Water → Methyl 2-butyl-1-[(2'-cyanobiphenyl-4-yl)methyl]benzimidazole-4-carboxylate

HRID 1655452노트

반응식

HRID 1655452 반응식
[CH2:1]([C:5]1[NH:6][C:7]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([O:16][CH3:17])=[O:15])[C:8]=2[N:9]=1)[CH2:2][CH2:3][CH3:4].[H-].[Na+].[C:20]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[C:28]1[CH:35]=[CH:34][C:31]([CH2:32]Cl)=[CH:30][CH:29]=1)#[N:21].O>CN(C=O)C>[CH2:1]([C:5]1[N:6]([CH2:32][C:31]2[CH:30]=[CH:29][C:28]([C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=3[C:20]#[N:21])=[CH:35][CH:34]=2)[C:7]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([O:16][CH3:17])=[O:15])[C:8]=2[N:9]=1)[CH2:2][CH2:3][CH3:4]

참가 물질

6

반응물 4

HCID 962WaterHCID 24758Sodium hydrideHCID 14987323Methyl 2-butyl-1H-benzimidazole-4-carboxylateHCID 217117564'-(chloromethyl)-[1,1'-Biphenyl]-2-carbonitrile

생성물 1

HCID 19792178Methyl 2-butyl-1-[(2'-cyanobiphenyl-4-yl)methyl]benzimidazole-4-carboxylate수율 84.1%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of methyl 2-butylbenzimidazole-7-carboxylate (1.5 g) in DMF (15 ml) was added sodium hydride (60% oil, 0.13 g) under ice-cooling. The mixture was stirred for 20 minutes and there was added 4-(2-cyanophenyl)benzyl chloride (1.5 g). The resultant mixture was stirred for further 5 hours at room temperature and there was added water, followed by extraction with ethyl acetate. The organic layer was washed with water and dried. The solvent was evaporated to dryness, and the residue was purified by column chromatography on silica gel to give a pale yellow oil (2.3 g, 82%).

후처리

  1. temperaturecooling
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed with water
  4. customdried
  5. customThe solvent was evaporated to dryness
  6. customthe residue was purified by column chromatography on silica gel

출처 및 근거

ORD 기록
ord-769cf82ef30c4ec4ae3819443034eb3a
출처 데이터셋
uspto-grants-1993_10
특허 번호
US05250554

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