1febdd2b21d2"
  },
  {
    "input_text": "A solution of 2-mercaptoimidazole (2 g.) and 3-aminopropanol (1.14 ml.) in hydrobromic acid (48%, 25 ml.) was heated under reflux for 25 hours. The reaction mixture was evaporated to dryness and the oily residual solid recrystallised twice from ethanol/ether to give 2-(3-aminopropylmercapto)imidazole dihydrobromide (3.55 g.) m.p. 160\u00b0-162\u00b0.",
    "output_reaction_inputs": {
      "m1_m2_m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "2-mercaptoimidazole"
              }
            ],
            "amount": {
              "mass": {
                "value": 2.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "3-aminopropanol"
              }
            ],
            "amount": {
              "volume": {
                "value": 1.14,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "hydrobromic acid"
              }
            ],
            "amount": {
              "volume": {
                "value": 25.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-8a713f0db7994c2c8ab4fe887150ebd3"
  },
  {
    "input_text": "4-(2-Aminoethoxymethyl)imidazole (2.24 g.) was caused to react with methyl isothiocyanate (1.21 g.) in isopropyl alcohol (25 ml.) in the usual way. The crude product was purified by chromatography on a column of silica gel with ethyl acetate as eluant and subsequently on a dry column of alumina, using chloroform. The final product was recrystallised from ethyl acetate to give N-methyl-N'-[2-(4-imidazolylmethoxy)ethyl]thiourea (0.80 g.), m.p. 96\u00b0-98\u00b0. (Found: C, 44.6; H, 6.5; N, 26.0; S, 14.7. C8H14N4OS requires: C, 44.8; H, 6.6; N, 26.2; S, 15.0).",
    "output_reaction_inputs": {
      "m1": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "4-(2-Aminoethoxymethyl)imidazole"
              }
            ],
            "amount": {
              "mass": {
                "value": 2.24,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      },
      "m2_m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "methyl isothiocyanate"
              }
            ],
            "amount": {
              "mass": {
                "value": 1.21,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "isopropyl alcohol"
              }
            ],
            "amount": {
              "volume": {
                "value": 25.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-2c095da33828438e87bbba14e5aed065"
  },
  {
    "input_text": "Reacting 4-hydroxymethyl-3-methylisothiazole (3.0 g.) with cysteamine hydrochloride (2.8 g.) in 48% aqueous hydrobromic acid (50 ml.) by the procedure of Example 1 gives 3-methyl-4-[(2-aminoethyl)thiomethyl]-isothiazole hydrobromide. The base is obtained by basifying with aqueous potassium carbonate, extracting with chloroform, drying the extracts over magnesium sulphate and concentrating. Reacting the amine (5.0 g.) with methyl isothiocyanate (1.94 g.) in ethanol (25 ml.) under reflux for 30 minutes and purifying the product on a column of alumina with benzene as eluant gives N-methyl-N'-[2-(3-methyl-4-isothiazolylmethylthio)ethyl]thiourea. (Found: C, 40.8; H, 5.9; N, 16.1; S, 36.4. C9H15N3S3 requires: C, 41.3; H, 5.8; N, 16.1; S, 36.8).",
    "output_reaction_inputs": {
      "m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "hydrobromic acid"
              }
            ],
            "amount": {
              "volume": {
                "value": 50.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      },
      "m1": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "4-hydroxymethyl-3-methylisothiazole"
              }
            ],
            "amount": {
              "mass": {
                "value": 3.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      },
      "m2": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "cysteamine hydrochloride"
              }
            ],
            "amount": {
              "mass": {
                "value": 2.8,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-058beeef5c6542b2bcfda4f522165585"
  },
  {
    "input_text": "A solution of 3-chloromethylisoxazole (5.8 g.) and cysteamine hydrochloride (6.25 g.) in aqueous hydrobromic acid (48%, 100 ml.) was heated under reflux for 6 hours. Concentration in the presence of water and subsequently n-propanol, followed by recrystallisation of the residue from isopropyl alcohol-ethanol afforded 3-[(2-aminoethyl)-thiomethyl]isoxazole hydrobromide, m.p. 131\u00b0-133\u00b0. (Found: Br, 33.6; S, 13.7. C6H10N2OS.HBr requires: Br, 33.4; S, 13.4).",
    "output_reaction_inputs": {
      "m1_m2_m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "3-chloromethylisoxazole"
              }
            ],
            "amount": {
              "mass": {
                "value": 5.8,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "cysteamine hydrochloride"
              }
            ],
            "amount": {
              "mass": {
                "value": 6.25,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "hydrobromic acid"
              }
            ],
            "amount": {
              "volume": {
                "value": 100.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-6a073502be6d4a2ba933d6587ac78c05"
  },
  {
    "input_text": "Ethoxyacetyl chloride (57 g.) was added slowly to a stirred solution of 4-methylthiosemicarbazide (53.5 g.) in dry pyridine (500 ml.) at 0\u00b0-5\u00b0. The mixture was allowed to attain room temperature and stirring was continued for 18 hours. Following concentration under reduced pressure the residue was treated with a solution of sodium (21.4 g.) in ethanol (500 ml.) and the mixture was heated under reflux for 24 hours. Following concentration and acidification with hydrochloric acid a solid was obtained. After partial concentration the solid was collected and recrystallised from ethyl acetate to give 3-ethoxymethyl-4-methyl-1,2,4-triazoline-5-thione (53 g.), m.p. 137\u00b0-138\u00b0.",
    "output_reaction_inputs": {
      "m1_m2_m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "Ethoxyacetyl chloride"
              }
            ],
            "amount": {
              "mass": {
                "value": 57.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "4-methylthiosemicarbazide"
              }
            ],
            "amount": {
              "mass": {
                "value": 53.5,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "pyridine"
              }
            ],
            "amount": {
              "volume": {
                "value": 500.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "stirring": {
        "type": "CUSTOM",
        "details": "stirring"
      },
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-729759af8efd4529bdfa58c13348db6d"
  },
  {
    "input_text": "A solution of 4-hydroxymethyl-5-methylimidazole hydrochloride (30.0 g.) and cysteamine hydrochloride (23.0 g.) in acetic acid (200 ml.) was heated under reflux for 10 hours. Following cooling to 15\u00b0-20\u00b0, the solid which crystallised was collected and washed with isopropyl alcohol to give 4-methyl-5-[(2-aminoethyl)thiomethyl]imidazole dihydrochloride (45.5 g.), m.p. 189\u00b0-192\u00b0.",
    "output_reaction_inputs": {
      "m1_m2_m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "4-hydroxymethyl-5-methylimidazole hydrochloride"
              }
            ],
            "amount": {
              "mass": {
                "value": 30.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "cysteamine hydrochloride"
              }
            ],
            "amount": {
              "mass": {
                "value": 23.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "acetic acid"
              }
            ],
            "amount": {
              "volume": {
                "value": 200.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-ee7c0aba780a4dc5b3a344e0bb790ffa"
  },
  {
    "input_text": "Potassium carbonate (7.75 g.) was added to a solution of 4-methyl-5-[(2-aminoethyl)thiomethyl]imidazole dihydrochloride (14.6 g.) in water (120 ml.). The solution was stored at room temperature for 15 minutes, then evaporated to dryness, extracted with isopropyl alcohol and the extracts are concentrated to dryness to give 4-methyl-5-[(2-aminoethyl)thiomethyl]imidazole.",
    "output_reaction_inputs": {
      "m1_m2_m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "Potassium carbonate"
              }
            ],
            "amount": {
              "mass": {
                "value": 7.75,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "4-methyl-5-[(2-aminoethyl)thiomethyl]imidazole dihydrochloride"
              }
            ],
            "amount": {
              "mass": {
                "value": 14.6,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "water"
              }
            ],
            "amount": {
              "volume": {
                "value": 120.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-b73d55a6d2bd48a08fc3d83505e5ce07"
  },
  {
    "input_text": "A solution of 4-methyl-5-[(2-aminoethyl)thiomethyl]imidazole (17.0 g.) and N-cyano-N',S-dimethylisothiourea (11.2 g.) in acetonitrile (500 ml.) was heated under reflux for 24 hours. Following concentration, the residue was chromatographed on a column of silica gel with acetonitrile as eluant and the product obtained was finally recrystallised from acetonitrile-ether to yield N-cyano-N'-methyl-N\"-[2-((4-methyl-5-imidazolyl)methylthio)ethyl]guanidine, m.p. 141\u00b0-2\u00b0. (Found: C, 47.2; H, 6.4; N, 33.4; S, 12.4. C10H16N6S requires: C, 47.6; H, 6.4; N, 33.3; S, 12.7).",
    "output_reaction_inputs": {
      "m1_m2_m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "4-methyl-5-[(2-aminoethyl)thiomethyl]imidazole"
              }
            ],
            "amount": {
              "mass": {
                "value": 17.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "N-cyano-N',S-dimethylisothiourea"
              }
            ],
            "amount": {
              "mass": {
                "value": 11.2,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "acetonitrile"
              }
            ],
            "amount": {
              "volume": {
                "value": 500.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-b5887e51aec640619a6a48d281bfeb1e"
  },
  {
    "input_text": "(i) Potassium carbonate (7.75 g.) was added to a solution of 4-methyl-5-[(2-aminoethyl)thiomethyl]imidazole dihydrochloride (14.6 g.) in water (120 ml.). The solution was stirred at room temperature for 15 minutes and methyl isothiocyanate (5.15 g.) was added. After heating under reflux for 30 minutes, the solution was slowly cooled to 5\u00b0. The product (13.1 g.) was collected and recrystallised from water to give N-methyl-N'-[2-((4-methyl-5-imidazolyl)methylthio)ethyl]thiourea, m.p. 150\u00b0-152\u00b0.",
    "output_reaction_inputs": {
      "m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "methyl isothiocyanate"
              }
            ],
            "amount": {
              "mass": {
                "value": 5.15,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      },
      "m1_m2_m4": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "Potassium carbonate"
              }
            ],
            "amount": {
              "mass": {
                "value": 7.75,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "4-methyl-5-[(2-aminoethyl)thiomethyl]imidazole dihydrochloride"
              }
            ],
            "amount": {
              "mass": {
                "value": 14.6,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "water"
              }
            ],
            "amount": {
              "volume": {
                "value": 120.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "temperature": {
        "control": {
          "type": "AMBIENT"
        }
      },
      "stirring": {
        "type": "CUSTOM",
        "details": "The solution was stirred at room temperature for 15 minutes"
      },
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-391da366c8c644da98fa5dc2cd69fd78"
  },
  {
    "input_text": "Lead cyanamide (3.0 g.) was added to a solution of N-methyl-N'-[2-((4-methyl-5-imidazolyl)methylthio)ethyl]thiourea (2.44 g.) in acetonitrile (50 ml.). Dimethylformamide (20 ml.) was added subsequently and the suspension was heated under reflux, with stirring, for 24 hours. Filtration, followed by concentration under reduced pressure and purification of the product by chromatography on a column of silica gel with acetonitrile as eluant and recrystallisation from the same solvent afforded N-cyano-N'-methyl-N\"-[2-((4-methyl-5-imidazolyl)methylthio)ethyl]guanidine, m.p. 139\u00b0-141\u00b0. (Found: C, 47.3; H, 6.6; N, 33.4; S, 12.6. C10N16N6S requires: C, 47.6; H, 6.4; N, 33.3; S, 12.7).",
    "output_reaction_inputs": {
      "m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "Dimethylformamide"
              }
            ],
            "amount": {
              "volume": {
                "value": 20.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      },
      "m1_m2_m4": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "Lead cyanamide"
              }
            ],
            "amount": {
              "mass": {
                "value": 3.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "N-methyl-N'-[2-((4-methyl-5-imidazolyl)methylthio)ethyl]thiourea"
              }
            ],
            "amount": {
              "mass": {
                "value": 2.44,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "acetonitrile"
              }
            ],
            "amount": {
              "volume": {
                "value": 50.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "stirring": {
        "type": "CUSTOM",
        "details": "with stirring, for 24 hours"
      },
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-b091e1c318974a46962039d13b50a5d8"
  },
  {
    "input_text": "A solution of homocysteamine hydrochloride (22.0 g.) and 4-hydroxymethyl-5-methylimidazole hydrochloride (25.6 g.) in aqueous hydrobromic acid (500 ml.) was heated under reflux for one hour. Concentration under reduced pressure, followed by recrystallisation from methanol-isopropyl alcohol afforded 4-methyl-5-[(3-aminopropyl)thiomethyl]-imidazole dihydrobromide (24.5 g.), m.p. 200.5\u00b0-202.5\u00b0.",
    "output_reaction_inputs": {
      "m1_m2_m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "homocysteamine hydrochloride"
              }
            ],
            "amount": {
              "mass": {
                "value": 22.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "4-hydroxymethyl-5-methylimidazole hydrochloride"
              }
            ],
            "amount": {
              "mass": {
                "value": 25.6,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "hydrobromic acid"
              }
            ],
            "amount": {
              "volume": {
                "value": 500.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-5c03afb5b75a493baa34d35232237405"
  },
  {
    "input_text": "The reaction of N-methyl-N'-[3-((4-methyl-5-imidazolyl)methylthio)propyl]thiourea (5.9 g.) with lead cyanamide (17.5 g.) by a procedure similar to that described in Example 3(b) afforded N-cyano-N'-methyl-N\"- [3-((4-methyl-5-imidazolyl)methylthio)propyl]guanidine (0.91 g.), m.p. 156\u00b0-158\u00b0, following chromatography on silica gel with successive elution by chloroformethyl acetate (1:1), ethyl acetate and ethyl acetate isopropyl alcohol (5:1) and final recrystallisation from isopropyl alcohol-ether. (Found: C, 49.5; H, 7.0; S, 12.0. C11H18N6S requires: C, 49.6; H, 6.8; S, 12.0).",
    "output_reaction_inputs": {
      "m1_m2": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "N-methyl-N'-[3-((4-methyl-5-imidazolyl)methylthio)propyl]thiourea"
              }
            ],
            "amount": {
              "mass": {
                "value": 5.9,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "lead cyanamide"
              }
            ],
            "amount": {
              "mass": {
                "value": 17.5,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-e67ded9da77941ffaad5bb78cb02a13b"
  },
  {
    "input_text": "A solution of N-cyano-N'-[2-((4-methyl-5-imidazolyl)methylthio)ethyl]-S-methylisothiourea (2.69 g.) and n-propylamine (1.1 g.) in ethanol (50 ml.) was heated under reflux for 6 hours. Concentration, followed by chromatographic purification on a column of silica gel with ethyl acetate-isopropyl alcohol (4:1) as eluant and final recrystallisation from aqueous isopropyl alcohol afforded N-cyano-N'-[2-((4-methyl-5-imidazolyl)methylthio)ethyl]-N\"-propylguanidine (2.0 g.) m.p. 108\u00b0-110\u00b0. (Found: C, 51.4; H, 7.4; N, 30.0; S, 11.4. C12H20N6S requires: C, 51.4: H, 7.2; N, 30.0; S, 11.4).",
    "output_reaction_inputs": {
      "m1_m2_m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "N-cyano-N'-[2-((4-methyl-5-imidazolyl)methylthio)ethyl]-S-methylisothiourea"
              }
            ],
            "amount": {
              "mass": {
                "value": 2.69,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "n-propylamine"
              }
            ],
            "amount": {
              "mass": {
                "value": 1.1,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "ethanol"
              }
            ],
            "amount": {
              "volume": {
                "value": 50.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-8738f166817849ef929d37cb5a7a9a5b"
  },
  {
    "input_text": "Sulphuryl chloride (286 g.) was added dropwise to a solution of ethyl 3-oxopentanoate (300 g.) in chloroform (250 ml.) at 10\u00b0-15\u00b0. Following addition the mixture was stirred overnight at room temperature, heated under reflux for 0.5 hour and cooled. After washing with water, sodium bicarbonate and water, the solution was dried (sodium sulphate), concentrated and fractionated to yield ethyl 2-chloro-3-oxopentanoate, b.p. 94\u00b0-96\u00b0/14 mm.",
    "output_reaction_inputs": {
      "m1_m2_m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "Sulphuryl chloride"
              }
            ],
            "amount": {
              "mass": {
                "value": 286.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "ethyl 3-oxopentanoate"
              }
            ],
            "amount": {
              "mass": {
                "value": 300.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "chloroform"
              }
            ],
            "amount": {
              "volume": {
                "value": 250.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "temperature": {
        "control": {
          "type": "AMBIENT"
        }
      },
      "stirring": {
        "type": "CUSTOM",
        "details": "was stirred overnight at room temperature"
      },
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-26755ecdc6db434492a289a0aa44ffe0"
  },
  {
    "input_text": "A solution of sodium nitrate (43.8 g.) in water (92 ml.) was added dropwise, with stirring, to a solution of ethyl isobutyrylacetate (100.3 g.) in acetic acid (80 ml.) at 0\u00b0. After stirring at 0\u00b0 for 30 minutes then at room temperature for 3 hours, (100 ml.) was added and the mixture extracted with ether. The extracts were washed with water, saturated sodium bicarbonate solution and water. After drying (CaSO4), the solution was evaporated to give ethyl 2-oximino-4-methyl-3-oxopentanoate (112 g.) as a crude oil.",
    "output_reaction_inputs": {
      "m1_m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "sodium nitrate"
              }
            ],
            "amount": {
              "mass": {
                "value": 43.8,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "water"
              }
            ],
            "amount": {
              "volume": {
                "value": 92.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      },
      "m2_m4": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "ethyl isobutyrylacetate"
              }
            ],
            "amount": {
              "mass": {
                "value": 100.3,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "acetic acid"
              }
            ],
            "amount": {
              "volume": {
                "value": 80.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "stirring": {
        "type": "CUSTOM",
        "details": "After stirring at 0\u00b0 for 30 minutes"
      },
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-8d4ff632d2a94c64a222977c90cbf04b"
  },
  {
    "input_text": "A solution of 2-mercaptoimidazole (2 g.) and 3-aminopropanol (1.14 ml.) in hydrobromic acid (48%, 25 ml.) was heated under reflux for 25 hours. The reaction mixture was evaporated to dryness and the oily residual solid recrystallized twice from ethanol/ether to give 2-(3-aminopropylthio)imidazole dihydrobromide (3.55 g.), m.p. 160\u00b0-162\u00b0.",
    "output_reaction_inputs": {
      "m1_m2_m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "2-mercaptoimidazole"
              }
            ],
            "amount": {
              "mass": {
                "value": 2.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "3-aminopropanol"
              }
            ],
            "amount": {
              "volume": {
                "value": 1.14,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "hydrobromic acid"
              }
            ],
            "amount": {
              "volume": {
                "value": 25.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-865fbe2fa6ed42b7923c4dd39c820837"
  },
  {
    "input_text": "Sodium (13.5 g.) was added over 3 hours to propane-1,3-diol (450 ml.) under nitrogen at 70\u00b0 with stirring. This solution was added over 20 minutes to a stirred solution of 4-chloromethylimidazole hydrochloride (50.0 g.) under nitrogen at 40\u00b0-60\u00b0. Subsequent heating at 60\u00b0-65\u00b0 for 3 hours followed by overnight cooling, filtration and concentration gave 4-(3-hydroxypropoxy)methylimidazole. Subsequent reaction with thionyl chloride gave 4-(3-chloropropoxy)methylimidazole hydrochloride (38.3 g.).",
    "output_reaction_inputs": {
      "m1_m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "Sodium"
              }
            ],
            "amount": {
              "mass": {
                "value": 13.5,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "propane-1,3-diol"
              }
            ],
            "amount": {
              "volume": {
                "value": 450.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      },
      "m2": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "4-chloromethylimidazole hydrochloride"
              }
            ],
            "amount": {
              "mass": {
                "value": 50.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "stirring": {
        "type": "CUSTOM",
        "details": "with stirring"
      },
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-b38b962c375a4a22a0b85394dd1d7556"
  },
  {
    "input_text": "A solution of 3-chloromethylisoxazole (5.8 g.) and cysteamine hydrochloride (6.25 g.) in aqueous hydrobromic acid (48%, 100 ml) was heated under reflux for 6 hours. Concentration in the presence of water and subsequently n-propanol, followed by recrystallisation of the residue from isopropyl alcohol-ethanol afforded 3-[(2-aminoethyl)thiomethyl]isoxazole hydrobromide, m.p. 131\u00b0-133\u00b0. (Found: Br, 33.6; S, 13.7. C6H10N2O S. H Br requires: Br, 33.4; S, 13.4).",
    "output_reaction_inputs": {
      "m1_m2_m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "3-chloromethylisoxazole"
              }
            ],
            "amount": {
              "mass": {
                "value": 5.8,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "cysteamine hydrochloride"
              }
            ],
            "amount": {
              "mass": {
                "value": 6.25,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "hydrobromic acid"
              }
            ],
            "amount": {
              "volume": {
                "value": 100.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-32415a5bef084031ba38baa64bbf028e"
  },
  {
    "input_text": "Combine 10.1 g (0.1 mole) 5-amino-1,2,3-thiadiazole, 75 ml of tetrahydrofurane and 11.5 ml (0.106 mole) of phenyl isocyanate. Further add 0.1 ml of triethylamine as catalyst. After standing overnight, the first crystals will have precipitated. The solvent is removed by evaporation under vacuum, and the residue is recrystallized from isopropanol.",
    "output_reaction_inputs": {
      "m1": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "5-amino-1,2,3-thiadiazole"
              }
            ],
            "amount": {
              "mass": {
                "value": 10.1,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      },
      "m2": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "phenyl isocyanate"
              }
            ],
            "amount": {
              "volume": {
                "value": 11.5,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      },
      "m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "triethylamine"
              }
            ],
            "amount": {
              "volume": {
                "value": 0.1,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "CATALYST"
          }
        ]
      },
      "m4": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "tetrahydrofurane"
              }
            ],
            "amount": {
              "volume": {
                "value": 75.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-1ef7bc88388c487bbc15151dfc435f0e"
  },
  {
    "input_text": "14.1 g (0.10 mol) of \u03b3-chlorobutyryl chloride in 50 ml of chloroform are added dropwise in the course of 1 hour, at 10\u00b0-15\u00b0 C., to a solution of 17.7 g (0.10 mol) of 1,3-diamino-4,6-dichlorobenzene and 8.7 g (0.11 mol) of pyridine in 500 ml of chloroform. The mixture is then stirred for 2 hours at room temperature, the solution is washed with water and filtered through 40 g of silica gel and the filtrate is concentrated. The resulting product is recrystallised from hexane/toluene. Yield: 13.5 g; melting point 125\u00b0-128\u00b0 C.",
    "output_reaction_inputs": {
      "m1_m4_m2_m3_m5": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "\u03b3-chlorobutyryl chloride"
              }
            ],
            "amount": {
              "mass": {
                "value": 14.1,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "1,3-diamino-4,6-dichlorobenzene"
              }
            ],
            "amount": {
              "mass": {
                "value": 17.7,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "pyridine"
              }
            ],
            "amount": {
              "mass": {
                "value": 8.7,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "chloroform"
              }
            ],
            "amount": {
              "volume": {
                "value": 50.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "chloroform"
              }
            ],
            "amount": {
              "volume": {
                "value": 500.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "temperature": {
        "control": {
          "type": "AMBIENT"
        }
      },
      "stirring": {
        "type": "CUSTOM",
        "details": "The mixture is then stirred for 2 hours at room temperature"
      },
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-cfba03b869d04abab857aa706c5eff06"
  },
  {
    "input_text": "13.5 g (0.05 mol) of N-(3-amino-4,6-dichlorophenyl)-\u03b3-chlorobutyramide, 200 ml of tetrahydrofurane and 100 ml of 1 N NaOH solution are stirred for 5 hours at 50\u00b0 C. After the mixture has been allowed to cool, it is extracted three times with 300 ml of ethyl acetate and the extracts are washed with water, dried with magnesium sulphate and concentrated. The resulting product is recrystallised from toluene/ethyl acetate. Yield: 8.5 g; melting point 168\u00b0-170\u00b0 C.",
    "output_reaction_inputs": {
      "m1_m3_m2": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "N-(3-amino-4,6-dichlorophenyl)-\u03b3-chlorobutyramide"
              }
            ],
            "amount": {
              "mass": {
                "value": 13.5,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "NaOH"
              }
            ],
            "amount": {
              "volume": {
                "value": 100.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "tetrahydrofurane"
              }
            ],
            "amount": {
              "volume": {
                "value": 200.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-2c2b21ecf2b848f9bd3c00a20922cf99"
  },
  {
    "input_text": "6.2 g of lithium aluminium hydride are introduced into 200 ml of absolute tetrahydrofuran. 26 g (0.12 mol) of 1-(3'-amino-4',6'-dimethylphenyl)-piperidin-2-one are added in portions, with stirring. The mixture is then refluxed for 1 hour. Excess LiAlH4 is destroyed with ethyl acetate. 2 N Hcl is added to the mixture until the pH is 4-5, ether is added and the mixture is extracted twice with 2 N KOH solution. The organic phase is washed with water and saturated NaCl solution, dried with MgSO4, clarified with active charcoal and evaporated. The residue is distilled in a bulb tube. This gives 18.2 g (73%) of a yellow oil (boiling point 140\u00b0/0.001 mm Hg).",
    "output_reaction_inputs": {
      "m2": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "1-(3'-amino-4',6'-dimethylphenyl)-piperidin-2-one"
              }
            ],
            "amount": {
              "mass": {
                "value": 26.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      },
      "m1_m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "lithium aluminium hydride"
              }
            ],
            "amount": {
              "mass": {
                "value": 6.2,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "tetrahydrofuran"
              }
            ],
            "amount": {
              "volume": {
                "value": 200.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "stirring": {
        "type": "CUSTOM",
        "details": "with stirring"
      },
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-6523d336c32147acb589d32f1f061f72"
  },
  {
    "input_text": "6 g of tert.-butyl peroctoate in 30 g of methane phosphonous acid methyl ester and 116 g of 1-methyl-1-oxophospholine are added dropwise to 282 g of oxygen-free methane phosphonous acid methyl ester at 120\u00b0 C. with stirring. The reaction time is 90 minutes. Excess methane phosphonous acid methyl ester and a small quantity of 1-methyl-oxophospholine are distilled off. The residue, consisting of 205 g of 1-methyl-1-oxophospholanyl-methyl phosphinic acid methyl ester is purified by distillation under vacuum (bp1 mm : 210\u00b0 to 220\u00b0 C.) to yield 186 g of pure product which solidifies very slowly to stellate crystals which begin to reliquefy at 70\u00b0 C. Acid saponification leads to isomeric 1-methyl-1-oxophospholanylmethyl phosphinic acids of the idealized constitution: ##STR17##",
    "output_reaction_inputs": {
      "m3_m1_m2": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "1-methyl-1-oxophospholine"
              }
            ],
            "amount": {
              "mass": {
                "value": 116.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "oxygen"
              }
            ],
            "amount": {
              "mass": {
                "value": 282.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "methane phosphonous acid methyl ester"
              }
            ],
            "amount": {
              "mass": {
                "value": 30.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "stirring": {
        "type": "CUSTOM",
        "details": "with stirring"
      },
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-3a0b11b509fc43e882b4cf004b5b9e93"
  },
  {
    "input_text": "A solution of 1.45 g (0.01 mole) of 4-methylbenzoylcyanide, 1.5 g (0.01 mole) of methyl 1-methylpyrrole-2-acetate and 40 mg (0.25 mmoles) of trichloroacetic acid in 4 ml of ether was stirred at 25\u00b0 under nitrogen for 21 days. The precipitated solid was collected by filtration and washed with cold ether, than hexane. The combined filtrates were evaporated in vacuo. A second crop of crystals was taken from hexane. After recrystallization from toluene:hexane was obtained, 0.46 g (16 percent yield) of methyl 5-[cyanohydroxy(4-methylphenyl)-methyl]-1-methylpyrrole-2-acetate mp 117\u00b0-118\u00b0. H1NMR CDCl3 2.35 (s, 3 H); 3.35 (s, 3 H); 3.55 (s, 2H); 3.65 (s, 3 H); 5.90 (d, 1 H); 6.05 (d, 1H); 7.15 (d, 2H); 7.35 (d, 2H). MS m/e 281, 280, 266, 212 IRnujol 3425, 1700 cm-1.",
    "output_reaction_inputs": {
      "m1_m2_m3_m4": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "4-methylbenzoylcyanide"
              }
            ],
            "amount": {
              "mass": {
                "value": 1.45,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "methyl 1-methylpyrrole-2-acetate"
              }
            ],
            "amount": {
              "mass": {
                "value": 1.5,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "trichloroacetic acid"
              }
            ],
            "amount": {
              "mass": {
                "value": 40.0,
                "units": "MILLIGRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "ether"
              }
            ],
            "amount": {
              "volume": {
                "value": 4.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-b2dca4c3d0d54749a8892380e6b6ad9b"
  },
  {
    "input_text": "3.2 g of N-(1-iso-propylthio-2,2,2-trichloroethyl)-2-acetoxybenzamide, 30 ml of ethanol and 0.5 ml of 35% hydrochloric acid were mixed together and the reaction was effected while stirring under reflux for two hours. The solvent was distilled off, and the contents were washed with water and dried to obtain 2.7 g of N-(1-iso-propylthio-2,2,2-trichloroethyl)-2-hydroxybenzamide as white crystals.",
    "output_reaction_inputs": {
      "m1_m3_m2": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "N-(1-iso-propylthio-2,2,2-trichloroethyl)-2-acetoxybenzamide"
              }
            ],
            "amount": {
              "mass": {
                "value": 3.2,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "hydrochloric acid"
              }
            ],
            "amount": {
              "volume": {
                "value": 0.5,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "ethanol"
              }
            ],
            "amount": {
              "volume": {
                "value": 30.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "stirring": {
        "type": "CUSTOM",
        "details": "while stirring"
      },
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-56f7bb581b564a3bb931d05bd7dab494"
  },
  {
    "input_text": "13 g of ethyl chlorocarbonate was added to the mixture of 3.4 g of N-(1-n-butylthio-2,2,2-trichloroethyl)-2-hydroxybenzamide and 50 ml of acetone under stirring, and 1.0 g of triethylamine was added dropwise thereto at 0\u00b0-5\u00b0 C. After effecting the reaction at room temperature for one hour, the solvent was distilled off under reduced pressure, 50 ml of water was added thereto and the solution was extracted with ethyl acetate. After washing the extract with water and drying, the solvent was distilled off to obtain 3.2 g of N-(1-n-butylthio-2,2,2-trichloroethyl)-2-ethoxycarbonyloxybenzamide as a brown oily substance. nD25 1.5350",
    "output_reaction_inputs": {
      "m1_m2_m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "ethyl chlorocarbonate"
              }
            ],
            "amount": {
              "mass": {
                "value": 13.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "N-(1-n-butylthio-2,2,2-trichloroethyl)-2-hydroxybenzamide"
              }
            ],
            "amount": {
              "mass": {
                "value": 3.4,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "acetone"
              }
            ],
            "amount": {
              "volume": {
                "value": 50.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      },
      "m4": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "triethylamine"
              }
            ],
            "amount": {
              "mass": {
                "value": 1.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "stirring": {
        "type": "CUSTOM",
        "details": "under stirring"
      },
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-edfb54964f1d4ad2977e45a8425ce162"
  },
  {
    "input_text": "14.2 g of N-(1-hydroxy-2,2,2-trichloroethyl)-2-hydroxybenzamide was mixed with 100 ml of dichloromethane, 7.2 g of thionyl chloride and 0.1 g of N,N-dimethylformamide and the reaction was effected while stirring under reflux for three hours. The solvent was distilled off to obtain N-(1,2,2,2-tetrachloroethyl)-2-hydroxybenzamide (m.p.: 113\u00b0-113.5\u00b0 C.). Without taking this out, 100 ml of dichloromethane and 3.8 g of iso-propyl mercaptan were added thereto and then 4.0 g of pyridine was also added dropwise. After effecting the reaction at room temperature for one hour, water was added thereto, the dichloromethane layer was separated out, dried and concentrated to obtain 16.2 g of N-(1-iso-propylthio-2,2,2-trichloroethyl)-2-hydroxybenzamide as white crystals.",
    "output_reaction_inputs": {
      "m1_m2_m3_m4": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "N-(1-hydroxy-2,2,2-trichloroethyl)-2-hydroxybenzamide"
              }
            ],
            "amount": {
              "mass": {
                "value": 14.2,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "dichloromethane"
              }
            ],
            "amount": {
              "volume": {
                "value": 100.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "thionyl chloride"
              }
            ],
            "amount": {
              "mass": {
                "value": 7.2,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "N,N-dimethylformamide"
              }
            ],
            "amount": {
              "mass": {
                "value": 0.1,
                "units": "GRAM"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "stirring": {
        "type": "CUSTOM",
        "details": "while stirring"
      },
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-c3badd86b64043d884bd0efa09f8ad8d"
  },
  {
    "input_text": "To 14.2 g of N-(1-hydroxy-2,2,2-trichloroethyl)-2-hydroxybenzamide were added 100 ml of dichloromethane, 0.1 g of N,N-dimethylformamide and 7.2 g of thionyl chloride, and the reaction was effected while stirring under reflux for three hours. Excess thionyl chloride was distilled off together with the solvent under reduced pressure to obtain 15.1 g of N-(1,2,2,2-tetrachloroethyl)-2-hydroxybenzamide.",
    "output_reaction_inputs": {
      "m1_m4_m3_m2": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "N-(1-hydroxy-2,2,2-trichloroethyl)-2-hydroxybenzamide"
              }
            ],
            "amount": {
              "mass": {
                "value": 14.2,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "thionyl chloride"
              }
            ],
            "amount": {
              "mass": {
                "value": 7.2,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "N,N-dimethylformamide"
              }
            ],
            "amount": {
              "mass": {
                "value": 0.1,
                "units": "GRAM"
              }
            },
            "reactionRole": "CATALYST"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "dichloromethane"
              }
            ],
            "amount": {
              "volume": {
                "value": 100.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "stirring": {
        "type": "CUSTOM",
        "details": "while stirring"
      },
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-459cddabb48c419d843d31c9c199fd5e"
  },
  {
    "input_text": "8.6 g of methyl acrylate are added dropwise to 5.9 g of isopropylamine under ice-cooling and stirring. The mixture is further stirred at room temperature for 5 hours. Then, the reaction mixture is distilled under reduced pressure. 12.3 g of methyl 3-isopropylaminopropionate are thereby obtained as a colorless oil. Yield: 84.5%",
    "output_reaction_inputs": {
      "m1_m2": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "methyl acrylate"
              }
            ],
            "amount": {
              "mass": {
                "value": 8.6,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "isopropylamine"
              }
            ],
            "amount": {
              "mass": {
                "value": 5.9,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "stirring": {
        "type": "CUSTOM",
        "details": "stirring"
      },
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-7dfae0682b68414e90c1265e1b945c02"
  },
  {
    "input_text": "27.8 g of n-butyl acrylate are added dropwise to 15.6 g of isopropylamine under ice-cooling and stirring. The mixture is further stirred at room temperature for 5 hours. Then, the reaction mixture is distilled under reduced pressure. 33 g of n-butyl 3-isopropylaminopropionate are thereby obtained as a colorless oil.",
    "output_reaction_inputs": {
      "m1_m2": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "n-butyl acrylate"
              }
            ],
            "amount": {
              "mass": {
                "value": 27.8,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "isopropylamine"
              }
            ],
            "amount": {
              "mass": {
                "value": 15.6,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "stirring": {
        "type": "CUSTOM",
        "details": "stirring"
      },
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-d42ee4e8e4e0404a92f1e89e2d71d7b0"
  },
  {
    "input_text": "A solution of benzonitrile (103 g) in ethylene glycol (310 g) was heated at reflux under substantially anhydrous conditions for 3 days. The reaction mixture was cooled and added to a mixture of ice and water (about 300 ml). The resulting mixture was extracted with ether (3\u00d7300 ml) and the combined ether extract back-washed with water (2\u00d7300 ml) and then with a saturated sodium chloride solution (300 ml). The ether solution was dried over anhydrous sodium sulfate. The ether was evaporated and the residual oil distilled to give 108 g (65% of theoretical) of ethylene glycol monobenzoate, b.p. 132\u00b0-135\u00b0 C./1.5 mm Hg.",
    "output_reaction_inputs": {
      "m2": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "water"
              }
            ],
            "amount": {
              "volume": {
                "value": 300.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      },
      "m1_m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "benzonitrile"
              }
            ],
            "amount": {
              "mass": {
                "value": 103.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "ethylene glycol"
              }
            ],
            "amount": {
              "mass": {
                "value": 310.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-4dfc0403728b4be38744dc6e3e984b5d"
  },
  {
    "input_text": "2-Chloro-9-(2-hydroxyethoxymethyl)adenine (0.83 g) was added with stirring to 95% hydrazine (11 ml) and the resulting solution stirred 1 hour under nitrogen. Excess hydrazine was removed by distillation in a rotary evaporator at a bath temperature of 30\u00b0 C. followed by co-evaporation twice with ethyl acetate. The residue was thoroughly triturated with methanol to give a quantitative yield (0.8 g) of white to cream colored-2-hydrazino-9-(2-hydroxyethoxymethyl) adenine, m.p. 220\u00b0-222\u00b0 C.",
    "output_reaction_inputs": {
      "m1": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "2-Chloro-9-(2-hydroxyethoxymethyl)adenine"
              }
            ],
            "amount": {
              "mass": {
                "value": 0.83,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      },
      "m2": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "hydrazine"
              }
            ],
            "amount": {
              "volume": {
                "value": 11.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "stirring": {
        "type": "CUSTOM",
        "details": "the resulting solution stirred 1 hour under nitrogen"
      },
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-4c7de4d0072e41c9b73fedd8fd7d0e03"
  },
  {
    "input_text": "A mixture of 2-azido-9-(2hydroxyethoxymethyl)adenine (0.41 g) and 10% palladium on charcoal (80 mg) in ethanol (41 ml) was shaken under hydrogen at 50 psi for 3.5 hours. The catalyst was removed by filtration through a celite pad and washed thoroughly with ethanol and water. The solvent was removed by evaporation under reduced pressure giving a quantitative yield (0.37 g) of nearly pure (one spot on TLC) 2-amino-9-(2-hydroxyethoxymethyl)adenine, m.p. 183\u00b0-184\u00b0 C. after recrystallization from n-propanol.",
    "output_reaction_inputs": {
      "m1_m2_m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "2-azido-9-(2hydroxyethoxymethyl)adenine"
              }
            ],
            "amount": {
              "mass": {
                "value": 0.41,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "palladium on charcoal"
              }
            ],
            "amount": {
              "mass": {
                "value": 80.0,
                "units": "MILLIGRAM"
              }
            },
            "reactionRole": "CATALYST"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "ethanol"
              }
            ],
            "amount": {
              "volume": {
                "value": 41.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "stirring": {
        "type": "CUSTOM",
        "details": "was shaken under hydrogen at 50 psi for 3.5 hours"
      },
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-4f3eff8c299644d1bfcd7abae285d881"
  },
  {
    "input_text": "Thiourea (0.28 g) was added to a refluxing solution of 2-amino-6-chloro-9-(2-benzoyloxyethoxymethyl)purine (1.27 g) in isopropanol (40 ml). The reaction mixture was heated at reflux for 11/2 hours and then chilled. 9-(2-benzoyloxyethoxymethyl)-thioguanine (0.58 g, m.p. 199\u00b0-202\u00b0 C.) was removed by filtration. This was added to 40 ml of aqueous ammonia (about 7 N) and the mixture heated on a steam bath for 10 minutes and then stirred overnight at room temperature. The water and ammonia were removed in vacuo and the residue triturated with acetone and then with ether to remove benzamide. The remaining solid was recrystallized twice from water to give yellow flakes of 9-(2-hydroxyethoxymethyl)thioguanine (0.26 g, m.p. 251\u00b0-254\u00b0 C.).",
    "output_reaction_inputs": {
      "m1_m2_m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "Thiourea"
              }
            ],
            "amount": {
              "mass": {
                "value": 0.28,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "2-amino-6-chloro-9-(2-benzoyloxyethoxymethyl)purine"
              }
            ],
            "amount": {
              "mass": {
                "value": 1.27,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "isopropanol"
              }
            ],
            "amount": {
              "volume": {
                "value": 40.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "temperature": {
        "control": {
          "type": "AMBIENT"
        }
      },
      "stirring": {
        "type": "CUSTOM",
        "details": "stirred overnight at room temperature"
      },
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-0282396aac7e4c6098c5d9a1f7e4280f"
  },
  {
    "input_text": "A mixture of 9-(2-hydroxyethoxymethyl)guanine (0.25 g), succinic anhydride (0.55 g) and pyridine (50 ml) was heated under anhydrous conditions on a steam bath overnight. The solvent was evaporated under reduced pressure at \u222040\u00b0 C., the last trace being removed azeotropically with toluene. The residue was triturated with acetone and the product removed by filtration. Recrystallization from methanol afforded 9-{2-(3-carboxypropionyloxy)ethoxymethyl}guanine, m.p. 203\u00b0-207\u00b0 C. (sinter 190\u00b0 C.), in 44% yield.",
    "output_reaction_inputs": {
      "m1_m2_m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "9-(2-hydroxyethoxymethyl)guanine"
              }
            ],
            "amount": {
              "mass": {
                "value": 0.25,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "succinic anhydride"
              }
            ],
            "amount": {
              "mass": {
                "value": 0.55,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "pyridine"
              }
            ],
            "amount": {
              "volume": {
                "value": 50.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-995dabbb899d4676b65cd66a9465f548"
  },
  {
    "input_text": "A mixture 9-(2-Hydroxyethoxymethyl)thioguanine (0.7 g), methyl iodide (0.2 ml), Dowex HCO3- resin (1.7 g) and methanol (200 ml) was stirred overnight at room temperature. The resin was removed by filtration, washed with methanol and the combined filtration evaporated, and the residue recrystallized from isopropanol and then from acetone to give 2-amino-6-methylthio-9-(2-hydroxyethoxymethyl)purine, m.p. 188\u00b0-191\u00b0 C. in 38% yield.",
    "output_reaction_inputs": {
      "m1_m2_m3_m4": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "9-(2-Hydroxyethoxymethyl)thioguanine"
              }
            ],
            "amount": {
              "mass": {
                "value": 0.7,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "methyl iodide"
              }
            ],
            "amount": {
              "volume": {
                "value": 0.2,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "HCO3-"
              }
            ],
            "amount": {
              "mass": {
                "value": 1.7,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "methanol"
              }
            ],
            "amount": {
              "volume": {
                "value": 200.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-75eaadbae4f04da5b4251f3e64644afd"
  },
  {
    "input_text": "A mixture of 9-(3-benzoyloxypropoxymethyl)guanine (0.5 g) and aqueous 45% methylamine (10 ml) was stirred overnight at room temperature. Excess methylamine and water was evaporated at \u222030\u00b0 C. under reduced pressure and the residue recrystallized from ethanol to give 9-(3-hydroxypropoxymethyl)guanine (0.24 g), m.p. 223\u00b0 C. (with resolidification), as the 0.1/2 hydrate.",
    "output_reaction_inputs": {
      "m1_m2": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "9-(3-benzoyloxypropoxymethyl)guanine"
              }
            ],
            "amount": {
              "mass": {
                "value": 0.5,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "methylamine"
              }
            ],
            "amount": {
              "volume": {
                "value": 10.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "temperature": {
        "control": {
          "type": "AMBIENT"
        }
      },
      "stirring": {
        "type": "CUSTOM",
        "details": "was stirred overnight at room temperature"
      },
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-d8c081b912a64017be073f54fec08031"
  },
  {
    "input_text": "A solution of 9-(2-hydroxyethoxymethyl)guanine (4.73 g) in 97% formic acid (24 ml) was stirred at room temperature overnight. The amber solution was diluted with about 200 ml of dry ether and chilled. The resulting white precipitate was filtered, dried and recrystallized from dry dimethylformamide to give 9-(2-formyloxyethoxymethyl)guanine (3.6 g, m.p. 225\u00b0-227\u00b0 C.).",
    "output_reaction_inputs": {
      "m1_m2": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "9-(2-hydroxyethoxymethyl)guanine"
              }
            ],
            "amount": {
              "mass": {
                "value": 4.73,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "formic acid"
              }
            ],
            "amount": {
              "volume": {
                "value": 24.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      },
      "m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "ether"
              }
            ],
            "amount": {
              "volume": {
                "value": 200.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-22fb52c1062f40b9968b5a4b0584da80"
  },
  {
    "input_text": "A solution of 2-amino-9-(2-hydroxyethoxymethyl)adenine (0.5 g) in 97% formic acid (2.5 ml) was stirred in an ice bath for 3 hours, and then at room temperature overnight. Dry ether (80 ml) was added and the mixture chilled. The solid was removed by filtration and dissolved in hot acetonitrile (125 ml); residual solids were removed by filtration. The filtrate was applied to a column containing silica gel (14 g) in acetonitrile. The column was eluted with dry acetone. The eluate was evaporated and the residual solid recrystallized from acetonitrile to give 2-amino-9-(2-formyloxyethoxymethyl)adenine (93 mg, m.p. 238\u00b0-240\u00b0 C.).",
    "output_reaction_inputs": {
      "m1_m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "2-amino-9-(2-hydroxyethoxymethyl)adenine"
              }
            ],
            "amount": {
              "mass": {
                "value": 0.5,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "formic acid"
              }
            ],
            "amount": {
              "volume": {
                "value": 2.5,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      },
      "m2": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "ether"
              }
            ],
            "amount": {
              "volume": {
                "value": 80.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-4cab48eb95094fc29a0e731b76fd03d6"
  },
  {
    "input_text": "A mixture of 2.20 g (6.12 mmol) of 9-(2-benzoyloxyethoxymethyl)-2-methylthioadenine and 100 ml of 40% aqueous methylamine was heated on a steam bath with occasional agitation for one hour. The solution was cooled and spin evaporated in vacuo. The resultant oil was leached with five 40 ml portions of hot ether to give a solid; yield, 1.31 g (84%), m.p. 174\u00b0-176\u00b0. Recrystallization from ethanol gave the analytical sample of 9-(2-hydroxyethoxymethyl)-2-methylthioadenine; \u03bbmax (\u03b5\u00d710-3) (10% EtOH in solvent) pH 1-270 (16.7),291 (sh) (11.9), H2O and pH 13-276 (15.2) nm; nmr (DMSO-d6), 2.49 (3H, S), 3.55 (4H, S), 4.65 (1H, br S), 5.55 (2H, S), 7.31 (2H, S), 8.15 (1H, S) \u03b4.",
    "output_reaction_inputs": {
      "m1_m2": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "9-(2-benzoyloxyethoxymethyl)-2-methylthioadenine"
              }
            ],
            "amount": {
              "mass": {
                "value": 2.2,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "methylamine"
              }
            ],
            "amount": {
              "volume": {
                "value": 100.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-80677927fbb04d7684ff8c043286d64a"
  },
  {
    "input_text": "A mixture of 9-(2-hydroxyethoxymethyl)guanine (4.6 g), dry dimethylformamide (46 ml), acetic anhydride (16 ml) and dry pyridine (24 ml) was stirred at room temperature overnight. The resulting white solid was removed by filtration and dissolved in warm dimethylformamide (100 ml), pyridine (10 ml) and acetic anhydride (8 ml) added and the mixture stirred for 18 hr. The white solid formed was removed by filtration, washed with ethyl acetate and recrystallized from dimethylformamide to give 9-(2-acetyloxyethoxymethyl)guanine (3.3 g), m.p. 240\u00b0-241\u00b0 C.",
    "output_reaction_inputs": {
      "m1_m2_m3_m4": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "9-(2-hydroxyethoxymethyl)guanine"
              }
            ],
            "amount": {
              "mass": {
                "value": 4.6,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "dimethylformamide"
              }
            ],
            "amount": {
              "volume": {
                "value": 46.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "acetic anhydride"
              }
            ],
            "amount": {
              "volume": {
                "value": 16.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "pyridine"
              }
            ],
            "amount": {
              "volume": {
                "value": 24.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "temperature": {
        "control": {
          "type": "AMBIENT"
        }
      },
      "stirring": {
        "type": "CUSTOM",
        "details": "was stirred at room temperature overnight"
      },
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-8da2c2cc5acb4e91b35107c024093b4d"
  },
  {
    "input_text": "2.3 g of Na is dissolved in 80 ml of ethanol; 21.1 g of 6-ethoxy-2-mercaptobenzothiazole is added and the mixture is stirred until solution takes place. 25.7 g of 2-bromo-2-phenylpropionic acid ethyl ester is then added and the mixture is stirred overnight at 20\u00b0 and worked up in the customary manner to give 2-(6-ethoxybenzothiazol-2-ylthio)-2-phenylpropionic acid ethyl ester, m.p. 92\u00b0-94\u00b0.",
    "output_reaction_inputs": {
      "m2": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "6-ethoxy-2-mercaptobenzothiazole"
              }
            ],
            "amount": {
              "mass": {
                "value": 21.1,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      },
      "m1_m4": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "Na"
              }
            ],
            "amount": {
              "mass": {
                "value": 2.3,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "ethanol"
              }
            ],
            "amount": {
              "volume": {
                "value": 80.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      },
      "m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "2-bromo-2-phenylpropionic acid ethyl ester"
              }
            ],
            "amount": {
              "mass": {
                "value": 25.7,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "stirring": {
        "type": "CUSTOM",
        "details": "the mixture is stirred until solution"
      },
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-5c0abd857c1c4d749eae13239a2f515f"
  },
  {
    "input_text": "18.2 g of 2-mercapto-2-phenylacetic acid methyl ester is added to a suspension of 2.4 g of NaH in 200 ml of DMF and the mixture is stirred until the evolution of gas has ceased. 17 g of 2-chlorobenzothiazole (or 21.5 g of 2-bromobenzothiazole) is then introduced. The mixture is stirred for 5 hours at 80\u00b0 and is worked up in the customary manner to give 2-(benzothiazol-2-ylthio)-2-phenylacetic acid methyl ester, in the form of an oil.",
    "output_reaction_inputs": {
      "m3_m4": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "2-chlorobenzothiazole"
              }
            ],
            "amount": {
              "mass": {
                "value": 17.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "2-bromobenzothiazole"
              }
            ],
            "amount": {
              "mass": {
                "value": 21.5,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      },
      "m1_m2_m5": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "2-mercapto-2-phenylacetic acid methyl ester"
              }
            ],
            "amount": {
              "mass": {
                "value": 18.2,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "NaH"
              }
            ],
            "amount": {
              "mass": {
                "value": 2.4,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "DMF"
              }
            ],
            "amount": {
              "volume": {
                "value": 200.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "stirring": {
        "type": "CUSTOM",
        "details": "the mixture is stirred until the evolution of gas"
      },
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-75d9164de36b4c3fa3658f3996a3c7f7"
  },
  {
    "input_text": "6 g of 2-(6-ethoxybenzothiazol-2-ylthio)-2-phenylpropionic acid ethyl ester and 6 g of KOH in 100 ml of ethanol are stirred at 20\u00b0; the mixture is evaporated; the residue is dissolved in water; and the solution is washed with ether, acidified with hydrochloric acid and extracted with CH2Cl2. The phases are separated and the organic phase is dried and evaporated to give 2-(6-ethoxybenzothiazol-2-ylthio)-2-phenylpropionic acid. M.p. 152\u00b0-153\u00b0 (from CCl4).",
    "output_reaction_inputs": {
      "m1_m2_m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "2-(6-ethoxybenzothiazol-2-ylthio)-2-phenylpropionic acid ethyl ester"
              }
            ],
            "amount": {
              "mass": {
                "value": 6.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "KOH"
              }
            ],
            "amount": {
              "mass": {
                "value": 6.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "ethanol"
              }
            ],
            "amount": {
              "volume": {
                "value": 100.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-9e18616d8c23471e9f13d90026eeb3b5"
  },
  {
    "input_text": "2-(4-Chlorophenylthio)acetamidoxime (21.7 g, 0.1 mol) was stirred in toluene (150 ml) whilst a solution of chloroacetyl chloride (11.3 g, 0.1 mol) in toluene (50 ml) was added dropwise over 20 minutes. The thick suspension was refluxed for 1 hour to give a black mixture which was cooled and then extracted with water and ether. The ether extracts were evaporated to give a brown oil which was chromatographed on silica gel (200 g) and eluted with ether/hexane (2:3) to give 5-chloromethyl-3-(4-chlorophenylthiomethyl)-1,2,4-oxadiazole.",
    "output_reaction_inputs": {
      "m1_m3_m2_m4": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "2-(4-Chlorophenylthio)acetamidoxime"
              }
            ],
            "amount": {
              "mass": {
                "value": 21.7,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "chloroacetyl chloride"
              }
            ],
            "amount": {
              "mass": {
                "value": 11.3,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "toluene"
              }
            ],
            "amount": {
              "volume": {
                "value": 150.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "toluene"
              }
            ],
            "amount": {
              "volume": {
                "value": 50.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-8bc5b6dcf1274343ba0f68ccfd92fe99"
  },
  {
    "input_text": "2-Dimethylaminobenzenethiol (1.67 g, 0.011 mol) was dissolved in a solution of sodium methoxide (0.59 g) in methanol (50 ml) and 5-chloromethyl-3-(4-chlorophenylthiomethyl)-1,2,4-oxadiazole (3.0 g 0.011 mol) was added dropwise with stirring. After a further 10 min. stirring the solution was filtered and evaporated to leave a brown oil, which was purified by chromatography on silica gel elution with hexane/ether (3:2) giving 3-(4-chlorophenylthiomethyl)-5-(2-dimethylaminophenylthiomethyl)-1,2,4-oxadiazole as a colourless oil, mass spectrum M+1 392; refractive index 1.6263.",
    "output_reaction_inputs": {
      "m1_m3_m4_m2": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "2-Dimethylaminobenzenethiol"
              }
            ],
            "amount": {
              "mass": {
                "value": 1.67,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "5-chloromethyl-3-(4-chlorophenylthiomethyl)-1,2,4-oxadiazole"
              }
            ],
            "amount": {
              "mass": {
                "value": 3.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "sodium methoxide"
              }
            ],
            "amount": {
              "mass": {
                "value": 0.59,
                "units": "GRAM"
              }
            },
            "reactionRole": "SOLVENT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "methanol"
              }
            ],
            "amount": {
              "volume": {
                "value": 50.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "stirring": {
        "type": "CUSTOM",
        "details": "with stirring"
      },
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-72da56557c4e456ab34dea5da02c4f35"
  },
  {
    "input_text": "4-Bromobenzenethiol (3.78 g, 0.02 mol) was added to a solution of sodium (0.46 g, 0.02 mol) in ethanol (50 ml.) and 3,5-di-(chloromethyl)-1,2,4-oxadiazole (1.67 g, 0.01 mol) was added dropwise. The solution was then filtered and evaporated to give a solid which was recrystallised from isopropanol to give 3,5-di-(4-bromophenylthiomethyl)-1,2,4-oxadiazole, m.p. 80\u00b0.",
    "output_reaction_inputs": {
      "m1_m2_m4_m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "4-Bromobenzenethiol"
              }
            ],
            "amount": {
              "mass": {
                "value": 3.78,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "sodium"
              }
            ],
            "amount": {
              "mass": {
                "value": 0.46,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "3,5-di-(chloromethyl)-1,2,4-oxadiazole"
              }
            ],
            "amount": {
              "mass": {
                "value": 1.67,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "ethanol"
              }
            ],
            "amount": {
              "volume": {
                "value": 50.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-556bc0e14ebc447da967ec4af9df9acf"
  },
  {
    "input_text": "95 g (0.30 M) of rac-5-(o-fluorophenyl)-1,3-dihydro-3-methyl-7-nitro-2H-1,4-benzodiazepin-2-one are dissolved in 1 liter of absolute acetone and treated with 60 g of powdered potassium carbonate and 43 g of dimethyl sulphate. The mixture is stirred at room temperature for 4 hours and left to stand in a refrigerator for 48 hours. The mixture is then concentrated, treated with ice-water and extracted several times with methylene chloride. The organic solution is dried over sodium sulphate, filtered and concentrated. The residue is crystallised from ethyl acetate/petroleum ether, there being obtained rac-5-(o-fluorophenyl)-1,3-dihydro-1,3-dimethyl-7-nitro-2H-1,4-benzodiazepin-2-one which melts at 154\u00b0-156\u00b0 C.",
    "output_reaction_inputs": {
      "m2_m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "potassium carbonate"
              }
            ],
            "amount": {
              "mass": {
                "value": 60.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "dimethyl sulphate"
              }
            ],
            "amount": {
              "mass": {
                "value": 43.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      },
      "m1_m4": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "rac-5-(o-fluorophenyl)-1,3-dihydro-3-methyl-7-nitro-2H-1,4-benzodiazepin-2-one"
              }
            ],
            "amount": {
              "mass": {
                "value": 95.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "acetone"
              }
            ],
            "amount": {
              "volume": {
                "value": 1.0,
                "units": "LITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "temperature": {
        "control": {
          "type": "AMBIENT"
        }
      },
      "stirring": {
        "type": "CUSTOM",
        "details": "The mixture is stirred at room temperature for 4 hours"
      },
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-dd4eafacf81644cea594457d4abe3803"
  },
  {
    "input_text": "85 g (0.26 M) of rac-5-(o-fluorophenyl)-1,3-dihydro-1,3-dimethyl-7-nitro-2H-1,4-benzodiazepin-2-one are dissolved in 700 ml of concentrated hydrochloric acid and treated slowly with 180 g of stannous chloride. After about 15 minutes, the mixture is cooled with ice and then concentrated on a rotary evaporator. The residue is dissolved in ice-water, slowly made alkaline with 200 g of sodium carbonate in 1 liter of water and extracted several times with methylene chloride. The organic solution is dried over sodium sulphate, filtered and concentrated. The residue is crystallised from ethyl acetate and there is obtained rac-7-amino-5(o-fluorophenyl)-1,3-dihydro-1,3-dimethyl-2H-1,4-benzodiazepin-2-one which melts at 178\u00b0-180\u00b0 C.",
    "output_reaction_inputs": {
      "m2": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "stannous chloride"
              }
            ],
            "amount": {
              "mass": {
                "value": 180.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      },
      "m1_m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "rac-5-(o-fluorophenyl)-1,3-dihydro-1,3-dimethyl-7-nitro-2H-1,4-benzodiazepin-2-one"
              }
            ],
            "amount": {
              "mass": {
                "value": 85.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "hydrochloric acid"
              }
            ],
            "amount": {
              "volume": {
                "value": 700.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-80a8fe5e178e4ac2a43cdf7f0f191005"
  },
  {
    "input_text": "57.5 g (0.18 M) of (S)-5-(o-fluorophenyl)-1,3-dihydro-3-methyl-7-nitro-2H-1,4-benzodiazepin-2-one are dissolved in 600 ml of absolute acetone. The solution is treated with 48 g of powdered potassium carbonate and 21 ml of methyl iodide and stirred at room temperature for 5 hours. The mixture is concentrated and the residue is treated with ice-water and extracted several times with methylene chloride. The methylene chloride solution is washed with water, dried over sodium sulphate, filtered and concentrated. The residue is crystallised from ether/petroleum ether and there is obtained (S)-5-(o-fluorophenyl)-1,3-dihydro-1,3-dimethyl-7-nitro-2H-1,4-benzodiazepin-2-one which melts at 118\u00b0-126\u00b0 C. with decomposition; [\u03b1]25D =+563.1\u00b0 (n methylene chloride; 1%).",
    "output_reaction_inputs": {
      "m1_m4": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "(S)-5-(o-fluorophenyl)-1,3-dihydro-3-methyl-7-nitro-2H-1,4-benzodiazepin-2-one"
              }
            ],
            "amount": {
              "mass": {
                "value": 57.5,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "acetone"
              }
            ],
            "amount": {
              "volume": {
                "value": 600.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      },
      "m2_m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "potassium carbonate"
              }
            ],
            "amount": {
              "mass": {
                "value": 48.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "methyl iodide"
              }
            ],
            "amount": {
              "volume": {
                "value": 21.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "temperature": {
        "control": {
          "type": "AMBIENT"
        }
      },
      "stirring": {
        "type": "CUSTOM",
        "details": "stirred at room temperature for 5 hours"
      },
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-f9e393b6a40d4d5291c42d9bcdfe38cd"
  },
  {
    "input_text": "11.1 g (0.03 M) of 1-[5-(o-fluorophenyl)-2,3-dihydro-1-methyl-2-oxo-1H-1,4-benzodiazepin-7-yl]-3-(2-hydroxyethyl)urea are stirred at room temperature for 18 hours in 150 ml of acetonitrile with 3.9 ml of acetyl chloride and 9 g of powdered potassium carbonate. The mixture is concentrated on a rotary evaporator and the residue is purified on a 500 g silica gel column using methylene chloride/ethanol as the eluting agent. After crystallisation from ethyl acetate, there is obtained 2-[3-[5-(o-fluorophenyl)-2,3-dihydro-1-methyl-2-oxo-1H-1,4-benzodiazepin-7-yl]-ureido]ethyl acetate which melts at 196\u00b0-198\u00b0 C.",
    "output_reaction_inputs": {
      "m1_m4_m2_m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "1-[5-(o-fluorophenyl)-2,3-dihydro-1-methyl-2-oxo-1H-1,4-benzodiazepin-7-yl]-3-(2-hydroxyethyl)urea"
              }
            ],
            "amount": {
              "mass": {
                "value": 11.1,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "acetyl chloride"
              }
            ],
            "amount": {
              "volume": {
                "value": 3.9,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "potassium carbonate"
              }
            ],
            "amount": {
              "mass": {
                "value": 9.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "acetonitrile"
              }
            ],
            "amount": {
              "volume": {
                "value": 150.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-7be5b7297aee4294a63d8870473b2a67"
  },
  {
    "input_text": "3.7 g of 1-(2-chloroethyl)-3-[6-chloro-5-(o-fluorophenyl)-2,3-dihydro-1-methyl-2-oxo-1H-1,4-benzodiazepin-7-yl]urea dissolved in 100 ml of acetonitrile are treated with 1.83 g of potassium acetate and 4.21 g of 18-crown-6. The mixture is then stirred at room temperature for 5 days, concentrated, treated with water/methylene chloride and the aqueous solution is extracted several times with methylene chloride. The organic solution is dried with sodium sulphate, filtered and concentrated. The residue is purified on a 350 g silica gel column using ethyl acetate as the eluting agent and crystallised from ethanol/ether. There is obtained 2-[3-[6-chloro-5-(o-fluorophenyl)-2,3-dihydro-1-methyl-2-oxo-1H-1,4-benzodiazepin-7-yl]ureido]ethyl acetate.",
    "output_reaction_inputs": {
      "m1_m4": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "1-(2-chloroethyl)-3-[6-chloro-5-(o-fluorophenyl)-2,3-dihydro-1-methyl-2-oxo-1H-1,4-benzodiazepin-7-yl]urea"
              }
            ],
            "amount": {
              "mass": {
                "value": 3.7,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "acetonitrile"
              }
            ],
            "amount": {
              "volume": {
                "value": 100.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      },
      "m2_m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "potassium acetate"
              }
            ],
            "amount": {
              "mass": {
                "value": 1.83,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "18-crown-6"
              }
            ],
            "amount": {
              "mass": {
                "value": 4.21,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "temperature": {
        "control": {
          "type": "AMBIENT"
        }
      },
      "stirring": {
        "type": "CUSTOM",
        "details": "The mixture is then stirred at room temperature for 5 days"
      },
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-afb0ad81616e453ca6e60b58c358b12b"
  },
  {
    "input_text": "Crude 7-allyloxy-4-methylcoumarin (83.5 g, 0.381 mol) was dissolved in 250 ml of diethyl aniline with heating, and the solution was allowed to reflux for two hours. After the solution had cooled and some product had precipitated, petroleum ether (b.p. 30\u00b0-60\u00b0 C., 760 ml) was added. A brown precipitate formed and was collected by filtration, washed with three small portions of petroleum ether, and dried in vacuo to obtain the crude product. Recrystallization from 600 ml of 95% EtOH gave the pure product (53.5 g, 74% recovery, 65% yield) of mp 192.5\u00b0-195.0\u00b0 C. (lit. 193\u00b0-194\u00b0 C.). TLC showed only a single spot.",
    "output_reaction_inputs": {
      "m1_m2": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "7-allyloxy-4-methylcoumarin"
              }
            ],
            "amount": {
              "mass": {
                "value": 83.5,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "diethyl aniline"
              }
            ],
            "amount": {
              "volume": {
                "value": 250.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-121167d53c244955836c4dd8d04576b3"
  },
  {
    "input_text": "A solution of sodium (29.8 g, 1.296 mol) in dry, absolute ethanol (1400 ml.) was added to 7-acetoxy-4-methyl-8-(2', 3'-dibromopropyl)coumarin (108.1 g, 0.259 mol). The mixture was allowed to reflux for one hour and 45 minutes with magnetic stirring. The cooled mixture was poured into a mixture of ice (2800 g) and 3.5% HCl (2800 ml.) and stirred. A yellow precipitate was collected by filtration, washed first with three portions (600 ml.) of 5% NaOH, second with one portion (600 ml.) of 3.5% HCl, third with three portions (600 ml.) of water, and then dried in vacuo to obtain crude 4,8-dimethylisopsoralen (48.6 g, 87.6% yield, mp. 160\u00b0-174\u00b0 C.). Recrystallization from 95% ethanol (1500 ml.) gave the pure product (33.7 g, 68% recovery, 61% yield) mp. 176\u00b0-178\u00b0 C. (lit.2 182\u00b0-183\u00b0 C.).",
    "output_reaction_inputs": {
      "m3_m4": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "ice"
              }
            ],
            "amount": {
              "mass": {
                "value": 2800.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "HCl"
              }
            ],
            "amount": {
              "volume": {
                "value": 2800.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      },
      "m5_m2": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "7-acetoxy-4-methyl-8-(2', 3'-dibromopropyl)coumarin"
              }
            ],
            "amount": {
              "mass": {
                "value": 108.1,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "ethanol"
              }
            ],
            "amount": {
              "volume": {
                "value": 1400.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      },
      "m1": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "sodium"
              }
            ],
            "amount": {
              "mass": {
                "value": 29.8,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "stirring": {
        "type": "CUSTOM",
        "details": "stirred"
      },
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-62f3b4ac62cb4278aa5e2423a5cf313c"
  },
  {
    "input_text": "The procedure is as in Example 1, starting from 8.8 g of fluorobenzene instead of the 9.9 g of anisol and from 20 g instead of from 15.7 g of 3-(1-benzoyl 4-piperidyl) propionic acid. 25.5 g of crude 3-(1-benzoyl 4-piperidyl) 1-(4-fluorophenyl) 1-propanone in the form of an oil are obtained.",
    "output_reaction_inputs": {
      "m2": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "3-(1-benzoyl 4-piperidyl) propionic acid"
              }
            ],
            "amount": {
              "mass": {
                "value": 15.7,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      },
      "m1": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "fluorobenzene"
              }
            ],
            "amount": {
              "mass": {
                "value": 8.8,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-92c7f755c66c44fb925797974aa488e6"
  },
  {
    "input_text": "In Example 1 the 9.9 g of anisole and the 15.7 g of 3-(1-benzoyl 4-piperidyl) propionic acid are substituted by 185 ml of 1,2 dichlorobenzene and 35 g of 3-(1-benzoyl 4-piperidyl) propionic acid respectively. The reaction is effected at 100\u00b0 C. and without solvent. 51.1 g of crude 1-(3,4-dichlorophenyl) 3-(1-benzoyl 4-piperidyl) 1-propanone in the form of an oil which crystallizes slowly are obtained.",
    "output_reaction_inputs": {
      "m2": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "3-(1-benzoyl 4-piperidyl) propionic acid"
              }
            ],
            "amount": {
              "mass": {
                "value": 15.7,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      },
      "m4": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "1,2 dichlorobenzene"
              }
            ],
            "amount": {
              "volume": {
                "value": 185.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      },
      "m1": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "anisole"
              }
            ],
            "amount": {
              "mass": {
                "value": 9.9,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      },
      "m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "3-(1-benzoyl 4-piperidyl) propionic acid"
              }
            ],
            "amount": {
              "mass": {
                "value": 35.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-00dfe80d22d94c26b46ffe088526d577"
  },
  {
    "input_text": "The procedure is as in Example 1, starting from 18 g of chlorobenzene instead of 9.9 g of anisol, 350 ml of carbon disulfide instead of 157 ml and 35 g instead of 15.7 g of 3-(1-benzoyl 4-piperidyl) propionic acid. 40.1 g of crude 1-(4-chlorophenyl) 3-(1-benzoyl 4-piperidyl) 1-propanone are obtained in the form of an oil which crystallizes.",
    "output_reaction_inputs": {
      "m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "carbon disulfide"
              }
            ],
            "amount": {
              "volume": {
                "value": 350.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      },
      "m1": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "chlorobenzene"
              }
            ],
            "amount": {
              "mass": {
                "value": 18.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      },
      "m2": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "3-(1-benzoyl 4-piperidyl) propionic acid"
              }
            ],
            "amount": {
              "mass": {
                "value": 15.7,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-012a3a87a68944188cc83cb3e4fbdb56"
  },
  {
    "input_text": "A mixture of 2-(2-dimethylaminophenylthio)acetamidoxime (1.0 g), triethylorthoformate (1.5 ml) and boron trifluoride etherate (0.015 ml) was warmed at 70\u00b0 whence a solution soon formed. Heating at 70\u00b0 was continued for 5 hours, the reaction mixture cooled and solvent removed by evaporation under reduced pressure. The residual oil was taken up in diethyl ether, washed with 5% aqueous sodium carbonate solution and water, dried and evaporated to dryness under reduced pressure. The residue was distilled under reduced pressure to give 3-(2-dimethylaminophenylthiomethyl)-1,2,4-oxadiazole as a colourless oil, b.p. 119\u00b0 (0.07 mm Hg).",
    "output_reaction_inputs": {
      "m1_m2_m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "2-(2-dimethylaminophenylthio)acetamidoxime"
              }
            ],
            "amount": {
              "mass": {
                "value": 1.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "triethylorthoformate"
              }
            ],
            "amount": {
              "volume": {
                "value": 1.5,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "boron trifluoride etherate"
              }
            ],
            "amount": {
              "volume": {
                "value": 0.015,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-69f9fef448a24feb8765b4eb8ad06143"
  },
  {
    "input_text": "Sodium (1.27 g; 0.055 mol) was dissolved in absolute ethanol (50 ml) and to this was added 2-aminothiophenol (7.38 g; 0.059 mol). To the resulting solution was added 3-chloromethyl-1,2,4-oxadiazole (6.59 g; 0.055 mol) dropwise over 10 minutes. The resulting mixture was then stirred at ambient temperature for 30 minutes, sodium chloride removed by filtration and the filtrate was evaporated to dryness under reduced pressure to give 3-(2-aminophenylthiomethyl)-1,2,4-oxadiazole which was re-crystallised from isopropanol; m.p. 57\u00b0.",
    "output_reaction_inputs": {
      "m1_m4": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "Sodium"
              }
            ],
            "amount": {
              "mass": {
                "value": 1.27,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "ethanol"
              }
            ],
            "amount": {
              "volume": {
                "value": 50.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      },
      "m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "3-chloromethyl-1,2,4-oxadiazole"
              }
            ],
            "amount": {
              "mass": {
                "value": 6.59,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      },
      "m2": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "2-aminothiophenol"
              }
            ],
            "amount": {
              "mass": {
                "value": 7.38,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "temperature": {
        "control": {
          "type": "AMBIENT"
        }
      },
      "stirring": {
        "type": "CUSTOM",
        "details": "The resulting mixture was then stirred at ambient temperature for 30 minutes"
      },
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-8a42b7c4c1d94c35863f966d25765d11"
  },
  {
    "input_text": "A solution of ethyl chloroformate (0.55 g) in benzene (10 ml) was added dropwise to a solution of 3-(2-aminophenylthiomethyl)-1,2,4-oxadiazole (2.07 g) in benzene (10 ml). The reaction mixture was then stirred for 2 days, filtered and the filtrate evaporated under reduced pressure to give an oil which crystallised on standing. Re-crystallisation from isopropanol gave 3-(2-ethoxycarbonylaminophenylthiomethyl)-1,2,4-oxadiazole, m.p. 55\u00b0.",
    "output_reaction_inputs": {
      "m1_m3_m2_m4": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "ethyl chloroformate"
              }
            ],
            "amount": {
              "mass": {
                "value": 0.55,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "3-(2-aminophenylthiomethyl)-1,2,4-oxadiazole"
              }
            ],
            "amount": {
              "mass": {
                "value": 2.07,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "benzene"
              }
            ],
            "amount": {
              "volume": {
                "value": 10.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "benzene"
              }
            ],
            "amount": {
              "volume": {
                "value": 10.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "stirring": {
        "type": "CUSTOM",
        "details": "The reaction mixture was then stirred for 2 days"
      },
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-c2b1806fbbdb457392ca9e5d57664cd3"
  },
  {
    "input_text": "A solution of benzylchloroformate (3.79 g) and 3-(2-aminophenylthiomethyl)-1,2,4-oxadiazole (3.1 g) in dioxan (75 ml) containing potassium carbonate (3.15 g) was refluxed for 1 hour. Solvent was then removed by evaporation under reduced pressure to give a colourless solid which was re-crystallised from hexane to give 3-(2-benzyloxycarbonylaminophenylthiomethyl)-1,2,4-oxadiazole, m.p. 41\u00b0.",
    "output_reaction_inputs": {
      "m1_m2_m4_m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "benzylchloroformate"
              }
            ],
            "amount": {
              "mass": {
                "value": 3.79,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "3-(2-aminophenylthiomethyl)-1,2,4-oxadiazole"
              }
            ],
            "amount": {
              "mass": {
                "value": 3.1,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "potassium carbonate"
              }
            ],
            "amount": {
              "mass": {
                "value": 3.15,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "dioxan"
              }
            ],
            "amount": {
              "volume": {
                "value": 75.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-44be2cb32f404a8c93de1ca7462d8589"
  },
  {
    "input_text": "A mixture of 3-(2-aminophenylthiomethyl)1,2,4-oxadiazole (4.14 g), 4-chlorobenzoyl chloride (3.68 g), sodium hydroxide (0.8 g) and water (15 ml) was stirred at 25\u00b0 for 4 hours. Crude product was recovered by filtration and crystallised from ethanol to give 3-[2-(4-chlorobenzamido)phenylthiomethyl]-1,2,4-oxadiazole, m.p. 103\u00b0.",
    "output_reaction_inputs": {
      "m1_m2_m3_m4": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "3-(2-aminophenylthiomethyl)1,2,4-oxadiazole"
              }
            ],
            "amount": {
              "mass": {
                "value": 4.14,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "4-chlorobenzoyl chloride"
              }
            ],
            "amount": {
              "mass": {
                "value": 3.68,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "sodium hydroxide"
              }
            ],
            "amount": {
              "mass": {
                "value": 0.8,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "water"
              }
            ],
            "amount": {
              "volume": {
                "value": 15.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "stirring": {
        "type": "CUSTOM",
        "details": "was stirred at 25\u00b0 for 4 hours"
      },
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-f61fb53e20f44433a9af42aa9ac33463"
  },
  {
    "input_text": "Methanesulphonyl chloride (1.39 g) was added dropwise to a cooled solution of 3-(2-aminophenylthiomethyl)-1,2,4-oxadiazole (3.1 g) in pyridine (12 ml). The reaction mixture was then poured into water (75 ml) the so formed solid removed by filtration and crystallised from ethanol to give 3-(2-methylsulphonamidophenylthiomethyl)-1,2,4-oxadiazole, m.p. 106\u00b0.",
    "output_reaction_inputs": {
      "m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "water"
              }
            ],
            "amount": {
              "volume": {
                "value": 75.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      },
      "m1_m2_m4": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "Methanesulphonyl chloride"
              }
            ],
            "amount": {
              "mass": {
                "value": 1.39,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "3-(2-aminophenylthiomethyl)-1,2,4-oxadiazole"
              }
            ],
            "amount": {
              "mass": {
                "value": 3.1,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "pyridine"
              }
            ],
            "amount": {
              "volume": {
                "value": 12.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-7d0737f2ea4f42e69f5b2de7e77e5887"
  },
  {
    "input_text": "A mixture of 3-(2-aminophenylthiomethyl)1,2,4-oxadiazole (2.07 g; 10-2 mol) and 1,2-epoxy-3-phenoxy propane (1.5 g; 10-2 mol) was warmed on a steam bath during 48 hours. The so produced mixture was chromatographed on silica gel, elution with diethyl ether/hexane (1:1) producing 2-hydroxy-1-[2-(1,2,4-oxadiazol-3-yl-methylthio)anilino]-3-phenoxypropane as a colourless oil.",
    "output_reaction_inputs": {
      "m1_m2": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "3-(2-aminophenylthiomethyl)1,2,4-oxadiazole"
              }
            ],
            "amount": {
              "mass": {
                "value": 2.07,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "1,2-epoxy-3-phenoxy propane"
              }
            ],
            "amount": {
              "mass": {
                "value": 1.5,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-5dd18a6e32de4b42a97e22bb18fc1e61"
  },
  {
    "input_text": "2-Aminobenzenethiol (5.0 g, 0.04 mol) was dissolved in a solution of sodium (0.92 g, 0.04 mol) in ethanol (50 ml) and 3,5-di(chloromethyl)-1,2,4-oxadiazole (3.3 g, 0.02 mol) was added. After filtration of the mixture, the filtrate was collected and the solvent removed to yield the crude product which on re-crystallisation from isopropanol gave 3,5,-di-(2-aminophenylthiomethyl)-1,2,4-oxadiazole, m.p. 68\u00b0.",
    "output_reaction_inputs": {
      "m1_m2_m4_m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "2-Aminobenzenethiol"
              }
            ],
            "amount": {
              "mass": {
                "value": 5.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "sodium"
              }
            ],
            "amount": {
              "mass": {
                "value": 0.92,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "3,5-di(chloromethyl)-1,2,4-oxadiazole"
              }
            ],
            "amount": {
              "mass": {
                "value": 3.3,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "ethanol"
              }
            ],
            "amount": {
              "volume": {
                "value": 50.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-5a924ee670364408a20f4cc11a37d940"
  },
  {
    "input_text": "2-Aminobenzenethiol (3.75 g, 0.03 mol) was added to a solution of sodium (0,06 mol, 1.38 g) in ethanol (50 ml). Solid chloroacetamidoxime hydrochloride (4.35 g, 0.03 mol) was added in one portion. After stirring for 10 minutes the reaction mixture was filtered and the filtrate evaporated to dryness to give the crude product which was re-crystallised from iso-propanol to give 2-(2-aminophenylthio) acetamidoxime, m.p. 80\u00b0.",
    "output_reaction_inputs": {
      "m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "chloroacetamidoxime hydrochloride"
              }
            ],
            "amount": {
              "mass": {
                "value": 4.35,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      },
      "m1_m2_m4": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "2-Aminobenzenethiol"
              }
            ],
            "amount": {
              "mass": {
                "value": 3.75,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "sodium"
              }
            ],
            "amount": {
              "mass": {
                "value": 1.38,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "ethanol"
              }
            ],
            "amount": {
              "volume": {
                "value": 50.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "stirring": {
        "type": "CUSTOM",
        "details": "After stirring for 10 minutes the reaction mixture"
      },
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-bdcb37078c0b4a949a7d43c71085ffca"
  },
  {
    "input_text": "A mixture of 2-dimethylaminoethanol (2.23 g), N,N1 -dimethylthiourea (2.6 g) and aqueous hydrobromic acid (48%, 20 ml) was boiled under reflux for 50 hours and evaporated to dryness. The residue was recrystallised from a mixture of methanol and ethanol to give the dihydrobromide of the title compound (5.6 g) m.p. 198\u00b0-199\u00b0.",
    "output_reaction_inputs": {
      "m2_m3_m4": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "2-dimethylaminoethanol"
              }
            ],
            "amount": {
              "mass": {
                "value": 2.23,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "N,N1 -dimethylthiourea"
              }
            ],
            "amount": {
              "mass": {
                "value": 2.6,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "hydrobromic acid"
              }
            ],
            "amount": {
              "volume": {
                "value": 20.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-63d179611f024bd1ad2279dc64a1524d"
  },
  {
    "input_text": "A solution of 80 g of 3-chlorophenyl-carboxylic acid chloride in 100 ml of anhydrous benzene was added dropwise with stirring at 10\u00b0 C. to a mixture of 5.87 g of 4-chlorophenol, 46.1 g of triethylamine and 250 ml of anhydrous benzene and the mixture was stirred overnight at room temperature. The mixture was vacuum filtered and the filtrate was evaporated to dryness to obtain 122 g of raw product which was crystallized from 200 ml of a 2-8 ethyl ether-petroleum ether (b.p.=60\u00b0-80\u00b0 C.) mixture to obtain 116 g of 4-chlorophenyl 3-chlorobenzoate melting at 72\u00b0 C.",
    "output_reaction_inputs": {
      "m2_m3_m5": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "4-chlorophenol"
              }
            ],
            "amount": {
              "mass": {
                "value": 5.87,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "triethylamine"
              }
            ],
            "amount": {
              "mass": {
                "value": 46.1,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "benzene"
              }
            ],
            "amount": {
              "volume": {
                "value": 250.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      },
      "m1_m4": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "3-chlorophenyl-carboxylic acid chloride"
              }
            ],
            "amount": {
              "mass": {
                "value": 80.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "benzene"
              }
            ],
            "amount": {
              "volume": {
                "value": 100.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "temperature": {
        "control": {
          "type": "AMBIENT"
        }
      },
      "stirring": {
        "type": "CUSTOM",
        "details": "the mixture was stirred overnight at room temperature"
      },
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-9df484c451d94b2b9590ff7158f1f6a5"
  },
  {
    "input_text": "51 g of 2-[4-(3-aminobenzamido)phenyl]-1-formylhydrazine and 29 g of calcium carbonate were dispersed in a mixture of 120 ml of dioxane and 120 ml of water. To the dispersion, 25 g of thiophosgene was added under cooling with ice. After reacting under cooling with ice for 3 hours, the crystals deposited were collected by filtration to obtain 42 g of the object compound.",
    "output_reaction_inputs": {
      "m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "thiophosgene"
              }
            ],
            "amount": {
              "mass": {
                "value": 25.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      },
      "m1_m2_m4_m5": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "2-[4-(3-aminobenzamido)phenyl]-1-formylhydrazine"
              }
            ],
            "amount": {
              "mass": {
                "value": 51.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "calcium carbonate"
              }
            ],
            "amount": {
              "mass": {
                "value": 29.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "dioxane"
              }
            ],
            "amount": {
              "volume": {
                "value": 120.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "water"
              }
            ],
            "amount": {
              "volume": {
                "value": 120.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-b7b1c3330d9943a89384b0a504dd24f4"
  },
  {
    "input_text": "60 g (0.3 mol) of 1,4-dihydroxy-2-naphthoic acid was added to 150 ml of 2-bromoethanol and, under heating at 90\u00b0 C. with stirring, hydrogen chloride gas was bubbled into the mixture during a reaction period of 2 hours. The mixture was cooled to from 10\u00b0 to 20\u00b0 C. and the crystals precipitated were collected by filtration to obtain 47.4 g (50% yield) of 1-hydroxy-4-(\u03b2-bromoethoxy)-2-naphthoic acid.",
    "output_reaction_inputs": {
      "m1_m2": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "1,4-dihydroxy-2-naphthoic acid"
              }
            ],
            "amount": {
              "mass": {
                "value": 60.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "2-bromoethanol"
              }
            ],
            "amount": {
              "volume": {
                "value": 150.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "temperature": {
        "setpoint": {
          "value": 90.0,
          "units": "CELSIUS"
        }
      },
      "stirring": {
        "type": "CUSTOM",
        "details": "with stirring"
      },
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-0b1588d9ef2e4873b79a10b0727c565f"
  },
  {
    "input_text": "1,8-Diaminonaphthalene (15.82 g.; 0.10 mole) and m-trifluoromethylbenzoyl chloride (20.8 g.; 0.10 mole) were reacted in the same procedures as reported in Example 1, yielding 33.3 g. (95.4% yield) of 2-(m-trifluoromethylphenyl)-1H-perimidine hydrochloride, m.p. 280\u00b0 C. (dec), mass spectrum m/e 312.",
    "output_reaction_inputs": {
      "m1_m2": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "1,8-Diaminonaphthalene"
              }
            ],
            "amount": {
              "mass": {
                "value": 15.82,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "m-trifluoromethylbenzoyl chloride"
              }
            ],
            "amount": {
              "mass": {
                "value": 20.8,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-9c153cf251474587bbf779aec045c62b"
  },
  {
    "input_text": "1,8-Diaminonaphthalene (1.04 grams; 0.00656 mole) and p-pentafluoroethoxybenzoyl chloride (1.8 grams; 0.00656 mole) were reacted in the procedures of Example 3, yielding 2.25 grams of product (82.7% yield), m.p., 240\u00b0 C. (dec.), mass spectrum m/e 378.",
    "output_reaction_inputs": {
      "m1_m2": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "1,8-Diaminonaphthalene"
              }
            ],
            "amount": {
              "mass": {
                "value": 1.04,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "p-pentafluoroethoxybenzoyl chloride"
              }
            ],
            "amount": {
              "mass": {
                "value": 1.8,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-5d5a9964617249ab90e294e713446b26"
  },
  {
    "input_text": "A solution of 5-amino-2-chloronicotinonitrile (5.0 g, 0.033 m), 2,5-dimethoxytetrahydrofuran (11 g, 0.085 m) and acetic anhydride (20 ml) was heated at reflux with stirring. After two hours, the solution was concentrated to dryness under reduced pressure (20 mm). The residue was triturated with CCl4 and filtered to yield 5.2 g (78% yield) of 2-chloro-5-(1-pyrrolyl)nicotinonitrile, m.p.=144\u00b0-146\u00b0.",
    "output_reaction_inputs": {
      "m1_m2_m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "5-amino-2-chloronicotinonitrile"
              }
            ],
            "amount": {
              "mass": {
                "value": 5.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "2,5-dimethoxytetrahydrofuran"
              }
            ],
            "amount": {
              "mass": {
                "value": 11.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "acetic anhydride"
              }
            ],
            "amount": {
              "volume": {
                "value": 20.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "stirring": {
        "type": "CUSTOM",
        "details": "with stirring"
      },
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-fd962f039f2b49eaa56712343fad21d4"
  },
  {
    "input_text": "A mixture of 6 (9.8 g, 0.024 mol), AgNO3 (8.8 g, 0.052 mol), EtOH (100 ml) and H2O (25 mL) was heated on a steam bath for 1 hour. The yellow solid was filtered and the solution concentrated to dryness. The residue was treated with H2O and extracted with CHCl3 (3X). The organic layer was dried, filtered and concentrated to dryness. Distillation of the resulting oil at 105\u00b0-135\u00b0 C. at 0.5 mm gave 3.0 g (48%) of 3; 1H NMR (CDCl3) 1.45\u03b4(3H, t, J=7), 4.4 (2H, q, J=7, 8.6 (1H, d, J=2),/8.9 (1H, d, J =2) and 10.1 (1H, s).",
    "output_reaction_inputs": {
      "m1_m3_m2_m4": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "6"
              }
            ],
            "amount": {
              "mass": {
                "value": 9.8,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "EtOH"
              }
            ],
            "amount": {
              "volume": {
                "value": 100.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "AgNO3"
              }
            ],
            "amount": {
              "mass": {
                "value": 8.8,
                "units": "GRAM"
              }
            },
            "reactionRole": "CATALYST"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "H2O"
              }
            ],
            "amount": {
              "volume": {
                "value": 25.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-05d381b2dcbd419bb2f97774b142a164"
  },
  {
    "input_text": "A mixture of 7 (2.3 g, 0.005 mol), AgNO3 (2.5 g, 0.015 mol) and EtOH (25 mL) was heated on a steam bath. After 1 hour, H2O (25 mL) was added and the yellow solid filtered off. The solution was concentrated to dryness and the residue treated with H2O and extracted with CHCl3 (3X). The CHCl3 layers were washed with NaHSO3 solution, dried, filtered and concentrated to dryness to yield 0.8 g (78%) of 8; 1H NMR (CDCl3) 1.4\u03b4(6H, t, J=7), 4.45 (4H, q, J=7), 8.6 (1H, d, J=3) and 9.0 (1H, d, J=3).",
    "output_reaction_inputs": {
      "m1_m4_m2": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "7"
              }
            ],
            "amount": {
              "mass": {
                "value": 2.3,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "EtOH"
              }
            ],
            "amount": {
              "volume": {
                "value": 25.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "AgNO3"
              }
            ],
            "amount": {
              "mass": {
                "value": 2.5,
                "units": "GRAM"
              }
            },
            "reactionRole": "CATALYST"
          }
        ]
      },
      "m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "H2O"
              }
            ],
            "amount": {
              "volume": {
                "value": 25.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-20e8831ee7a24370b1cd754eee4727a4"
  },
  {
    "input_text": "To a stirred suspension of 3-hydroxy-3,4-dimethyoctylamine (4.91 g; 28.38 mmole) and anhydrous sodium carbonate (5 g) in dry etanol (40 ml) was added ethyl chloroformate (3.65 g; 33.6 mmole) in dry ethanol (25 ml), over 30 min. The mixture was heated under reflux for 1 hr and then poured into water (200 ml). The product was extracted into diethyl ether (3\u00d7100 ml), and the combined organic layers washed with dilute hydrochloric acid (1\u00d7100 ml) and brine (1\u00d7100 ml) and dried. (Na2SO4). Evaporation in vacuo gave ethyl N-[3-hydroxy-3,4-dimethyloctyl]-carbamate (6.2 g; 891).",
    "output_reaction_inputs": {
      "m1_m2_m5": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "3-hydroxy-3,4-dimethyoctylamine"
              }
            ],
            "amount": {
              "mass": {
                "value": 4.91,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "sodium carbonate"
              }
            ],
            "amount": {
              "mass": {
                "value": 5.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "etanol"
              }
            ],
            "amount": {
              "volume": {
                "value": 40.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      },
      "m3_m6": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "ethyl chloroformate"
              }
            ],
            "amount": {
              "mass": {
                "value": 3.65,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "ethanol"
              }
            ],
            "amount": {
              "volume": {
                "value": 25.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      },
      "m4": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "water"
              }
            ],
            "amount": {
              "volume": {
                "value": 200.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-bcf083b948a34c09861b5529754dfe93"
  },
  {
    "input_text": "A solution of 4 -amino-2-chlorophenol (21.5 g; 0.15 mol) in ethylacetate (400 ml) is cooled to 0\u00b0 C. and then methyl isocyanate (18.6 g; 0.15 mol) added slowly. The solution is stirred for one hour and then evaporated under vacuum to afford 30 g of title product, m.p. 188\u00b0-189\u00b0 C.",
    "output_reaction_inputs": {
      "m1_m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "4 -amino-2-chlorophenol"
              }
            ],
            "amount": {
              "mass": {
                "value": 21.5,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "ethylacetate"
              }
            ],
            "amount": {
              "volume": {
                "value": 400.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      },
      "m2": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "methyl isocyanate"
              }
            ],
            "amount": {
              "mass": {
                "value": 18.6,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "stirring": {
        "type": "CUSTOM",
        "details": "The solution is stirred for one hour"
      },
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-a6afcc2e87764f1a9ce8be1b6f529a89"
  },
  {
    "input_text": "A mixture of 3-[3-chloro-4-(phenethyloxy)phenyl]-1,1-dimethylurea (16.68 g; 0.0523 mol), n-butanol (300 ml) and 50% aqueous sodium hydroxide (50 ml) is refluxed for 1.5 hours, and then poured onto 500 ml crushed ice. The resultant mixture is extracted with ether (2\u00d7200 ml). The ether solution is washed with brine, dried over potassium carbonate and cooled in an ice bath. Dry hydrochloric acid gas is bubbled through the solution. The precipitated amine hydrochloride is collected to afford 10.46 g (0.0368 mol) of product, a white solid, m.p. 198\u00b0-204\u00b0 C.",
    "output_reaction_inputs": {
      "m1_m3_m2": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "3-[3-chloro-4-(phenethyloxy)phenyl]-1,1-dimethylurea"
              }
            ],
            "amount": {
              "mass": {
                "value": 16.68,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "sodium hydroxide"
              }
            ],
            "amount": {
              "volume": {
                "value": 50.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "n-butanol"
              }
            ],
            "amount": {
              "volume": {
                "value": 300.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-8c03fcfc1e2241dc9327513dc2b5bc42"
  },
  {
    "input_text": "To a mixture of water (50 ml), ethanol (50 ml) and 50% aqueous sodium hydroxide (25 ml) is added 3-chloro-4-(phenethyloxy)aniline hydrochloride (8.25 g; 0.0290 mol). When the solid is all dissolved, the solution is extracted with ether (3\u00d7100 ml). The ether solution is washed with brine, dried over potassium carbonate and concentrated under vacuum to yield 5.16 g (77%) of a tan oil. This oil is distilled at 140\u00b0 C. under 0.005 ml vacuum to afford the product, a colorless liquid.",
    "output_reaction_inputs": {
      "m1_m4_m2": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "water"
              }
            ],
            "amount": {
              "volume": {
                "value": 50.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "sodium hydroxide"
              }
            ],
            "amount": {
              "volume": {
                "value": 25.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "ethanol"
              }
            ],
            "amount": {
              "volume": {
                "value": 50.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      },
      "m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "3-chloro-4-(phenethyloxy)aniline hydrochloride"
              }
            ],
            "amount": {
              "mass": {
                "value": 8.25,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-ba747bf6921f452da748698f0b95c17e"
  },
  {
    "input_text": "A mixture of 3-{3-chloro-4-[3-(2-phenyl-1,3-dioxolan-2-yl)propoxy]phenyl}-1,1-dimethylurea (2.03 g; 0.005 mol), tetrahydrofuran (10 ml) and 10% aqueous hydrochloric acid (2 ml) is stirred overnight. The reaction mixture is poured into brine (100 ml) and extracted with methylene chloride. The organic layer is washed with water, dried and evaporated to afford the product: 1.69 g of an off-white solid. Recrystallization from a toluene-hexane mixture (50 ml) yields 1.33 g of cream colored needles, m.p. 129\u00b0-130\u00b0 C.",
    "output_reaction_inputs": {
      "m1_m2_m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "3-{3-chloro-4-[3-(2-phenyl-1,3-dioxolan-2-yl)propoxy]phenyl}-1,1-dimethylurea"
              }
            ],
            "amount": {
              "mass": {
                "value": 2.03,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "tetrahydrofuran"
              }
            ],
            "amount": {
              "volume": {
                "value": 10.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "hydrochloric acid"
              }
            ],
            "amount": {
              "volume": {
                "value": 2.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      },
      "m5": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "brine"
              }
            ],
            "amount": {
              "volume": {
                "value": 100.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      },
      "m4": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "off-white solid"
              }
            ],
            "amount": {
              "mass": {
                "value": 1.69,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "stirring": {
        "type": "CUSTOM",
        "details": "is stirred overnight"
      },
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-1c830e65fe2348868fcc6875ef511b3c"
  },
  {
    "input_text": "Ethyl 2-(2-amino-4-thiazolyl)-2-ethoxyiminoacetate (syn isomer, 5 g.) was added to a mixture of 1 N sodium hydroxide (45.9 ml.) and ethanol (30 ml.) and stirred at room temperature for 5 hours. After removing ethanol from the resultant solution under reduced pressure, the residue was dissolved in water (60 ml.) and adjusted to pH 2.0 with 10% hydrochloric acid. The solution was subjected to salting-out, and the precipitates were collected by filtration and dried to give 2-(2-amino-4-thiazolyl)-2-ethoxyiminoacetic acid (syn isomer, 2.9 g.).",
    "output_reaction_inputs": {
      "m1_m2_m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "Ethyl 2-(2-amino-4-thiazolyl)-2-ethoxyiminoacetate"
              }
            ],
            "amount": {
              "mass": {
                "value": 5.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "sodium hydroxide"
              }
            ],
            "amount": {
              "volume": {
                "value": 45.9,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "ethanol"
              }
            ],
            "amount": {
              "volume": {
                "value": 30.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "temperature": {
        "control": {
          "type": "AMBIENT"
        }
      },
      "stirring": {
        "type": "CUSTOM",
        "details": "stirred at room temperature for 5 hours"
      },
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-0da63e3cf1c54ca195528ac86b7c28f1"
  },
  {
    "input_text": "2-(2-Aminothiazol-4-yl)-2-ethoxyiminoacetic acid (syn isomer, 100 g.), formic acid (85.5 g.) and acetic anhydride (190.1 g.) were treated in a similar manner to that of Example F-(5) to give 2-(2-formamidothiazol-4-yl)-2-ethoxyiminoacetic acid (syn isomer, 99.1 g.).",
    "output_reaction_inputs": {
      "m1_m3_m2": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "2-(2-Aminothiazol-4-yl)-2-ethoxyiminoacetic acid"
              }
            ],
            "amount": {
              "mass": {
                "value": 100.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "acetic anhydride"
              }
            ],
            "amount": {
              "mass": {
                "value": 190.1,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "formic acid"
              }
            ],
            "amount": {
              "mass": {
                "value": 85.5,
                "units": "GRAM"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-4b3d65695c43465f9d806e4bfa98bb9a"
  },
  {
    "input_text": "To a suspension of ethyl 2-hydroxyimino-3-oxobutyrate (syn isomer, 15 g.) and potassium carbonate (19.8 g.) in acetone (75 ml.) was added dropwise propyliodide (16.2 g.) with stirring, and the mixture was stirred at ambient temperature for 1,5 hours. The insoluble substance was collected by filtration and washed with acetone. The washings and the filtrate were combined and evaporated to dryness under reduced pressure. To the resultant residue was added water and the aqueous solution was extracted twice with chloroform. The extract was washed with an aqueous solution of sodium chloride, dried over magnesium sulfate, and then evaporated to dryness under reduced pressure to give ethyl 3-oxo-2-propoxyiminobutyrate (syn isomer, 15.4 g.), oil.",
    "output_reaction_inputs": {
      "m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "propyliodide"
              }
            ],
            "amount": {
              "mass": {
                "value": 16.2,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      },
      "m1_m2_m4": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "ethyl 2-hydroxyimino-3-oxobutyrate"
              }
            ],
            "amount": {
              "mass": {
                "value": 15.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "potassium carbonate"
              }
            ],
            "amount": {
              "mass": {
                "value": 19.8,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "acetone"
              }
            ],
            "amount": {
              "volume": {
                "value": 75.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "stirring": {
        "type": "CUSTOM",
        "details": "with stirring"
      },
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-b966754f79cf4834b4a42cca46d929d5"
  },
  {
    "input_text": "Ethyl 3-oxo-2-propoxyiminobutyrate (syn isomer, 15.4 g.) and sulfuryl chloride (10.6 g.) were dissolved in acetic acid (15.4 ml.), warmed at 35\u00b0 to 45\u00b0 C. for 10 minutes with stirring and then stirred at ambient temperature for additional 6 hours. The reaction mixture was poured into ice-water (200 ml.) and the resultant mixture was extracted twice with chloroform. The extract was washed with an aqueous solution of sodium chloride, twice a saturated aqueous solution of sodium bicarbonate and once with water in turn, dried over magnesium sulfate, and then evaporated to dryness under reduced pressure to give ethyl 4-chloro-3-oxo-2-propoxyiminobutyrate (syn isomer, 15.4 g.), oil.",
    "output_reaction_inputs": {
      "m1_m2_m4": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "Ethyl 3-oxo-2-propoxyiminobutyrate"
              }
            ],
            "amount": {
              "mass": {
                "value": 15.4,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "sulfuryl chloride"
              }
            ],
            "amount": {
              "mass": {
                "value": 10.6,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "acetic acid"
              }
            ],
            "amount": {
              "volume": {
                "value": 15.4,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      },
      "m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "ice water"
              }
            ],
            "amount": {
              "volume": {
                "value": 200.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "stirring": {
        "type": "CUSTOM",
        "details": "with stirring"
      },
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-eed38966fb844a228579db43b09ec00d"
  },
  {
    "input_text": "2-(2-Aminothiazol-4-yl)-2-n-propoxyiminoacetic acid (syn isomer, 21.8 g.), acetic anhydride (38.8 g.) and formic acid (17.5 g.) were treated in a similar manner to that of Example F-(5), and then the obtained oil was triturated with diisopropyl ether to give 2-(2-formamidothiazol-4-yl)-2-n-propoxyiminoacetic acid (syn isomer, 19.2 g.), mp. 164\u00b0 C. (dec.).",
    "output_reaction_inputs": {
      "m1_m2_m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "2-(2-Aminothiazol-4-yl)-2-n-propoxyiminoacetic acid"
              }
            ],
            "amount": {
              "mass": {
                "value": 21.8,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "acetic anhydride"
              }
            ],
            "amount": {
              "mass": {
                "value": 38.8,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "formic acid"
              }
            ],
            "amount": {
              "mass": {
                "value": 17.5,
                "units": "GRAM"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-d6387ea5292a480aaa6b1fbbd9aab24b"
  },
  {
    "input_text": "Ethyl 2-hydroxyimino-3-oxobutyrate (syn isomer, 30 g.), iso-propyl iodode (32.5 g.), potassium carbonate (39.5 g.) and acetone (150 ml.) were treated in a similar manner to that of Example D-(1) to give ethyl 2-iso-propoxyimino-3-oxobutyrate (syn isomer, 35.4 g.), oil.",
    "output_reaction_inputs": {
      "m1_m2_m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "Ethyl 2-hydroxyimino-3-oxobutyrate"
              }
            ],
            "amount": {
              "mass": {
                "value": 30.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "potassium carbonate"
              }
            ],
            "amount": {
              "mass": {
                "value": 39.5,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "acetone"
              }
            ],
            "amount": {
              "volume": {
                "value": 150.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-d6be50192c104d7fba89a7295a2d6214"
  },
  {
    "input_text": "Ethyl 2-iso-propoxyimino-3-oxobutyrate (syn isomer 35.4 g.), sulfuryl chloride (24.5 g.) and acetic acid (35.4 ml.) were treated in a similar manner to that of Example D-(2) to give ethyl 4-chloro-3-oxo-2-iso-propoxyiminobutyrate (syn isomer, 41.5 g.), oil.",
    "output_reaction_inputs": {
      "m1_m2_m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "Ethyl 2-iso-propoxyimino-3-oxobutyrate"
              }
            ],
            "amount": {
              "mass": {
                "value": 35.4,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "sulfuryl chloride"
              }
            ],
            "amount": {
              "mass": {
                "value": 24.5,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "acetic acid"
              }
            ],
            "amount": {
              "volume": {
                "value": 35.4,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-65624b7a364746ef997abcbc983b741e"
  },
  {
    "input_text": "Ethyl 4-chloro-3-oxo-2-iso-propoxyiminobutyrate (syn isomer, 41.5 g.), thiourea (13.4 g.), sodium acetate (14.4 g.), water (110 ml.) and ethanol (110 ml.) were treated in a similar manner to that of Example D-(3) to give ethyl 2-(2-aminothiazol-4-yl)-2-iso-propoxyiminoacetate (syn isomer, 27.3 g.), mp. 162\u00b0 to 164\u00b0 C.",
    "output_reaction_inputs": {
      "m1_m2_m3_m4_m5": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "Ethyl 4-chloro-3-oxo-2-iso-propoxyiminobutyrate"
              }
            ],
            "amount": {
              "mass": {
                "value": 41.5,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "thiourea"
              }
            ],
            "amount": {
              "mass": {
                "value": 13.4,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "sodium acetate"
              }
            ],
            "amount": {
              "mass": {
                "value": 14.4,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "water"
              }
            ],
            "amount": {
              "volume": {
                "value": 110.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "ethanol"
              }
            ],
            "amount": {
              "volume": {
                "value": 110.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-9c0939ecd1414d79bf64d22081b27c5a"
  },
  {
    "input_text": "n-Butyl iodide (46.9 g.) was added dropwise to a stirred suspension of ethyl 2-hydroxyimino-3-oxobutyrate (syn isomer, 40 g.), potassium carbonate (52.7 g.) and acetone (200 ml.) under ice-cooling over 5 minutes, and stirred at room temperature for 4 hours. The resultant solution was filtered, and washed with acetone. The filtrate and washing solution were combined together and concentrated in vacuo. After adding water (300 ml.) to the residue, the solution was extracted with methylene chloride three times. The solution was washed with a saturated aqueous solution of sodium chloride, dried over magnesium sulfate and concentrated in vacuo to give ethyl 2-n-butoxyimino-3-oxobutyrate (syn isomer, 48.8 g.), oil.",
    "output_reaction_inputs": {
      "m1_m2_m3_m4": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "n-Butyl iodide"
              }
            ],
            "amount": {
              "mass": {
                "value": 46.9,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "ethyl 2-hydroxyimino-3-oxobutyrate"
              }
            ],
            "amount": {
              "mass": {
                "value": 40.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "potassium carbonate"
              }
            ],
            "amount": {
              "mass": {
                "value": 52.7,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "acetone"
              }
            ],
            "amount": {
              "volume": {
                "value": 200.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "temperature": {
        "control": {
          "type": "AMBIENT"
        }
      },
      "stirring": {
        "type": "CUSTOM",
        "details": "stirred at room temperature for 4 hours"
      },
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-2e59defc5632424d80e722324b7e478f"
  },
  {
    "input_text": "Ethyl 2-hydroxyimino-3-oxobutyrate (syn isomer, 40 g.), N,N-dimethylformamide (200 ml.), potassium carbonate (52.7 g.) and iso-butyl bromide (34.94 g.) were treated in a similar manner to that of Example F-(1) to give ethyl 2-iso-butoxyimino-3-oxo-butyrate (syn isomer, 42 g.).",
    "output_reaction_inputs": {
      "m1_m4_m2_m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "Ethyl 2-hydroxyimino-3-oxobutyrate"
              }
            ],
            "amount": {
              "mass": {
                "value": 40.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "potassium carbonate"
              }
            ],
            "amount": {
              "mass": {
                "value": 52.7,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "iso-butyl bromide"
              }
            ],
            "amount": {
              "mass": {
                "value": 34.94,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "N,N-dimethylformamide"
              }
            ],
            "amount": {
              "volume": {
                "value": 200.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-8fa481d1577a4c9fb50f071f0f617767"
  },
  {
    "input_text": "Ethyl 2-iso-butoxyimino-4-chloro-3-oxobutyrate (syn isomer, 31.9 g.), thiourea (9.72 g.), sodium acetate 3-hydrate (17.4 g.), ethanol (120 ml.) and water (80 ml.) were treated in a similar manner to that of Example F-(3) to give ethyl 2-(2-aminothiazol-4-yl)-2-iso-butoxyiminoacetate (syn isomer, 17.6 g.), mp 122\u00b0 to 124\u00b0 C.",
    "output_reaction_inputs": {
      "m1_m2_m3_m4_m5": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "Ethyl 2-iso-butoxyimino-4-chloro-3-oxobutyrate"
              }
            ],
            "amount": {
              "mass": {
                "value": 31.9,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "thiourea"
              }
            ],
            "amount": {
              "mass": {
                "value": 9.72,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "sodium acetate 3-hydrate"
              }
            ],
            "amount": {
              "mass": {
                "value": 17.4,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "ethanol"
              }
            ],
            "amount": {
              "volume": {
                "value": 120.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "water"
              }
            ],
            "amount": {
              "volume": {
                "value": 80.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-49124fd9d9cd402999243745e359f808"
  },
  {
    "input_text": "2-(2-Aminothiazol-4-yl)-2-iso-butoxyiminoacetic acid (syn isomer, 11.5 g.), acetic anhydride (19.3 g.) and formic acid (8.7 g.) were treated in a similar manner to that of Example F-(5) to give 2-(2-formamidothiazol-4-yl)-2-iso-butoxyiminoacetic acid (syn isomer, 11.15 g.), mp 163\u00b0 C. (dec.).",
    "output_reaction_inputs": {
      "m1_m2_m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "2-(2-Aminothiazol-4-yl)-2-iso-butoxyiminoacetic acid"
              }
            ],
            "amount": {
              "mass": {
                "value": 11.5,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "acetic anhydride"
              }
            ],
            "amount": {
              "mass": {
                "value": 19.3,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "formic acid"
              }
            ],
            "amount": {
              "mass": {
                "value": 8.7,
                "units": "GRAM"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-ac46e42ef5084082a7325a049be55802"
  },
  {
    "input_text": "Ethyl 2-hydroxyimino-3-oxobutyrate (syn isomer, 30 g.), N,N-dimethylformamide (100 ml.), potassium carbonate (39.5 g.) and cyclohexyl bromide (31.1 g.) were treated in a similar manner to that of Example F-(1) to give ethyl 2-cyclohexyloxyimino-3-oxobutyrate (syn isomer, 41.8 g.), oil.",
    "output_reaction_inputs": {
      "m1_m4_m2_m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "Ethyl 2-hydroxyimino-3-oxobutyrate"
              }
            ],
            "amount": {
              "mass": {
                "value": 30.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "potassium carbonate"
              }
            ],
            "amount": {
              "mass": {
                "value": 39.5,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "cyclohexyl bromide"
              }
            ],
            "amount": {
              "mass": {
                "value": 31.1,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "N,N-dimethylformamide"
              }
            ],
            "amount": {
              "volume": {
                "value": 100.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-701ba944fdf647e7804a7d8ca7d9deb4"
  },
  {
    "input_text": "Ethyl 2-cyclohexyloxyimino-3-oxobutyrate (syn isomer, 41.3 g.), acetic acid (41.3 ml.) and sulfuryl chloride (23.8 g.) were treated in a similar manner to that of Example F-(2) to give ethyl 4-chloro-2-cyclohexyloxyimino-3-oxobutyrate (syn isomer, 27.8 g.), oil.",
    "output_reaction_inputs": {
      "m1_m3_m2": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "Ethyl 2-cyclohexyloxyimino-3-oxobutyrate"
              }
            ],
            "amount": {
              "mass": {
                "value": 41.3,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "sulfuryl chloride"
              }
            ],
            "amount": {
              "mass": {
                "value": 23.8,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "acetic acid"
              }
            ],
            "amount": {
              "volume": {
                "value": 41.3,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-9cb89b3517bc444e938c036b23a03b4c"
  },
  {
    "input_text": "Ethyl 2-hydroxyimino-3-oxobutyrate (syn isomer, 56.7 g.), N,N-dimethylformamide (280 ml.), potassium carbonate (72.3 g.) and propargyl bromide (43 g.) were treated in a similar manner to that of Example F-(1) to give ethyl 2-propargyloxyimino-3-oxobutyrate (syn isomer, 71.2 g.).",
    "output_reaction_inputs": {
      "m1_m4_m2_m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "Ethyl 2-hydroxyimino-3-oxobutyrate"
              }
            ],
            "amount": {
              "mass": {
                "value": 56.7,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "potassium carbonate"
              }
            ],
            "amount": {
              "mass": {
                "value": 72.3,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "propargyl bromide"
              }
            ],
            "amount": {
              "mass": {
                "value": 43.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "N,N-dimethylformamide"
              }
            ],
            "amount": {
              "volume": {
                "value": 280.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-93256dfdb79d4f24bbc7c35201d81d1f"
  },
  {
    "input_text": "Ethyl 2-propargyloxyimino-3-oxobutyrate (syn isomer, 71.2 g.), acetic acid (81 ml.) and sulfuryl chloride (50.2 g.) were treated in a similar manner to that of Example F-(2) to give ethyl 4-chloro-3-oxo-2-propargyloxyiminobutyrate (syn isomer, 61.6 g.), oil.",
    "output_reaction_inputs": {
      "m1_m3_m2": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "Ethyl 2-propargyloxyimino-3-oxobutyrate"
              }
            ],
            "amount": {
              "mass": {
                "value": 71.2,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "sulfuryl chloride"
              }
            ],
            "amount": {
              "mass": {
                "value": 50.2,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "acetic acid"
              }
            ],
            "amount": {
              "volume": {
                "value": 81.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-cad7738d1e0549d9b66b39d16a101ecf"
  },
  {
    "input_text": "Ethyl 4-chloro-3-oxo-2-propargyloxyiminobutyrate (syn isomer, 61 g.), thiourea (20 g.), sodium acetate 3-hydrate (35.8 g.), water (150 ml.), and ethanol (180 ml.) were treated in a similar manner to that of Example F-(3) to give ethyl 2-(2-aminothiazol-4-yl)-2-propargyloxyiminoacetate (syn isomer, 35.6 g.).",
    "output_reaction_inputs": {
      "m1_m2_m3_m4_m5": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "Ethyl 4-chloro-3-oxo-2-propargyloxyiminobutyrate"
              }
            ],
            "amount": {
              "mass": {
                "value": 61.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "thiourea"
              }
            ],
            "amount": {
              "mass": {
                "value": 20.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "sodium acetate 3-hydrate"
              }
            ],
            "amount": {
              "mass": {
                "value": 35.8,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "water"
              }
            ],
            "amount": {
              "volume": {
                "value": 150.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "ethanol"
              }
            ],
            "amount": {
              "volume": {
                "value": 180.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-fb6b1bd0edbf46529f31a1679c19eba9"
  },
  {
    "input_text": "Ethyl 2-hydroxyimino-3-oxobutyrate (syn isomer, 40 g.), N,N-dimethylformaide (200 ml.), potassium carbonate (52 g.) and n-hexyl bromide (41.4 g.) were treated in a similar manner to that of Example F-(1) to give ethyl 2-n-hexyloxyimino-3-oxobutyrate (syn isomer, 60.7 g.), oil.",
    "output_reaction_inputs": {
      "m1_m2_m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "Ethyl 2-hydroxyimino-3-oxobutyrate"
              }
            ],
            "amount": {
              "mass": {
                "value": 40.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "potassium carbonate"
              }
            ],
            "amount": {
              "mass": {
                "value": 52.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "n-hexyl bromide"
              }
            ],
            "amount": {
              "mass": {
                "value": 41.4,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-6557900439f44e58a53bb01be2ea714d"
  },
  {
    "input_text": "Ethyl 2-n-hexyloxyimino-3-oxobutyrate (syn isomer, 60.7 g.), acetic acid (61 ml.) and sulfuryl chloride (34.7 g.) were treated in a similar manner to that of Example F-(2) to give ethyl 2-n-hexyloxyimino-4-chloro-3-oxobutyrate (syn isomer, 55.6 g.).",
    "output_reaction_inputs": {
      "m1_m3_m2": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "Ethyl 2-n-hexyloxyimino-3-oxobutyrate"
              }
            ],
            "amount": {
              "mass": {
                "value": 60.7,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "sulfuryl chloride"
              }
            ],
            "amount": {
              "mass": {
                "value": 34.7,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "acetic acid"
              }
            ],
            "amount": {
              "volume": {
                "value": 61.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-7558a9c526f149efa1a78b0b2b12d61d"
  },
  {
    "input_text": "Ethyl 2-n-hexyloxyimino-4-chloro-3-oxobutyrate (syn isomer, 55.6 g.), thiourea (15.2 g.), sodium acetate 3-hydrate (27.2 g), ethanol (280 ml.) and water (140 ml.) were treated in a similar manner to that of Example F-(3) to give ethyl 2-(2-aminothiazol-4-yl)-2-n-hexyloxyiminoacetate (syn isomer, 29.3 g.) mp 77\u00b0 to 78\u00b0 C.",
    "output_reaction_inputs": {
      "m1_m2_m3_m4_m5": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "Ethyl 2-n-hexyloxyimino-4-chloro-3-oxobutyrate"
              }
            ],
            "amount": {
              "mass": {
                "value": 55.6,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "thiourea"
              }
            ],
            "amount": {
              "mass": {
                "value": 15.2,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "sodium acetate 3-hydrate"
              }
            ],
            "amount": {
              "mass": {
                "value": 27.2,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "ethanol"
              }
            ],
            "amount": {
              "volume": {
                "value": 280.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "water"
              }
            ],
            "amount": {
              "volume": {
                "value": 140.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-f0a12c4072424d2f9897351aa2149fe9"
  },
  {
    "input_text": "Ethyl 2-hydroxyimino-3-oxobutyrate (syn isomer, 40 g.), N,N-dimethylformamide (200 ml.), potassium carbonate (52 g.) and pentyl bromide (37.9 g.) were treated in a similar manner to that of Example F-(1) to give ethyl 2-pentyloxyimino-3-oxobutyrate (syn isomer, 57.5 g.), oil.",
    "output_reaction_inputs": {
      "m1_m4_m2_m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "Ethyl 2-hydroxyimino-3-oxobutyrate"
              }
            ],
            "amount": {
              "mass": {
                "value": 40.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "potassium carbonate"
              }
            ],
            "amount": {
              "mass": {
                "value": 52.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "pentyl bromide"
              }
            ],
            "amount": {
              "mass": {
                "value": 37.9,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "N,N-dimethylformamide"
              }
            ],
            "amount": {
              "volume": {
                "value": 200.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-c5f477b17dc64c7883e52d8c38d9ee46"
  },
  {
    "input_text": "Ethyl 2-pentyloxyimino-3-oxobutyrate (syn isomer, 57.5 g.), acetic acid (58.5 ml.) and sulfuryl chloride (20.9 ml.) were treated in a similar manner to that of Example F-(2) to give ethyl 2-pentyloxyimino-4-chloro-3-oxobutyrate (syn isomer, 51.1 g.), oil.",
    "output_reaction_inputs": {
      "m1_m3_m2": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "Ethyl 2-pentyloxyimino-3-oxobutyrate"
              }
            ],
            "amount": {
              "mass": {
                "value": 57.5,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "sulfuryl chloride"
              }
            ],
            "amount": {
              "volume": {
                "value": 20.9,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "acetic acid"
              }
            ],
            "amount": {
              "volume": {
                "value": 58.5,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-6d8ccc0e89f646978bf051b39c45f9ea"
  },
  {
    "input_text": "Ethyl 2-pentyloxyimino-4-chloro-3-oxobutyrate (syn isomer, 51.1 g.), thiourea (14.7 g.), sodium acetate trihydrate (26.4 g.), ethanol (175 ml.) and water (125 ml.), were treated in a similar manner to that of Example F-(3) to give ethyl 2-(2-aminothiazol-4-yl)-2-pentyloxyiminoacetate (syn isomer, 28.7 g.), mp. 86\u00b0 to 88\u00b0 C.",
    "output_reaction_inputs": {
      "m1_m2_m3_m4_m5": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "Ethyl 2-pentyloxyimino-4-chloro-3-oxobutyrate"
              }
            ],
            "amount": {
              "mass": {
                "value": 51.1,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "thiourea"
              }
            ],
            "amount": {
              "mass": {
                "value": 14.7,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "sodium acetate trihydrate"
              }
            ],
            "amount": {
              "mass": {
                "value": 26.4,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "ethanol"
              }
            ],
            "amount": {
              "volume": {
                "value": 175.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "water"
              }
            ],
            "amount": {
              "volume": {
                "value": 125.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-c8352299e64b4ce2b64804c5d1d1ef20"
  },
  {
    "input_text": "2-(2-Aminothiazol-4-yl)-2-pentyloxyiminoacetic acid (syn isomer, 15 g.), acetic anhydride (23.8 g.) and formic acid (10.7 g.) were treated in a similar manner to that of Example F-(5) to give 2-(2-formamidothiazol-4-yl)-2-pentyloxyiminoacetic acid (syn isomer, 14.7 g.), mp 125\u00b0 C. (dec.).",
    "output_reaction_inputs": {
      "m1_m2_m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "2-(2-Aminothiazol-4-yl)-2-pentyloxyiminoacetic acid"
              }
            ],
            "amount": {
              "mass": {
                "value": 15.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "acetic anhydride"
              }
            ],
            "amount": {
              "mass": {
                "value": 23.8,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "formic acid"
              }
            ],
            "amount": {
              "mass": {
                "value": 10.7,
                "units": "GRAM"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-7bc5ae9b977d47ca88cf3726337a0d93"
  },
  {
    "input_text": "A solution of ethyl 2-(2-tritylaminothiazol-4-yl)-2-allyloxyiminoacetate (syn isomer, 8.7 g.), 50% formic acid (42.5 ml.) and tetrahydrofuran (42.5 ml.) was stirred at 60\u00b0 C. for 40 minutes. After concentrating the resultant solution in vacuo, the residue was dissolved in ethyl acetate, washed with an aqueous solution of sodium bicarbonate and a saturated aqueous solution of sodium chloride in turn, and dried over magnesium sulfate. After concentrating the resultant solution in vacuo, the residue was subjected to column chromatography on silica gel with benzene and ethyl acetate in turn, to give ethyl 2-(2-aminothiazol-4-yl)-2-allyloxyiminoacetate (syn isomer, 3.7 g.), mp. 102\u00b0 to 104\u00b0 C.",
    "output_reaction_inputs": {
      "m1_m2_m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "ethyl 2-(2-tritylaminothiazol-4-yl)-2-allyloxyiminoacetate"
              }
            ],
            "amount": {
              "mass": {
                "value": 8.7,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "formic acid"
              }
            ],
            "amount": {
              "volume": {
                "value": 42.5,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "tetrahydrofuran"
              }
            ],
            "amount": {
              "volume": {
                "value": 42.5,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-b22541bc37194929badbb49a0f90a44f"
  },
  {
    "input_text": "Ethyl 2-hydroxyimino-3-oxobutyrate (syn isomer, 60 g.), 1-bromo-2-chloroethane (54.1 g.), potassium carbonate (78 g.) and N,N-dimethylformamide (200 ml.) were treated in a similar manner to that of Example F-(1) to give ethyl 2-(2-chloroethoxyimino)-3-oxobutyrate (syn isomer, 83.6 g.), oil.",
    "output_reaction_inputs": {
      "m1_m2_m3_m4": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "Ethyl 2-hydroxyimino-3-oxobutyrate"
              }
            ],
            "amount": {
              "mass": {
                "value": 60.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "1-bromo-2-chloroethane"
              }
            ],
            "amount": {
              "mass": {
                "value": 54.1,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "potassium carbonate"
              }
            ],
            "amount": {
              "mass": {
                "value": 78.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "N,N-dimethylformamide"
              }
            ],
            "amount": {
              "volume": {
                "value": 200.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-bb61d4b92462405f8afe5f9384ff9a33"
  },
  {
    "input_text": "Ethyl 2-(2-chloroethoxyimino)-3-oxobutyrate (syn isomer, 83.6 g.), sulfury chloride (52.4 g.) and acetic acid (83.6 ml.) were treated in a similar manner to that of Example F-(2) to give Ethyl 2-(2-chloroethoxyimino)-3-oxo-4-chlorobutyrate (syn isomer, 68 g.), oil.",
    "output_reaction_inputs": {
      "m1_m2_m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "Ethyl 2-(2-chloroethoxyimino)-3-oxobutyrate"
              }
            ],
            "amount": {
              "mass": {
                "value": 83.6,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "chloride"
              }
            ],
            "amount": {
              "mass": {
                "value": 52.4,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "acetic acid"
              }
            ],
            "amount": {
              "volume": {
                "value": 83.6,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-0206a2634f4f4577a5e6ba39c4db8c50"
  },
  {
    "input_text": "Ethyl 2-(2-chloroethoxyimino)-3-oxo-4-chlorobutyrate (syn isomer, 68 g.), thiourea (20.2 g.), sodium acetate trihydrate (36.2 g.), ethanol (270 ml.) and water (170 ml.) were treated in a similar manner to that of Example F-(3) to give ethyl 2-(2-aminothiazol-4-yl)-2-(2-chloroethoxyimino)acetate (syn isomer, 33.7 g.), mp 126\u00b0 to 128\u00b0 C.",
    "output_reaction_inputs": {
      "m1_m2_m3_m4_m5": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "Ethyl 2-(2-chloroethoxyimino)-3-oxo-4-chlorobutyrate"
              }
            ],
            "amount": {
              "mass": {
                "value": 68.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "thiourea"
              }
            ],
            "amount": {
              "mass": {
                "value": 20.2,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "sodium acetate trihydrate"
              }
            ],
            "amount": {
              "mass": {
                "value": 36.2,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "ethanol"
              }
            ],
            "amount": {
              "volume": {
                "value": 270.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "water"
              }
            ],
            "amount": {
              "volume": {
                "value": 170.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-21273b1437d54c01956ef7db82ca7cbe"
  },
  {
    "input_text": "2-(2-Aminothiazol-4-yl)-2-(2-chloroethoxyimino)acetic acid (syn isomer, 15 g.), acetic anhydride (24.5 g.), formic acid (11.0 g.) and tetrahydrofuran (50 ml.) were treated in a similar manner to that of Example F-(5) to give 2-(2-formamidothiazol-4-yl)-2-(2-chloroethoxyimino)acetic acid (syn isomer, 13.4 g.), mp 155\u00b0 C. (dec.).",
    "output_reaction_inputs": {
      "m1_m2_m3_m4": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "2-(2-Aminothiazol-4-yl)-2-(2-chloroethoxyimino)acetic acid"
              }
            ],
            "amount": {
              "mass": {
                "value": 15.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "acetic anhydride"
              }
            ],
            "amount": {
              "mass": {
                "value": 24.5,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "formic acid"
              }
            ],
            "amount": {
              "mass": {
                "value": 11.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "tetrahydrofuran"
              }
            ],
            "amount": {
              "volume": {
                "value": 50.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-3191c892ff9e4404bdf642e91ec90c41"
  },
  {
    "input_text": "7-{2-(2-Formamido-4-thiazolyl)-2-methoxyiminoacetamido}-3-chloro-3-cephem-4-carboxylic acid(syn isomer, 0.4 g.) was suspended in methanol (15 ml.). After adding conc-hydrochloric acid (0.16 g.) to the suspension, the mixture was stirred at room temperature for 2.5 hours. Methanol was distilled off from the resultant mixture under reduced pressure, and the residue was dissolved in water (15 ml.). The solution was washed with ethyl acetate (30 ml.) and dichloromethane (30 ml.) in turn. To the acqueous layer was introduced nitrogen gas to remove the remaining organic solvent completely, and the solution was lyophilized to give 7-{2-(2-amino-4-thiazolyl)-2-methoxyiminoacetamido}-3-chloro-3-cephem-4-carboxylic acid hydrochloride (syn isomer 0.35 g.), m.p. 170\u00b0 to 180\u00b0 C. (dec.)",
    "output_reaction_inputs": {
      "m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "methanol"
              }
            ],
            "amount": {
              "volume": {
                "value": 15.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      },
      "m2": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "hydrochloric acid"
              }
            ],
            "amount": {
              "mass": {
                "value": 0.16,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      },
      "m1": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "7-{2-(2-Formamido-4-thiazolyl)-2-methoxyiminoacetamido}-3-chloro-3-cephem-4-carboxylic acid"
              }
            ],
            "amount": {
              "mass": {
                "value": 0.4,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "temperature": {
        "control": {
          "type": "AMBIENT"
        }
      },
      "stirring": {
        "type": "CUSTOM",
        "details": "the mixture was stirred at room temperature for 2.5 hours"
      },
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-1861750d23ef446faabc0221721671fb"
  },
  {
    "input_text": "7-[2-{2-(2,2,2-Trifluoroacetamido)-4-thiazolyl}--2-methoxyiminoacetamido]-2,3-dimethyl-3-cephem-4-carboxylic acid (syn isomer, 0.86 g.) was dissolved in an aqueous solution (9 ml.) containing sodium acetate trihydrate (2.3 g.), and the solution was stirred at room temperature for 19 hours. After removing the insoluble substance from the resultant mixture by filtration, the filtrate was adjusted to around pH 2.5 with 10% hydrochloric acid under ice-cooling. The precipitates were collected by filtration, washed with water and dried to give 7-{2-(2-amino-4-thiazolyl)-2-methoxyiminoacetamido}-2,3-dimethyl-3-cephem-4-carboxylic acid (syn isomer, 0.16 g.).",
    "output_reaction_inputs": {
      "m2": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "sodium acetate trihydrate"
              }
            ],
            "amount": {
              "mass": {
                "value": 2.3,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      },
      "m1": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "7-[2-{2-(2,2,2-Trifluoroacetamido)-4-thiazolyl}--2-methoxyiminoacetamido]-2,3-dimethyl-3-cephem-4-carboxylic acid"
              }
            ],
            "amount": {
              "mass": {
                "value": 0.86,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "temperature": {
        "control": {
          "type": "AMBIENT"
        }
      },
      "stirring": {
        "type": "CUSTOM",
        "details": "the solution was stirred at room temperature for 19 hours"
      },
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-94e2038b3a2d4ad9a71d3371c334c5f9"
  },
  {
    "input_text": "7-{2-(2-Formamido-4-thiazolyl)-2-methoxyiminoacetamido}-3-cephem-4-carboxylic acid (syn isomer, 95 mg.) was suspended in methanol (4 ml.). To the suspension was added conc. hydrochloric acid (110 mg.) and the solution was stirred at room temperature for 4 hours. After distilling methanol under reduced pressure, the residue was dissolved in water (30 ml.) and the aqueous solution was washed with ethyl acetate (10 ml.) and dichloromethane (15 ml.) in turn. Nitrogen gas was introduced into the aqueous solution to exclude the remaining organic solvent, and the aqueous solution was lyophilized to give 7-{2-(2-amino-4-thiazolyl)-2-methoxyiminoacetamido)-3-cephem-4-carboxylic acid hydrochloride (syn isomer, 83 mg.), m.p. 180\u00b0 to 190\u00b0 C. (dec.)",
    "output_reaction_inputs": {
      "m2": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "hydrochloric acid"
              }
            ],
            "amount": {
              "mass": {
                "value": 110.0,
                "units": "MILLIGRAM"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      },
      "m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "methanol"
              }
            ],
            "amount": {
              "volume": {
                "value": 4.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      },
      "m1": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "7-{2-(2-Formamido-4-thiazolyl)-2-methoxyiminoacetamido}-3-cephem-4-carboxylic acid"
              }
            ],
            "amount": {
              "mass": {
                "value": 95.0,
                "units": "MILLIGRAM"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "temperature": {
        "control": {
          "type": "AMBIENT"
        }
      },
      "stirring": {
        "type": "CUSTOM",
        "details": "the solution was stirred at room temperature for 4 hours"
      },
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-0511639093f44883a5dc39e3328f0692"
  },
  {
    "input_text": "7-[2-(2-Amino-4-thiazolyl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylic acid(syn-isomer: 5 g.) was gradually added to an aqueous solution (30 ml.) of sodium bicarbonate (1.04 g.) at 35\u00b0 to 40\u00b0 C., and stirred at 50\u00b0 to 53\u00b0 C. for 30 minutes. After removing the insoluble substance from the resultant solution, the filtrate was treated with activated charcoal (0.3 g.), and filtered. The filtrate was lyophilized to give sodium 7-[2-(2-amino-4-thiazolyl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylate (syn-isomer: 4.2 g.).",
    "output_reaction_inputs": {
      "m1_m2": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "7-[2-(2-Amino-4-thiazolyl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylic acid"
              }
            ],
            "amount": {
              "mass": {
                "value": 5.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "sodium bicarbonate"
              }
            ],
            "amount": {
              "volume": {
                "value": 30.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "stirring": {
        "type": "CUSTOM",
        "details": "stirred at 50\u00b0 to 53\u00b0 C. for 30 minutes"
      },
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-d527fb9ddaf448209b2e9b11414eb1c7"
  },
  {
    "input_text": "7-[2-(2-Aminothiazol-4-yl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylic acid (syn isomer, 1.15 g.) was added to an aqueous solution of calcium hydroxide (0.111 g.) in water (100 ml.), and the solution was stirred at room temperature for 10 minutes. After the solution was filtered, the filtrate was lyophilized to give calcium 7-[2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylate (syn isomer, 1.2 g.).",
    "output_reaction_inputs": {
      "m1_m2_m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "7-[2-(2-Aminothiazol-4-yl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylic acid"
              }
            ],
            "amount": {
              "mass": {
                "value": 1.15,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "calcium hydroxide"
              }
            ],
            "amount": {
              "mass": {
                "value": 0.111,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "water"
              }
            ],
            "amount": {
              "volume": {
                "value": 100.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "temperature": {
        "control": {
          "type": "AMBIENT"
        }
      },
      "stirring": {
        "type": "CUSTOM",
        "details": "the solution was stirred at room temperature for 10 minutes"
      },
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-2e4b85b4d0d34837b3b432c677ee2ca8"
  },
  {
    "input_text": "7-[2-(2-Aminothiazol-4-yl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylic acid (syn isomer, 1.15 g.) was added to a suspension of magnesium hydroxide (0.088 g.) in water (100 ml.), and the mixture was stirred at 70\u00b0 C. for 30 minutes to give a solution. After the resultant solution was filtered, the filtrate was lyophilized to give magnesium 7-[2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylate (syn isomer, 1.1 g.).",
    "output_reaction_inputs": {
      "m1_m2_m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "7-[2-(2-Aminothiazol-4-yl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylic acid"
              }
            ],
            "amount": {
              "mass": {
                "value": 1.15,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "magnesium hydroxide"
              }
            ],
            "amount": {
              "mass": {
                "value": 0.088,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "water"
              }
            ],
            "amount": {
              "volume": {
                "value": 100.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "temperature": {
        "setpoint": {
          "value": 70.0,
          "units": "CELSIUS"
        }
      },
      "stirring": {
        "type": "CUSTOM",
        "details": "the mixture was stirred at 70\u00b0 C. for 30 minutes"
      },
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-f03e65c096fc4beaba3125fc5510e664"
  },
  {
    "input_text": "Sodium 7-[2-(2-aminothiazol-4-yl)-2- methoxyiminoacetamido]-3-cephem-4-carboxylate (syn isomer, 1.21 g.) was added to a solution of lysine hydrochloride (0.55 g.) in water (12 ml.). The solution was lyophilized to give a lysine salt of 7-[2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylic acid (syn isomer, 1.6 g.).",
    "output_reaction_inputs": {
      "m2_m3_m4": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "Sodium 7-[2-(2-aminothiazol-4-yl)-2- methoxyiminoacetamido]-3-cephem-4-carboxylate"
              }
            ],
            "amount": {
              "mass": {
                "value": 1.21,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "lysine hydrochloride"
              }
            ],
            "amount": {
              "mass": {
                "value": 0.55,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "water"
              }
            ],
            "amount": {
              "volume": {
                "value": 12.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-def780177ae749078882479830c01fe8"
  },
  {
    "input_text": "Sodium 7-[2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylate (syn isomer, 15 g.) was dissolved in water (13 ml.) at 35\u00b0 to 45\u00b0 C. under stirring. Warmed ethanol (52 ml., 30\u00b0 C.) was added dropwise to the stirred solution, and stirred at the same temperature for 5 minutes and then at room temperature for 2 hours. The precipitates were collected by filtration, washed with ethanol and dried under reduced pressure to give plates of sodium 7-[2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylate dihydrate (syn isomer, 13.45 g.).",
    "output_reaction_inputs": {
      "m2": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "ethanol"
              }
            ],
            "amount": {
              "volume": {
                "value": 52.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      },
      "m1_m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "Sodium 7-[2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylate"
              }
            ],
            "amount": {
              "mass": {
                "value": 15.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "water"
              }
            ],
            "amount": {
              "volume": {
                "value": 13.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "stirring": {
        "type": "CUSTOM",
        "details": "under stirring"
      },
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-2a0b187bb2bd4a69a37860c32e44b6db"
  },
  {
    "input_text": "7-{2-(2-Formamido-4-thiazolyl)-2-methoxyiminoacetamido}-3-chloro-3-cephem-4-carboxylic acid (anti isomer, 0.4 g.) was suspended in methanol (15 ml.). Conc. hydrochloric acid (0.16 g.) was added to the suspension and the mixture was stirred at room temperature for 5 hours. The precipitates were collected by filtration, washed with a mixed solvent of methanol and diethyl ether (1:1), and dried to give 7-{2-(2-amino-4-thiazolyl)-2-methoxyiminoacetamido}-3-chloro-3-cephem-4-carboxylic acid hydrochloride (anti isomer, 0.31 g.), m.p. above than 250\u00b0 C.",
    "output_reaction_inputs": {
      "m2": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "hydrochloric acid"
              }
            ],
            "amount": {
              "mass": {
                "value": 0.16,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      },
      "m1": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "7-{2-(2-Formamido-4-thiazolyl)-2-methoxyiminoacetamido}-3-chloro-3-cephem-4-carboxylic acid"
              }
            ],
            "amount": {
              "mass": {
                "value": 0.4,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      },
      "m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "methanol"
              }
            ],
            "amount": {
              "volume": {
                "value": 15.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "temperature": {
        "control": {
          "type": "AMBIENT"
        }
      },
      "stirring": {
        "type": "CUSTOM",
        "details": "the mixture was stirred at room temperature for 5 hours"
      },
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-92dbd84efb8b41ec8300b388dbe8c810"
  },
  {
    "input_text": "2-(2-Formamidothiazol-4-yl)-2-iso-butoxyiminoacetic acid (syn isomer, 6.48 g.), N,N-dimethylformamide (2.10 g.), phosphoryl chloride (4.40 g.), tetrahydrofuran (110 ml.), 4-nitrobenzyl 7-amino-3-cephem-4-carboxylate (8.23 g.), acetone (16 ml.) and water (16 ml.) were treated in a similar manner to that of Example 15-(1) to give 4-nitrobenzyl 7-[2-(2formamidothiazol-4-yl)-2-iso-butoxyiminoacetamido]-3-cephem-4-carboxylate (syn isomer, 12.8 g.).",
    "output_reaction_inputs": {
      "m1_m2_m3_m7_m4_m6_m5": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "2-(2-Formamidothiazol-4-yl)-2-iso-butoxyiminoacetic acid"
              }
            ],
            "amount": {
              "mass": {
                "value": 6.48,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "N,N-dimethylformamide"
              }
            ],
            "amount": {
              "mass": {
                "value": 2.1,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "phosphoryl chloride"
              }
            ],
            "amount": {
              "mass": {
                "value": 4.4,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "4-nitrobenzyl 7-amino-3-cephem-4-carboxylate"
              }
            ],
            "amount": {
              "mass": {
                "value": 8.23,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "water"
              }
            ],
            "amount": {
              "volume": {
                "value": 16.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "acetone"
              }
            ],
            "amount": {
              "volume": {
                "value": 16.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "tetrahydrofuran"
              }
            ],
            "amount": {
              "volume": {
                "value": 110.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-36a31ac5fa1c4c069ad224ff1d8e6690"
  },
  {
    "input_text": "4-Nitrobenzyl 7-[2-(2-formamidothiazol-4-yl)-2-isobutoxyiminoacetamido]-3-cephem-4-carboxylate (syn isomer, 14.2 g.), 10% palladium carbon (5.7 g.), methanol (57 ml.), tetrahydrofuran (142 ml.), acetic acid (1 ml.) and water (10 ml.) were treated in a similar manner to that of Example 15-(2) to give 7-[2-(2-formamidothiazol-4-yl)-2-isobutoxyiminoacetamido]-3-cephem-4-carboxylic acid (syn isomer, 4.25 g.).",
    "output_reaction_inputs": {
      "m1_m5_m2_m3_m4_m6": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "4-Nitrobenzyl 7-[2-(2-formamidothiazol-4-yl)-2-isobutoxyiminoacetamido]-3-cephem-4-carboxylate"
              }
            ],
            "amount": {
              "mass": {
                "value": 14.2,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "methanol"
              }
            ],
            "amount": {
              "volume": {
                "value": 57.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "tetrahydrofuran"
              }
            ],
            "amount": {
              "volume": {
                "value": 142.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "acetic acid"
              }
            ],
            "amount": {
              "volume": {
                "value": 1.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "palladium carbon"
              }
            ],
            "amount": {
              "mass": {
                "value": 5.7,
                "units": "GRAM"
              }
            },
            "reactionRole": "CATALYST"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "water"
              }
            ],
            "amount": {
              "volume": {
                "value": 10.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-7f9b42caa2814fdb9730cb29dd8c43da"
  },
  {
    "input_text": "7-[2-(2-formamidothiazol-4-yl)-2-iso-butoxyiminoacetamido]-3-cephem-4-carboxylic acid (syn isomer, 4.1 g.), conc. hydrochloric acid (3.65 g.) and methanol (61.5 ml.) were treated in a similar manner to that of Example 15-(3) to give 7-[2-(2-aminothiazol-4-yl)-2-iso-butoxyiminoacetamido]-3-cephem-4-carboxylic acid (syn isomer, 2.4 g.).",
    "output_reaction_inputs": {
      "m1_m2_m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "7-[2-(2-formamidothiazol-4-yl)-2-iso-butoxyiminoacetamido]-3-cephem-4-carboxylic acid"
              }
            ],
            "amount": {
              "mass": {
                "value": 4.1,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "hydrochloric acid"
              }
            ],
            "amount": {
              "mass": {
                "value": 3.65,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "methanol"
              }
            ],
            "amount": {
              "volume": {
                "value": 61.5,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-209a6d361d2b4a55a8a64653086a25d2"
  },
  {
    "input_text": "2-(2-Formamidothiazol-4-yl)-2-cyclohexyloxyiminoacetic acid (syn isomer, 0.9 g.), N,N-dimethylformamide (266 mg.), phosphoryl chloride (557 mg.), tetrahydrofuran (20 ml.), 4-nitrobenzyl 7-amino-3-cephem-4-carboxylate (1.05 g.), acetone (3 ml.) and water (3 ml.) were treated in a similar manner to that of Example 15-(1) to give 4-nitrobenzyl 7-[2-(2-formamidothiazol-4-yl)-2-cyclohexyloxyiminoacetamido]-3-cephem-4-carboxylate (syn isomer, 1.69 g.).",
    "output_reaction_inputs": {
      "m1_m2_m3_m7_m4_m6_m5": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "2-(2-Formamidothiazol-4-yl)-2-cyclohexyloxyiminoacetic acid"
              }
            ],
            "amount": {
              "mass": {
                "value": 0.9,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "N,N-dimethylformamide"
              }
            ],
            "amount": {
              "mass": {
                "value": 266.0,
                "units": "MILLIGRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "phosphoryl chloride"
              }
            ],
            "amount": {
              "mass": {
                "value": 557.0,
                "units": "MILLIGRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "4-nitrobenzyl 7-amino-3-cephem-4-carboxylate"
              }
            ],
            "amount": {
              "mass": {
                "value": 1.05,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "water"
              }
            ],
            "amount": {
              "volume": {
                "value": 3.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "acetone"
              }
            ],
            "amount": {
              "volume": {
                "value": 3.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "tetrahydrofuran"
              }
            ],
            "amount": {
              "volume": {
                "value": 20.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-01d4c12e294248eea9837313867f1fe7"
  },
  {
    "input_text": "4-Nitrobenzyl 7-[2-(2-formamidothiazol-4-yl)-2-cyclohexyloxyiminoacetamido]-3-cephem-4-carboxylate (syn isomer, 2.0 g.), 10% palladium carbon (0.8 g.), methanol (8 ml.), tetrahydrofuran (20 ml.), acetic acid (0.14 ml.) and water (1.4 ml.) were treated in a similar manner to that of Example 15-(2) to give 7-[2-(2-formamidothiazol-4-yl)-2-cyclohexyloxyiminoacetamido]-3-cephem-4-carboxylic acid (syn isomer, 0.77 g.).",
    "output_reaction_inputs": {
      "m1_m5_m2_m3_m4_m6": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "4-Nitrobenzyl 7-[2-(2-formamidothiazol-4-yl)-2-cyclohexyloxyiminoacetamido]-3-cephem-4-carboxylate"
              }
            ],
            "amount": {
              "mass": {
                "value": 2.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "methanol"
              }
            ],
            "amount": {
              "volume": {
                "value": 8.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "tetrahydrofuran"
              }
            ],
            "amount": {
              "volume": {
                "value": 20.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "acetic acid"
              }
            ],
            "amount": {
              "volume": {
                "value": 0.14,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "palladium carbon"
              }
            ],
            "amount": {
              "mass": {
                "value": 0.8,
                "units": "GRAM"
              }
            },
            "reactionRole": "CATALYST"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "water"
              }
            ],
            "amount": {
              "volume": {
                "value": 1.4,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-675b557fe314446dac194c61f3a98fd7"
  },
  {
    "input_text": "7-[2-(2-Formamidothiazol-4-yl)-2-cyclohexyloxyiminoacetamido]-3-cephem-4-carboxylic acid (syn isomer, 0.72 g.), methanol (10.8 ml.) and conc. hydrochloric acid (0.61 g.) were treated in a similar manner to that of Example 15-(3) to give 7-[2-(2-aminothiazol-4-yl)-2-cyclohexyloxyiminoacetamido]-3-cephem-4-carboxylic acid (syn isomer, 0.28 g.).",
    "output_reaction_inputs": {
      "m1_m3_m2": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "7-[2-(2-Formamidothiazol-4-yl)-2-cyclohexyloxyiminoacetamido]-3-cephem-4-carboxylic acid"
              }
            ],
            "amount": {
              "mass": {
                "value": 0.72,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "hydrochloric acid"
              }
            ],
            "amount": {
              "mass": {
                "value": 0.61,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "methanol"
              }
            ],
            "amount": {
              "volume": {
                "value": 10.8,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-74cd741deb8c4763bf2048f684ec13d3"
  },
  {
    "input_text": "A suspension of 7-[2-(2-formamidothiazol-4-yl)-2-n-propoxyiminoacetamido]-3-chloro-3-cephem-4-carboxylic acid (syn isomer, 1.5 g.), conc. hydrochloric acid (0.7 ml.) and methanol (30 ml.) was stirred at room temperature for 1.5 hours. After removing methanol from the resultant solution in vacuo, water (30 ml.) was added to the residue. After the solution was adjusted to pH 7.5 with a saturated aqueous solution of sodium bicarbonate, the insoluble substance was removed by filtration. The filtrate was adjusted to pH 3 with 10% hydrochloric acid. The precipitates were collected by filtration and dried over phosphorus pentoxide to give 7-[2-(2-aminothiazol-4-yl)-2-n-propoxyiminoacetamido]-3-chloro-3-cephem-4-carboxylic acid (syn isomer, 0.6 g.).",
    "output_reaction_inputs": {
      "m1_m2_m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "7-[2-(2-formamidothiazol-4-yl)-2-n-propoxyiminoacetamido]-3-chloro-3-cephem-4-carboxylic acid"
              }
            ],
            "amount": {
              "mass": {
                "value": 1.5,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "hydrochloric acid"
              }
            ],
            "amount": {
              "volume": {
                "value": 0.7,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "methanol"
              }
            ],
            "amount": {
              "volume": {
                "value": 30.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "temperature": {
        "control": {
          "type": "AMBIENT"
        }
      },
      "stirring": {
        "type": "CUSTOM",
        "details": "was stirred at room temperature for 1.5 hours"
      },
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-b9a2e49f30a24132801032ad35ec3c2d"
  },
  {
    "input_text": "2-(2-Aminothiazol-4-yl)-2-n-hexyloxyiminoacetic acid (syn isomer, 3 g.), water (0.15 g.), phosphoryl chloride (3.8 g.), trimethylsilyacetamide (10.7 g.), N,N-dimethylformamide (1.0 g.), tetrahydrofuran (50 ml.) and 7-amino-3-cephem-4-carboxylic acid (2.0 g.) were treated in a similar manner to that of Example 18 to give 7-[2-(2-aminothiazole-4-yl)-2-n-hexyloxyiminoacetamido]-3-cephem-4-carboxylic acid (syy isomer, 1.1 g.).",
    "output_reaction_inputs": {
      "m1_m2_m3_m6_m5_m4": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "2-(2-Aminothiazol-4-yl)-2-n-hexyloxyiminoacetic acid"
              }
            ],
            "amount": {
              "mass": {
                "value": 3.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "water"
              }
            ],
            "amount": {
              "mass": {
                "value": 0.15,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "phosphoryl chloride"
              }
            ],
            "amount": {
              "mass": {
                "value": 3.8,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "7-amino-3-cephem-4-carboxylic acid"
              }
            ],
            "amount": {
              "mass": {
                "value": 2.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "tetrahydrofuran"
              }
            ],
            "amount": {
              "volume": {
                "value": 50.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "N,N-dimethylformamide"
              }
            ],
            "amount": {
              "mass": {
                "value": 1.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-8048c7fe72a84ad5b3056c5ab81d9353"
  },
  {
    "input_text": "2-(2-Formamidothiazol-4-yl)-2-pentyloxyiminoacetic acid (syn isomer, 4.14 g.), 4-nitrobenzyl 7-amino-3-cephem-4-carboxylate (4.5 g.), N,N-dimethylformamide (1.41 g.), phosphoryl chloride (2.96 g.), tetrahydrofuran (72 ml.), acetone (15 ml.) and water (15 ml.) were treated in a similar manner to that of Example 15 -(1) to give 4-nitrobenzyl 7-[2-(2-formamidothiazol-4-yl)-2-pentyloxyiminoacetamido]-3-cephem-4-carboxylate (syn isomer, 8.1 g.).",
    "output_reaction_inputs": {
      "m1_m2_m3_m4_m7_m6_m5": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "2-(2-Formamidothiazol-4-yl)-2-pentyloxyiminoacetic acid"
              }
            ],
            "amount": {
              "mass": {
                "value": 4.14,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "4-nitrobenzyl 7-amino-3-cephem-4-carboxylate"
              }
            ],
            "amount": {
              "mass": {
                "value": 4.5,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "N,N-dimethylformamide"
              }
            ],
            "amount": {
              "mass": {
                "value": 1.41,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "phosphoryl chloride"
              }
            ],
            "amount": {
              "mass": {
                "value": 2.96,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "water"
              }
            ],
            "amount": {
              "volume": {
                "value": 15.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "acetone"
              }
            ],
            "amount": {
              "volume": {
                "value": 15.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "tetrahydrofuran"
              }
            ],
            "amount": {
              "volume": {
                "value": 72.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-1d1e858a07fc44e393dbb0889aaa0903"
  },
  {
    "input_text": "4-Nitrobenzyl 7-[2-(2-formamidothiazol-4-yl)-2-pentyloxyiminoacetamido]-3-cephem-4-carboxylate (syn isomer, 8 g.), 10% palladium carbon (3.6 g.), methanol (36 ml.), tetrahydrofuran (90 ml.), acetic acid (0.63 g.) and water (6.3 ml.) were treated in a similar manner to that of Example 15 -(2) to give 7-[2-(2-formamidothiazol-4-yl)-2-pentyloxyiminoacetamido]-3-cephem-4-carboxylic acid (syn isomer, 3.4 g.).",
    "output_reaction_inputs": {
      "m1_m5_m2_m3_m4_m6": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "4-Nitrobenzyl 7-[2-(2-formamidothiazol-4-yl)-2-pentyloxyiminoacetamido]-3-cephem-4-carboxylate"
              }
            ],
            "amount": {
              "mass": {
                "value": 8.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "methanol"
              }
            ],
            "amount": {
              "volume": {
                "value": 36.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "tetrahydrofuran"
              }
            ],
            "amount": {
              "volume": {
                "value": 90.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "acetic acid"
              }
            ],
            "amount": {
              "mass": {
                "value": 0.63,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "palladium carbon"
              }
            ],
            "amount": {
              "mass": {
                "value": 3.6,
                "units": "GRAM"
              }
            },
            "reactionRole": "CATALYST"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "water"
              }
            ],
            "amount": {
              "volume": {
                "value": 6.3,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-cf889c4b16fa47e2ab45067176143c89"
  },
  {
    "input_text": "7-[2-(2-Formamidothiazol-4-yl)-2-pentyloxyiminoacetamido]-3-cephem-4-carboxylic acid (syn isomer, 3.3 g.), conc. hydrochloric acid (2.80 g.), tetrahydrofuran (20 ml.) and methanol (50 ml.) were treated in a similar manner to that of Example 15-(3) to give 7-[2-(2-aminothiazol-4-yl)-2-pentyloxyiminoacetamido]-3-cephem-4-carboxylic acid (syn isomer, 2.3 g.)",
    "output_reaction_inputs": {
      "m1_m2_m3_m4": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "7-[2-(2-Formamidothiazol-4-yl)-2-pentyloxyiminoacetamido]-3-cephem-4-carboxylic acid"
              }
            ],
            "amount": {
              "mass": {
                "value": 3.3,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "hydrochloric acid"
              }
            ],
            "amount": {
              "mass": {
                "value": 2.8,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "tetrahydrofuran"
              }
            ],
            "amount": {
              "volume": {
                "value": 20.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "methanol"
              }
            ],
            "amount": {
              "volume": {
                "value": 50.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-eaec10dd51124532a072c1145da74a7a"
  },
  {
    "input_text": "2-(2-Formamidothiazol-4-yl)-2-ethoxycarbonylmethoxyiminoacetic acid (syn isomer, 1.35 g.), 4-nitrobenzyl 7-amino-3-cephem-4-carboxylate (1.54 g.), N,N-dimethylformamide (393 mg.), phosphoryl chloride (825 mg.), tetrahydrofuran (21.2 ml.), acetone (3.9 ml.) and water (3.9 ml.) were treated in a similar manner to that of Example 15- (1) to give 4-nitrobenzyl 7-[2-(2-formamidothiazol-4-yl)-2-ethoxycarbonylmethoxyiminoacetamido]-3-cephem-4-carboxylate (syn isomer 2.52 g.).",
    "output_reaction_inputs": {
      "m1_m2_m3_m4_m7_m6_m5": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "2-(2-Formamidothiazol-4-yl)-2-ethoxycarbonylmethoxyiminoacetic acid"
              }
            ],
            "amount": {
              "mass": {
                "value": 1.35,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "4-nitrobenzyl 7-amino-3-cephem-4-carboxylate"
              }
            ],
            "amount": {
              "mass": {
                "value": 1.54,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "N,N-dimethylformamide"
              }
            ],
            "amount": {
              "mass": {
                "value": 393.0,
                "units": "MILLIGRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "phosphoryl chloride"
              }
            ],
            "amount": {
              "mass": {
                "value": 825.0,
                "units": "MILLIGRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "water"
              }
            ],
            "amount": {
              "volume": {
                "value": 3.9,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "acetone"
              }
            ],
            "amount": {
              "volume": {
                "value": 3.9,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "tetrahydrofuran"
              }
            ],
            "amount": {
              "volume": {
                "value": 21.2,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-3f6b26f7610748fca3c7e8b014f21b67"
  },
  {
    "input_text": "4-Nitrobenzyl 7-[2-(2-formamidothiazol-4-yl)-2-ethoxycarbonylmethoxyiminoacetamido]-3-cephem-4-carboxylate (syn isomer, 2.52 g.), 10% palladium carbon (1.3 g.) ethanol (13 ml.), tetrahydrofuran (25 ml.), acetic acid (0.22 ml.) and water (2.2 ml.) were treated in a similar manner to that of Example 15-(2) to give 7-[2-(2-formamidothiazol-4-yl)-2-ethoxycarbonylmethoxyiminoacetamido]-3-cephem-4-carboxylic acid (syn isomer, 0.4 g.).",
    "output_reaction_inputs": {
      "m1_m5_m2_m3_m4_m6": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "4-Nitrobenzyl 7-[2-(2-formamidothiazol-4-yl)-2-ethoxycarbonylmethoxyiminoacetamido]-3-cephem-4-carboxylate"
              }
            ],
            "amount": {
              "mass": {
                "value": 2.52,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "ethanol"
              }
            ],
            "amount": {
              "volume": {
                "value": 13.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "tetrahydrofuran"
              }
            ],
            "amount": {
              "volume": {
                "value": 25.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "acetic acid"
              }
            ],
            "amount": {
              "volume": {
                "value": 0.22,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "palladium carbon"
              }
            ],
            "amount": {
              "mass": {
                "value": 1.3,
                "units": "GRAM"
              }
            },
            "reactionRole": "CATALYST"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "water"
              }
            ],
            "amount": {
              "volume": {
                "value": 2.2,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-2b856ce1e65d4c60850c26416a796e89"
  },
  {
    "input_text": "A solution of 7-[2-(2-formamidothiazol-4-yl)-2-ethoxycarbonylmethoxyiminoacetamido]-3-cephem-4-carboxylic acid (syn isomer, 0.35 g.), conc.hydrochloric acid (0.39 g.), ethanol (5.3 ml.) and tetrahydrofuran (8 ml.) was stirred at room temperature for 4.5 hours. After the resultant solution was concentrated in vacuo, the residue was dissolved in an aqueous solution of sodium bicarbonate, treated with activated charcoal and filtered. The filtrate was adjusted to pH 3.5 with 10% hydrochloric acid under ice cooling. The precipitates were collected by filtration, washed with water and dried to give 7-[2-(2-aminothiazol-4-yl)-2-ethoxycarbonylmethoxyiminoacetamido]-3-cephem-4-carboxylic acid (syn isomer, 0.1 g.).",
    "output_reaction_inputs": {
      "m1": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "7-[2-(2-formamidothiazol-4-yl)-2-ethoxycarbonylmethoxyiminoacetamido]-3-cephem-4-carboxylic acid"
              }
            ],
            "amount": {
              "mass": {
                "value": 0.35,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      },
      "m2_m3_m4": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "hydrochloric acid"
              }
            ],
            "amount": {
              "mass": {
                "value": 0.39,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "ethanol"
              }
            ],
            "amount": {
              "volume": {
                "value": 5.3,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "tetrahydrofuran"
              }
            ],
            "amount": {
              "volume": {
                "value": 8.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-093bbf1c180944e99804477a816fbbf3"
  },
  {
    "input_text": "A suspension of 7-[2-(2-formamidothiazol-4-yl)-2-(2,2,2-trifluoroethoxyimino)acetamido]-3-cephem-4-carboxylic acid (syn isomer, 1.5 g.), conc. hydrochloric acid (1.3 ml.), tetrahydrofuran (10 ml.) and methanol (30 ml.) was treated in a similar manner to that of Example 21-(3) to give 7-[2-(2-aminothiazol-4-yl)-2-(2,2,2-trifluoroethoxyimino)acetamido]-3-cephem-4-carboxylic acid (syn isomer, 1.1 g.).",
    "output_reaction_inputs": {
      "m1_m2_m3_m4": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "7-[2-(2-formamidothiazol-4-yl)-2-(2,2,2-trifluoroethoxyimino)acetamido]-3-cephem-4-carboxylic acid"
              }
            ],
            "amount": {
              "mass": {
                "value": 1.5,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "hydrochloric acid"
              }
            ],
            "amount": {
              "volume": {
                "value": 1.3,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "tetrahydrofuran"
              }
            ],
            "amount": {
              "volume": {
                "value": 10.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "methanol"
              }
            ],
            "amount": {
              "volume": {
                "value": 30.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-0d8eeb6507b04ee9a6f791d787ba93df"
  },
  {
    "input_text": "A solution of 2-(2-formamidothiazol-4-yl)-2-(2-chloroethoxyimino)acetic acid (syn isomer, 3.47 g.), N,N-dimethylformamide (1.1 g.) and phosphoryl chloride (2.3 g.) in ethyl acetate (35 ml.), and a solution of 7-amino-3-cephem-4-carboxylic acid (2.5 g.) and bis(trimethylsilyl)acetamide (12.7 g.) in ethyl acetate (25 ml.) were treated in a similar manner to that of Example 15-(1) to give 7-[2-(2-formamidothiazol-4-yl)-2-(2-chloroethoxyimino)acetamido]-3-cephem-4-carboxylic acid (syn isomer, 1.85 g.).",
    "output_reaction_inputs": {
      "m1_m7_m2_m5_m3_m4_m6": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "2-(2-formamidothiazol-4-yl)-2-(2-chloroethoxyimino)acetic acid"
              }
            ],
            "amount": {
              "mass": {
                "value": 3.47,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "phosphoryl chloride"
              }
            ],
            "amount": {
              "mass": {
                "value": 2.3,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "7-amino-3-cephem-4-carboxylic acid"
              }
            ],
            "amount": {
              "mass": {
                "value": 2.5,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "bis(trimethylsilyl)acetamide"
              }
            ],
            "amount": {
              "mass": {
                "value": 12.7,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "ethyl acetate"
              }
            ],
            "amount": {
              "volume": {
                "value": 35.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "ethyl acetate"
              }
            ],
            "amount": {
              "volume": {
                "value": 25.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "N,N-dimethylformamide"
              }
            ],
            "amount": {
              "mass": {
                "value": 1.1,
                "units": "GRAM"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-f95e5f2d5a46400393b2f53a6e960086"
  },
  {
    "input_text": "7-[2-(2-Formamidothiazol-4-yl)-2-(2-chloroethoxyimino)acetamido]-3-cephem-4-carboxylic acid (syn isomer, 1.8 g.), conc. hydrochloric acid (1.6 g.), methanol (27 ml.) and tetrahydrofuran (40 ml.) were treated in a similar manner to that of Example 15-(3) to give 7-[2-(2-aminothiazol-4-yl)-2-(2-chloroethoxyimino)acetamido]-3-cephem-4-carboxylic acid (syn isomer, 1.4 g.).",
    "output_reaction_inputs": {
      "m1_m2_m3_m4": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "7-[2-(2-Formamidothiazol-4-yl)-2-(2-chloroethoxyimino)acetamido]-3-cephem-4-carboxylic acid"
              }
            ],
            "amount": {
              "mass": {
                "value": 1.8,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "hydrochloric acid"
              }
            ],
            "amount": {
              "mass": {
                "value": 1.6,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "methanol"
              }
            ],
            "amount": {
              "volume": {
                "value": 27.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "tetrahydrofuran"
              }
            ],
            "amount": {
              "volume": {
                "value": 40.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-ff08473e359a458c8c653a1b314ac564"
  },
  {
    "input_text": "A solution of 2-(2-formamidothiazol-4-yl)-2-(tert-butoxycarbonylmethoxyimino)acetic acid (syn isomer, 3.2 g.), N,N-dimethylformamide (0.852 g.) and phosphoryl chloride (1.79 g.) in ethyl acetate (34 ml.) and a solution of 7-amino-3-cephem-4-carboxylic acid (1.95 g.) and bis(trimethylsilyl)acetamide (9.9 g.) in ethyl acetate (19.5 ml.) were treated in a similar manner to that of Example 15-(1) to give 7-[2-(2-formamidothiazol-4-yl)-2-(tert-butoxycarbonylmethoxyimino)acetamido]-3-cephem-4-carboxylic acid (syn isomer, 2.9 g.).",
    "output_reaction_inputs": {
      "m1_m7_m2_m5_m3_m4_m6": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "2-(2-formamidothiazol-4-yl)-2-(tert-butoxycarbonylmethoxyimino)acetic acid"
              }
            ],
            "amount": {
              "mass": {
                "value": 3.2,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "phosphoryl chloride"
              }
            ],
            "amount": {
              "mass": {
                "value": 1.79,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "7-amino-3-cephem-4-carboxylic acid"
              }
            ],
            "amount": {
              "mass": {
                "value": 1.95,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "bis(trimethylsilyl)acetamide"
              }
            ],
            "amount": {
              "mass": {
                "value": 9.9,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "ethyl acetate"
              }
            ],
            "amount": {
              "volume": {
                "value": 34.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "ethyl acetate"
              }
            ],
            "amount": {
              "volume": {
                "value": 19.5,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "N,N-dimethylformamide"
              }
            ],
            "amount": {
              "mass": {
                "value": 0.852,
                "units": "GRAM"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-b47ffec89d424cc2980a0a8f7d786a6e"
  },
  {
    "input_text": "A solution of 2-(2-formamidothiazol-4-yl)-2-(2,2,2-trifluoroethoxyimino)acetic acid (syn isomer, 0.9 g.), N,N-dimethylformamide (0.24 g.) and phosphoryl chloride (0.5 g.) in ethyl acetate (10 ml.) and a solution of 4-nitrobenzyl 7-amino-3-chloro-3-cephem-4-carboxylate hydrochloride (1.23 g.) and trimethylsilylacetamide (2.8 g.) in ethyl acetate (20 ml.) were treated in a similar manner to that of Example 21-(1) to give 4-nitrobenzyl 7-[2-(2-formamidothiazol-4-yl)-2-(2,2,2-trifluoroethoxyimino)acetamido]-3-chloro-3-cephem-4-carboxylate (syn isomer, 1.9 g.).",
    "output_reaction_inputs": {
      "m1_m7_m2_m5_m3_m4_m6": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "2-(2-formamidothiazol-4-yl)-2-(2,2,2-trifluoroethoxyimino)acetic acid"
              }
            ],
            "amount": {
              "mass": {
                "value": 0.9,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "phosphoryl chloride"
              }
            ],
            "amount": {
              "mass": {
                "value": 0.5,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "4-nitrobenzyl 7-amino-3-chloro-3-cephem-4-carboxylate hydrochloride"
              }
            ],
            "amount": {
              "mass": {
                "value": 1.23,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "trimethylsilylacetamide"
              }
            ],
            "amount": {
              "mass": {
                "value": 2.8,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "ethyl acetate"
              }
            ],
            "amount": {
              "volume": {
                "value": 10.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "ethyl acetate"
              }
            ],
            "amount": {
              "volume": {
                "value": 20.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "N,N-dimethylformamide"
              }
            ],
            "amount": {
              "mass": {
                "value": 0.24,
                "units": "GRAM"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-d581e025aca542a483a5bf20db834a5b"
  },
  {
    "input_text": "A suspension of 4-nitrobenzyl 7-[2-(2-formamidothiazol-4-yl)-2-(2,2,2-trifluoroethoxyimino)acetamido]-3-chloro-3-cephem-4-carboxylate (syn isomer, 1.8 g.) and 10% palladium carbon (0.9 g.) in methanol (20 ml.) and tetrahydrofuran (20 ml.) was treated in a similar manner to that of Example 21-(2) to give 7-[2-(2-formamidothiazol-4-yl)-2-(2,2,2-trifluoroethoxyimino)acetamido]-3-chloro-3-cephem-4-carboxylic acid (syn isomer, 1.0 g.).",
    "output_reaction_inputs": {
      "m1_m4_m2_m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "4-nitrobenzyl 7-[2-(2-formamidothiazol-4-yl)-2-(2,2,2-trifluoroethoxyimino)acetamido]-3-chloro-3-cephem-4-carboxylate"
              }
            ],
            "amount": {
              "mass": {
                "value": 1.8,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "methanol"
              }
            ],
            "amount": {
              "volume": {
                "value": 20.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "tetrahydrofuran"
              }
            ],
            "amount": {
              "volume": {
                "value": 20.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "palladium carbon"
              }
            ],
            "amount": {
              "mass": {
                "value": 0.9,
                "units": "GRAM"
              }
            },
            "reactionRole": "CATALYST"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-1d154c7b79a54e5294b48024046f9a20"
  },
  {
    "input_text": "7-[2-(2-Formamidothiazol-4-yl)-2-(2,2,2-trifluoroethoxyimino)acetamido]-3-chloro-3-cephem-4-carboxylic acid (syn isomer, 0.7 g.), conc.hydrochloric acid (0.43 ml.) and methanol (16 ml.) were treated in a similar manner to that of Example 21-(3) to give 7-[2-(2-aminothiazol-4-yl)-2-(2,2,2-trifluoroethoxyimino)acetamido]-3-chloro-3-cephem-4-carboxylic acid (syn isomer, 0.65 g.).",
    "output_reaction_inputs": {
      "m2_m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "hydrochloric acid"
              }
            ],
            "amount": {
              "volume": {
                "value": 0.43,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "methanol"
              }
            ],
            "amount": {
              "volume": {
                "value": 16.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      },
      "m1": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "7-[2-(2-Formamidothiazol-4-yl)-2-(2,2,2-trifluoroethoxyimino)acetamido]-3-chloro-3-cephem-4-carboxylic acid"
              }
            ],
            "amount": {
              "mass": {
                "value": 0.7,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-1d5bf5c23c7945b1a304ae3a212a4f54"
  },
  {
    "input_text": "A solution of 2-(2-formamidothiazol-4-yl)-2-butoxyiminoacetic acid (syn isomer, 1.5 g.), N,N-dimethylformamide (440 mg.) and phosphoryl chloride (920 mg.) in ethyl acetate (12 ml.) and a solution of 4-nitrobenzyl 7-amino-3-chloro-3-cephem-4-carboxylate (2.03 g.), trimethylsilylacetamide (7 g.) and bis(trimethylsilyl)acetamide (2 ml.) in ethyl acetate (25 ml.) were treated in a similar manner to that of Example 21-(1) to give 4-nitrobenzyl 7-[2-(2-formamidothiazol-4-yl)-2-butoxyiminoacetamido]-3-chloro-3-cephem-4-carboxylate (syn isomer, 2.8 g.), yellow powder.",
    "output_reaction_inputs": {
      "m1_m8_m2_m6_m3_m4_m5_m7": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "2-(2-formamidothiazol-4-yl)-2-butoxyiminoacetic acid"
              }
            ],
            "amount": {
              "mass": {
                "value": 1.5,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "phosphoryl chloride"
              }
            ],
            "amount": {
              "mass": {
                "value": 920.0,
                "units": "MILLIGRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "4-nitrobenzyl 7-amino-3-chloro-3-cephem-4-carboxylate"
              }
            ],
            "amount": {
              "mass": {
                "value": 2.03,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "trimethylsilylacetamide"
              }
            ],
            "amount": {
              "mass": {
                "value": 7.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "bis(trimethylsilyl)acetamide"
              }
            ],
            "amount": {
              "volume": {
                "value": 2.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "ethyl acetate"
              }
            ],
            "amount": {
              "volume": {
                "value": 12.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "ethyl acetate"
              }
            ],
            "amount": {
              "volume": {
                "value": 25.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "N,N-dimethylformamide"
              }
            ],
            "amount": {
              "mass": {
                "value": 440.0,
                "units": "MILLIGRAM"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-528a3c318c514457afbcb388f137742f"
  },
  {
    "input_text": "A mixture of 4-nitrobenzyl 7-[2-(2-formamidothiazol-4-yl)-2-butoxyiminoacetamido]-3-chloro-3-cephem-4-carboxylate (syn isomer, 2.7 g.), 10% palladium carbon (1.3 g.), water (4 ml.), acetic acid (0.4 ml.), methanol (27 ml.) and tetrahydrofuran (54 ml.) was treated in a similar manner to that of Example 21-(2) to give 7-[2-(2-formamidothiazol-4-yl)-2-butoxyiminoacetamido]-3-chloro-3-cephem-4-carboxylic acid (syn isomer, 1.4 g.), pale yellow powder.",
    "output_reaction_inputs": {
      "m1_m5_m2_m3_m4_m6": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "4-nitrobenzyl 7-[2-(2-formamidothiazol-4-yl)-2-butoxyiminoacetamido]-3-chloro-3-cephem-4-carboxylate"
              }
            ],
            "amount": {
              "mass": {
                "value": 2.7,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "water"
              }
            ],
            "amount": {
              "volume": {
                "value": 4.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "acetic acid"
              }
            ],
            "amount": {
              "volume": {
                "value": 0.4,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "methanol"
              }
            ],
            "amount": {
              "volume": {
                "value": 27.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "palladium carbon"
              }
            ],
            "amount": {
              "mass": {
                "value": 1.3,
                "units": "GRAM"
              }
            },
            "reactionRole": "CATALYST"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "tetrahydrofuran"
              }
            ],
            "amount": {
              "volume": {
                "value": 54.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-d1cade454db64ae489f919eb9fc953af"
  },
  {
    "input_text": "A mixture of 7-[2-(2-formamidothiazol-4-yl)-2-butoxyiminoacetamido]-3-chloro-3-cephem-4-carboxylic acid (syn isomer, 1.3 g.), conc. hydrochloric acid (1.3 ml.) and methanol (20 ml.) was treated in a similar manner to that of Example 21-(3) to give 7-[2-(2-aminothiazol-4-yl)-2-butoxyiminoacetamido]-3-chloro-3-cephem-4-carboxylic acid (syn isomer, 1.2 g.), pale yellow powder.",
    "output_reaction_inputs": {
      "m1_m2_m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "7-[2-(2-formamidothiazol-4-yl)-2-butoxyiminoacetamido]-3-chloro-3-cephem-4-carboxylic acid"
              }
            ],
            "amount": {
              "mass": {
                "value": 1.3,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "hydrochloric acid"
              }
            ],
            "amount": {
              "volume": {
                "value": 1.3,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "methanol"
              }
            ],
            "amount": {
              "volume": {
                "value": 20.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-5c3fdf5217a044b6b21db486ce8eaa15"
  },
  {
    "input_text": "A solution of 2-(2-formamidothiazol-4-yl)-2-butoxyiminoacetic acid (syn isomer, 1.09 g.), N,N-dimethylformamide (322 mg.) and phosphoryl chloride (675 mg.) in ethyl acetate (9.2 ml.) and a solution of 4-nitrobenzyl 7-amino-3-methoxy-3-cephem-4-carboxylate hydrochloride (1.5 g.), trimethylsilylacetamide (5 g.) and bis(trimethylsilyl)acetamide (2 ml.) in ethyl acetate (30 ml.) were treated in a similar manner to that of Example 3-(1) to give 4-nitrobenzyl 7-[2-(2-formamidothiazol-4-yl)-2-butoxyiminoacetamido]-3-methoxy-3-cephem-4-carboxylate (syn isomer, 1.8 g.).",
    "output_reaction_inputs": {
      "m1_m8_m2_m6_m3_m4_m5_m7": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "2-(2-formamidothiazol-4-yl)-2-butoxyiminoacetic acid"
              }
            ],
            "amount": {
              "mass": {
                "value": 1.09,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "phosphoryl chloride"
              }
            ],
            "amount": {
              "mass": {
                "value": 675.0,
                "units": "MILLIGRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "4-nitrobenzyl 7-amino-3-methoxy-3-cephem-4-carboxylate hydrochloride"
              }
            ],
            "amount": {
              "mass": {
                "value": 1.5,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "trimethylsilylacetamide"
              }
            ],
            "amount": {
              "mass": {
                "value": 5.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "bis(trimethylsilyl)acetamide"
              }
            ],
            "amount": {
              "volume": {
                "value": 2.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "ethyl acetate"
              }
            ],
            "amount": {
              "volume": {
                "value": 9.2,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "ethyl acetate"
              }
            ],
            "amount": {
              "volume": {
                "value": 30.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "N,N-dimethylformamide"
              }
            ],
            "amount": {
              "mass": {
                "value": 322.0,
                "units": "MILLIGRAM"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-ad71202fecfd4782b90d91a4de1b8576"
  },
  {
    "input_text": "A mixture of 4-nitrobenzyl 7-[2-(2-formamidothiazol-4-yl)-2-butoxyiminoacetamido]-3-methoxy-3-cephem-4-carboxylate (syn isomer, 1.7 g.), 10% palladium carbon (1 g.), water (3 ml.), acetic acid (0.3 ml.), methanol (20 ml.) and tetrahydrofuran (35 ml.) was treated in a similar manner to that of Example 15-(2) to give 7-[2-(2-formamidothiazol-4-yl)-2-butoxyiminoacetamido]-3-methoxy-3-cephem-4-carboxylic acid (syn isomer, 1 g.), yellow powder.",
    "output_reaction_inputs": {
      "m1_m5_m2_m3_m4_m6": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "4-nitrobenzyl 7-[2-(2-formamidothiazol-4-yl)-2-butoxyiminoacetamido]-3-methoxy-3-cephem-4-carboxylate"
              }
            ],
            "amount": {
              "mass": {
                "value": 1.7,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "water"
              }
            ],
            "amount": {
              "volume": {
                "value": 3.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "acetic acid"
              }
            ],
            "amount": {
              "volume": {
                "value": 0.3,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "methanol"
              }
            ],
            "amount": {
              "volume": {
                "value": 20.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "palladium carbon"
              }
            ],
            "amount": {
              "mass": {
                "value": 1.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "CATALYST"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "tetrahydrofuran"
              }
            ],
            "amount": {
              "volume": {
                "value": 35.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-5e76bb3b0bc34fbb92dfa1eeefc7a2c3"
  },
  {
    "input_text": "Thiourea (0.14 g.) was added to a solution of 4-nitrobenzyl 7-[2-(2-bromoacetyl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylate (syn-isomer: 0.8 g.) in ethanol (20 ml.) and water (5 ml.), and stirred at room temperature for 3.5 hours. The resultant solution was concentrated under reduced pressure, and to the residue were added water and ethyl acetate. The ethyl acetate layer was separated, washed with water, dried over magnesium sulfate and concentrated under reduced pressure to give the crude product (0.6 g.). The product was purified by column chromatography on silica gel (eluent:benzene and ethyl acetate (8:2) to give 4-nitrobenzyl 7-[2-(2-amino-4-thiazolyl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylate (syn-isomer:0.21 g.), mp 165\u00b0 to 170\u00b0 C. (dec.).",
    "output_reaction_inputs": {
      "m1_m2_m3_m4": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "Thiourea"
              }
            ],
            "amount": {
              "mass": {
                "value": 0.14,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "4-nitrobenzyl 7-[2-(2-bromoacetyl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylate"
              }
            ],
            "amount": {
              "mass": {
                "value": 0.8,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "ethanol"
              }
            ],
            "amount": {
              "volume": {
                "value": 20.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "water"
              }
            ],
            "amount": {
              "volume": {
                "value": 5.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "temperature": {
        "control": {
          "type": "AMBIENT"
        }
      },
      "stirring": {
        "type": "CUSTOM",
        "details": "stirred at room temperature for 3.5 hours"
      },
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-924b59ef09754e13ae71e6961c85e3d5"
  },
  {
    "input_text": "A solution of 2-(2-formamidothiazol-4-yl)-2-n-hexyloxyiminoacetic acid (syn isomer, 3.24 g.), N,N-dimethylformamide (0.951 g.), and phosphoryl chloride (2.00 g.) in ethyl acetate (20 ml.), and a solution of 4-nitrobenzyl 7-amino-3-chloro-3-cephem-4-carboxylate hydrochloride (4 g.) in a mixture of acetone (20 ml.), water (20 ml.) and tetrahydrofuran (400 ml.) were treated in a similar manner to that of Example 21-(1) to give 4-nitrobenzyl 7-[2-(2-formamidothiazol-4-yl)-2-n-hexyloxyiminoacetamido]-3-chloro-3-cephem-4-carboxylate (syn isomer, 5.78 g.).",
    "output_reaction_inputs": {
      "m1_m2_m3_m5_m4_m6_m8_m7": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "2-(2-formamidothiazol-4-yl)-2-n-hexyloxyiminoacetic acid"
              }
            ],
            "amount": {
              "mass": {
                "value": 3.24,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "N,N-dimethylformamide"
              }
            ],
            "amount": {
              "mass": {
                "value": 0.951,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "phosphoryl chloride"
              }
            ],
            "amount": {
              "mass": {
                "value": 2.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "4-nitrobenzyl 7-amino-3-chloro-3-cephem-4-carboxylate hydrochloride"
              }
            ],
            "amount": {
              "mass": {
                "value": 4.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "ethyl acetate"
              }
            ],
            "amount": {
              "volume": {
                "value": 20.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "acetone"
              }
            ],
            "amount": {
              "volume": {
                "value": 20.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "tetrahydrofuran"
              }
            ],
            "amount": {
              "volume": {
                "value": 400.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "water"
              }
            ],
            "amount": {
              "volume": {
                "value": 20.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-8236e5a2fd6c42ff94a230ffd83b4c37"
  },
  {
    "input_text": "A mixture of 4-nitrobenzyl 7-[2-(2-formamidothiazol-4-yl)-2-n-hexyloxyiminoacetamido]-3-chloro-3-cephem-4-carboxylate (syn isomer, 5.6 g.), acetic acid (0.4 ml.), 10% palladium carbon (2.24 g.), water (4 ml.), methanol (23 ml.) and tetrahydrofuran (56 ml.) was treated in a similar manner to that of Example 21-(2) to give 7-[2-(2-formamidothiazol-4-yl)-2-n-hexyloxyiminoacetamido]-3-chloro-3-cephem-4-carboxylic acid (syn isomer, 2.5 g.).",
    "output_reaction_inputs": {
      "m1_m2_m5_m3_m4_m6": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "4-nitrobenzyl 7-[2-(2-formamidothiazol-4-yl)-2-n-hexyloxyiminoacetamido]-3-chloro-3-cephem-4-carboxylate"
              }
            ],
            "amount": {
              "mass": {
                "value": 5.6,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "acetic acid"
              }
            ],
            "amount": {
              "volume": {
                "value": 0.4,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "water"
              }
            ],
            "amount": {
              "volume": {
                "value": 4.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "methanol"
              }
            ],
            "amount": {
              "volume": {
                "value": 23.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "palladium carbon"
              }
            ],
            "amount": {
              "mass": {
                "value": 2.24,
                "units": "GRAM"
              }
            },
            "reactionRole": "CATALYST"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "tetrahydrofuran"
              }
            ],
            "amount": {
              "volume": {
                "value": 56.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-29ec0e1e13ee4e018c3636bf79972922"
  },
  {
    "input_text": "A mixture of 7-[2-(2-formamidothiazol-4-yl)-2-n-hexyloxyiminoacetamido]-3-chloro-3-cephem-4-carboxylic acid (syn isomer, 2.4 g.), conc. hydrochloric acid (1.84 g.), methanol (36 ml.) and tetrahydrofuran (30 ml.) was stirred at 30\u00b0 C. for 2 hours. The resultant solution was concentrated in vacuo. Water (60 ml.) was added to the residue and the precipitates were collected by filtration, washed with water and dried over phosphorus pentoxide to give 7-[2-(2-aminothiazol-4-yl)-2-n-hexyloxyiminoacetamido]-3-chloro-3-cephem-4-carboxylic acid (syn isomer, 1.86 g.).",
    "output_reaction_inputs": {
      "m1_m2_m3_m4": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "7-[2-(2-formamidothiazol-4-yl)-2-n-hexyloxyiminoacetamido]-3-chloro-3-cephem-4-carboxylic acid"
              }
            ],
            "amount": {
              "mass": {
                "value": 2.4,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "hydrochloric acid"
              }
            ],
            "amount": {
              "mass": {
                "value": 1.84,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "methanol"
              }
            ],
            "amount": {
              "volume": {
                "value": 36.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "tetrahydrofuran"
              }
            ],
            "amount": {
              "volume": {
                "value": 30.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "temperature": {
        "setpoint": {
          "value": 30.0,
          "units": "CELSIUS"
        }
      },
      "stirring": {
        "type": "CUSTOM",
        "details": "was stirred at 30\u00b0 C. for 2 hours"
      },
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-9c9e0516c92843d38d2dbd3623516656"
  },
  {
    "input_text": "A mixture of 7-[2-(2-formamidothiazol-4-yl)-2-propargyloxyiminoacetamido]-3-chloro-3-cephem-4-carboxylic acid (syn isomer, 1.4 g.), conc. hydrochloric acid (1.4 ml.) and methanol (20 ml.) was treated in a similar manner to that of Example 51-(2) to give 7-[2-(2-aminothiazol-4-yl)-2-propargyloxyiminoacetamido]-3-chloro-3-cephem-4-carboxylic acid (syn isomer, 0.7 g.), yellowish white powder.",
    "output_reaction_inputs": {
      "m1_m2_m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "7-[2-(2-formamidothiazol-4-yl)-2-propargyloxyiminoacetamido]-3-chloro-3-cephem-4-carboxylic acid"
              }
            ],
            "amount": {
              "mass": {
                "value": 1.4,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "hydrochloric acid"
              }
            ],
            "amount": {
              "volume": {
                "value": 1.4,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "methanol"
              }
            ],
            "amount": {
              "volume": {
                "value": 20.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-27dbb4a39bf34897ab8288734d1b7b87"
  },
  {
    "input_text": "Thiourea (11 mg.) and a solution of 7-[2-(2-bromoacetyl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylic acid (syn isomer, 30 mg.) in ethanol (2 ml.) were treated in a similar manner to that of Example 36-(4) to give 7-[2-(2-amino-4-thiazolyl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylic acid (syn isomer). The product was identified with an authentic sample by thin layer chromatography.",
    "output_reaction_inputs": {
      "m1_m2_m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "Thiourea"
              }
            ],
            "amount": {
              "mass": {
                "value": 11.0,
                "units": "MILLIGRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "7-[2-(2-bromoacetyl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylic acid"
              }
            ],
            "amount": {
              "mass": {
                "value": 30.0,
                "units": "MILLIGRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "ethanol"
              }
            ],
            "amount": {
              "volume": {
                "value": 2.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-9e18ff75dba845c385a5dc885be2d36a"
  },
  {
    "input_text": "A solution of 4-nitrobenzyl 7-amino-3-chloro-3-cephem-4-carboxylate hydrochloride (15.0 g.), bis(trimethylsilyl)acetamide (11.3 g.) and trimethylsilylacetamide (9.7 g.) in tetrahydrofuran (300 ml.), a solution of diketene (3.41 ml.) in methylene chloride (4 ml.), a solution of bromine (2.27 ml.) in methylene chloride (4 ml.), a solution of sodium nitrite (3.1 g.) in water (20 ml.) and a solution of thiourea (4.0 g.) in water (40 ml.) were treated in a similar manner to that of Example 37-(1) to give 4-nitrobenzyl 7-[2-(2-aminothiazol-4-yl)-2-hydroxyiminoacetamido]-3-chloro-3-cephem-4-carboxylate (syn isomer, 10.4 g.).",
    "output_reaction_inputs": {
      "m1_m2_m3_m8_m4_m9_m5_m10_m6_m11_m7_m12": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "4-nitrobenzyl 7-amino-3-chloro-3-cephem-4-carboxylate hydrochloride"
              }
            ],
            "amount": {
              "mass": {
                "value": 15.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "bis(trimethylsilyl)acetamide"
              }
            ],
            "amount": {
              "mass": {
                "value": 11.3,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "trimethylsilylacetamide"
              }
            ],
            "amount": {
              "mass": {
                "value": 9.7,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "diketene"
              }
            ],
            "amount": {
              "volume": {
                "value": 3.41,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "bromine"
              }
            ],
            "amount": {
              "volume": {
                "value": 2.27,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "sodium nitrite"
              }
            ],
            "amount": {
              "mass": {
                "value": 3.1,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "thiourea"
              }
            ],
            "amount": {
              "mass": {
                "value": 4.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "tetrahydrofuran"
              }
            ],
            "amount": {
              "volume": {
                "value": 300.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "methylene chloride"
              }
            ],
            "amount": {
              "volume": {
                "value": 4.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "methylene chloride"
              }
            ],
            "amount": {
              "volume": {
                "value": 4.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "water"
              }
            ],
            "amount": {
              "volume": {
                "value": 20.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "water"
              }
            ],
            "amount": {
              "volume": {
                "value": 40.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-ce8162567ad04ea7b2e7f4ba6c8612ee"
  },
  {
    "input_text": "4-Nitrobenzyl 7-[2-(2-aminothiazol-4-yl)-2-hydroxyiminoacetamido]-3-chloro-3-cephem-4-carboxylate (syn isomer, 5.0 g.), 10% palladium carbon (3.0 g.), methanol (100 ml.), water (10 ml.) and tetrahydrofuran (150 ml.) were treated in a similar manner to that of Example 37-(2), to give 7-[2-(2-aminothiazol-4-yl)-2-hydroxyiminoacetamido]-3-chloro-3-cephem-4-carboxylic acid (syn isomer, 1.28 g.).",
    "output_reaction_inputs": {
      "m1_m4_m2_m3_m5": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "4-Nitrobenzyl 7-[2-(2-aminothiazol-4-yl)-2-hydroxyiminoacetamido]-3-chloro-3-cephem-4-carboxylate"
              }
            ],
            "amount": {
              "mass": {
                "value": 5.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "methanol"
              }
            ],
            "amount": {
              "volume": {
                "value": 100.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "water"
              }
            ],
            "amount": {
              "volume": {
                "value": 10.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "palladium carbon"
              }
            ],
            "amount": {
              "mass": {
                "value": 3.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "CATALYST"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "tetrahydrofuran"
              }
            ],
            "amount": {
              "volume": {
                "value": 150.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-afd5d8bea6494369995a7f10d921f78d"
  },
  {
    "input_text": "Ethyl 2-hydroxyimino-3-oxobutyrate (syn isomer, 100 g.), N,N-dimethylformamide (300 ml.), potassium carbonate (130 g.) and bromooctane (121 g.) were treated in a similar manner to that of Example F-(1) to give ethyl 2-n-octyloxyimino-3-oxobutyrate (syn isomer, 165.5 g.), oil.",
    "output_reaction_inputs": {
      "m1_m4_m2_m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "Ethyl 2-hydroxyimino-3-oxobutyrate"
              }
            ],
            "amount": {
              "mass": {
                "value": 100.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "potassium carbonate"
              }
            ],
            "amount": {
              "mass": {
                "value": 130.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "bromooctane"
              }
            ],
            "amount": {
              "mass": {
                "value": 121.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "N,N-dimethylformamide"
              }
            ],
            "amount": {
              "volume": {
                "value": 300.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-b57cad909c484eab9ababe1f581630c3"
  },
  {
    "input_text": "Ethyl 2-n-octyloxyimino-3-oxobutyrate (syn isomer, 165.5 g.), sulfuryl chloride (84.7 g.) and acetic acid (165 ml.) were treated in a similar manner to that of Example F-(2) to give ethyl 2-n-octyloxyimino-4-chloro-3-oxobutyrate (syn isomer, 169.6 g.), oil.",
    "output_reaction_inputs": {
      "m1_m2_m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "Ethyl 2-n-octyloxyimino-3-oxobutyrate"
              }
            ],
            "amount": {
              "mass": {
                "value": 165.5,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "sulfuryl chloride"
              }
            ],
            "amount": {
              "mass": {
                "value": 84.7,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "acetic acid"
              }
            ],
            "amount": {
              "volume": {
                "value": 165.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-84818f8f3e0042bd93ce1895070b4593"
  },
  {
    "input_text": "Ethyl 2-n-octyloxyimino-4-chloro-3-oxobutyrate (syn isomer, 169.6 g.), thiourea (42.3 g.), sodium acetate trihydrate (75.5 g.), water (420 ml.) and ethanol (1020 ml.) were treated in a similar manner to that of Example F-(3) to give ethyl 2-(2-aminothiazol-4-yl)-2-n-octyloxyiminoacetate (syn isomer, 65 g.), mp. 77\u00b0 to 78\u00b0 C.",
    "output_reaction_inputs": {
      "m1_m2_m3_m4_m5": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "Ethyl 2-n-octyloxyimino-4-chloro-3-oxobutyrate"
              }
            ],
            "amount": {
              "mass": {
                "value": 169.6,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "thiourea"
              }
            ],
            "amount": {
              "mass": {
                "value": 42.3,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "sodium acetate trihydrate"
              }
            ],
            "amount": {
              "mass": {
                "value": 75.5,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "water"
              }
            ],
            "amount": {
              "volume": {
                "value": 420.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "ethanol"
              }
            ],
            "amount": {
              "volume": {
                "value": 1020.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-0e1f07f45c5249f9aaa19d95e7c1d773"
  },
  {
    "input_text": "2-(2-Aminothiazol-4-yl)-2-n-octyloxyiminoacetic acid (syn isomer, 20 g.), acetic anhydride (27.3 g.) and formic acid (12.3 g.) were treated in a similar manner to that of Example F-(5) to give 2-(2-formamidothiazol-4-yl)-2-n-octyloxyiminoacetic acid (syn isomer, 21.3 g.), mp. 122\u00b0 C. (dec.).",
    "output_reaction_inputs": {
      "m1_m2_m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "2-(2-Aminothiazol-4-yl)-2-n-octyloxyiminoacetic acid"
              }
            ],
            "amount": {
              "mass": {
                "value": 20.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "acetic anhydride"
              }
            ],
            "amount": {
              "mass": {
                "value": 27.3,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "formic acid"
              }
            ],
            "amount": {
              "mass": {
                "value": 12.3,
                "units": "GRAM"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-3f72c691daf8447ebce653425a01b412"
  },
  {
    "input_text": "7-[2-(2-Formamidothiazol-4-yl)-4-n-octyloxyiminoacetamido]-3-cephem-4-carboxylic acid (syn isomer, 8.0 g.), conc. hydrochloric acid (6.23 g.), tetrahydrofuran (15 ml.) and methanol (120 ml.) were treated in a similar manner to that of Example 21-(3) to give 7-[2-(2-aminothiazol-4-yl)-2-n-octyloxyiminoacetamido]-3-cephem-4-carboxylic acid (syn isomer, 6.95 g.).",
    "output_reaction_inputs": {
      "m1_m2_m3_m4": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "7-[2-(2-Formamidothiazol-4-yl)-4-n-octyloxyiminoacetamido]-3-cephem-4-carboxylic acid"
              }
            ],
            "amount": {
              "mass": {
                "value": 8.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "hydrochloric acid"
              }
            ],
            "amount": {
              "mass": {
                "value": 6.23,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "tetrahydrofuran"
              }
            ],
            "amount": {
              "volume": {
                "value": 15.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "methanol"
              }
            ],
            "amount": {
              "volume": {
                "value": 120.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-0c2c785ecfa241609d6ea296e4eb0fb5"
  },
  {
    "input_text": "To acetic anhydride (32 g.) was added formic acid (14.4 g. ) under ice-coolind and stirred at 40\u00b0 to 45\u00b0 C. for an hour. 2-(2-Aminothiazol-4-yl)-2-cyclopentyloxyiminoacetic acid (syn isomer, 20 g.) and tetrahydrofuran (100 ml.) were added to the solution under ice-cooling and stirred at 35\u00b0 C. for 3 hours. After the solution was concentrated in vacuo, the residue was pulverized with diisopropyl ether, and dried over phosphorus pentoxide to give 2-(2-formamidothiazol-4-yl)-2-cyclopentyloxyiminoacetic acid (syn isomer, 9.04 g.), mp. 158\u00b0 C. (dec.).",
    "output_reaction_inputs": {
      "m1_m2": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "acetic anhydride"
              }
            ],
            "amount": {
              "mass": {
                "value": 32.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "formic acid"
              }
            ],
            "amount": {
              "mass": {
                "value": 14.4,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      },
      "m3_m4": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "2-(2-Aminothiazol-4-yl)-2-cyclopentyloxyiminoacetic acid"
              }
            ],
            "amount": {
              "mass": {
                "value": 20.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "tetrahydrofuran"
              }
            ],
            "amount": {
              "volume": {
                "value": 100.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "stirring": {
        "type": "CUSTOM",
        "details": "stirred at 40\u00b0 to 45\u00b0 C. for an hour"
      },
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-65b7210098e64242bcc5096926491051"
  },
  {
    "input_text": "A solution of 2-(2-formamidothiazol-4-yl)-2-cyclopentyloxyiminoacetic acid (syn isomer, 1.5 g.), phosphoryl chloride (974 mg.), N,N-dimethylformamide (464 mg.) and tetrahydrofuran (15 ml.) and a solution of 7-amino-3-cephem-4-carboxylic acid (1.38 g.) in 50% aqueous acetone (14 ml.) were treated in a similar manner to that of Example 15-(1) to give 7-[2-(2-formamidothiazol-4-yl)-2-cyclopentyloxyiminoacetamido]-3-cephem-4-carboxylic acid (syn isomer, 1.75 g.).",
    "output_reaction_inputs": {
      "m1_m2_m3_m6_m4_m5": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "2-(2-formamidothiazol-4-yl)-2-cyclopentyloxyiminoacetic acid"
              }
            ],
            "amount": {
              "mass": {
                "value": 1.5,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "phosphoryl chloride"
              }
            ],
            "amount": {
              "mass": {
                "value": 974.0,
                "units": "MILLIGRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "N,N-dimethylformamide"
              }
            ],
            "amount": {
              "mass": {
                "value": 464.0,
                "units": "MILLIGRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "7-amino-3-cephem-4-carboxylic acid"
              }
            ],
            "amount": {
              "mass": {
                "value": 1.38,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "acetone"
              }
            ],
            "amount": {
              "volume": {
                "value": 14.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "tetrahydrofuran"
              }
            ],
            "amount": {
              "volume": {
                "value": 15.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-908157d5f4814009a76a9e3e5f0a1bb8"
  },
  {
    "input_text": "7-[2-(2-formamidothiazol-4-yl)-2cyclopentyloxyiminoacetamido]-3-cephem-4-carboxylic acid (syn isomer, 1.7 g.) in methanol (17 ml.) and tetrahydrofuran (5 ml.), and conc. hydrochloric acid (1.5 g.) were treated in a similar manner to that of Example 15-(3) to give 7-[2-(2-aminothiazol-4-yl)-2cyclopentyloxyiminoacetamido]-3cephem-4-carboxylic acid (syn isomer, 1.3 g.).",
    "output_reaction_inputs": {
      "m1_m3_m4_m2": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "7-[2-(2-formamidothiazol-4-yl)-2cyclopentyloxyiminoacetamido]-3-cephem-4-carboxylic acid"
              }
            ],
            "amount": {
              "mass": {
                "value": 1.7,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "hydrochloric acid"
              }
            ],
            "amount": {
              "mass": {
                "value": 1.5,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "methanol"
              }
            ],
            "amount": {
              "volume": {
                "value": 17.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "tetrahydrofuran"
              }
            ],
            "amount": {
              "volume": {
                "value": 5.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-ee56aefb750d4b92b9df81dde0efbe62"
  },
  {
    "input_text": "0.2 mol (25.2 g) of sodium sulphite is added, at ambient temperature, to a solution of 0.1 mol (32.7 g) of N-(\u03b2-mesylaminoethyl)-para-phenylenediamine sulphate in 150 ml of water, and 0.13 mol (13.17 g) of acetic anhydride is added gradually, whilst stirring. When the addition is complete, stirring is continued for one hour and the expected acetylated derivative which has precipitated in crystalline form is then filtered off. The product is drained, washed with water and dried in vacuo. After recrystallisation from alcohol and drying in vacuo, it melts at 130\u00b0 C.",
    "output_reaction_inputs": {
      "m1_m2_m4_m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "sodium sulphite"
              }
            ],
            "amount": {
              "mass": {
                "value": 25.2,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "N-(\u03b2-mesylaminoethyl)-para-phenylenediamine sulphate"
              }
            ],
            "amount": {
              "mass": {
                "value": 32.7,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "acetic anhydride"
              }
            ],
            "amount": {
              "mass": {
                "value": 13.17,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "water"
              }
            ],
            "amount": {
              "volume": {
                "value": 150.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "stirring": {
        "type": "CUSTOM",
        "details": "whilst stirring"
      },
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-eeefe92c406c44e98bdbe8f2962e95e7"
  },
  {
    "input_text": "0.037 mol (10 g) of 4-acetylamino-N-(\u03b2-mesylaminoethyl)-aniline is dissolved in 31 ml of boiling water. 7.4 g of sodium carbonate and 0.148 mol (18.5 g) of glycol bromohydrin are added, whilst stirring. After stirring for 4 hours in a boiling water bath, the reaction medium is filtered and the filtrate is then left to stand for 48 hours at 0\u00b0 C. The 4-acetylamino-N-(\u03b2-hydroxyethyl)-N-(\u03b2-mesylaminoethyl)-aniline which has precipitated in crystalline form is filtered off. After recrystallisation from boiling water and drying in vacuo, the products melts at 118\u00b0 C.",
    "output_reaction_inputs": {
      "m2_m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "sodium carbonate"
              }
            ],
            "amount": {
              "mass": {
                "value": 7.4,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "glycol bromohydrin"
              }
            ],
            "amount": {
              "mass": {
                "value": 18.5,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      },
      "m1_m4": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "4-acetylamino-N-(\u03b2-mesylaminoethyl)-aniline"
              }
            ],
            "amount": {
              "mass": {
                "value": 10.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "water"
              }
            ],
            "amount": {
              "volume": {
                "value": 31.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "stirring": {
        "type": "CUSTOM",
        "details": "whilst stirring"
      },
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-0e39a43fc665425db3e9973ade2eb8f6"
  },
  {
    "input_text": "A mixture of 68 g (0.652 mol) of 2-ethyl-6-methylaniline, 45 g (0.326 mol) of powdered potassium carbonate and 30 ml of dimethylformamide was heated to 100\u00b0 C. and 63 g (0.326 mol) of 3-bromomethyl-4-methyl-1,2,5-thiadiazole were added dropwise, while stirring. The mixture was stirred at 100\u00b0 C. for a further 5 hours, the inorganic precipitate was filtered off and the filtrate was distilled. 59.4 g (77.4% of theory) of 2-ethyl-6-methyl-N-(4-methyl-1,2,5-thiadiazol-3-yl-methyl)-aniline of boiling point 160\u00b0-163\u00b0 C./0.3 mm Hg were obtained. ##STR18##",
    "output_reaction_inputs": {
      "m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "3-bromomethyl-4-methyl-1,2,5-thiadiazole"
              }
            ],
            "amount": {
              "mass": {
                "value": 63.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      },
      "m1_m2_m4": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "2-ethyl-6-methylaniline"
              }
            ],
            "amount": {
              "mass": {
                "value": 68.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "potassium carbonate"
              }
            ],
            "amount": {
              "mass": {
                "value": 45.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "dimethylformamide"
              }
            ],
            "amount": {
              "volume": {
                "value": 30.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "temperature": {
        "setpoint": {
          "value": 100.0,
          "units": "CELSIUS"
        }
      },
      "stirring": {
        "type": "CUSTOM",
        "details": "while stirring"
      },
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-e8fc492b5c2f4ae68b3b0b8401702e63"
  },
  {
    "input_text": "A solution of butyl lithium (0.05 moles) in hexane (31.25 ml), was treated with 2,2,6,6-tetramethylpiperidine (8.5 ml), followed by THF (100 ml) under an inert atmosphere at 0\u00b0 C. A solution of N-methylcaprolactam (6.25 ml, 50 mM) in THF (20 ml) was added, the mixture stirred for 30 minutes and treated with a solution of butyl lithium (0.05 mole) in hexane (31.25 ml). After 15 minutes, o-chloroanisole (6.2 ml) was added and the mixture stirred for fifteen hours at ambient temperature.",
    "output_reaction_inputs": {
      "m9": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "THF"
              }
            ],
            "amount": {
              "volume": {
                "value": 100.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      },
      "m1_m6_m2": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "butyl lithium"
              }
            ],
            "amount": {
              "moles": {
                "value": 0.05,
                "units": "MOLE"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "2,2,6,6-tetramethylpiperidine"
              }
            ],
            "amount": {
              "volume": {
                "value": 8.5,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "hexane"
              }
            ],
            "amount": {
              "volume": {
                "value": 31.25,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      },
      "m5": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "o-chloroanisole"
              }
            ],
            "amount": {
              "volume": {
                "value": 6.2,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      },
      "m4_m8": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "butyl lithium"
              }
            ],
            "amount": {
              "moles": {
                "value": 0.05,
                "units": "MOLE"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "hexane"
              }
            ],
            "amount": {
              "volume": {
                "value": 31.25,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      },
      "m3_m7": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "N-methylcaprolactam"
              }
            ],
            "amount": {
              "volume": {
                "value": 6.25,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "THF"
              }
            ],
            "amount": {
              "volume": {
                "value": 20.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "stirring": {
        "type": "CUSTOM",
        "details": "the mixture stirred for 30 minutes"
      },
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-8e88b4b1248e459c99e854fbe4ee5c99"
  },
  {
    "input_text": "To a solution of 600 mg of the oxime (V) in a mixture of 10 ml of dimethoxyethane and 5 ml of water, was added 6 ml of 16% titanium trichloride and the mixture was kept at 50\u00b0 to 60\u00b0 C. for 30 minutes under an argon atmosphere. After cooling, the mixture was admixed with 20 ml of water and extracted with methylene chloride. The extract was washed with an aqueous sodium bicarbonate solution, then with an aqueous sodium chloride solution, dried over magnesium sulfate, and concentrated in vacuo to give 425 mg of an oil. This oil was chromatographed over silica gel to give 305 mg of an oil (IV): nD20 1.4787; MS: m/e 168 (M+).",
    "output_reaction_inputs": {
      "m4": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "titanium trichloride"
              }
            ],
            "amount": {
              "volume": {
                "value": 6.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "CATALYST"
          }
        ]
      },
      "m1_m2_m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "oxime"
              }
            ],
            "amount": {
              "mass": {
                "value": 600.0,
                "units": "MILLIGRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "dimethoxyethane"
              }
            ],
            "amount": {
              "volume": {
                "value": 10.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "water"
              }
            ],
            "amount": {
              "volume": {
                "value": 5.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      },
      "m5": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "water"
              }
            ],
            "amount": {
              "volume": {
                "value": 20.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-ee0d561e59244332b3e4e8486cac0721"
  },
  {
    "input_text": "To a solution of 400 mg of the hydroxyketone (IV) in 8 ml of methylene chloride, while being cooled in ice, were added 770 mg of m-chloroperbenzoic acid and 480 mg of sodium hydrogencarbonate. The mixture was stirred overnight at room temperature and then treated with 10 ml of 10% sodium thiosulfate solution. The aqueous layer was separated and extracted three time with methylene chloride. The combined methylene chloride layer was washed with saturated aqueous sodium bicarbonate solution, then with an aqueous sodium chloride solution, dried over magnesium sulfate, and concentrated in vacuo to give 415 mg of a colorless oil (III); nD20 1.4845; MS: m/e 169 (M+ --CH3), 166 (M+ --H2O).",
    "output_reaction_inputs": {
      "m4": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "sodium thiosulfate"
              }
            ],
            "amount": {
              "volume": {
                "value": 10.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      },
      "m1_m5": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "hydroxyketone"
              }
            ],
            "amount": {
              "mass": {
                "value": 400.0,
                "units": "MILLIGRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "methylene chloride"
              }
            ],
            "amount": {
              "volume": {
                "value": 8.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      },
      "m2_m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "m-chloroperbenzoic acid"
              }
            ],
            "amount": {
              "mass": {
                "value": 770.0,
                "units": "MILLIGRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "sodium hydrogencarbonate"
              }
            ],
            "amount": {
              "mass": {
                "value": 480.0,
                "units": "MILLIGRAM"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "temperature": {
        "control": {
          "type": "AMBIENT"
        }
      },
      "stirring": {
        "type": "CUSTOM",
        "details": "The mixture was stirred overnight at room temperature"
      },
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-7be15e461ed84d0c87a29e41c9bbc3d7"
  },
  {
    "input_text": "N-(4-Chlorophenyl)benzene-1,2-diamine (11.2 g) was added to diethyl oxalate (50 ml) and the mixture heated under reflux for 2 hours. The mixture was cooled and ethanol (40 ml) was added. The precipitated solid was filtered off and recrystallised from ethanol giving the title compound (11.2 g) mp>300\u00b0 C.",
    "output_reaction_inputs": {
      "m1_m2": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "N-(4-Chlorophenyl)benzene-1,2-diamine"
              }
            ],
            "amount": {
              "mass": {
                "value": 11.2,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "diethyl oxalate"
              }
            ],
            "amount": {
              "volume": {
                "value": 50.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      },
      "m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "ethanol"
              }
            ],
            "amount": {
              "volume": {
                "value": 40.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-5f67bd962ece4c348acec0776cac1378"
  },
  {
    "input_text": "1-(4-Chlorophenyl)-1,2-dihydro-3-(N,N-diethylamino)ethylaminoquinoxalin-2-one (5.0 g) was dissolved in chloroform (150 ml) and dry hydrogen chloride was bubbled through the solution for 10 minutes. The precipitate was dried and recrystallised from ethanol giving the title compound mp >240\u00b0 C.",
    "output_reaction_inputs": {
      "m1_m2": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "1-(4-Chlorophenyl)-1,2-dihydro-3-(N,N-diethylamino)ethylaminoquinoxalin-2-one"
              }
            ],
            "amount": {
              "mass": {
                "value": 5.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "chloroform"
              }
            ],
            "amount": {
              "volume": {
                "value": 150.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-a21151614f2b40ed92f2eff4c8947795"
  },
  {
    "input_text": "To a solution of N-(4-methoxyphenyl)benzene-1,2-diamine (9.0 g) in ethanol (150 ml) was added a solution of alloxan monohydrate (6.7 g) in water (150 ml) and the mixture was stirred for 30 minutes. The precipitate was filtered off and recrystallised from glacial acetic acid giving the title compound mp 236\u00b0-238\u00b0 C.",
    "output_reaction_inputs": {
      "m1_m3_m2_m4": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "N-(4-methoxyphenyl)benzene-1,2-diamine"
              }
            ],
            "amount": {
              "mass": {
                "value": 9.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "alloxan monohydrate"
              }
            ],
            "amount": {
              "mass": {
                "value": 6.7,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "ethanol"
              }
            ],
            "amount": {
              "volume": {
                "value": 150.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "water"
              }
            ],
            "amount": {
              "volume": {
                "value": 150.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "stirring": {
        "type": "CUSTOM",
        "details": "the mixture was stirred for 30 minutes"
      },
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-62625e2fe9614868958e51327dbb292d"
  },
  {
    "input_text": "To a stirred solution of 3-chloro-1-(4-chlorophenyl)-1,2-dihydroquinoxalin-2-one (20.0 g) in glacial acetic acid (250 ml) was added zinc powder (20.0 g) in small portions during 30 minutes. After a further 15 minutes the mixture was filtered, water was added and the product was extracted into dichloromethane. Evaporation of the solvent and recrystallisation of the residue from ethanol gave the sub-title compound mp 196\u00b0-199\u00b0 C.",
    "output_reaction_inputs": {
      "m1_m2_m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "3-chloro-1-(4-chlorophenyl)-1,2-dihydroquinoxalin-2-one"
              }
            ],
            "amount": {
              "mass": {
                "value": 20.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "acetic acid"
              }
            ],
            "amount": {
              "volume": {
                "value": 250.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "zinc"
              }
            ],
            "amount": {
              "mass": {
                "value": 20.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "CATALYST"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-6589aa323e094b04bd62c6f58317520a"
  },
  {
    "input_text": "A solution of 1-(4-chlorophenyl)-1,2,3,4-tetrahydroquinoxalin-2-one (8.2 g) in dichloromethane (50 ml) was stirred with manganese dioxide (10.0 g) for 4 hours. The mixture was filtered, evaporated, and the residue was recrystallised from ethanol giving the title compound mp 169\u00b0-171\u00b0 C.",
    "output_reaction_inputs": {
      "m1_m2_m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "1-(4-chlorophenyl)-1,2,3,4-tetrahydroquinoxalin-2-one"
              }
            ],
            "amount": {
              "mass": {
                "value": 8.2,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "dichloromethane"
              }
            ],
            "amount": {
              "volume": {
                "value": 50.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "manganese dioxide"
              }
            ],
            "amount": {
              "mass": {
                "value": 10.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "CATALYST"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-b812400383414fb39423b3d7606178bf"
  },
  {
    "input_text": "13.2 gm of N-(2-hydroxy-propyl)-benzimidazolone were dissolved in 150 ml of dioxane, and after addition of 8 ml of SOCl2 the mixture was refluxed for one hour. After evaporation in vacuo, the residue was dissolved in ethyl acetate, and the solution was washed with a sodium bicarbonate solution and water, and dried over Na2SO4. After distilling off the solvent, 13.4 gm of N-(2-chloro-propyl)-benzimidazolone were obtained.",
    "output_reaction_inputs": {
      "m2": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "SOCl2"
              }
            ],
            "amount": {
              "volume": {
                "value": 8.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      },
      "m1_m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "N-(2-hydroxy-propyl)-benzimidazolone"
              }
            ],
            "amount": {
              "mass": {
                "value": 13.2,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "dioxane"
              }
            ],
            "amount": {
              "volume": {
                "value": 150.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-1feec8aed7a74538a89a21b306c36355"
  },
  {
    "input_text": "To a solution of 6,7-dichloro-2,3-dihydro-2-hydroxymethylbenzofuran (10.4 gm.) in acetone (200 ml.) cooled to 20\u00b0 C. is added an oxidizing solution prepared from chromium trioxide (6.0 g.), concentrated sulfuric acid (5.3 ml.) and water (43 ml.) over a one-half hour period. The reaction mixture is stirred at 25\u00b0 C. for 18 hours. The acetone layer is separated from the precipitated chromium salts, added to water (600 ml.) and extracted with ether (2\u00d7150 ml.). The ether extract is washed with water then extracted with aqueous sodium bicarbonate. Acidification of the basic solution gives 3.4 g. of 6,7-dichloro-2,3-dihydrobenzofuran-2-carboxylic acid which is purified by reprecipitation from aqueous sodium hydroxide with aqueous hydrochloric acid.",
    "output_reaction_inputs": {
      "m5_m2_m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "sulfuric acid"
              }
            ],
            "amount": {
              "volume": {
                "value": 5.3,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "water"
              }
            ],
            "amount": {
              "volume": {
                "value": 43.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "chromium trioxide"
              }
            ],
            "amount": {
              "mass": {
                "value": 6.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "CATALYST"
          }
        ]
      },
      "m1_m4": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "6,7-dichloro-2,3-dihydro-2-hydroxymethylbenzofuran"
              }
            ],
            "amount": {
              "mass": {
                "value": 10.4,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "acetone"
              }
            ],
            "amount": {
              "volume": {
                "value": 200.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "temperature": {
        "setpoint": {
          "value": 25.0,
          "units": "CELSIUS"
        }
      },
      "stirring": {
        "type": "CUSTOM",
        "details": "The reaction mixture is stirred at 25\u00b0 C. for 18 hours"
      },
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-ad2eb912455c492f8f452620271b6696"
  },
  {
    "input_text": "A solution of 6,7-dichloro-2,3-dihydrobenzofuran-2-carboxylic acid (70 g.) conc. sulfuric acid (2 ml.) and ethanol (250 ml.) is refluxed for 2 hours. The ethanol is distilled at reduced pressure and the residue is suspended in saturated sodium bicarbonate and extracted with ether. The ether solution is washed with brine, dried over magnesium sulfate and the ether distilled at reduced pressure. The 6,7-dichloro-2,3-dihydrobenzofuran-2-carboxylic acid ethyl ester is used without further purification in the following synthesis.",
    "output_reaction_inputs": {
      "m1_m2_m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "6,7-dichloro-2,3-dihydrobenzofuran-2-carboxylic acid"
              }
            ],
            "amount": {
              "mass": {
                "value": 70.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "sulfuric acid"
              }
            ],
            "amount": {
              "volume": {
                "value": 2.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "ethanol"
              }
            ],
            "amount": {
              "volume": {
                "value": 250.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-b523152ade4e47c5a03f19c7517aab86"
  },
  {
    "input_text": "2.8 ml of 98% acetic acid anhydride were added under an inert atmosphere to a solution of 7.6 g of N,N-dimethyl-\u03b3-(4-amino-phenoxy)-benzene-propanamine in 80 ml of benzene and the mixture was stirred for 45 minutes. 50 ml of 2 N sodium hydroxide were added thereto and the decanted organic phase was washed with aqueous sodium chloride solution and was dried, treated with activated carbon and filtered. The filtrate was evaporated to dryness to obtain 9 g of N-[4-(3-dimethylamino-1-phenyl-propyloxy)-phenyl]acetamide.",
    "output_reaction_inputs": {
      "m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "sodium hydroxide"
              }
            ],
            "amount": {
              "volume": {
                "value": 50.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      },
      "m1_m2_m4": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "acetic acid anhydride"
              }
            ],
            "amount": {
              "volume": {
                "value": 2.8,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "N,N-dimethyl-\u03b3-(4-amino-phenoxy)-benzene-propanamine"
              }
            ],
            "amount": {
              "mass": {
                "value": 7.6,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "benzene"
              }
            ],
            "amount": {
              "volume": {
                "value": 80.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "stirring": {
        "type": "CUSTOM",
        "details": "the mixture was stirred for 45 minutes"
      },
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-1fca68c93d4e4bb3b720bc61f81769d9"
  },
  {
    "input_text": "95 g (0.30 M) of rac-5-(o-fluorophenyl)-1,3-dihydro-3-methyl-7-nitro-2H-1,4-benzodiazepin-2-one are dissolved in 1 liter of absolute acetone and treated with 60 g of powdered potassium carbonate and 43 g of dimethyl sulphate. The mixture is stirred at room temperature for 4 hours and left to stand in a refrigerator for 48 hours. The mixture is then concentrated, treated with ice-water and extracted several times with methylene chloride. The organic solution is dried over sodium sulphate, filtered and concentrated. The residue is crystallised from ethyl acetate/petroleum ether, there being obtained rac-5-(o-fluorophenyl)-1,3-dihydro-1,3-dimethyl-7-nitro-2H-1,4-benzodiazepin-2-one which melts at 154\u00b0-156\u00b0 C.",
    "output_reaction_inputs": {
      "m1_m4": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "rac-5-(o-fluorophenyl)-1,3-dihydro-3-methyl-7-nitro-2H-1,4-benzodiazepin-2-one"
              }
            ],
            "amount": {
              "mass": {
                "value": 95.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "acetone"
              }
            ],
            "amount": {
              "volume": {
                "value": 1.0,
                "units": "LITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      },
      "m2_m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "potassium carbonate"
              }
            ],
            "amount": {
              "mass": {
                "value": 60.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "dimethyl sulphate"
              }
            ],
            "amount": {
              "mass": {
                "value": 43.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "temperature": {
        "control": {
          "type": "AMBIENT"
        }
      },
      "stirring": {
        "type": "CUSTOM",
        "details": "The mixture is stirred at room temperature for 4 hours"
      },
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-4595af9d84234d3abdd4d2bba58beb2c"
  },
  {
    "input_text": "85 g (0.26 M) of rac-5-(o-fluorophenyl)-1,3-dihydro-1,3-dimethyl-7-nitro-2H-1,4-benzodiazepin-2-one are dissolved in 700 ml of concentrated hydrochloric acid and treated slowly with 180 g of stannous chloride. After about 15 minutes, the mixture is cooled with ice and then concentrated on a rotary evaporator. The residue is dissolved in ice-water, slowly made alkaline with 200 g of sodium carbonate in 1 liter of water and extracted several times with methylene chloride. The organic solution is dried over sodium sulphate, filtered and concentrated. The residue is crystallised from ethyl acetate and there is obtained rac-7-amino-5-(o-fluorophenyl)-1,3-dihydro-1,3-dimethyl-2H-1,4-benzodiazepin-2-one which melts at 178\u00b0-180\u00b0 C.",
    "output_reaction_inputs": {
      "m1_m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "rac-5-(o-fluorophenyl)-1,3-dihydro-1,3-dimethyl-7-nitro-2H-1,4-benzodiazepin-2-one"
              }
            ],
            "amount": {
              "mass": {
                "value": 85.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "hydrochloric acid"
              }
            ],
            "amount": {
              "volume": {
                "value": 700.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      },
      "m2": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "stannous chloride"
              }
            ],
            "amount": {
              "mass": {
                "value": 180.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-a862b04fc90e4603b470204c02f91c96"
  },
  {
    "input_text": "57.5 g (0.18 M) of (S)-5-(o-fluorophenyl)-1,3-dihydro-3-methyl-7-nitro-2H-1,4-benzodiazepin-2-one are dissolved in 600 ml of absolute acetone. The solution is treated with 48 g of powdered potassium carbonate and 21 ml of methyl iodide and stirred at room temperature for 5 hours. The mixture is concentrated and the residue is treated with ice-water and extracted several times with methylene chloride. The methylene chloride solution is washed with water, dried over sodium sulphate, filtered and concentrated. The residue is crystallised from ether/petroleum ether and there is obtained (S)-5-(o-fluorophenyl)-1,3-dihydro-1,3-dimethyl-7-nitro-2H-1,4-benzodiazepin-2-one which melts at 118\u00b0-126\u00b0 C. with decomposition; [\u03b1]25D =+563.1\u00b0 (in methylene chloride; 1%).",
    "output_reaction_inputs": {
      "m2_m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "potassium carbonate"
              }
            ],
            "amount": {
              "mass": {
                "value": 48.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "methyl iodide"
              }
            ],
            "amount": {
              "volume": {
                "value": 21.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      },
      "m1_m4": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "(S)-5-(o-fluorophenyl)-1,3-dihydro-3-methyl-7-nitro-2H-1,4-benzodiazepin-2-one"
              }
            ],
            "amount": {
              "mass": {
                "value": 57.5,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "acetone"
              }
            ],
            "amount": {
              "volume": {
                "value": 600.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "temperature": {
        "control": {
          "type": "AMBIENT"
        }
      },
      "stirring": {
        "type": "CUSTOM",
        "details": "stirred at room temperature for 5 hours"
      },
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-42e43699364b489fbb33a1ac84b78d6e"
  },
  {
    "input_text": "11.1 g (0.03 M) of 1-[5-(o-fluorophenyl)-2,3-dihydro-1-methyl-2-oxo-1H-1,4-benzodiazepin-7-yl]-3-(2-hydroxyethyl)urea are stirred at room temperature for 18 hours in 150 ml of acetonitrile with 3.9 ml of acetyl chloride and 9 g of powdered potassium carbonate. The mixture is concentrated on a rotary evaporator and the residue is purified on a 500 g silica gel column using methylene chloride/ethanol as the eluting agent. After crystallisation from ethyl acetate, there is obtained 2-[3-[5-(o-fluorophenyl)-2,3-dihydro-1-methyl-2-oxo-1H-1,4-benzodiazepin-7-yl]ureido]ethyl acetate which melts at 196\u00b0-198\u00b0 C.",
    "output_reaction_inputs": {
      "m1_m4_m2_m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "1-[5-(o-fluorophenyl)-2,3-dihydro-1-methyl-2-oxo-1H-1,4-benzodiazepin-7-yl]-3-(2-hydroxyethyl)urea"
              }
            ],
            "amount": {
              "mass": {
                "value": 11.1,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "acetyl chloride"
              }
            ],
            "amount": {
              "volume": {
                "value": 3.9,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "potassium carbonate"
              }
            ],
            "amount": {
              "mass": {
                "value": 9.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "acetonitrile"
              }
            ],
            "amount": {
              "volume": {
                "value": 150.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-62469bd849684a538fac7385de8c0622"
  },
  {
    "input_text": "3.7 g 1-(2-chloroethyl)-3-[6-chloro-5-(o-fluorophenyl)-2,3-dihydro-1-methyl-2-oxo-1H-1,4-benzodiazepin-7-yl]urea dissolved in 100 ml of acetonitrile are treated with 1.83 g of potassium acetate and 4.21 g of 18-crown-6. The mixture is then stirred at room temperature for 5 days, concentrated, treated with water/methylene chloride and the aqueous solution is extracted several times with methylene chloride. The organic solution is dried with sodium sulphate, filtered and concentrated. The residue is purified on a 350 g silica gel column using ethyl acetate as the eluting agent and crystallised from ethanol/ether. There is obtained 2-[3-[6-chloro-5-(o-fluorophenyl)-2,3-dihydro-1-methyl-2-oxo-1H-1,4-benzodiazepin-7-yl]ureido]ethyl acetate.",
    "output_reaction_inputs": {
      "m1_m4": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "1-(2-chloroethyl)-3-[6-chloro-5-(o-fluorophenyl)-2,3-dihydro-1-methyl-2-oxo-1H-1,4-benzodiazepin-7-yl]urea"
              }
            ],
            "amount": {
              "mass": {
                "value": 3.7,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "acetonitrile"
              }
            ],
            "amount": {
              "volume": {
                "value": 100.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      },
      "m2_m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "potassium acetate"
              }
            ],
            "amount": {
              "mass": {
                "value": 1.83,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "18-crown-6"
              }
            ],
            "amount": {
              "mass": {
                "value": 4.21,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "temperature": {
        "control": {
          "type": "AMBIENT"
        }
      },
      "stirring": {
        "type": "CUSTOM",
        "details": "The mixture is then stirred at room temperature for 5 days"
      },
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-8decbb0a85144a1a84e0a14db4719ebc"
  },
  {
    "input_text": "A solution of 3.36 g (10 millimoles) of 2-(4-(4-chlorobenzoyl)phenoxy)-2-methylpropionoyl chloride in 15 ml of acetone were added, slowly under stirring at room temperature, to a solution of 2.1 g (20 millimoles) of diethanolamine in 30 ml of acetone.",
    "output_reaction_inputs": {
      "m1_m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "2-(4-(4-chlorobenzoyl)phenoxy)-2-methylpropionoyl chloride"
              }
            ],
            "amount": {
              "mass": {
                "value": 3.36,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "acetone"
              }
            ],
            "amount": {
              "volume": {
                "value": 15.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      },
      "m2_m4": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "diethanolamine"
              }
            ],
            "amount": {
              "mass": {
                "value": 2.1,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "acetone"
              }
            ],
            "amount": {
              "volume": {
                "value": 30.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-2544e38ff82147a8b46aa81d8a5f6e70"
  },
  {
    "input_text": "60 g (0.3 mol) of 1,4-dihydroxy-2-naphthoic acid was added to 150 ml of 2,3-dibromopropanol and, under heating at 90\u00b0 C. with stirring, hydrogen chloride gas was bubbled in the mixture during a reaction period of 2 hours. The mixture was cooled to 10\u00b0 to 20\u00b0 C. and the crystals precipitated were collected by filteration to obtain 42.4 g (35% yield) of 1-hydroxy-4-(\u03b2,\u03b3-dibromopropyloxy)-2-naphthoic acid.",
    "output_reaction_inputs": {
      "m1_m2": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "1,4-dihydroxy-2-naphthoic acid"
              }
            ],
            "amount": {
              "mass": {
                "value": 60.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "2,3-dibromopropanol"
              }
            ],
            "amount": {
              "volume": {
                "value": 150.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "temperature": {
        "setpoint": {
          "value": 90.0,
          "units": "CELSIUS"
        }
      },
      "stirring": {
        "type": "CUSTOM",
        "details": "with stirring"
      },
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-871727e329864f6f9d3d0279cb7bc2d2"
  },
  {
    "input_text": "60 g (0.3 mol) of 1,4-dihydroxy-2-naphthoic acid was added to 150 ml of 2-bromoethanol and, under heating at 90\u00b0 C. with stirring, hydrogen chloride gas was bubbled into the mixture during a reaction period of 2 hours. The mixture was then cooled to from 10\u00b0 to 20\u00b0 C. and the crystals precipitated were collected by filtration to obtain 47.4 g (50% yield) of 1-hydroxy-4-(\u03b2-bromoethoxy)-2-naphthoic acid.",
    "output_reaction_inputs": {
      "m1_m2": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "1,4-dihydroxy-2-naphthoic acid"
              }
            ],
            "amount": {
              "mass": {
                "value": 60.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "2-bromoethanol"
              }
            ],
            "amount": {
              "volume": {
                "value": 150.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "temperature": {
        "setpoint": {
          "value": 90.0,
          "units": "CELSIUS"
        }
      },
      "stirring": {
        "type": "CUSTOM",
        "details": "with stirring"
      },
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-513037ecc1254dad9b895a2c7a80966c"
  },
  {
    "input_text": "Sodium bicarbonate (1.7 g, 0.02 mole) and glycine ethyl ester hydrochloride (1.4 g, 0.01 mole) were dissolved in water (10 ml) and a solution of 2,3-dimethyl-2-isopropylbutanoyl chloride (1.6 g, 0.009 mole) in ether (10 ml) was added. The mixture was stirred vigorously at room temperature for 2 hours. After 16 hours at room temperature the ether layer was separated and dried (MgSO4). Removal of the solvent left a white solid which was recrystallised from ether/petroleum ether to give N-(2,3-dimethyl-2-isopropylbutanoyl)glycine ethyl ester, mp. 74.5\u00b0-75.5\u00b0.",
    "output_reaction_inputs": {
      "m1_m2_m4": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "Sodium bicarbonate"
              }
            ],
            "amount": {
              "mass": {
                "value": 1.7,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "glycine ethyl ester hydrochloride"
              }
            ],
            "amount": {
              "mass": {
                "value": 1.4,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "water"
              }
            ],
            "amount": {
              "volume": {
                "value": 10.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      },
      "m3_m5": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "2,3-dimethyl-2-isopropylbutanoyl chloride"
              }
            ],
            "amount": {
              "mass": {
                "value": 1.6,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "ether"
              }
            ],
            "amount": {
              "volume": {
                "value": 10.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "temperature": {
        "control": {
          "type": "AMBIENT"
        }
      },
      "stirring": {
        "type": "CUSTOM",
        "details": "The mixture was stirred vigorously at room temperature for 2 hours"
      },
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-790d24fe12e946e6a4cd5825d5835508"
  },
  {
    "input_text": "A solution of 2-sec-butyl-2,3-dimethylpentanoyl chloride (2.0 g) in benzene (10 ml) was added to a stirred solution of ethanolamine (2.0 g) in benzene (100 ml). After 16 hours the benzene solution was washed with dilute hydrochloric acid and water, dried (MgSO4) and concentrated to give a pale yellow syrup. Distillation of this syrup gave N-(2-hydroxyethyl)-2-sec-butyl-2,3-dimethylpentanamide bp. 125\u00b0-130\u00b0/0.3 mm which slowly solidified on standing.",
    "output_reaction_inputs": {
      "m1_m3_m2_m4": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "2-sec-butyl-2,3-dimethylpentanoyl chloride"
              }
            ],
            "amount": {
              "mass": {
                "value": 2.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "ethanolamine"
              }
            ],
            "amount": {
              "mass": {
                "value": 2.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "benzene"
              }
            ],
            "amount": {
              "volume": {
                "value": 10.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "benzene"
              }
            ],
            "amount": {
              "volume": {
                "value": 100.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-360b1778c9524cf09c1bdc684f0e02a4"
  },
  {
    "input_text": "To lithium aluminum hydride solution (3.9 M; 120 ml) diluted with anhydrous ether (750 ml) is added dropwise 150 g of ethyl 3-chloro-4-cyclohexylphenylglyoxylate with stirring, under nitrogen. The mixture is diluted with 250 ml of ether, and is stirred for 2 hours. The reaction mixture is acidified with 10% hydrochloric acid (450 ml) and extracted with ether/tetrahydrofuran. The aqueous fraction is washed three times with 50 ml portions of ether. The combined ether fractions are washed with water until neutral to litmus, and is dried over potassium carbonate. The ether is removed and the residue is triturated with n-hexane, filtered and air-dried to give 1-(3-chloro-4-cyclohexylphenyl)-1,2-ethanediol.",
    "output_reaction_inputs": {
      "m5": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "ether"
              }
            ],
            "amount": {
              "volume": {
                "value": 250.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      },
      "m2": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "ethyl 3-chloro-4-cyclohexylphenylglyoxylate"
              }
            ],
            "amount": {
              "mass": {
                "value": 150.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      },
      "m1_m4": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "lithium aluminum hydride"
              }
            ],
            "amount": {
              "volume": {
                "value": 120.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "ether"
              }
            ],
            "amount": {
              "volume": {
                "value": 750.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      },
      "m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "hydrochloric acid"
              }
            ],
            "amount": {
              "volume": {
                "value": 450.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "stirring": {
        "type": "CUSTOM",
        "details": "with stirring, under nitrogen"
      },
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-82d63ea03e384ceba20eade100c9a6f7"
  },
  {
    "input_text": "Powdered ethyl \u03b1,\u03b2-dibromo-\u03b2-(3-chloro-4-cyclohexyl)propionate (33.0 g.) is added portion-wise to 20% ethanolic potassium hydroxide (135 ml) at room temperature. The mixture is refluxed on a steam bath for 6 hours. The alcohol is evaporated and the residue is dissolved in water and covered with ether and is acidified with cold, dilute hydrochloric acid. The ether layer is washed with water, saline, and dried over sodium sulfate. The ether is removed to give a residue which is triturated with carbon tetrachloride. Recrystallization is carried out from acetic acid-water. This material is digested and triturated with boiling carbon tetrachloride to give 3-chloro-4-cyclohexylpropiolic acid.",
    "output_reaction_inputs": {
      "m1_m2": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "ethyl \u03b1,\u03b2-dibromo-\u03b2-(3-chloro-4-cyclohexyl)propionate"
              }
            ],
            "amount": {
              "mass": {
                "value": 33.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "potassium hydroxide"
              }
            ],
            "amount": {
              "volume": {
                "value": 135.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-83d329ea911f47a7a6c850b803b09ec6"
  },
  {
    "input_text": "To a solution of 1-(2-tetrahydropyranyloxy)-trans-5-nonen-2-yne (61.5 g) in methanol (250 ml) was added 4% oxalic acid (250 ml). The reaction mixture was refluxed for 2 hours and concentrated under reduced pressure to give a residue, which was extracted with ether, washed with water, dried over magnesium sulfate and concentrated under reduced pressure to give a yellowish oily residue. The oily residue was distilled under reduced pressure to give colorless oily trans-5-nonen-2-yne-1-ol (37 g).",
    "output_reaction_inputs": {
      "m1_m3_m2": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "1-(2-tetrahydropyranyloxy)-trans-5-nonen-2-yne"
              }
            ],
            "amount": {
              "mass": {
                "value": 61.5,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "oxalic acid"
              }
            ],
            "amount": {
              "volume": {
                "value": 250.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "methanol"
              }
            ],
            "amount": {
              "volume": {
                "value": 250.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-eedc9e2a0c75415689799839c63b7a25"
  },
  {
    "input_text": "To a solution of trans, trans, trans-2,4,7-undecatrien-1-ol (3.4 g) in chloroform (300 ml) was added manganese dioxide (30 g). The reaction mixture was stirred for 60 hours at ambient temperature. After the manganese dioxide was removed by filtration, the resultant mixture was concentrated under reduced pressure to give a yellowish oily residue, which was subjected to a column chromatography on silica gel (developing solvent: chloroform) to give colorless oily trans, trans, trans-2,4,7-undecatrienal (2 g).",
    "output_reaction_inputs": {
      "m1_m2_m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "trans-2,4,7-undecatrien-1-ol"
              }
            ],
            "amount": {
              "mass": {
                "value": 3.4,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "chloroform"
              }
            ],
            "amount": {
              "volume": {
                "value": 300.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "manganese dioxide"
              }
            ],
            "amount": {
              "mass": {
                "value": 30.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "CATALYST"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "temperature": {
        "control": {
          "type": "AMBIENT"
        }
      },
      "stirring": {
        "type": "CUSTOM",
        "details": "The reaction mixture was stirred for 60 hours at ambient temperature"
      },
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-ceef52dd2440451dbcf39f839d66cc1e"
  },
  {
    "input_text": "To a solution of trans, trans-2,4-nonadien-1-ol (20 g) in chloroform (400 ml) was added manganese dioxide (125 g). The mixture was stirred for 11 hours at ambient temperature and then filtered. The filtrate was concentrated under reduced pressure to give an oily residue, which was subjected to a column chromatography on silica gel (developing solvent: chloroform). The eluate was concentrated under reduced pressure to give colorless oily trans, trans-2,4-nonadienal (9 g).",
    "output_reaction_inputs": {
      "m1_m2_m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "trans-2,4-nonadien-1-ol"
              }
            ],
            "amount": {
              "mass": {
                "value": 20.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "chloroform"
              }
            ],
            "amount": {
              "volume": {
                "value": 400.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "manganese dioxide"
              }
            ],
            "amount": {
              "mass": {
                "value": 125.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "CATALYST"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "temperature": {
        "control": {
          "type": "AMBIENT"
        }
      },
      "stirring": {
        "type": "CUSTOM",
        "details": "The mixture was stirred for 11 hours at ambient temperature"
      },
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-9941ce206cff4f14aaf6db444c754b16"
  },
  {
    "input_text": "To a solution of trans, trans, trans-2,4,6-undecatrien-1-ol (7.2 g) in chloroform (300 ml) was added manganese dioxide (50 g) and then the mixture was stirred for 15 hours at ambient temperature. The resultant mixture was filtered and the filtrate was concentrated under reduced pressure to give an oily residue, which was subjected to a column chromatography on silica gel (developing solvent: chloroform). The eluate was concentrated under reduced pressure to give oily trans, trans, trans-2,4,6-undecatrienal (5.5. g).",
    "output_reaction_inputs": {
      "m1_m2_m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "trans-2,4,6-undecatrien-1-ol"
              }
            ],
            "amount": {
              "mass": {
                "value": 7.2,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "chloroform"
              }
            ],
            "amount": {
              "volume": {
                "value": 300.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "manganese dioxide"
              }
            ],
            "amount": {
              "mass": {
                "value": 50.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "CATALYST"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "temperature": {
        "control": {
          "type": "AMBIENT"
        }
      },
      "stirring": {
        "type": "CUSTOM",
        "details": "the mixture was stirred for 15 hours at ambient temperature"
      },
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-fa87428232d441e2be2380ca12c4839d"
  },
  {
    "input_text": "To a cold solution of 180 g of 3-isopropyl-3-methyl-5H-imidazo[2,1-a]isoindole-2-(3H),5-dione in 300 ml of dry tetrahydrofuran in a pressure bottle is added 68 g of dimethylamine. The bottle is sealed and the mixture heated to 50\u00b0 C. with stirring for 16 hours. The mixture is cooled, and the contents of the bottle transferred to a flask. The solvent is then removed in vacuo. The crystalline residue is then suspended in ether, filtered, washed with ether, and air-dried to give 195 g of o-(5-isopropyl-5-methyl-4-oxo-2-imidazolin-2-yl)-N,N-dimethylbenzamide, melting point 144\u00b0-146\u00b0 C. This product is recrystallized from acetonitrile to give an analytically pure product, melting point 147\u00b0-150\u00b0 C.",
    "output_reaction_inputs": {
      "m1_m3_m2": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "3-isopropyl-3-methyl-5H-imidazo[2,1-a]isoindole-2-(3H),5-dione"
              }
            ],
            "amount": {
              "mass": {
                "value": 180.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "dimethylamine"
              }
            ],
            "amount": {
              "mass": {
                "value": 68.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "tetrahydrofuran"
              }
            ],
            "amount": {
              "volume": {
                "value": 300.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "temperature": {
        "setpoint": {
          "value": 50.0,
          "units": "CELSIUS"
        }
      },
      "stirring": {
        "type": "CUSTOM",
        "details": "with stirring for 16 hours"
      },
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-642b27ccbf224b80b20dc80a38af0b5f"
  },
  {
    "input_text": "3,5-Bis(trimethylsilyloxy)-1,2,4-triazine (2.5 g) and 2-chlorotetrahydropyran (1.8 g) are dissolved in dimethylformamide (1 ml), and the mixture is stirred overnight at room temperature and concentrated in vacuo. The residue is column-chromatographed over silica gel using a mixture of acetone/n-hexane (1/3) as an eluent. The first major fraction gives 1.0 g (40%) of 2,4-bis(tetrahydro-2-pyranyl)-3,5-dioxo-2,3,4,5-tetrahydro-1,2,4-triazine (Compound No. 87) (yield, 1.0 g; 36%), the second gives 4-(tetrahydro-2-pyranyl)-3,5-dioxo-2,3,4,5-tetrahydro-1,2,4-triazine (Compound No. 88) (yield, 0.8 g; 40%) and the third gives 2-(tetrahydro-2-pyranyl)-3,5-dioxo-2,3,4,5-tetrahydro-1,2,4-triazine (Compound No. 100) (yield, 0.6 g; 30%). Compound Nos. 87 and 88 melt at 32\u00b0 C. and 116\u00b0 C., respectively.",
    "output_reaction_inputs": {
      "m1_m2_m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "3,5-Bis(trimethylsilyloxy)-1,2,4-triazine"
              }
            ],
            "amount": {
              "mass": {
                "value": 2.5,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "2-chlorotetrahydropyran"
              }
            ],
            "amount": {
              "mass": {
                "value": 1.8,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "dimethylformamide"
              }
            ],
            "amount": {
              "volume": {
                "value": 1.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "temperature": {
        "control": {
          "type": "AMBIENT"
        }
      },
      "stirring": {
        "type": "CUSTOM",
        "details": "the mixture is stirred overnight at room temperature"
      },
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-dc0f92aaa36443ad9beeea8d601fede7"
  },
  {
    "input_text": "2-(4-Methylbenzoyloxymethyl)-3,5-dioxo-hexahydro-1,2,4-triazine (1.0 g) is dissolved in methanol (60 ml), and the mixture is added with sodium methoxide (0.21 g) and stirred at room temperature for 30 minutes. The methanol is removed in vacuo, and the resulting white crystals are thoroughly washed with ethanol to give 2-(4-methylbenzoyloxymethyl)-3,5-dioxo-4-sodio-hexahydro-1,2,4-triazine (Compound No. 74). Yield, 0.84 g (77.8%). M.P., 225\u00b0-235\u00b0 C. (decomp.).",
    "output_reaction_inputs": {
      "m2": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "sodium methoxide"
              }
            ],
            "amount": {
              "mass": {
                "value": 0.21,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      },
      "m1_m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "2-(4-Methylbenzoyloxymethyl)-3,5-dioxo-hexahydro-1,2,4-triazine"
              }
            ],
            "amount": {
              "mass": {
                "value": 1.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "methanol"
              }
            ],
            "amount": {
              "volume": {
                "value": 60.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "temperature": {
        "control": {
          "type": "AMBIENT"
        }
      },
      "stirring": {
        "type": "CUSTOM",
        "details": "stirred at room temperature for 30 minutes"
      },
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-44f5ae61552c43e991351d740ddb6eb1"
  },
  {
    "input_text": "3,5-Dioxo-4-sodio-2,3,4,5-tetrahydro-1,2,4-triazine monohydrate (770 mg) dissolved in water (60 ml) is hydrogenated for 4 hours in the presence of platinum oxide (100 mg) at atmospheric pressure. The catalyst is filtered off, and the filtrate is concentrated in vacuo to give a colorless transparent liquid. The liquid is dissolved in ethanol (30 ml), and the solvent is then removed in vacuo to give amorphous solids of 3,5-dioxo-4-sodio-hexahydro-1,2,4-triazine dihydrate (Compound No. 4). Yield, 850 mg (98.2%). Softening temperature, 122.3\u00b0 C.",
    "output_reaction_inputs": {
      "m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "ethanol"
              }
            ],
            "amount": {
              "volume": {
                "value": 30.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      },
      "m1_m2": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "3,5-Dioxo-4-sodio-2,3,4,5-tetrahydro-1,2,4-triazine monohydrate"
              }
            ],
            "amount": {
              "mass": {
                "value": 770.0,
                "units": "MILLIGRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "water"
              }
            ],
            "amount": {
              "volume": {
                "value": 60.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      },
      "m4": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "platinum oxide"
              }
            ],
            "amount": {
              "mass": {
                "value": 100.0,
                "units": "MILLIGRAM"
              }
            },
            "reactionRole": "CATALYST"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-eb59e34e835c404aadd0bc4c26631abd"
  },
  {
    "input_text": "4-Chloro-3,5-dinitro-o-xylene (10.0 grams, 0.043 mole) and i-propylamine (10.1 grams, 0.17 mole) are mixed and refluxed for 12 hours using an efficient reflux condenser. The mixture is then cooled and poured into 100 ml. of 5% hydrochloric acid and extracted with diethyl ether. The ether extract is dried over magnesium sulfate. Removal of the drying agent and solvent leaves an orange oil which readily solidifies. The product is recrystallized from methanol to give 8.7 grams (80%) of an orange solid with melting point 69\u00b0 C. to 70\u00b0 C.",
    "output_reaction_inputs": {
      "m1_m2": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "4-Chloro-3,5-dinitro-o-xylene"
              }
            ],
            "amount": {
              "mass": {
                "value": 10.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "i-propylamine"
              }
            ],
            "amount": {
              "mass": {
                "value": 10.1,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-690bd2cc884646198f5a54bc15ab045e"
  },
  {
    "input_text": "A finely powdered mixture of 15.5 grams (0.051 mole) of 3,5-dinitro-4-chloro-o-toluamide is heated with 12 grams (0.084 mole) of phosphorus pentoxide for 15 minutes at 300\u00b0 C. to 350\u00b0 C. The resulting nitrile is distilled from the reaction flask. Recrystallization of the solidified product from methanol gives the desired product as an analytically pure material.",
    "output_reaction_inputs": {
      "m1": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "3,5-dinitro-4-chloro-o-toluamide"
              }
            ],
            "amount": {
              "mass": {
                "value": 15.5,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      },
      "m2": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "phosphorus pentoxide"
              }
            ],
            "amount": {
              "mass": {
                "value": 12.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-ca7e3011ee1840028dc2e094a7f333ee"
  },
  {
    "input_text": "Methyl 2-methyl-5-nitrobenzyl ether (11.5 g) was dissolved in 125 ml of absolute ethanol. To this was added a solution of sodium sulfide monohydrate (48.3 g) and sodium bicarbonate (16.7 g) in 75 ml of water. The resulting mixture was refluxed until tlc indicated all the starting material was gone. The mixture was then concentrated in vacuo to an oily solid. Methylene chloride was added and the mixture filtered. The methylene chloride layer was separated and dried. After removal of the drying agent, the solvent was concentrated in vacuo to give 9.3 g of a mobile orange liquid,",
    "output_reaction_inputs": {
      "m2_m3_m5": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "sodium sulfide monohydrate"
              }
            ],
            "amount": {
              "mass": {
                "value": 48.3,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "sodium bicarbonate"
              }
            ],
            "amount": {
              "mass": {
                "value": 16.7,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "water"
              }
            ],
            "amount": {
              "volume": {
                "value": 75.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      },
      "m1_m4": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "Methyl 2-methyl-5-nitrobenzyl ether"
              }
            ],
            "amount": {
              "mass": {
                "value": 11.5,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "ethanol"
              }
            ],
            "amount": {
              "volume": {
                "value": 125.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-df7e9dc2ce2d4eb493814bf8209d69b9"
  },
  {
    "input_text": "To 120 ml of concentrated sulfuric acid is added 53.6 g of o-methylacetophenone, while cooling at -10\u00b0. To this cold, stirred solution is added a mixture of 32 ml of 70% nitric acid and 48 ml of concentrated sulfuric acid. The reaction solution is stirred for 21/2 hours between -9\u00b0 and 0\u00b0 and then poured over 800 g of ice. The mixture is extracted with ether and the organic phase washed with water, saturated Na2CO3 solutions, water and finally brine. The ether solution is dried over MgSO4 and evaporated to dryness to give 56.2 g of a pale yellow oil. The oil is crystallized from 95% ethanol to give 25.4 g of product, mp about 50\u00b0 C. Recrystallization from hexane afforded product mp 53\u00b0-55\u00b0 C.",
    "output_reaction_inputs": {
      "m4_m1": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "o-methylacetophenone"
              }
            ],
            "amount": {
              "mass": {
                "value": 53.6,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "sulfuric acid"
              }
            ],
            "amount": {
              "volume": {
                "value": 120.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      },
      "m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "ice"
              }
            ],
            "amount": {
              "mass": {
                "value": 800.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      },
      "m2_m5": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "nitric acid"
              }
            ],
            "amount": {
              "volume": {
                "value": 32.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "sulfuric acid"
              }
            ],
            "amount": {
              "volume": {
                "value": 48.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "stirring": {
        "type": "CUSTOM",
        "details": "To this cold, stirred solution"
      },
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-2a3fabf976654d99bffe4c8c39b9b879"
  },
  {
    "input_text": "A mixture of 4-chloro-\u03b1-methoxy-5-nitro-o-toluic acid (3.6 g.) and phosphorus pentachloride (3.0 g.) in 120 ml of benzene is refluxed for thirty minutes. The mixture is then concentrated in vacuo and the residue boiled with 200 ml of hexane and filtered hot. The filtrate is partially concentrated and chilled to give 2.5 g. of white solid with mp 63\u00b0-65\u00b0.",
    "output_reaction_inputs": {
      "m1_m2_m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "4-chloro-\u03b1-methoxy-5-nitro-o-toluic acid"
              }
            ],
            "amount": {
              "mass": {
                "value": 3.6,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "phosphorus pentachloride"
              }
            ],
            "amount": {
              "mass": {
                "value": 3.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "benzene"
              }
            ],
            "amount": {
              "volume": {
                "value": 120.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-fa347dcbadae44e2b78b16e93a9d7d65"
  },
  {
    "input_text": "A sample of 4-chloro-\u03b1-methoxy-5-nitro-o-toluamide (0.8 g) is added to phosphorus oxychloride (10 ml) and the slurry gradually heated to reflux. After about 10 minutes at reflux, all the solid has dissolved giving a clear yellow solution. The solution is concentrated in vacuo and the crude residue is portioned between ether and water. The ether layer is separated and dried. Removal of the drying agent and concentration of the filtrate in vacuo leaves a crude solid (0.7 g.) with mp 57\u00b0-59\u00b0.",
    "output_reaction_inputs": {
      "m1_m2": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "4-chloro-\u03b1-methoxy-5-nitro-o-toluamide"
              }
            ],
            "amount": {
              "mass": {
                "value": 0.8,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "phosphorus oxychloride"
              }
            ],
            "amount": {
              "volume": {
                "value": 10.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-126a01c6f0b3494b90e6e74c054d1fa2"
  },
  {
    "input_text": "A mixture of methyl 2-methyl-5-nitrobenzyl ether (12 g, 0.066 M), methoxyacetone [20 g (used as solvent)], 2-naphthalenesulfonic acid (0.3 g) and 5% Pt/C (0.7 g) is shaken on a Parr hydrogenator maintaining the temperature below 40\u00b0 with external cooling. The theoretical amount of hydrogen (0.26 M) is consumed and further uptake ceases after 2 hours.",
    "output_reaction_inputs": {
      "m1_m2_m3_m4": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "methyl 2-methyl-5-nitrobenzyl ether"
              }
            ],
            "amount": {
              "mass": {
                "value": 12.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "methoxyacetone"
              }
            ],
            "amount": {
              "mass": {
                "value": 20.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "2-naphthalenesulfonic acid"
              }
            ],
            "amount": {
              "mass": {
                "value": 0.3,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "Pt/C"
              }
            ],
            "amount": {
              "mass": {
                "value": 0.7,
                "units": "GRAM"
              }
            },
            "reactionRole": "CATALYST"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "stirring": {
        "type": "CUSTOM",
        "details": "is shaken on a Parr hydrogenator"
      },
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-b471310070f544c69f0660f3394fbeee"
  },
  {
    "input_text": "N-[2-[(Acetylthio)methyl]-4-methyl-1-oxopentyl]glycine (0.5 g) is dissolved in 30 ml of ethyl acetate along with p-nitrophenol (0.2 g). This solution is cooled to 5\u00b0 C., N,N'-dicyclohexylcarbodiimide (0.4 g) is added portionwise and the reaction mixture is stirred at 5\u00b0 for about 16 hours. The dicyclohexyl urea is filtered off and the filtrate is concentrated thoroughly in vacuo. Isopropyl ether is added to the residue and allowed to sit for about 16 hours. The crystalline solid is filtered to yield 0.4 g of product, melting point 95\u00b0-100\u00b0 C.",
    "output_reaction_inputs": {
      "m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "N,N'-dicyclohexylcarbodiimide"
              }
            ],
            "amount": {
              "mass": {
                "value": 0.4,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      },
      "m1_m4_m2": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "N-[2-[(Acetylthio)methyl]-4-methyl-1-oxopentyl]glycine"
              }
            ],
            "amount": {
              "mass": {
                "value": 0.5,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "p-nitrophenol"
              }
            ],
            "amount": {
              "mass": {
                "value": 0.2,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "ethyl acetate"
              }
            ],
            "amount": {
              "volume": {
                "value": 30.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "temperature": {
        "setpoint": {
          "value": 5.0,
          "units": "CELSIUS"
        }
      },
      "stirring": {
        "type": "CUSTOM",
        "details": "the reaction mixture is stirred at 5\u00b0 for about 16 hours"
      },
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-4ff5f6ce19d44d26bab42629294b0bd9"
  },
  {
    "input_text": "A solution of p-hydroxybenzoic acid (19.2 g., 150 mmole) in 10% aqueous sodium hydroxide (120 ml.) is added to dimethylsulfoxide (DMSO) (480 ml.) previously heated to 80\u00b0 C. n-Octyl bromide (28.95 g., 150 mmole) is added dropwise to the solution. The reaction mixture is stirred for 4 hours at room temperature after which it is poured into ice water (1200 ml.). Conc. hydrochloric acid (30 ml.) is added, and the mixture is allowed to stand until precipitation is complete. The precipitate is collected, dried, and crystallized from acetonitrile-water. m.p. 97\u00b0-99\u00b0 C.",
    "output_reaction_inputs": {
      "m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "n-Octyl bromide"
              }
            ],
            "amount": {
              "mass": {
                "value": 28.95,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      },
      "m5": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "hydrochloric acid"
              }
            ],
            "amount": {
              "volume": {
                "value": 30.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      },
      "m4": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "ice water"
              }
            ],
            "amount": {
              "volume": {
                "value": 1200.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      },
      "m1_m6_m2": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "p-hydroxybenzoic acid"
              }
            ],
            "amount": {
              "mass": {
                "value": 19.2,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "dimethylsulfoxide"
              }
            ],
            "amount": {
              "volume": {
                "value": 480.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "sodium hydroxide"
              }
            ],
            "amount": {
              "volume": {
                "value": 120.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "temperature": {
        "control": {
          "type": "AMBIENT"
        }
      },
      "stirring": {
        "type": "CUSTOM",
        "details": "The reaction mixture is stirred for 4 hours at room temperature after which it"
      },
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-f87f175aed394f3ea24240f0a30f29d7"
  },
  {
    "input_text": "This time, 10 mmols of N-methyl-2,6-dimethyl-4-pyridone were used and 117 g of phosgene were introduced in the course of 2 and a half hours. A yield of 89% of 2-ethylhexanoyl chloride was obtained, after distillation.",
    "output_reaction_inputs": {
      "m1": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "N-methyl-2,6-dimethyl-4-pyridone"
              }
            ],
            "amount": {
              "moles": {
                "value": 10.0,
                "units": "MILLIMOLE"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      },
      "m2": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "phosgene"
              }
            ],
            "amount": {
              "mass": {
                "value": 117.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-209d2b095a704f55823227365638158b"
  },
  {
    "input_text": "The procedure described in Example 1 was used and was applied to a solution of 1 mol of benzoic acid in 140 g of xylene. The reaction was carried out in the presence of 10 mmols of N-butyl-4-pyridone. 120 g of phosgene were introduced in the course of 2 hours 40 minutes. The yield obtained after distillation is 98.5%. Infra-red spectrometry did not reveal any trace of benzoic anhydride in the residue. The latter was recycled and a further batch of one mol of benzoic acid was introduced into the reactor. 120 g of phosgene are introduced in the course of 3 hours and the usual cycle is followed. A yield of 96% of benzoyl chloride was obtained after distillation. The residue still showed no traces of anhydride in infra-red spectrometry.",
    "output_reaction_inputs": {
      "m6": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "xylene"
              }
            ],
            "amount": {
              "mass": {
                "value": 140.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      },
      "m1": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "benzoic acid"
              }
            ],
            "amount": {
              "moles": {
                "value": 1.0,
                "units": "MOLE"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      },
      "m4": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "benzoic acid"
              }
            ],
            "amount": {
              "moles": {
                "value": 1.0,
                "units": "MOLE"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      },
      "m2": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "N-butyl-4-pyridone"
              }
            ],
            "amount": {
              "moles": {
                "value": 10.0,
                "units": "MILLIMOLE"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      },
      "m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "phosgene"
              }
            ],
            "amount": {
              "mass": {
                "value": 120.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      },
      "m5": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "phosgene"
              }
            ],
            "amount": {
              "mass": {
                "value": 120.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-a73fc58458ef4359b5c314e2ff1fc9f7"
  },
  {
    "input_text": "A mixture of N-ethoxycarbonylcyanoacetamide (42 g), triethylorthoformate (40 g) and acetic anhydride (100 ml) is heated at reflux for one hour. The reaction is allowed to stand until cool and then is filtered, washing with ether, to yield \u03b1-cyano-\u03b2-ethoxy-N-ethoxycarbonylacrylamide.",
    "output_reaction_inputs": {
      "m1_m2_m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "N-ethoxycarbonylcyanoacetamide"
              }
            ],
            "amount": {
              "mass": {
                "value": 42.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "triethylorthoformate"
              }
            ],
            "amount": {
              "mass": {
                "value": 40.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "acetic anhydride"
              }
            ],
            "amount": {
              "volume": {
                "value": 100.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-c15e5390453a4046b6a0903e8829e8f7"
  },
  {
    "input_text": "A mixture of \u03b1-cyano-\u03b2-(2,6-dimethylanilino)-N-ethoxycarbonylacrylamide (1.2 g) and about 10 ml of p-cymene is heated at reflux for about 1.5 hour. After cooling on standing, the crystalline product is collected by filtering and washing with ether to yield 5-cyano-1-(2,6-dimethylphenyl)uracil, m.p. 267\u00b0-269\u00b0.",
    "output_reaction_inputs": {
      "m1_m2": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "\u03b1-cyano-\u03b2-(2,6-dimethylanilino)-N-ethoxycarbonylacrylamide"
              }
            ],
            "amount": {
              "mass": {
                "value": 1.2,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "p-cymene"
              }
            ],
            "amount": {
              "volume": {
                "value": 10.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-ae5a8e8150e641f68942589431275530"
  },
  {
    "input_text": "A mixture of 8.8 g (0.03 mol) of \u03b1-cyano-\u03b2-(4-chloroanilino)-N-ethoxycarbonylacrylamide and 40 ml of ortho-dichlorobenzene is heated at reflux. After about 2 hours, crystals appear and the mixture is allowed to cool to room temperature. The mixture is filtered to yield 5-cyano-1-(4-chlorophenyl)uracil, m.p. 236\u00b0-239\u00b0.",
    "output_reaction_inputs": {
      "m1_m2": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "\u03b1-cyano-\u03b2-(4-chloroanilino)-N-ethoxycarbonylacrylamide"
              }
            ],
            "amount": {
              "mass": {
                "value": 8.8,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "ortho-dichlorobenzene"
              }
            ],
            "amount": {
              "volume": {
                "value": 40.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "temperature": {
        "control": {
          "type": "AMBIENT"
        }
      },
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-5f29e2571ed8423bb285087692fc82c8"
  },
  {
    "input_text": "To 10.0 g of \u03b1-cyano-\u03b2-ethoxy-N-ethoxycarbonylacrylamide dissolved in about 40 ml of hot ethanol is added 6.45 g of 2,6-difluoroaniline in 15 ml of ethanol. The reaction mixture is stirred at reflux for about 6 hours, cooled and filtered to yield \u03b1-cyano-\u03b2-(2,6-difluoroanilino)-N-ethoxycarbonylacrylamide, white solid (12.61 g), which is added to 60 ml of tetralin and heated at reflux for 5 hours. The mixture is allowed to cool, filtered and washed with ether to yield 10.21 g of 5-cyano-1-(2,6-difluorophenyl)uracil, white solid.",
    "output_reaction_inputs": {
      "m2_m4": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "\u03b1-cyano-\u03b2-ethoxy-N-ethoxycarbonylacrylamide"
              }
            ],
            "amount": {
              "mass": {
                "value": 10.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "ethanol"
              }
            ],
            "amount": {
              "volume": {
                "value": 40.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      },
      "m3_m5": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "2,6-difluoroaniline"
              }
            ],
            "amount": {
              "mass": {
                "value": 6.45,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "ethanol"
              }
            ],
            "amount": {
              "volume": {
                "value": 15.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "stirring": {
        "type": "CUSTOM",
        "details": "The reaction mixture is stirred"
      },
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-bfdb5b271ee541b690e490df43bc1e13"
  },
  {
    "input_text": "A mixture of \u03b1-cyano-\u03b2-ethoxy-N-ethoxycarbonylacrylamide (10 g) and 45 ml of ethanol is heated to effect dissolution. Then 8.12 g of p-trifluoromethylaniline in 10 ml of ethanol is added and the mixture heated at reflux for 45 minutes. The mixture is cooled and filtered to give 14.01 g of \u03b1-cyano-\u03b2-(4-trifluoromethylanilino)-N-ethoxycarbonylacrylamide, which is added to about 60 ml of tetralin and heated at reflux for several hours. On formation of precipitate, the mixture is allowed to cool and then filtered, washed with ether, to yield 5-cyano-1-(4-trifluoromethylphenyl)uracil, m.p. 230.5\u00b0-231.5\u00b0.",
    "output_reaction_inputs": {
      "m1_m4": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "\u03b1-cyano-\u03b2-ethoxy-N-ethoxycarbonylacrylamide"
              }
            ],
            "amount": {
              "mass": {
                "value": 10.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "ethanol"
              }
            ],
            "amount": {
              "volume": {
                "value": 45.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      },
      "m2_m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "p-trifluoromethylaniline"
              }
            ],
            "amount": {
              "mass": {
                "value": 8.12,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "ethanol"
              }
            ],
            "amount": {
              "volume": {
                "value": 10.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-87ec9cf3b80f4dda893b00e06c9fd81d"
  },
  {
    "input_text": "Following the above procedure, p-methoxyaniline (0.05 mol) is reacted with \u03b1-cyano-\u03b2-ethoxy-N-ethoxycarbonyl-acrylamide (0.05 mol) to yield \u03b1-cyano-\u03b2-(4-methoxyanilino)-N-ethoxycarbonylacrylamide, which is cyclized by heating in tetralin to yield 5-cyano-1-(4-methoxyphenyl)uracil, m.p. 304.5\u00b0-306.5\u00b0.",
    "output_reaction_inputs": {
      "m1": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "p-methoxyaniline"
              }
            ],
            "amount": {
              "moles": {
                "value": 0.05,
                "units": "MOLE"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      },
      "m2": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "\u03b1-cyano-\u03b2-ethoxy-N-ethoxycarbonyl-acrylamide"
              }
            ],
            "amount": {
              "moles": {
                "value": 0.05,
                "units": "MOLE"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-a4a076162024446dbb5ca70c65f8face"
  },
  {
    "input_text": "3-Fluoroaniline (0.05 mol) is reacted with \u03b1-cyano-\u03b2-ethoxy-N-ethoxycarbonylacrylamide (0.05 mol) to yield \u03b1-cyano-\u03b2-(3-fluoroanilino)-N-ethoxycarbonylacrylamide, m.p. 169.5\u00b0-171.0\u00b0, which is heated at reflux in tetralin to yield 5-cyano-1-(3-fluorophenyl)uracil, m.p. 245.5\u00b0-246.5\u00b0.",
    "output_reaction_inputs": {
      "m1_m2": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "3-Fluoroaniline"
              }
            ],
            "amount": {
              "moles": {
                "value": 0.05,
                "units": "MOLE"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "\u03b1-cyano-\u03b2-ethoxy-N-ethoxycarbonylacrylamide"
              }
            ],
            "amount": {
              "moles": {
                "value": 0.05,
                "units": "MOLE"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-abbda641fdcb4c4b9440402fe091f25f"
  },
  {
    "input_text": "To a mixture of 5-cyano-1-(2,6-dimethylphenyl)uracil (0.1 mol) and 80 ml of five percent sodium hydroxide solution, with stirring, is slowly added dimethyl sulfate (0.1 mol). The reaction mixture is stirred for about 2 hours and then filtered, washed with water and dried to yield 5-cyano-1-(2,6-dimethylphenyl)-3-methyluracil, m.p. 198.2\u00b0-199.5\u00b0.",
    "output_reaction_inputs": {
      "m2": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "dimethyl sulfate"
              }
            ],
            "amount": {
              "moles": {
                "value": 0.1,
                "units": "MOLE"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      },
      "m1_m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "5-cyano-1-(2,6-dimethylphenyl)uracil"
              }
            ],
            "amount": {
              "moles": {
                "value": 0.1,
                "units": "MOLE"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "sodium hydroxide"
              }
            ],
            "amount": {
              "volume": {
                "value": 80.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "stirring": {
        "type": "CUSTOM",
        "details": "with stirring"
      },
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-ee416237c73b47f1bed088a9973a89a8"
  },
  {
    "input_text": "A mixture of 5-cyano-1-(2,6-dimethylphenyl)uracil (0.01 mol) and 30 ml of 48% HBr is heated at reflux for about 10 hours. After cooling, the solid product is collected by filtering, washed with water and dried to yield 1-(2,6-dimethylphenyl)uracil.",
    "output_reaction_inputs": {
      "m1_m2": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "5-cyano-1-(2,6-dimethylphenyl)uracil"
              }
            ],
            "amount": {
              "moles": {
                "value": 0.01,
                "units": "MOLE"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "HBr"
              }
            ],
            "amount": {
              "volume": {
                "value": 30.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-a9395aac069f4d26976a99ec99bb4f71"
  },
  {
    "input_text": "5.6 g (0.02 mole) of pGlu-His-OMe are dissolved in 200 cc of MeOH and treated while cold for 2 hours with 4.8 g (6\u00d70.02 mole) of NaOH. The solution which is obtained is acidified to pH 4.5 with 6\u00d70.02 mole of HCl. After being evaporated to dryness under vacuum at 50\u00b0 C., the pGlu-His-OH is obtained, and this can be used without any additional purification. White solid; yield is quantitative.",
    "output_reaction_inputs": {
      "m2": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "NaOH"
              }
            ],
            "amount": {
              "mass": {
                "value": 4.8,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      },
      "m1_m4": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "pGlu-His-OMe"
              }
            ],
            "amount": {
              "mass": {
                "value": 5.6,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "MeOH"
              }
            ],
            "amount": {
              "volume": {
                "value": 200.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      },
      "m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "HCl"
              }
            ],
            "amount": {
              "moles": {
                "value": 0.02,
                "units": "MOLE"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-a4b42c020d9d4a54b4bdea09ec029a33"
  },
  {
    "input_text": "A mixture of 6.7 g (18 mmole) of methyl-2-methoxycarbonyl-6,6-dimethyl-6-sila-n-hexadecanoate (from step C) in 50 ml of methanol and 3.0 g (about 48 mmole) of potassium hydroxide (powder) in 50 ml of methanol is refluxed for 45 min. The resulting mixture is then concentrated to a solid. Dilute hydrochloric acid (2N) is then added to the solid (in excess, to acid pH) and the mixture extracted with methylene chloride. The extract is dried, then concentrated to a residue. The residue is heated to 160\u00b0-170\u00b0 under reduced pressure (approx. 15 mm Hg), for 1 hour, then distilled under high vacuum through a jacketed Vigreux column to obtain refined title product of this step (as the main fraction) at 145\u00b0-140\u00b0 at 0.101-0.090 mm Hg.",
    "output_reaction_inputs": {
      "m1_m3_m2_m4": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "methyl-2-methoxycarbonyl-6,6-dimethyl-6-sila-n-hexadecanoate"
              }
            ],
            "amount": {
              "mass": {
                "value": 6.7,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "potassium hydroxide"
              }
            ],
            "amount": {
              "mass": {
                "value": 3.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "methanol"
              }
            ],
            "amount": {
              "volume": {
                "value": 50.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "methanol"
              }
            ],
            "amount": {
              "volume": {
                "value": 50.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-b28593799bc44db4a2e2d86c5bc9b74e"
  },
  {
    "input_text": "To 0.36 g of 3,4-dimethoxyphenethylamine was added 0.46 g of N-(2-carbamoyl-5-chlorophenyl)glycine and the mixture was stirred at 175\u00b0 to 185\u00b0 C. for 6 hours under nitrogen atmosphere. After cooling, the mixture was dissolved in 50 ml of chloroform and the chloroform solution was filtered to remove insoluble materials. The filtrate was washed with 5% hydrochloric acid, a 5% aqueous sodium carbonate solution and water and then dried. The solvent was evaporated in vacuo, and the residue was subjected to column chromatography on silica gel (15 g) and eluted with a mixture of chloroform and methanol (50:1 by volume). The eluate was concentrated to give 0.44 g of 2-(2-carbamoyl-5-chlorophenylamino)-N-(3,4-dimethoxyphenethyl)acetamide as colorless needles having a melting point of 167.5\u00b0-169\u00b0 C.",
    "output_reaction_inputs": {
      "m1_m2": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "3,4-dimethoxyphenethylamine"
              }
            ],
            "amount": {
              "mass": {
                "value": 0.36,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "N-(2-carbamoyl-5-chlorophenyl)glycine"
              }
            ],
            "amount": {
              "mass": {
                "value": 0.46,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      },
      "m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "chloroform"
              }
            ],
            "amount": {
              "volume": {
                "value": 50.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "stirring": {
        "type": "CUSTOM",
        "details": "the mixture was stirred at 175\u00b0 to 185\u00b0 C. for 6 hours under nitrogen atmosphere"
      },
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-85a476f0c50c4da49095a556ec2b89e2"
  },
  {
    "input_text": "100 ml of dimethylformamide was added to a mixture of 25.8 g of 2-chloro-N-(3,4-dimetoxyphenethyl)acetamide, 13.6 g of m-aminobenzamide, 15.0 g of sodium iodide and 20.0 g of calcium carbonate, and the mixture was stirred at 60\u00b0 C. for 4 hours. The same procedure as described in Example 1 was followed to obtain 2-(3-carbamoylphenylamino)-N-(3,4-dimethoxyphenethyl)acetamide. The product was converted to the corresponding hydrochloride salt as described in Example 5. The salt was recrystallized from a mixture of methanol and diethyl ether to obtain 21.7 g of 2-(3-carbamoylphenylamino)-N-(3,4-dimethoxyphenethyl)acetamide hydrochloride having a melting point of 142\u00b0-155\u00b0 C. (dec.).",
    "output_reaction_inputs": {
      "m5_m1_m2_m3_m4": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "2-chloro-N-(3,4-dimetoxyphenethyl)acetamide"
              }
            ],
            "amount": {
              "mass": {
                "value": 25.8,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "m-aminobenzamide"
              }
            ],
            "amount": {
              "mass": {
                "value": 13.6,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "sodium iodide"
              }
            ],
            "amount": {
              "mass": {
                "value": 15.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "calcium carbonate"
              }
            ],
            "amount": {
              "mass": {
                "value": 20.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "dimethylformamide"
              }
            ],
            "amount": {
              "volume": {
                "value": 100.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "temperature": {
        "setpoint": {
          "value": 60.0,
          "units": "CELSIUS"
        }
      },
      "stirring": {
        "type": "CUSTOM",
        "details": "the mixture was stirred at 60\u00b0 C. for 4 hours"
      },
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-d127022fb13e40e8b21bad5422700896"
  },
  {
    "input_text": "A suspension of 1 g of 2-(3-carbamoylphenylamino)-N-(3,4-dimethoxyphenethyl)acetamide hydrochloride in 20 ml of water was vigorously stirred, whereupon the mixture became a viscous liquid at once and subsequently crystals were formed again. After stirring was continued for 30 minutes, the crystals were collected by filtration, washed with water and then air-dried by allowing to stand at room temperature for 10 days to obtain 0.88 g of 2-(3-carbamoylphenylamino)-N-(3,4-dimethoxyphenethyl)acetamide trihydrate as a crystalline powder having a melting point of 51\u00b0-56\u00b0 C.",
    "output_reaction_inputs": {
      "m1_m2": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "2-(3-carbamoylphenylamino)-N-(3,4-dimethoxyphenethyl)acetamide hydrochloride"
              }
            ],
            "amount": {
              "mass": {
                "value": 1.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "water"
              }
            ],
            "amount": {
              "volume": {
                "value": 20.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "stirring": {
        "type": "CUSTOM",
        "details": "was vigorously stirred, whereupon the mixture"
      },
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-582567d9709b416082f49249fa8be3ce"
  },
  {
    "input_text": "To 0.2 g of pulverized 2-(3-carbamoylphenylamino)-N-(3,4-dimethoxyphenethyl)acetamide was added 100 ml of water and the mixture was stirred at 60\u00b0 to 65\u00b0 C. for 30 minutes to dissolve the powder completely. The solution was then concentrated under reduced pressure at 60\u00b0 C. until about 40 ml of residual liquid was left, and allowed to stand at room temperature overnight. The colorless needles precipitated were collected by filtration, washed with water and then air-dried by allowing to stand at room temperature to obtain 0.13 g of 2-(3-carbamoylphenylamino)-N-(3,4-dimethoxyphenethyl)acetamide trihydrate having a melting point of 54\u00b0-57\u00b0 C.",
    "output_reaction_inputs": {
      "m1_m2": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "2-(3-carbamoylphenylamino)-N-(3,4-dimethoxyphenethyl)acetamide"
              }
            ],
            "amount": {
              "mass": {
                "value": 0.2,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "water"
              }
            ],
            "amount": {
              "volume": {
                "value": 100.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "stirring": {
        "type": "CUSTOM",
        "details": "the mixture was stirred at 60\u00b0 to 65\u00b0 C. for 30 minutes"
      },
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-f584edcc0fe4495a936c2f46d3771082"
  },
  {
    "input_text": "To a mixture of 6.8 g of 3-aminobenzamide, 5.5 g of methyl monochloroacetate and 10.0 g of calcium carbonate was added 30 ml of dimethylformamide and the mixture was stirred at 110\u00b0 to 120\u00b0 C. for 2 hours. The inorganic salt precipitated was filtered off and the filtrate was concentrated under reduced pressure. 50 ml of water was added to the resulting residue and the mixture was stirred to precipitate crystals. The crystals were collected by filtration, dried and recrystallized from a mixture of methanol and diethyl ether to obtain 5.7 g of N-(3-carbamoylphenyl)glycine methyl ester as colorless needles having a melting point of 146\u00b0-147\u00b0 C.",
    "output_reaction_inputs": {
      "m1_m2_m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "3-aminobenzamide"
              }
            ],
            "amount": {
              "mass": {
                "value": 6.8,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "methyl monochloroacetate"
              }
            ],
            "amount": {
              "mass": {
                "value": 5.5,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "calcium carbonate"
              }
            ],
            "amount": {
              "mass": {
                "value": 10.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      },
      "m4": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "dimethylformamide"
              }
            ],
            "amount": {
              "volume": {
                "value": 30.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "stirring": {
        "type": "CUSTOM",
        "details": "the mixture was stirred at 110\u00b0 to 120\u00b0 C. for 2 hours"
      },
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-d131304facaa4f75a93dc596b4b6bdb7"
  },
  {
    "input_text": "To n-butanol (100 ml.) add 5-cyano-salicylaldehyde (6 g.), 2-thiobarbituric acid (6 g.) and methanesulfonic acid (10 ml.) With stirring, heat the mixture to reflux for 11/2 hours. Cool, filter, and wash the solid with isopropanol and ether to yield 7-cyano-(1H,3H,5H)-(1)-benzopyrano-(2,3-d)-pyrimidine-4-one-2-thione.",
    "output_reaction_inputs": {
      "m4_m1_m2_m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "5-cyano-salicylaldehyde"
              }
            ],
            "amount": {
              "mass": {
                "value": 6.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "2-thiobarbituric acid"
              }
            ],
            "amount": {
              "mass": {
                "value": 6.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "methanesulfonic acid"
              }
            ],
            "amount": {
              "volume": {
                "value": 10.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "n-butanol"
              }
            ],
            "amount": {
              "volume": {
                "value": 100.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "stirring": {
        "type": "CUSTOM",
        "details": "With stirring"
      },
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-6443daa7b40a4185803feb655054d997"
  },
  {
    "input_text": "To a solution of 5-hydroxymethyl-salicylaldehyde (5.8 g.) and 2-thiobarbituric acid (6 g.) in n-butanol (100 ml.) add methanesulfonic acid (10 ml.) and heat to reflux, with stirring, for 1 hour. Cool, filter and wash the solid with ethanol and ether to yield 7-n-butyloxymethyl-(1H,3H,5H)-(1)-benzopyrano-(2,3-d)-pyrimidine-4-one-2-thione.",
    "output_reaction_inputs": {
      "m1_m2_m4_m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "5-hydroxymethyl-salicylaldehyde"
              }
            ],
            "amount": {
              "mass": {
                "value": 5.8,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "2-thiobarbituric acid"
              }
            ],
            "amount": {
              "mass": {
                "value": 6.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "methanesulfonic acid"
              }
            ],
            "amount": {
              "volume": {
                "value": 10.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "n-butanol"
              }
            ],
            "amount": {
              "volume": {
                "value": 100.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "stirring": {
        "type": "CUSTOM",
        "details": "with stirring, for 1 hour"
      },
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-e2191dd56f2446eeb0103dd94f1827d4"
  },
  {
    "input_text": "While stirring and with ice cooling, a solution of 17.6 g of t-butanol and 19.2 ml of pyridine in 60 ml of dichloromethane is dripped into a solution, cooled at 5\u00b0 C., of 62 g of \u03b1-chloro-\u03b1-(2,4-dichlorophenyl)-acetyl chloride in 60 ml of dichloromethane in such a manner that the temperature of the reaction mixture stays below 10\u00b0 C. After all the solution has been dripped in, the mixture is stirred overnight at room temperature, is then diluted with 100 ml of dichloromethane and extracted 5 times, each time with 100 ml of water. The organic phase is dried over magnesium sulfate and distilled after the solvent has been evaporated. There is obtained 58 g of \u03b1-chloro-\u03b1-(2,4-dichlorophenyl)-acetic acid t-butyl ester as a colorless oil; b.p. 98\u00b0-103\u00b0 C./0.13 mbar.",
    "output_reaction_inputs": {
      "m4": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "dichloromethane"
              }
            ],
            "amount": {
              "volume": {
                "value": 60.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      },
      "m3_m5": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "\u03b1-chloro-\u03b1-(2,4-dichlorophenyl)-acetyl chloride"
              }
            ],
            "amount": {
              "mass": {
                "value": 62.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "dichloromethane"
              }
            ],
            "amount": {
              "volume": {
                "value": 60.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      },
      "m1": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "t-butanol"
              }
            ],
            "amount": {
              "mass": {
                "value": 17.6,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      },
      "m6": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "dichloromethane"
              }
            ],
            "amount": {
              "volume": {
                "value": 100.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      },
      "m2": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "pyridine"
              }
            ],
            "amount": {
              "volume": {
                "value": 19.2,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "stirring": {
        "type": "CUSTOM",
        "details": "While stirring and with ice cooling"
      },
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-f400aa52fe434e649fda6c635634b4cc"
  },
  {
    "input_text": "A mixture of 8.29 g of the diethylamine salt of Step A of Example 5 and 24 ml of 50% aqueous formic acid was heated at 45\u00b0 C. for 15 minutes and was then vacuum filtered to remove triphenyl carbinol. The filtrate was evaporated to dryness under reduced pressure and the residue was taken up in ethanol several times to obtain 3.5 g of a product identical to that of Examples 5,6 and 7.",
    "output_reaction_inputs": {
      "m1_m2": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "diethylamine"
              }
            ],
            "amount": {
              "mass": {
                "value": 8.29,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "formic acid"
              }
            ],
            "amount": {
              "volume": {
                "value": 24.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "temperature": {
        "setpoint": {
          "value": 45.0,
          "units": "CELSIUS"
        }
      },
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-2a20b4d244914ed2b5e4956048cf6123"
  },
  {
    "input_text": "8.7 g (0.0365 mol) of 2,2-dimethyl-3-(3,3,3-trifluoro-2-methoxy-prop-1-enyl)-cyclopropanecarboxylic acid were dissolved in 100 ml of carbon tetrachloride, and 21 g of thionyl chloride were slowly added dropwise at 60\u00b0 C., while stirring. The mixture was then heated to the reflux temperature for 4 hours. After this reaction time, excess thionyl chloride and carbon tetrachloride were distilled off under a waterpump vacuum. The residue was distilled in vacuo. 6 g (64.2% of theory) of 2,2-dimethyl-3-(3,3,3-trifluoro-2-methoxy-prop-1-enyl)-cyclopropanecarboxylic acid chloride were obtained as a slightly yellow liquid with a boiling point of 80\u00b0 C./2 mbar.",
    "output_reaction_inputs": {
      "m1_m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "2,2-dimethyl-3-(3,3,3-trifluoro-2-methoxy-prop-1-enyl)-cyclopropanecarboxylic acid"
              }
            ],
            "amount": {
              "mass": {
                "value": 8.7,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "carbon tetrachloride"
              }
            ],
            "amount": {
              "volume": {
                "value": 100.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      },
      "m2": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "thionyl chloride"
              }
            ],
            "amount": {
              "mass": {
                "value": 21.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "stirring": {
        "type": "CUSTOM",
        "details": "while stirring"
      },
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-16ec1e3b80c84cdcb58119aa97e293c5"
  },
  {
    "input_text": "The same compound is also prepared as follows: 11.5 g of n-butyl isothiocyanate are added to 11.4 g of N,N-diethyl-acetamidine, whereupon the mixture becomes exothermic. The mixture is left to stand for 1 hour at 60\u00b0 and the resulting adduct is used in the following experiment. A mixture of 22.9 g of the crude product and 27.9 g of 4-chloro-3-nitro-phenacyl bromide in 200 ml of isopropanol is refluxed for 2 hours. The solution is worked up as described above, yielding 4-chloro-3-nitro-1-(4-methyl-2-n-butylamino-5-thiazoloyl)-benzene.",
    "output_reaction_inputs": {
      "m3_m4_m5": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "crude product"
              }
            ],
            "amount": {
              "mass": {
                "value": 22.9,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "4-chloro-3-nitro-phenacyl bromide"
              }
            ],
            "amount": {
              "mass": {
                "value": 27.9,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "isopropanol"
              }
            ],
            "amount": {
              "volume": {
                "value": 200.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      },
      "m1_m2": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "n-butyl isothiocyanate"
              }
            ],
            "amount": {
              "mass": {
                "value": 11.5,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "N,N-diethyl-acetamidine"
              }
            ],
            "amount": {
              "mass": {
                "value": 11.4,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-6b81f8a6adc64f01aa1cb27e58c9f2d5"
  },
  {
    "input_text": "7 g of 1-amino-2-nitro-4-(4-methyl-2-isobutylamino-5-thiazoloyl)-benzene are reduced with 40 g of stannous chloride in 150 ml of acetic acid analogously to Example 1. Oily 1,2-diamino-4-(4-methyl-2-isobutylamino-5-thiazoloyl)-benzene is obtained and this is used in the following step.",
    "output_reaction_inputs": {
      "m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "acetic acid"
              }
            ],
            "amount": {
              "volume": {
                "value": 150.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      },
      "m1": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "1-amino-2-nitro-4-(4-methyl-2-isobutylamino-5-thiazoloyl)-benzene"
              }
            ],
            "amount": {
              "mass": {
                "value": 7.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      },
      "m2": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "stannous chloride"
              }
            ],
            "amount": {
              "mass": {
                "value": 40.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-41489766065b499ab5de2a7514e5174b"
  },
  {
    "input_text": "The starting material is prepared as follows: A mixture of 3.7 g of N-acetyl-N',N'-dimethyl-thiourea and 7 g of 4-chloro-3-nitro-phenacyl bromide in 100 ml of isopropanol is refluxed for 2 hours, cooled and filtered. The residue is rendered basic and extracted with methylene chloride. The extract is dried and evaporated and the residue is recrystallised from a mixture of ethyl acetate and hexane, yielding 4-chloro-3-nitro-1-(4-methyl-2-dimethylamino-5-thiazoloyl)-benzene, which melts at 165\u00b0-169\u00b0.",
    "output_reaction_inputs": {
      "m1_m2_m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "N-acetyl-N',N'-dimethyl-thiourea"
              }
            ],
            "amount": {
              "mass": {
                "value": 3.7,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "4-chloro-3-nitro-phenacyl bromide"
              }
            ],
            "amount": {
              "mass": {
                "value": 7.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "isopropanol"
              }
            ],
            "amount": {
              "volume": {
                "value": 100.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-a354118cb09546babbb1b35628b7af3f"
  },
  {
    "input_text": "1.0 g (0.0035 mol) of (\u00b1)-trans-3-(Z-2-chloro-2-(4-chloro-phenyl)-vinyl)-2,2-dimethyl-cyclopropanecarboxylic acid were dissolved in 20 ml of carbon tetrachloride, and 5 ml of thionyl chloride were added dropwise slowly at 25\u00b0 C., while stirring. The mixture was then heated to the reflux temperature for 4 hours. After this reaction time, excess thionyl chloride and carbon tetrachloride were distilled off under a waterpump vacuum. Last residues of solvent were removed by brief incipient distillation at a bath temperature of 60\u00b0 C./2 mm Hg. 1.03 g (96.9% of theory) of (\u00b1)-trans-3-(Z-2-chloro-2-(4-chloro-phenyl)-vinyl)-2,2-dimethyl-cyclopropanecarboxylic acid chloride were obtained as an oily liquid. ##STR21##",
    "output_reaction_inputs": {
      "m2": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "thionyl chloride"
              }
            ],
            "amount": {
              "volume": {
                "value": 5.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      },
      "m1_m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "(\u00b1)-trans-3-(Z-2-chloro-2-(4-chloro-phenyl)-vinyl)-2,2-dimethyl-cyclopropanecarboxylic acid"
              }
            ],
            "amount": {
              "mass": {
                "value": 1.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "carbon tetrachloride"
              }
            ],
            "amount": {
              "volume": {
                "value": 20.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "stirring": {
        "type": "CUSTOM",
        "details": "while stirring"
      },
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-90c4267b33b840dc91ebb9f529a132b5"
  },
  {
    "input_text": "Palladium on charcoal (5%, 110 mg.) is added to a solution of 2-ethylidene-17\u03b2-methoxy-5\u03b1-androstan-3-one (Preparation 1, 1.5 g.) and shaken under hydrogen. The catalyst is removed by filtration and the filtrate is concentrated to dryness and chromatographed to give 2\u03b2-ethyl-17\u03b2-methoxy-5\u03b1-androstan-3-one.",
    "output_reaction_inputs": {
      "m2_m1": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "2-ethylidene-17\u03b2-methoxy-5\u03b1-androstan-3-one"
              }
            ],
            "amount": {
              "mass": {
                "value": 1.5,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "Palladium on charcoal"
              }
            ],
            "amount": {
              "mass": {
                "value": 110.0,
                "units": "MILLIGRAM"
              }
            },
            "reactionRole": "CATALYST"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "stirring": {
        "type": "CUSTOM",
        "details": "shaken under hydrogen"
      },
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-580dd025238242c3964e704182ed7ac8"
  },
  {
    "input_text": "Ethereal diazomethane (40 ml. generated from 3 g. of N-methyl-N'-nitro-N-nitrosoguinidine) is added to a mixture of 17\u03b2-methoxy-5\u03b1-androst-1-en-3-one (IV, Example 23, 1.0 g.) and palladium diacetate (10 mg.) in diethyl ether (20 ml.). After a few hours the organic diluents are removed by reduced pressure and the residue is column chromatographed thru silica gel (100 g.) eluting by gradient between ethyl acetate:SSB (5:95, 5 l.) and ethyl acetate:SSB (20:80, 5 l.). The appropriate fractions (TLC) are pooled and concentrated to give the title compound, m.p. 114\u00b0-118\u00b0; MS (m/e) 316, 301, 269, and 243; NMR (CDCl3) 0.77, 0.97, 3.23 and 3.34 \u03b4; CMR (CDCl3) 9.66 \u03b4.",
    "output_reaction_inputs": {
      "m1_m2_m4_m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "diazomethane"
              }
            ],
            "amount": {
              "volume": {
                "value": 40.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "17\u03b2-methoxy-5\u03b1-androst-1-en-3-one"
              }
            ],
            "amount": {
              "mass": {
                "value": 1.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "diethyl ether"
              }
            ],
            "amount": {
              "volume": {
                "value": 20.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "palladium diacetate"
              }
            ],
            "amount": {
              "mass": {
                "value": 10.0,
                "units": "MILLIGRAM"
              }
            },
            "reactionRole": "CATALYST"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-2eb83d9020dc472a9c5a97ebbfae12b8"
  },
  {
    "input_text": "Sodium borohydride (0.37 gms.) is added to a mixture of 17\u03b2-methoxy-5\u03b1-androstan-3-one (3 gms.) and isopropylalcohol (95%, 35 ml.). The mixture is stirred at 20\u00b0-25\u00b0 for one hour and then is concentrated to dryness. The residue is column chromatographed on a size C prepacked Merck silica gel column. Elution was performed with ethyl acetate:cyclohexane, 10:90. 6 Ml. fractions are collected. The appropriate fractions (TLC) are combined and concentrated to dryness. The residue is recrystallized from isopropyl ether to give 3\u03b1-hydroxy-17\u03b2-methoxy-5\u03b1-androstane, m.p. 164\u00b0-167\u00b0; IR (mull) 3290, 3220, 1120, 1110, 1005 cm-1 ; NMR (CDCl3) 0.72, 0.76, 0.9-2.0, 3.21, 3.3, and 4.01 \u03b4 and 3\u03b2-hydroxy-17\u03b2-methoxy-5\u03b1-androstane, m.p. 150\u00b0-152\u00b0; NMR (CDCl3) 0.75-2.0, 3.25, 3.37 and 3.6 \u03b4.",
    "output_reaction_inputs": {
      "m1_m2_m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "Sodium borohydride"
              }
            ],
            "amount": {
              "mass": {
                "value": 0.37,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "17\u03b2-methoxy-5\u03b1-androstan-3-one"
              }
            ],
            "amount": {
              "mass": {
                "value": 3.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "isopropylalcohol"
              }
            ],
            "amount": {
              "volume": {
                "value": 35.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "stirring": {
        "type": "CUSTOM",
        "details": "The mixture is stirred at 20\u00b0-25\u00b0 for one hour"
      },
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-bfcf29539a0d42edac5b7214a999a796"
  },
  {
    "input_text": "Following the addition of 4 ml of DBN (1,5-diazabicyclo-[4,3,0]-non-5-ene), 98.1 g (1 mole) of cyclohexane oxide (Aldrich) were added dropwise to 65 g of ethane thiol (1.05 moles) in 300 ml of methanol. The mixture was kept under reflux overnight in a steam bath, the reflux temperature rising from 325\u00b0 K. to 338\u00b0 K. After adjustment to pH~8 with carbon dioxide, the methanol was distilled off and the residue was fractionated in vacuo.",
    "output_reaction_inputs": {
      "m3_m4": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "ethane thiol"
              }
            ],
            "amount": {
              "mass": {
                "value": 65.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "methanol"
              }
            ],
            "amount": {
              "volume": {
                "value": 300.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      },
      "m1_m2": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "DBN"
              }
            ],
            "amount": {
              "volume": {
                "value": 4.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "cyclohexane oxide"
              }
            ],
            "amount": {
              "mass": {
                "value": 98.1,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-7ffeb1c1f2f740058d3cea42fe1632cd"
  },
  {
    "input_text": "6 g of methyl isocyanate in 15 ml of ethyl acetate were added dropwise at room temperature to a solution of 16.5 g of 1-amino-3,6-dithiaoctane in 40 ml of ethylacetate. The urea precipitated was recrystallised twice from methanol/water.",
    "output_reaction_inputs": {
      "m1_m3_m2_m4": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "methyl isocyanate"
              }
            ],
            "amount": {
              "mass": {
                "value": 6.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "1-amino-3,6-dithiaoctane"
              }
            ],
            "amount": {
              "mass": {
                "value": 16.5,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "ethyl acetate"
              }
            ],
            "amount": {
              "volume": {
                "value": 15.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "ethylacetate"
              }
            ],
            "amount": {
              "volume": {
                "value": 40.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-98b0d249dda34bff9b31a6ece2bf5710"
  },
  {
    "input_text": "14.0 g (0.07 mol) of 4-chlorobenzophenone, 10.0 g (0.93 mol) of 1-thioglycerol and 28.5 g (0.21 mol) of potassium carbonate in 60 ml of dimethylacetamide are kept at 110\u00b0 C. for 6 hours, under N2 gas and with stirring. After cooling, the reaction mixture is poured into 200 ml of water. The crude product, which is obtained in the form of an oil, is taken up in ethyl acetate, the solution is washed with water until neutral, dried over K2CO3 and concentrated, isopropanol is poured over the concentrate and the resulting mixture is stirred. The product, which is obtained in the form of crystals, is filtered off. 9.4 g (47%); melting point 86\u00b0-88\u00b0 C.",
    "output_reaction_inputs": {
      "m1_m2_m3_m5": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "4-chlorobenzophenone"
              }
            ],
            "amount": {
              "mass": {
                "value": 14.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "1-thioglycerol"
              }
            ],
            "amount": {
              "mass": {
                "value": 10.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "potassium carbonate"
              }
            ],
            "amount": {
              "mass": {
                "value": 28.5,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "dimethylacetamide"
              }
            ],
            "amount": {
              "volume": {
                "value": 60.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      },
      "m4": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "water"
              }
            ],
            "amount": {
              "volume": {
                "value": 200.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "stirring": {
        "type": "CUSTOM",
        "details": "with stirring"
      },
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-b16a223e0ba84ab59f7f53f99630190c"
  },
  {
    "input_text": "Into the same flask as in Example 1 are placed 400 ml of water, 87 g of sulfuric acid, 5 g of manganic sulfate and 100 g of p-methoxytoluene, and the mixture is stirred. Into a 1-liter beaker are placed 540 ml of water, 86 g of chromic anhydride and 246 g of sulfuric acid to prepare an oxidizing solution. The oxidation process of Example 2 is repeated in the same manner except that the reaction temperature is maintained at 80\u00b0 C for 21/3 hours. The reaction mixture is treated in the same manner as in Example 1, affording 70 g of anisaldehyde, 27 g of unreacted p-methoxytoluene and 5 g of the residue. Conversion 73%. Yield 86%. Aldehyde selectivity 80%.",
    "output_reaction_inputs": {
      "m7": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "sulfuric acid"
              }
            ],
            "amount": {
              "mass": {
                "value": 246.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      },
      "m8": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "water"
              }
            ],
            "amount": {
              "volume": {
                "value": 540.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      },
      "m9": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "water"
              }
            ],
            "amount": {
              "volume": {
                "value": 400.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      },
      "m6": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "chromic anhydride"
              }
            ],
            "amount": {
              "mass": {
                "value": 86.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      },
      "m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "sulfuric acid"
              }
            ],
            "amount": {
              "mass": {
                "value": 87.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      },
      "m5": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "p-methoxytoluene"
              }
            ],
            "amount": {
              "mass": {
                "value": 100.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      },
      "m4": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "manganic sulfate"
              }
            ],
            "amount": {
              "mass": {
                "value": 5.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "temperature": {
        "setpoint": {
          "value": 80.0,
          "units": "CELSIUS"
        }
      },
      "stirring": {
        "type": "CUSTOM",
        "details": "the mixture is stirred"
      },
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-de53053a72e44066b382014d1cb7aeb9"
  },
  {
    "input_text": "To a mixture of \u03b2-(2-aminomethyl-1,4-cyclohexadienyl)propionic acid (1.40 L g., 7.7 mmoles) and triethylamine (2.02 g., 20 mmoles) in 50% aqueous THF (20 ml.) was added a solution of t-butyl azidoformate (1.43 g., 10 mmoles) in THF (5 ml.) and the reaction mixture was stirred overnight at room temperature. The mixture was washed with ether (2\u00d720 ml) and the aqueous layer was acidified to pH 2 with dil. hydrochloric acid. The mixture was extracted with chloroform (4\u00d730 ml.) and the combined extracts were washed with water and dried. Evaporation of the extracts under reduced pressure afforded \u03b2-(2-tert.-butoxycarbonylaminomethyl-1,4-cyclohexadienyl)propionic acid as a colorless oil. Yield, 2.10 g. (97%).",
    "output_reaction_inputs": {
      "m1_m2_m4": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "\u03b2-(2-aminomethyl-1,4-cyclohexadienyl)propionic acid"
              }
            ],
            "amount": {
              "volume": {
                "value": 1.4,
                "units": "LITER"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "triethylamine"
              }
            ],
            "amount": {
              "mass": {
                "value": 2.02,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "THF"
              }
            ],
            "amount": {
              "volume": {
                "value": 20.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      },
      "m3_m5": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "t-butyl azidoformate"
              }
            ],
            "amount": {
              "mass": {
                "value": 1.43,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "THF"
              }
            ],
            "amount": {
              "volume": {
                "value": 5.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "temperature": {
        "control": {
          "type": "AMBIENT"
        }
      },
      "stirring": {
        "type": "CUSTOM",
        "details": "the reaction mixture was stirred overnight at room temperature"
      },
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-424610a688a043c1a85682f37bc1671f"
  },
  {
    "input_text": "A mixture of 3-aminomethyl-2-thienylacetic acid 8 (3.1 g, 18 m moles) and triethylamine (8 g, 80 m moles) in 50% aqueous acetone (80 ml) was added dropwise t-butoxycarbonyl azide (5.7 g, 40 m moles) over a period of 20 mins. at 0\u00b0 C. with vigorous stirring. The reaction mixture was stirred overnight at room temperature and concentrated under reduced pressure. The concentrate was washed with ether (2\u00d720 ml), adjusted to pH 2 with conc. HCl and extracted with ethyl acetate (2\u00d750 ml). The ethyl acetate extracts were washed with saturated aqueous sodium chloride, dried over MgSO4, treated with charcoal and evaporated under reduced pressure. The residue was triturated with n-hexane and crystallized from n-hexane and benzene to give 4.5 g (92%) of colorless needles 9, melting at 62\u00b0-63\u00b0 C.",
    "output_reaction_inputs": {
      "m1_m2_m4": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "3-aminomethyl-2-thienylacetic acid"
              }
            ],
            "amount": {
              "mass": {
                "value": 3.1,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "triethylamine"
              }
            ],
            "amount": {
              "mass": {
                "value": 8.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "acetone"
              }
            ],
            "amount": {
              "volume": {
                "value": 80.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      },
      "m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "t-butoxycarbonyl azide"
              }
            ],
            "amount": {
              "mass": {
                "value": 5.7,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "temperature": {
        "control": {
          "type": "AMBIENT"
        }
      },
      "stirring": {
        "type": "CUSTOM",
        "details": "The reaction mixture was stirred overnight at room temperature"
      },
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-3de54980351141beacb89d4be38c3269"
  },
  {
    "input_text": "To a stirred solution of 75.4 g (0.537 moles) of 4-hydroxy-4-methyl-1-octyne (Example 122), 104.9 g (1.54 moles) of imidazole, and 325 ml of dimethylformamide is added 65.2 g (0.60 moles) of chlorotrimethylsilane. After standing overnight the mixture is poured into 800 ml of hexane. The mixture is washed thoroughly with water followed by sodium bicarbonate solution and brine. The solution is dried over magnesium sulfate, filtered, and evaporated to give a liquid, p.m.r. specturm, \u03b4 1.26 (singlet, 3, CH3), 1.92 (triplet, 1, HC), 2.30 (doublet, 2, CH2).",
    "output_reaction_inputs": {
      "m5": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "hexane"
              }
            ],
            "amount": {
              "volume": {
                "value": 800.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      },
      "m1_m2_m3_m4": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "4-hydroxy-4-methyl-1-octyne"
              }
            ],
            "amount": {
              "mass": {
                "value": 75.4,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "imidazole"
              }
            ],
            "amount": {
              "mass": {
                "value": 104.9,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "dimethylformamide"
              }
            ],
            "amount": {
              "volume": {
                "value": 325.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "chlorotrimethylsilane"
              }
            ],
            "amount": {
              "mass": {
                "value": 65.2,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-6c56ff896b3a44389501ee9bda5c2793"
  },
  {
    "input_text": "To a stirred mixture of 24.5 g (55.6 mmoles) of 1-iodo-4-hydroxy-4-methyl-trans-octene (Example 130), 13.6 g (200 mmoles) of imidazole, and 75 ml of dimethylformamide is added 10.9 g (100 mmoles) of chlorotrimethylsilane. After standing overnight the mixture is poured into 250 ml of hexane. The mixture is washed thoroughly with water followed by brine and dried over magnesium sulfate. After removal of the solvent, the product is distilled to give a colorless liquid, bp 67.5\u00b0-68\u00b0 C. (0.07 mm).",
    "output_reaction_inputs": {
      "m1_m2_m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "1-iodo-4-hydroxy-4-methyl-trans-octene"
              }
            ],
            "amount": {
              "mass": {
                "value": 24.5,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "imidazole"
              }
            ],
            "amount": {
              "mass": {
                "value": 13.6,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "dimethylformamide"
              }
            ],
            "amount": {
              "volume": {
                "value": 75.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      },
      "m5": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "hexane"
              }
            ],
            "amount": {
              "volume": {
                "value": 250.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      },
      "m4": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "chlorotrimethylsilane"
              }
            ],
            "amount": {
              "mass": {
                "value": 10.9,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-ed36b3835b064322bc7d2847c6895a43"
  },
  {
    "input_text": "To a cold solution of 166 g of 4-hydroxy-1-octyne [Prostaglandins, 10, 289 (1975)], and 240 g of imidazole in one liter of dimethylformamide is added dropwise 202 g of chlorotrimethylsilane. The mixture is allowed to stand at room temperature for 2 to 3 days. The mixture is partitioned with water and hexane. The hexane layer is washed with brine, dried over magnesium sulfate, and concentrated. Distillation of the residue gives a colorless liquid, b.p. 38\u00b0 (0.2 mm).",
    "output_reaction_inputs": {
      "m1_m2_m4_m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "4-hydroxy-1-octyne"
              }
            ],
            "amount": {
              "mass": {
                "value": 166.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "imidazole"
              }
            ],
            "amount": {
              "mass": {
                "value": 240.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "chlorotrimethylsilane"
              }
            ],
            "amount": {
              "mass": {
                "value": 202.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "dimethylformamide"
              }
            ],
            "amount": {
              "volume": {
                "value": 1.0,
                "units": "LITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-33258338acb24023b97e26f003d6ebaf"
  },
  {
    "input_text": "To a stirred suspension of 6.15 g of pyridinium chlorochromate (Tetrahedron Letters, 1975, 2647) in 20 ml of methylene chloride is added 450 mg of sodium acetate. After 5 minutes, a solution of 3.64 g of 4-hydroxy-1-iodo trans-1-octene in 15 ml of methylene chloride is added in one portion. The dark mixture is stirred at room temperature for 75 minutes, diluted with 50 ml of ether, and decanted. The solid sludge is washed repeatedly with ether and decanted. The combined solutions are percolated through Florisil. The solution is concentrated to give an orange liquid, pmr spectrum (CDCl3): 3.20 (d,j=7 cps,=CHCH2CO).",
    "output_reaction_inputs": {
      "m1_m4": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "pyridinium chlorochromate"
              }
            ],
            "amount": {
              "mass": {
                "value": 6.15,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "methylene chloride"
              }
            ],
            "amount": {
              "volume": {
                "value": 20.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      },
      "m3_m5": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "4-hydroxy-1-iodo trans-1-octene"
              }
            ],
            "amount": {
              "mass": {
                "value": 3.64,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "methylene chloride"
              }
            ],
            "amount": {
              "volume": {
                "value": 15.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      },
      "m2": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "sodium acetate"
              }
            ],
            "amount": {
              "mass": {
                "value": 450.0,
                "units": "MILLIGRAM"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      },
      "m6": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "ether"
              }
            ],
            "amount": {
              "volume": {
                "value": 50.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "temperature": {
        "control": {
          "type": "AMBIENT"
        }
      },
      "stirring": {
        "type": "CUSTOM",
        "details": "The dark mixture is stirred at room temperature for 75 minutes"
      },
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-fcbbb3b3d903433483f73220e4a2c8f3"
  },
  {
    "input_text": "To a stirred solution of 50 g (0.29 moles) of p-fluorophenoxy acetic acid in one liter of absolute ethanol is added 10 ml of sulfuric acid. The mixture is heated to reflux for 18 hours, cooled to room temperature, and evaporated under vacuum. It is then poured onto 300 g of ice, extracted twice with 500 ml of ether, washed twice with 250 ml of a saturated solution of sodium bicarbonate, 100 ml of saturated sodium chloride solution, dried with magnesium sulfate, filtered and evaporated under vacuum giving 58 g of an oil. This is crystallized from 50 ml of hexane at -25\u00b0 C. to give 55 g (90%) of the subject product as colorless crystals, mp 32\u00b0-33\u00b0 C.",
    "output_reaction_inputs": {
      "m1_m3_m2": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "p-fluorophenoxy acetic acid"
              }
            ],
            "amount": {
              "mass": {
                "value": 50.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "sulfuric acid"
              }
            ],
            "amount": {
              "volume": {
                "value": 10.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "ethanol"
              }
            ],
            "amount": {
              "volume": {
                "value": 1.0,
                "units": "LITER"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "temperature": {
        "control": {
          "type": "AMBIENT"
        }
      },
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-66d76f2bad004111b0e5ed9d5fd66fd7"
  },
  {
    "input_text": "To a 0\u00b0 C. solution of 10 g (55 mmoles) of 3-hydroxy-4-p-fluorophenoxy-1-butyne (Example 157) in 75 ml of dry dimethylformamide and 88 g (130 mmoles) of imidazole is added dropwise, with stirring, 7.5 g (68 mmoles) of chlorotrimethylsilane. The mixture, while under an argon atmosphere, is stirred at room temperature for 18 hours, and then poured into 150 ml of hexane and 100 ml of ice-water. The organic phase is separated, washed with 50 ml of a brine solution, dried with magnesium sulfate, and evaporated under vacuum. This crude product is distilled under vacuum at 0.1 mm (bp 73\u00b0-75\u00b0 C.), to give 12.2 g (91%) of the subject compound as a colorless oily liquid.",
    "output_reaction_inputs": {
      "m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "chlorotrimethylsilane"
              }
            ],
            "amount": {
              "mass": {
                "value": 7.5,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      },
      "m4_m5": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "hexane"
              }
            ],
            "amount": {
              "volume": {
                "value": 150.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "ice water"
              }
            ],
            "amount": {
              "volume": {
                "value": 100.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      },
      "m1_m6_m2": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "3-hydroxy-4-p-fluorophenoxy-1-butyne"
              }
            ],
            "amount": {
              "mass": {
                "value": 10.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "imidazole"
              }
            ],
            "amount": {
              "mass": {
                "value": 88.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "dimethylformamide"
              }
            ],
            "amount": {
              "volume": {
                "value": 75.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "stirring": {
        "type": "CUSTOM",
        "details": "with stirring"
      },
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-19eb37b772b345ee9304926e23d7a9f0"
  },
  {
    "input_text": "To a stirred solution of 11.7 g of 3-hydroxy-1-iodo-3-methyl-1-octene (Example 184) and 7.4 g of imidazole in 45 ml of dry dimethylformamide is added dropwise 5.98 g of trimethylsilylchloride at 0\u00b0 C. under argon atmosphere. After stirring at 0\u00b0 C. for an additional 15 minutes, the solution is stirred at ambient temperature for 18 hours. The reaction mixture is poured into 600 ml of hexane and the resulting solution washed with water, saturated sodium chloride solution, dried over anhydrous magnesium sulfate and taken to dryness to furnish 14.7 g of oil. Distillation affords 13.4 g of clear oil; bp 65\u00b0 C. (0.05 mm); \u03bb max 6.21, 8.00, 9.90, 10.51, 11.90, 13.2\u03bc.",
    "output_reaction_inputs": {
      "m4": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "hexane"
              }
            ],
            "amount": {
              "volume": {
                "value": 600.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      },
      "m1_m2_m5_m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "3-hydroxy-1-iodo-3-methyl-1-octene"
              }
            ],
            "amount": {
              "mass": {
                "value": 11.7,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "imidazole"
              }
            ],
            "amount": {
              "mass": {
                "value": 7.4,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "trimethylsilylchloride"
              }
            ],
            "amount": {
              "mass": {
                "value": 5.98,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "dimethylformamide"
              }
            ],
            "amount": {
              "volume": {
                "value": 45.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "temperature": {
        "setpoint": {
          "value": 0.0,
          "units": "CELSIUS"
        }
      },
      "stirring": {
        "type": "CUSTOM",
        "details": "After stirring at 0\u00b0 C. for an additional 15 minutes"
      },
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-9b38102e50ab41779669d9c31c9a7787"
  },
  {
    "input_text": "To a cold solution of 166 g of 4-hydroxy-1-octyne [Prostaglandins, 10, 289 (1975)], and 240 g of imidazole in one liter of dimethylformamide is added dropwise 202 g of chlorotrimethylsilane. The mixture is allowed to stand at room temperature for 2 to 3 days. The mixture is partitioned with water and hexane. The hexane layer is washed with brine dried over magnesium sulfate, and concentrated. Distillation of the residue gives a colorless liquid, bp 38\u00b0 C. (0.2 mm).",
    "output_reaction_inputs": {
      "m1_m2_m4_m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "4-hydroxy-1-octyne"
              }
            ],
            "amount": {
              "mass": {
                "value": 166.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "imidazole"
              }
            ],
            "amount": {
              "mass": {
                "value": 240.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "chlorotrimethylsilane"
              }
            ],
            "amount": {
              "mass": {
                "value": 202.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "dimethylformamide"
              }
            ],
            "amount": {
              "volume": {
                "value": 1.0,
                "units": "LITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-e449db387ceb44a0b8de2666f727b645"
  },
  {
    "input_text": "To a stirred solution of 456 mg of 4-hydroxy-4-vinyl-1-iodo-trans-1-octene and 320 mg of imidazole in 1.0 ml of dimethylformamide is added 0.23 ml of chlorotrimethylsilane during 3 minutes. The mixture is stirred at room temperature for 22 hours and partitioned with a mixture of cold hexane and water. The hexane layer is washed repeatedly with water and then brine, dried over magnesium sulfate, and concentrated to give an oil, pmr spectrum (CDCl3): 0.13 (s, trimethylsiloxy group) and 2.32 (d, =CHCH2).",
    "output_reaction_inputs": {
      "m1_m2_m4_m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "4-hydroxy-4-vinyl-1-iodo-trans-1-octene"
              }
            ],
            "amount": {
              "mass": {
                "value": 456.0,
                "units": "MILLIGRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "imidazole"
              }
            ],
            "amount": {
              "mass": {
                "value": 320.0,
                "units": "MILLIGRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "chlorotrimethylsilane"
              }
            ],
            "amount": {
              "volume": {
                "value": 0.23,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "dimethylformamide"
              }
            ],
            "amount": {
              "volume": {
                "value": 1.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "temperature": {
        "control": {
          "type": "AMBIENT"
        }
      },
      "stirring": {
        "type": "CUSTOM",
        "details": "The mixture is stirred at room temperature for 22 hours"
      },
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-9ba5542e01ca42479ec4f1319a69c0b3"
  },
  {
    "input_text": "To a stirred solution of 27.8 g of 4-cyclopropyl-4-hydroxy-1-octyne (Example 190) and 33.3 g of imidazole in 130 ml of dimethylformamide at 5\u00b0 C. is added 24 ml of chlorotrimethylsilane during 5 minutes. The solution is stirred at ambient temperature for 17 hours and then partitioned with 600 ml of hexane and 250 ml of ice water. The hexane phase is separated and washed successively with water and brine. The solution is dried over magnesium sulfate and evaporated to give a liquid, pmr spectrum (CDCl3): \u03b40.12 (singlet, trimethylsiloxy group), 2.02 (triplet, HC\u2261C), and 2.45 (doublet, C\u2261CH2).",
    "output_reaction_inputs": {
      "m1_m2_m4_m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "4-cyclopropyl-4-hydroxy-1-octyne"
              }
            ],
            "amount": {
              "mass": {
                "value": 27.8,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "imidazole"
              }
            ],
            "amount": {
              "mass": {
                "value": 33.3,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "chlorotrimethylsilane"
              }
            ],
            "amount": {
              "volume": {
                "value": 24.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "dimethylformamide"
              }
            ],
            "amount": {
              "volume": {
                "value": 130.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "temperature": {
        "control": {
          "type": "AMBIENT"
        }
      },
      "stirring": {
        "type": "CUSTOM",
        "details": "The solution is stirred at ambient temperature for 17 hours"
      },
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-b53eacabecde47298a8932132e7d96d4"
  },
  {
    "input_text": "To a stirred solution of 55.4 g of 1-(2-propyn-1-yl)cyclohexanol [H. Gutmann, et al., Helv. Chim. Acta, 42, 179 (1959)] and 79 g of imidazole in 240 ml of DMF at 10\u00b0 C. initially is added 56 ml of chlorodimethylsilane during 10 minutes. The cloudy yellow solution is stirred at room temperature for 26 hours. The resulting mixture is partitioned between 1000 ml of hexane and 400 ml of water at 0\u00b0-5\u00b0 C. The hexane phase is washed successively with 6\u00d7200 ml of cold water and 200 ml of brine. The extract is dried over magnesium sulfate, filtered, and evaporated to give 85 g of colorless liquid, i.r. (film) :1240 and 830 cm-1 (trimethylsilyloxy group).",
    "output_reaction_inputs": {
      "m1_m2_m4_m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "1-(2-propyn-1-yl)cyclohexanol"
              }
            ],
            "amount": {
              "mass": {
                "value": 55.4,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "imidazole"
              }
            ],
            "amount": {
              "mass": {
                "value": 79.0,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "chlorodimethylsilane"
              }
            ],
            "amount": {
              "volume": {
                "value": 56.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "DMF"
              }
            ],
            "amount": {
              "volume": {
                "value": 240.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "SOLVENT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "temperature": {
        "control": {
          "type": "AMBIENT"
        }
      },
      "stirring": {
        "type": "CUSTOM",
        "details": "The cloudy yellow solution is stirred at room temperature for 26 hours"
      },
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-9f48946cad3f4f6bb2ebe3c8edcc83f2"
  },
  {
    "input_text": "To a stirred mixture of 31.5 g of 1-propargyl-1-trimethylsilyloxycyclohexane and 150 mg of azobisisobutyronitrile is added 41 ml of tri-n-butyltin hydride. The stirred mixture is heated to about 80\u00b0 C. The initial exothermic reaction is moderated, and the temperature is subsequently maintained at 130\u00b0-135\u00b0 C. for one hour.",
    "output_reaction_inputs": {
      "m3": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "tri-n-butyltin hydride"
              }
            ],
            "amount": {
              "volume": {
                "value": 41.0,
                "units": "MILLILITER"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      },
      "m1_m2": {
        "components": [
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "1-propargyl-1-trimethylsilyloxycyclohexane"
              }
            ],
            "amount": {
              "mass": {
                "value": 31.5,
                "units": "GRAM"
              }
            },
            "reactionRole": "REACTANT"
          },
          {
            "identifiers": [
              {
                "type": "NAME",
                "value": "azobisisobutyronitrile"
              }
            ],
            "amount": {
              "mass": {
                "value": 150.0,
                "units": "MILLIGRAM"
              }
            },
            "reactionRole": "REACTANT"
          }
        ]
      }
    },
    "output_reaction_conditions": {
      "temperature": {
        "setpoint": {
          "value": 80.0,
          "units": "CELSIUS"
        }
      },
      "conditionsAreDynamic": true,
      "details": "See reaction.notes.procedure_details."
    },
    "reaction_id": "ord-4877c4744df7475692645ff9a1e81581"
  }
]