Methanol → HCID 22768404, compound

HRID 1764510Notes

Reaction equation

HRID 1764510 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]=[C:10](SC)[CH:9]([CH2:14][CH:15]([CH3:17])[CH3:16])[N:8]=[C:7]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:6]=2[CH:24]=1.CO.O.[NH2:28][NH2:29]>O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]=[C:10]([NH:28][NH2:29])[CH:9]([CH2:14][CH:15]([CH3:17])[CH3:16])[N:8]=[C:7]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:6]=2[CH:24]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 24654Hydrazine hydrate (1:1)HCID 22768410HCID 22768410, compound

Product 1

HCID 22768404HCID 22768404, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 1.6 parts of 7-chloro-3-isobutyl-2-methylmercapto-5-phenyl-3H-1,4-benzodiazepine in 150 parts by volume of methanol is added 40 parts of 100% hydrazine hydrate. The mixture is refluxed for 4.5 hours and poured into water, followed by extraction with chloroform. The chloroform layer is washed with water, dried over sodium sulfate and the solvent is evaporated. Treatment of the residue with diethyl ether yields 7-chloro-2-hydrazino-3-isobutyl-5-phenyl-3H-1,4-benzodiazepine as crystals. Recrystallization from a mixture of chloroform and n-hexane yields colorless crystals melting at 168° C to 169° C.

Workup

  1. temperatureThe mixture is refluxed for 4.5 hours
  2. extractionfollowed by extraction with chloroform
  3. washThe chloroform layer is washed with water
  4. dry with materialdried over sodium sulfate
  5. customthe solvent is evaporated

Sources & evidence

ORD record
ord-55ede318d19944b6a2cbbf49f44abcb9
Source dataset
uspto-grants-1978_09
Patent number
US04116956

Reaction notes

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