Ammonia → HCID 53747560, compound

HRID 1378029Notes

Reaction equation

HRID 1378029 reaction equation
C(N1C=CN=C1)([N:3]1C=CN=C1)=O.[O:13]=[C:14]1[N:20]2[CH2:21][CH2:22][C@H:19]2[C:18]2=[C:23]([C:26]([OH:28])=O)[N:24]=[CH:25][N:17]2[C:16]2[CH:29]=[CH:30][S:31][C:15]1=2.N>CN(C)C=O>[O:13]=[C:14]1[N:20]2[CH2:21][CH2:22][C@H:19]2[C:18]2=[C:23]([C:26]([NH2:3])=[O:28])[N:24]=[CH:25][N:17]2[C:16]2[CH:29]=[CH:30][S:31][C:15]1=2

Participants

5

Reactant 3

HCID 222AmmoniaHCID 682631,1'-CarbonyldiimidazoleHCID 53899458HCID 53899458, compound

Product 1

HCID 53747560HCID 53747560, compoundYield 89.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

7.65 g (47 mmol) of 1,1'-carbonyldiimidazole were added portionwise to a suspension of 12.43 g (45 mmol) of (S)-8-oxo-11,11a-dihydro-8H,10H-azeto[1,2-a]imidazo[5,1-c]thieno[3,2-e][1,4]diazepine-1-carboxylic acid in 70 ml of dimethylformamide. The resulting pale brown solution was heated to 50° for 45 minutes. Subsequently, the solution was cooled to room temperature and 10.9 ml of aqueous ammonia solution were added dropwise. After stirring for a further 30 minutes the reaction mixture was poured into 100 ml of ice-water and the resulting precipitate was filtered off and rinsed with water, ethanol and subsequently with ether. After drying at 70°/10 Torr there were obtained 11.0 g (89%) of (S)-8-oxo-11,11a-dihydro-8H,10H-azeto[1,2-a]imidazo[5,1-c]thieno[3,2-e][1,4]diazepine-1-carboxamide as colourless crystals of m.p. >250°.

Workup

  1. temperatureThe resulting pale brown solution was heated to 50° for 45 minutes
  2. filtrationthe resulting precipitate was filtered off
  3. washrinsed with water, ethanol and subsequently with ether
  4. customAfter drying at 70°/10 Torr there

Sources & evidence

ORD record
ord-d1a6f3d1ac1d476e8fe59e18cb8a3e29
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

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