Sodium Methoxide → Methyl 1-[(2'-cyanobiphenyl-4-yl)methyl]-2-methoxybenzimidazole-7-carboxylate

HRID 397111Notes

Reaction equation

HRID 397111 reaction equation
C[O-].[Na+].[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12]1[CH:17]=[CH:16][C:15]([CH2:18][N:19]2[C:23]3[C:24]([C:28]([O:30][CH2:31]C)=[O:29])=[CH:25][CH:26]=[CH:27][C:22]=3[N:21]=[C:20]2[O:33][CH3:34])=[CH:14][CH:13]=1)#[N:5]>CO>[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12]1[CH:13]=[CH:14][C:15]([CH2:18][N:19]2[C:23]3[C:24]([C:28]([O:30][CH3:31])=[O:29])=[CH:25][CH:26]=[CH:27][C:22]=3[N:21]=[C:20]2[O:33][CH3:34])=[CH:16][CH:17]=1)#[N:5]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 22596778Ethyl 1-[(2'-cyanobiphenyl-4-yl)methyl]2-methoxybenzimidazole-7-carboxylate

Product 1

HCID 15654673Methyl 1-[(2'-cyanobiphenyl-4-yl)methyl]-2-methoxybenzimidazole-7-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of 5.2M sodium methoxide in methanol (0.5 ml) was added to a solution of ethyl 1-[(2′-cyanobiphenyl-4-yl)methyl]-2-methoxybenzimidazole-7-carboxylate (1.3 g) in methanol (50 ml). The mixture was heated for 4 hours under reflux. The reaction mixture was concentrated, and the precipitated crystals were collected by filtration. Recrystallization from methanol afforded colorless prisms (1.1 g, 85%), m.p. 149-150° C.

Workup

  1. temperatureThe mixture was heated for 4 hours
  2. temperatureunder reflux
  3. concentrationThe reaction mixture was concentrated
  4. filtrationthe precipitated crystals were collected by filtration
  5. customRecrystallization from methanol afforded colorless prisms (1.1 g, 85%), m.p. 149-150° C.

Sources & evidence

ORD record
ord-9feae4462d474e8fa62ed65dbf8f939c
Source dataset
uspto-grants-2003_08
Patent number
US06608210B2

Reaction notes

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