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

HRID 26054Notes

Reaction equation

HRID 26054 reaction equation
CO[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:4].[CH3:29][NH2:30].[K+].[Br-]>C(O)C>[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]([NH:30][CH3:29])=[O:4])=[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 6329MethylamineHCID 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 537838328-Chloro-6-(2-chlorophenyl)-N-methyl-1-methylthio-4H-imidazo [1,5-a][1,4]benzodiazepine-3-carboxamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2.1 g (0.005 mole) of 8-chloro-6-(2-chlorophenyl)-1-methylthio-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxylic acid methyl ester and 20 ml of a 28% solution of methylamine in ethanol was heated at 130° in a steel bomb for 18 hrs. The contents of the bomb were evaporated at reduced pressure to give a tan solid. Recrystallization from ethanol gave off-white prisms with mp 224°-227°. Uv λ max 218 mμ (ε=51,400) infl 245 (26,000) sh 275 (12,000); ir (KBr) 3410 cm-1 (NH) 1668, 1527 (CON).

Workup

  1. customThe contents of the bomb were evaporated at reduced pressure
  2. customto give a tan solid
  3. customRecrystallization from ethanol
  4. customgave off-white prisms with mp 224°-227°

Sources & evidence

ORD record
ord-012ec4f16acb45f89aaa7f7ecaec266f
Source dataset
uspto-grants-1979_04
Patent number
US04147875

Reaction notes

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