Ammonia → 8-Chloro-6-(2-chlorophenyl)-1-methylthio-4H-imidazo[1,5-a] [1,4]benzodiazepine-3-carboxamide

HRID 26053Notes

Reaction equation

HRID 26053 reaction equation
C[O:2][C:3]([C:5]1[N:6]=[C:7]([S:27][CH3:28])[N:8]2[C:14]3[CH:15]=[CH:16][C:17]([Cl:19])=[CH:18][C:13]=3[C:12]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[Cl:26])=[N:11][CH2:10][C:9]=12)=O.[NH3:29].[K+].[Br-]>CO>[Cl:19][C:17]1[CH:16]=[CH:15][C:14]2[N:8]3[C:7]([S:27][CH3:28])=[N:6][C:5]([C:3]([NH2:29])=[O:2])=[C:9]3[CH2:10][N:11]=[C:12]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[Cl:26])[C:13]=2[CH:18]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 253877Potassium BromideHCID 537434228-chloro-6-(2-chlorophenyl)-1-methylthio-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxylic acid methyl ester

Product 1

HCID 203945828-Chloro-6-(2-chlorophenyl)-1-methylthio-4H-imidazo[1,5-a] [1,4]benzodiazepine-3-carboxamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 3 g (0.007 mole) of 8-chloro-6-(2-chlorophenyl)-1-methylthio-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxylic acid methyl ester and 60 ml of 25% solution of ammonia in methanol was heated at 130° in a steel bomb for 18 hrs. The contents of the bomb were evaporated at reduced pressure to give light tan crystals, which were recrystallized from methanol/methylene chloride to yield light tan prisms with mp 270°-274° (dec.). Uv λ max 217 mμ (ε=47,200) infl 242 (23,200) sh 270 (11,500), ir (KBr) 3365, 3250, 3215, 3150 cm-1 (NH2) 1675, 1650, 1590 (CON).

Workup

  1. customThe contents of the bomb were evaporated at reduced pressure
  2. customto give light tan crystals, which
  3. customwere recrystallized from methanol/methylene chloride
  4. customto yield light tan prisms with mp 270°-274° (dec.)

Sources & evidence

ORD record
ord-e62f6bd06dca4c37ae3106c593afc6b0
Source dataset
uspto-grants-1979_04
Patent number
US04147875

Reaction notes

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