Sodium Bicarbonate → 2-oxo-7-(trifluoromethyl)-1-[3-(trifluoromethyl)benzyl]-2,3-dihydro-1H-benzimidazole-5-carbonitrile

HRID 495656Notes

Reaction equation

HRID 495656 reaction equation
Br[C:2]1[CH:22]=[C:21]([C:23]([F:26])([F:25])[F:24])[C:5]2[N:6]([CH2:10][C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:20])([F:19])[F:18])[CH:12]=3)[C:7](=[O:9])[NH:8][C:4]=2[CH:3]=1.[Cu][C:28]#[N:29].C(=O)(O)[O-].[Na+]>CN(C)C=O>[O:9]=[C:7]1[N:6]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:20])([F:19])[F:18])[CH:12]=2)[C:5]2[C:21]([C:23]([F:26])([F:25])[F:24])=[CH:22][C:2]([C:28]#[N:29])=[CH:3][C:4]=2[NH:8]1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 22327356HCID 22327356, compoundHCID 178418546HCID 178418546, compound2×

Product 1

HCID 223273832-oxo-7-(trifluoromethyl)-1-[3-(trifluoromethyl)benzyl]-2,3-dihydro-1H-benzimidazole-5-carbonitrileYield 93%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-bromo-7-(trifluoromethyl)-1-[3-(trifluoromethyl)benzyl]-1,3-dihydro-2H-benzimidazol-2-one (171.9 mg) and copper(I) cyanide (76.3 mg) in N,N-dimethylformamide (10 ml) was heated at reflux for 11 hours. Copper(I) cyanide (51.0 mg) was further added, and the mixture was heated at reflux for 13 hours. To the reaction mixture was added saturated aqueous sodium bicarbonate solution, and the mixture was extracted 5 times with chloroform. The organic layer was dried over anhydrous magnesium sulfate, and concentrated in vacuo to give the title compound (139.5 mg, 93%).

Workup

  1. temperatureat reflux for 11 hours
  2. temperaturethe mixture was heated
  3. temperatureat reflux for 13 hours
  4. extractionthe mixture was extracted 5 times with chloroform
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0983c4c76383489db44c577da7f8d2e2
Source dataset
uspto-grants-2005_09
Patent number
US06939887B2

Reaction notes

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