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

HRID 26059
Notes
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Reaction equation

HRID 26059 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 887MethanolSolvent
HCID 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-7ffa80c3b69c4f38a841588ed2defbd6
Source dataset
uspto-grants-1979_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04147875

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes