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

HRID 495620노트

반응식

HRID 495620 반응식
[Cl:1][C:2]1[CH:26]=[CH:25][CH:24]=[CH:23][C:3]=1[CH2:4][N:5]([C:11]1[C:16]([C:17]([F:20])([F:19])[F:18])=[CH:15][C:14]([NH2:21])=[CH:13][C:12]=1[NH2:22])[C:6](=[O:10])OCC.[H-].[Na+].C(=O)(O)[O-].[Na+]>C(O)C>[NH2:21][C:14]1[CH:15]=[C:16]([C:17]([F:18])([F:20])[F:19])[C:11]2[N:5]([CH2:4][C:3]3[CH:23]=[CH:24][CH:25]=[CH:26][C:2]=3[Cl:1])[C:6](=[O:10])[NH:22][C:12]=2[CH:13]=1

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 20827733Ethyl 2-chlorobenzyl[2,4-diamino-6-(trifluoromethyl)phenyl]carbamate

생성물 1

HCID 223273745-amino-1-(2-chlorobenzyl)-7-(trifluoromethyl)-1,3-dihydro-2H-benzimidazol-2-one수율 61%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

Ethyl 2-chlorobenzyl[2,4-diamino-6-(trifluoromethyl)phenyl]carbamate (85.6 mg) was dissolved in ethanol (10 ml), and to the solution was added sodium hydride (17.7 mg). The reaction mixture was heated at reflux for 24 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 (46.0 mg).

후처리

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 24 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)

출처 및 근거

ORD 기록
ord-5f92d9fbca3e4bc7aa638c6258538e88
출처 데이터셋
uspto-grants-2005_09
특허 번호
US06939887B2

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