Methanol → 7-Chloro-2-hydrazinyl-5-phenyl-3H-1,4-benzodiazepine

HRID 1764500Notes

Reaction equation

HRID 1764500 reaction equation
Cl.Cl.[NH2:3][C:4]1[CH2:10][N:9]=[C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:7]2[CH:17]=[C:18]([Cl:21])[CH:19]=[CH:20][C:6]=2[N:5]=1.CO.O.[NH2:25]N>O>[Cl:21][C:18]1[CH:19]=[CH:20][C:6]2[N:5]=[C:4]([NH:3][NH2:25])[CH2:10][N:9]=[C:8]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:7]=2[CH:17]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 24654Hydrazine hydrate (1:1)HCID 22768411HCID 22768411, compound

Product 1

HCID 123908747-Chloro-2-hydrazinyl-5-phenyl-3H-1,4-benzodiazepine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a suspension of 3.4 parts of 2-amino-7-chloro-5-phenyl-3H-1,4-benzodiazepine dihydrochloride in 60 parts by volume of methanol is added 1.25 parts of 80% hydrazine hydrate. The suspension is stirred for 40 minutes, diluted with water and extracted with methylene chloride. The extract is washed with water and dried over anhydrous sodium sulfate, followed by evaporation of the solvent. The residue is recrystallized from a mixture of methylene chloride and benzene to give 7-chloro-2-hydrazino-5-phenyl-3H-1,4-benzodiazepine as colorless prisms. Melting point: around 170° C (browning), 202° C to 204° C (decomposition).

Workup

  1. extractionextracted with methylene chloride
  2. washThe extract is washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. customfollowed by evaporation of the solvent
  5. customThe residue is recrystallized from a mixture of methylene chloride and benzene

Sources & evidence

ORD record
ord-078de181a570489b96126bab52ffb4ff
Source dataset
uspto-grants-1978_09
Patent number
US04116956

Reaction notes

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