Ammonia → HCID 22914476, compound

HRID 1378178Notes

Reaction equation

HRID 1378178 reaction equation
[Br:1][C:2]1[C:7]2[C:8](=[O:20])[N:9]([CH3:19])[CH2:10][C:11]3[N:12]([CH:13]=[N:14][C:15]=3[C:16](O)=[O:17])[C:6]=2[CH:5]=[CH:4][CH:3]=1.C(N1C=CN=C1)([N:23]1C=CN=C1)=O.N>CN(C)C=O.O>[Br:1][C:2]1[C:7]2[C:8](=[O:20])[N:9]([CH3:19])[CH2:10][C:11]3[N:12]([CH:13]=[N:14][C:15]=3[C:16]([NH2:23])=[O:17])[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 222AmmoniaHCID 682631,1'-CarbonyldiimidazoleHCID 22914630HCID 22914630, compound

Product 1

HCID 22914476HCID 22914476, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

24.9 g (74.1 mmol) of 7-bromo-5-methyl-6-oxo-5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxylic acid were suspended in 100 ml of N,N-dimethylformamide, treated at room temperature with 14.3 g (89 mmol) of 1,1'-carbonyldiimidazole and stirred at 70° for 30 minutes. 50 ml of 25% ammonia were added dropwise at 25°-30°. The reaction mixture was diluted with 200 ml of water and cooled to 0°, and the crystallizate was filtered off under suction and dried. There were obtained 21.6 g (86%) of 7-bromo-5-methyl-6-oxo-5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxamide of m.p. 278°-279°.

Workup

  1. temperaturecooled to 0°
  2. filtrationthe crystallizate was filtered off under suction
  3. customdried

Sources & evidence

ORD record
ord-a8e6ad1338b44b789509cd0d7ea4e99e
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

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