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

HRID 495624Notes

Reaction equation

HRID 495624 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:24]=[CH:25][CH:26]=1)[CH2:5][N:6]([C:12]1[C:17]([C:18]([F:21])([F:20])[F:19])=[CH:16][C:15]([NH2:22])=[CH:14][C:13]=1[NH2:23])[C:7](=O)[O:8]CC.[H-].[Na+].C(=O)(O)[O-].[Na+]>C(O)C>[NH2:22][C:15]1[CH:16]=[C:17]([C:18]([F:21])([F:20])[F:19])[C:12]2[N:6]([CH2:5][C:4]3[CH:24]=[CH:25][CH:26]=[C:2]([Cl:1])[CH:3]=3)[C:7](=[O:8])[NH:23][C:13]=2[CH:14]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 20827738Ethyl 3-chlorobenzyl[2,4-diamino-6-(trifluoromethyl)phenyl]carbamate

Product 1

HCID 223273805-amino-1-(3-chlorobenzyl)-7-(trifluoromethyl)-1,3-dihydro-2H-benzimidazol-2-oneYield 32%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 3-chlorobenzyl[2,4-diamino-6-(trifluoromethyl)phenyl]carbamate (110.3 mg) was dissolved in ethanol (10 ml), and to the solution was added sodium hydride (56.9 mg). The reaction mixture was heated at reflux for 5 hours. After allowing to cool, to the reaction mixture was added saturated aqueous sodium bicarbonate solution, and the mixture was extracted 4 times with chloroform. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. The resultant residue was purified by preparative TLC (2 mm, 20×20 cm, CHCl3-methanol=5:1) to give the title compound (31.1 mg).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 5 hours
  3. temperatureto cool, to the reaction mixture
  4. extractionthe mixture was extracted 4 times with chloroform
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe resultant residue was purified by preparative TLC (2 mm, 20×20 cm, CHCl3-methanol=5:1)

Sources & evidence

ORD record
ord-b64f743e1ec1462e9fddd2d483261b66
Source dataset
uspto-grants-2005_09
Patent number
US06939887B2

Reaction notes

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