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

HRID 860927Notes

Reaction equation

HRID 860927 reaction equation
C[O-].[Na+].[CH2:4]([O:6][C:7]([C:9]1[C:14]2[N:15]([CH2:20][C:21]3[CH:26]=[CH:25][C:24]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=4[C:33]#[N:34])=[CH:23][CH:22]=3)[C:16]([O:18][CH3:19])=[N:17][C:13]=2[CH:12]=[CH:11][CH:10]=1)=[O:8])C>CO>[C:33]([C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=1[C:24]1[CH:23]=[CH:22][C:21]([CH2:20][N:15]2[C:14]3[C:9]([C:7]([O:6][CH3:4])=[O:8])=[CH:10][CH:11]=[CH:12][C:13]=3[N:17]=[C:16]2[O:18][CH3:19])=[CH:26][CH:25]=1)#[N:34]

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-e258200b294f4015be298b2b5918b1a2
Source dataset
uspto-grants-2006_12
Patent number
US07153972B2

Reaction notes

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