Acetic Anhydride → 2-(2-Acetylhydrazino)-7-chloro-5-phenyl-3H-1,4-benzodiazepine

HRID 1764520Notes

Reaction equation

HRID 1764520 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]=[C:10]([NH:12][NH2:13])[CH2:9][N:8]=[C:7]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:6]=2[CH:20]=1.[C:21](OC(=O)C)(=[O:23])[CH3:22]>C(Cl)(Cl)Cl>[C:21]([NH:13][NH:12][C:10]1[CH2:9][N:8]=[C:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:6]2[CH:20]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=2[N:11]=1)(=[O:23])[CH3:22]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 123908747-Chloro-2-hydrazinyl-5-phenyl-3H-1,4-benzodiazepine

Product 1

HCID 6243742-(2-Acetylhydrazino)-7-chloro-5-phenyl-3H-1,4-benzodiazepine

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 1.4 parts of 7-chloro-2-hydrazino-5-phenyl-3H-1,4-benzodiazepine in 30 parts by volume of chloroform is added with stirring 0.47 part by volume of acetic anhydride. The mixture is stirred for 1 hour and washed with a saturated aqueous solution of sodium bicarbonate and then with water. The chloroform layer is dried over sodium sulfate and the solvent is evaporated. Addition of methanol yields 2-(2-acetylhydrazino)-7-chloro-5-phenyl-3H-1,4-benzodiazepine as white crystals. Recrystallization from a mixture of chloroform and methanol yields powdery crystals melting at 202° C to 204° C (effervescence).

Workup

  1. washwashed with a saturated aqueous solution of sodium bicarbonate
  2. dry with materialThe chloroform layer is dried over sodium sulfate
  3. customthe solvent is evaporated
  4. additionAddition of methanol

Sources & evidence

ORD record
ord-3497703aba8f4305828796528deab46a
Source dataset
uspto-grants-1978_09
Patent number
US04116956

Reaction notes

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