Ammonia → HCID 54053191, compound

HRID 1378239Notes

Reaction equation

HRID 1378239 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]3[CH:12]=[N:13][C:14]([C:15](O)=[O:16])=[C:10]3[C@@H:9]3[CH2:18][CH2:19][N:8]3[C:7](=[O:20])[C:6]=2[CH:21]=1.C(N1C=CN=C1)([N:24]1C=CN=C1)=O.C(=O)=O.N>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]3[CH:12]=[N:13][C:14]([C:15]([NH2:24])=[O:16])=[C:10]3[C@@H:9]3[CH2:18][CH2:19][N:8]3[C:7](=[O:20])[C:6]=2[CH:21]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 280Carbon DioxideHCID 682631,1'-CarbonyldiimidazoleHCID 54249109HCID 54249109, compound

Product 1

HCID 54053191HCID 54053191, compoundYield 92.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3.04 g (10.0 mmol) of (S)-7-chloro-12,12a-dihydro-9-oxo-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepine-1-carboxylic acid were suspended in 15 ml of N,N-dimethylformamide and treated portionwise at room temperature with 1.78 g (11.0 mmol) of 1,1'-carbonyldiimidazole. After the CO2 evolution had finished the clear brown solution was stirred at 50° for 30 min., cooled and treated dropwise at a temperature below 25° within about 10 min. with 2.5 ml of conc. ammonia. After stirring for 30 minutes the suspension obtained was evaporated and the residue was triturated with 30 ml of water. The white crystals were filtered off under suction and dried in a vacuum. There were obtained 2.8 g (92%) of (S)-7-chloro-12,12a-dihydro-9-oxo-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepine-1-carboxamide of m.p. 251°-253°.

Workup

  1. temperaturecooled
  2. stirringAfter stirring for 30 minutes the suspension
  3. customobtained
  4. customwas evaporated
  5. customthe residue was triturated with 30 ml of water
  6. filtrationThe white crystals were filtered off under suction
  7. customdried in a vacuum

Sources & evidence

ORD record
ord-97757a2519f0477f85f61789d4bb987b
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

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