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

HRID 1704005Notes

Reaction equation

HRID 1704005 reaction equation
C[O:2][C:3]([C:5]1[N:6]=[C:7]([Cl:27])[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.[NH3:28].[K+].[Br-]>CO.C(Cl)Cl>[Cl:26][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=1[C:12]1[C:13]2[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:14]=2[N:8]2[C:7]([Cl:27])=[N:6][C:5]([C:3]([NH2:28])=[O:2])=[C:9]2[CH2:10][N:11]=1

Participants

6

Reactant 3

HCID 222AmmoniaHCID 253877Potassium BromideHCID 541351956-(2-chlorophenyl)-1,8-dichloro-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxylic acid methyl ester

Product 1

HCID 203945796-(2-chlorophenyl)-1,8-dichloro-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxamide

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 0.5 g (0.0012 mole) of 6-(2-chlorophenyl)-1,8-dichloro-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxylic acid methyl ester and 20 ml of a 20% solution of ammonia in methanol was heated at 120°-125° in a steel bomb for 18 hrs. Evaporation of the solvent at reduced pressure gave an amorphous solid. The solid was dissolved in methylene chloride, washed with water, dried and evaporated at reduced pressure to give a tan, amorphous solid which crystallized when stirred with a small amount of boiling ether. Recrystallization from a solution of methanol and methylene chloride gave white crystals with mp 285°-288°. Uv λ 214 mμ (ε=44,300) sh 245 (26,500) sh 260 (16,400) sh 300 (600); ir (KBr) 3470, 3335 cm-1 (NH2) 1670 (CON).

Workup

  1. customEvaporation of the solvent at reduced pressure
  2. customgave an amorphous solid
  3. washwashed with water
  4. customdried
  5. customevaporated at reduced pressure
  6. customto give a tan, amorphous solid which
  7. customcrystallized when
  8. customRecrystallization from a solution of methanol and methylene chloride
  9. customgave white crystals with mp 285°-288°

Sources & evidence

ORD record
ord-c25f76041c9c483cb8fa2e0142061261
Source dataset
uspto-grants-1978_11
Patent number
US04125726

Reaction notes

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