Methanol → Methyl 2-butyl-1-[[2'-(1H-tetrazol-5-yl)biphenyl-4-yl]methyl]benzimidazole-7-carboxylate

HRID 653726Notes

Reaction equation

HRID 653726 reaction equation
[CH2:1]([C:5]1[N:9]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[C:23]3[NH:27][N:26]=[N:25][N:24]=3)=[CH:13][CH:12]=2)[C:8]2[C:28]([C:32]([OH:34])=[O:33])=[CH:29][CH:30]=[CH:31][C:7]=2[N:6]=1)[CH2:2][CH2:3][CH3:4].S(=O)(=O)(O)O.[CH3:40]O>>[CH2:1]([C:5]1[N:9]([CH2:10][C:11]2[CH:12]=[CH:13][C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[C:23]3[NH:27][N:26]=[N:25][N:24]=3)=[CH:15][CH:16]=2)[C:8]2[C:28]([C:32]([O:34][CH3:40])=[O:33])=[CH:29][CH:30]=[CH:31][C:7]=2[N:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 178441468HCID 178441468, compound

Product 1

HCID 178441473Methyl 2-butyl-1-[[2'-(1H-tetrazol-5-yl)biphenyl-4-yl]methyl]benzimidazole-7-carboxylate

Procedure

A mixture of 2-butyl-1-[[2'-(1H-tetrazol-5-yl)biphenyl-4-yl]methyl]benzimidazole-7-carboxylic acid (1.8 g) in methanol (18 ml) and conc. sulfuric acid (14.4 g) was heated for 24 hours under reflux. After removal of the solvent by evaporation, the residue was suspended with water, whose pH was adjusted to 3-4 with 1N-NaOH, followed by extraction with ethyl acetate. The organic layer was washed with water and dried. The solvent was removed by evaporation and the residue was purified by column chromatography on silica gel. Recrystallization from ethanol afforded colorless prisms (1.05 g), m.p. 153°-155° C.

Workup

  1. temperaturewas heated for 24 hours
  2. temperatureunder reflux
  3. customAfter removal of the solvent
  4. customby evaporation
  5. extractionfollowed by extraction with ethyl acetate
  6. washThe organic layer was washed with water
  7. customdried
  8. customThe solvent was removed by evaporation
  9. customthe residue was purified by column chromatography on silica gel
  10. customRecrystallization from ethanol afforded colorless prisms (1.05 g), m.p. 153°-155° C.

Sources & evidence

ORD record
ord-b2754afa0f6d4c0c804c30cba18d8841
Source dataset
uspto-grants-1992_07
Patent number
US05128356

Reaction notes

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