Ammonia → HCID 22914329, compound

HRID 1378229Notes

Reaction equation

HRID 1378229 reaction equation
C(N1C=CN=C1)([N:3]1C=CN=C1)=O.[Cl:13][C:14]1[CH:15]=[CH:16][C:17]2[N:23]3[CH:24]=[N:25][C:26]([C:27](O)=[O:28])=[C:22]3[CH2:21][N:20]([CH3:30])[C:19](=[O:31])[C:18]=2[CH:32]=1.C(=O)=O.N>CN(C)C=O>[Cl:13][C:14]1[CH:15]=[CH:16][C:17]2[N:23]3[CH:24]=[N:25][C:26]([C:27]([NH2:3])=[O:28])=[C:22]3[CH2:21][N:20]([CH3:30])[C:19](=[O:31])[C:18]=2[CH:32]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 280Carbon DioxideHCID 682631,1'-CarbonyldiimidazoleHCID 9994443HCID 9994443, compound

Product 1

HCID 22914329HCID 22914329, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2.7 g (16.8 mmol) of 1,1'-carbonyldiimidazole were added portionwise to a suspension of 4.7 g (16.0 mmol) of 8-chloro-5-methyl-6-oxo-5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxylic acid in 25 ml of N,N-dimethylformamide. After the CO2 evolution had finished the mixture was heated to 60° for 45 min. Subsequently, the solution was cooled to room temperature and 3.9 ml of conc. aqueous ammonia solution were added dropwise thereto. After stirring for a further 90 minutes the reaction mixture was poured into 90 ml of ice-water and stirred for 1 hr. The white crystals were filtered off under suction and washed with a small amount of water. After drying in a high vacuum there were obtained 3.84 g (83%) of 8-chloro-5-methyl-6-oxo-5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxamide of m.p. 275°-277°.

Workup

  1. temperaturewas heated to 60° for 45 min
  2. stirringstirred for 1 hr
  3. filtrationThe white crystals were filtered off under suction
  4. washwashed with a small amount of water
  5. customAfter drying in a high vacuum there

Sources & evidence

ORD record
ord-7190263ef07946fa9aaf226e3b3ff808
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

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