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

HRID 1764509Notes

Reaction equation

HRID 1764509 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:11][C:10](=S)[CH2:9][N:8]=[C:7]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:6]=2[CH:19]=1.CS(C)=O.O.[NH2:25][NH2:26]>C(O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]=[C:10]([NH:25][NH2:26])[CH2:9][N:8]=[C:7]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:6]=2[CH:19]=1

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 24654Hydrazine hydrate (1:1)HCID 826706Thionordiazepam

Product 1

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

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2.9 parts of 7-chloro-1,3-dihydro-5-phenyl-2H-1,4-benzodiazepine-2-thione in a mixture of 2.5 parts by volume of dimethylsulfoxide and 100 parts by volume of ethanol is added 5 parts by volume of 80% hydrazine hydrate, and the mixture is allowed to stand for 24 hours. After evaporation of the solvent under reduced pressure, the residue is diluted with water, followed by extraction with methylene chloride. The methylene chloride layer is dried over sodium sulfate and the solvent is evaporated. Treatment of the residue with benzene gives 7-chloro-2-hydrazino-5-phenyl-3H-1,4-benzodiazepine. Recrystallization from a mixture of methylene chloride and benzene gives crystals melting at 205° C to 207° C (decomposition) which are confirmed to be identical with the product prepared in Examples 1 and 9.

Workup

  1. customAfter evaporation of the solvent under reduced pressure
  2. additionthe residue is diluted with water
  3. extractionfollowed by extraction with methylene chloride
  4. dry with materialThe methylene chloride layer is dried over sodium sulfate
  5. customthe solvent is evaporated

Sources & evidence

ORD record
ord-f221792362f544ee8dbe13a14ae93a9e
Source dataset
uspto-grants-1978_09
Patent number
US04116956

Reaction notes

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