2-Methylimidazole → Estazolam

HRID 1764513

Reaction equation

HRID 1764513 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.Cl.[CH:22](N)=N.CC1NC=CN=1>O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]3[CH:22]=[N:13][N:12]=[C:10]3[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

Participants

5

Reactant 3

HCID 127492-MethylimidazoleHCID 10313058Methanimidamide, hydrochloride (1:1)HCID 123908747-Chloro-2-hydrazinyl-5-phenyl-3H-1,4-benzodiazepine

Product 1

HCID 3261Estazolam

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2.8 parts of 7-chloro-2-hydrazino-5-phenyl-3H-1,4-benzodiazepine, 2.4 parts of formamidine hydrochloride and 2.5 parts of 2-methylimidazole is fused at 160° C for 10 minutes. Water is added to the mixture, followed by extraction with methylene chloride. The methylene chloride layer is washed with water, dried over sodium sulfate and the solvent is evaporated, whereby 8-chloro-6-phenyl-4H-s-triazolo [4,3-a][1,4] benzodiazepine is yielded. Recrystallization from ethyl acetate yields colorless flakes melting at 226° C to 227° C.

Workup

  1. extractionfollowed by extraction with methylene chloride
  2. washThe methylene chloride layer is washed with water
  3. dry with materialdried over sodium sulfate
  4. customthe solvent is evaporated

Sources & evidence

ORD record
ord-2f9d688256f6492a8e3493b7ddfa1c2a
Source dataset
uspto-grants-1978_09
Patent number
US04116956

Linked notes

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