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

HRID 1655452Notes

Reaction equation

HRID 1655452 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-769cf82ef30c4ec4ae3819443034eb3a
Source dataset
uspto-grants-1993_10
Patent number
US05250554

Reaction notes

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