5-bromo-1-(2,4-dimethoxybenzyl)-7-(trifluoromethyl)-1,3-dihydro-2H-benzimidazol-2-one → 1-(2,4-dimethoxybenzyl)-2-oxo-7-(trifluoromethyl)-2,3-dihydro-1H-benzimidazole-5-carbonitrile

HRID 495662Notes

Reaction equation

HRID 495662 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][C:14]([O:17][CH3:18])=[CH:13][C:12]=3[O:19][CH3:20])[C:7](=[O:9])[NH:8][C:4]=2[CH:3]=1.[Cu][C:28]#[N:29]>CN(C)C=O>[CH3:20][O:19][C:12]1[CH:13]=[C:14]([O:17][CH3:18])[CH:15]=[CH:16][C:11]=1[CH2:10][N:6]1[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][C:7]1=[O:9]

Participants

4

Reactant 2

HCID 223273735-bromo-1-(2,4-dimethoxybenzyl)-7-(trifluoromethyl)-1,3-dihydro-2H-benzimidazol-2-oneHCID 178418546HCID 178418546, compound

Product 1

HCID 223274151-(2,4-dimethoxybenzyl)-2-oxo-7-(trifluoromethyl)-2,3-dihydro-1H-benzimidazole-5-carbonitrileYield 112.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-bromo-1-(2,4-dimethoxybenzyl)-7-(trifluoromethyl)-1,3-dihydro-2H-benzimidazol-2-one (1090.7 mg) and copper(I) cyanide (793.8 mg) in N,N-dimethylformamide (100 ml) was heated at reflux for 34 hours. The reaction mixture was concentrated in vacuo. To the resultant residue were added saturated aqueous sodium bicarbonate solution and water, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and concentrated in vacuo to give the title compound (1076.5 mg, quantitative yield). HPLC retention time: 30.54 min (condition 2).

Workup

  1. temperatureat reflux for 34 hours
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. additionTo the resultant residue were added saturated aqueous sodium bicarbonate solution and water
  4. extractionthe mixture was extracted with ethyl acetate
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a4d581d5c1264beda0f2868eda63c7c1
Source dataset
uspto-grants-2005_09
Patent number
US06939887B2

Reaction notes

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