Sodium ethoxide → Ethyl 1-((2'-cyano(1,1'-biphenyl)-4-yl)methyl)-2-ethoxy-1H-benzimidazole-7-carboxylate

HRID 1760866Notes

Reaction equation

HRID 1760866 reaction equation
Cl[C:2]1[N:6]([CH2:7][C:8]2[CH:13]=[CH:12][C:11]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[C:20]#[N:21])=[CH:10][CH:9]=2)[C:5]2[C:22]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[CH:23][CH:24]=[CH:25][C:4]=2[N:3]=1.[CH3:31][CH2:32][O-:33].[Na+]>C(O)C>[C:20]([C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[C:11]1[CH:12]=[CH:13][C:8]([CH2:7][N:6]2[C:5]3[C:22]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[CH:23][CH:24]=[CH:25][C:4]=3[N:3]=[C:2]2[O:33][CH2:32][CH3:31])=[CH:9][CH:10]=1)#[N:21]

Participants

4

Reactant 2

HCID 2723922Sodium ethoxideHCID 22596779Ethyl 2-chloro-1-[(2'-cyanobiphenyl-4-yl)methyl]benzimidazole-7-carboxylate

Product 1

HCID 15434963Ethyl 1-((2'-cyano(1,1'-biphenyl)-4-yl)methyl)-2-ethoxy-1H-benzimidazole-7-carboxylateYield 70%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl 2-chloro-1-[(2′-cyanobiphenyl-4-yl)-methyl]benzimidazole-7-carboxylate (1.0 g) in ethanol (30 ml) was added NaOEt (0.17 g) and the mixture was heated under reflux for 1 hour. The reaction mixture was concentrated to dryness. The resultant residue was dissolved in ethyl acetate and the solution was washed with water, and then dried. After evaporation of the solvent, the residue was purified by column chromatography on silica gel to give the title compound as colorless crystals(0.37 g, 70%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 1 hour
  3. concentrationThe reaction mixture was concentrated to dryness
  4. dissolutionThe resultant residue was dissolved in ethyl acetate
  5. washthe solution was washed with water
  6. customdried
  7. customAfter evaporation of the solvent
  8. customthe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-464f904faeff47c79075db812c09b690
Source dataset
uspto-grants-2005_01
Patent number
US06844443B2

Reaction notes

Loading…