Sodium hydride → 5-bromo-1-(2,4-dimethoxybenzyl)-7-(trifluoromethyl)-1,3-dihydro-2H-benzimidazol-2-one

HRID 495661Notes

Reaction equation

HRID 495661 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([Br:8])[CH:5]=[C:4]([C:9]([F:12])([F:11])[F:10])[C:3]=1[N:13]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][C:21]=1[O:28][CH3:29])[C:14](=[O:18])OCC.[H-].[Na+]>C(O)C>[Br:8][C:6]1[CH:5]=[C:4]([C:9]([F:10])([F:12])[F:11])[C:3]2[N:13]([CH2:19][C:20]3[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][C:21]=3[O:28][CH3:29])[C:14](=[O:18])[NH:1][C:2]=2[CH:7]=1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 22327363Ethyl 2-amino-4-bromo-6-(trifluoromethyl)phenyl(2,4-dimethoxybenzyl)carbamate

Product 1

HCID 223273735-bromo-1-(2,4-dimethoxybenzyl)-7-(trifluoromethyl)-1,3-dihydro-2H-benzimidazol-2-oneYield 106.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl 2-amino-4-bromo-6-(trifluoromethyl)phenyl(2,4-dimethoxybenzyl)carbamate (1.1345 g) in ethanol (75 ml) was added sodium hydride (60%) (225.5 mg). The reaction mixture was heated at reflux for 33 hours. The solvent was removed to about one third in vacuo. To the reaction mixture was added 1N hydrochloric acid, and the mixture was basified with saturated aqueous sodium bicarbonate solution, and extracted 5 times with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and concentrated in vacuo to give the title compound (1090.7 mg, quantitative yield). HPLC retention time: 34.49 min (condition 2).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 33 hours
  3. customThe solvent was removed to about one third in vacuo
  4. additionTo the reaction mixture was added 1N hydrochloric acid
  5. extractionextracted 5 times with ethyl acetate
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4d75e12d339a431abd8f965ec10996c9
Source dataset
uspto-grants-2005_09
Patent number
US06939887B2

Reaction notes

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