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

HRID 495644Notes

Reaction equation

HRID 495644 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([C:14]2[C:19]([C:20]([F:23])([F:22])[F:21])=[CH:18][C:17]([NH2:24])=[CH:16][C:15]=2[NH2:25])[C:9](=[O:13])OCC)=[CH:4][CH:3]=1.[H-].[Na+].C(=O)(O)[O-].[Na+]>C(O)C>[NH2:24][C:17]1[CH:18]=[C:19]([C:20]([F:21])([F:22])[F:23])[C:14]2[N:8]([C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=3)[C:9](=[O:13])[NH:25][C:15]=2[CH:16]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 20827747Ethyl 4-chlorophenyl[2,4-diamino-6-(trifluoromethyl)phenyl]carbamate

Product 1

HCID 223273675-amino-1-(4-chlorophenyl)-7-(trifluoromethyl)-1,3-dihydro-2H-benzimidazol-2-oneYield 70.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 4-chlorophenyl[2,4-diamino-6-(trifluoromethyl)phenyl]carbamate (1.2053 g) was dissolved in ethanol (20 ml), and to the solution was added sodium hydride (129.0 mg). The reaction mixture was heated at reflux for 9 hours. After allowing to cool, to the reaction mixture was added saturated aqueous sodium bicarbonate solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo. The resultant residue was purified by silica gel column (60 g, CHCl3:methanol=10:1→5:1) to give the title compound (0.7431 g, 70%).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 9 hours
  3. temperatureto cool, to the reaction mixture
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe resultant residue was purified by silica gel column (60 g, CHCl3:methanol=10:1→5:1)

Sources & evidence

ORD record
ord-ff96107e8768410ab531993305bd7f0d
Source dataset
uspto-grants-2005_09
Patent number
US06939887B2

Reaction notes

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