Methanol → HCID 178439902, compound

HRID 653725Notes

Reaction equation

HRID 653725 reaction equation
[CH2:1]([C:4]1[N:8]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[C:22]3[NH:26][N:25]=[N:24][N:23]=3)=[CH:12][CH:11]=2)[C:7]2[C:27]([C:31]([OH:33])=[O:32])=[CH:28][CH:29]=[CH:30][C:6]=2[N:5]=1)[CH2:2][CH3:3].S(=O)(=O)(O)O.[CH3:39]O>>[CH2:1]([C:4]1[N:8]([CH2:9][C:10]2[CH:11]=[CH:12][C:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[C:22]3[NH:26][N:25]=[N:24][N:23]=3)=[CH:14][CH:15]=2)[C:7]2[C:27]([C:31]([O:33][CH3:39])=[O:32])=[CH:28][CH:29]=[CH:30][C:6]=2[N:5]=1)[CH2:2][CH3:3]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 178439901HCID 178439901, compound

Product 1

HCID 178439902HCID 178439902, compound

Procedure

A mixture of 2-propyl-1-[[2'-(1H-tetrazol-5-yl)biphenyl-4-yl]methyl]benzimidazole-7-carboxylic acid (465 mg) and conc. sulfuric acid (7.2 g) in methanol (60 ml) was heated for 24 hours under reflux. After removal of solvent, the residue was suspended with water, to which was added 1N-NaOH to adjust to pH 3-4, followed by extraction with ethyl acetate. The organic layer was washed with water and dried, followed by evaporation of the solvent. The residue was purified by column chromatography on silica gel. Recrystallization from ethanol afforded colorless prisms (310 mg), m.p. 195°-196° C.

Workup

  1. temperaturewas heated for 24 hours
  2. temperatureunder reflux
  3. customAfter removal of solvent
  4. additionwas added 1N-NaOH
  5. extractionfollowed by extraction with ethyl acetate
  6. washThe organic layer was washed with water
  7. customdried
  8. customfollowed by evaporation of the solvent
  9. customThe residue was purified by column chromatography on silica gel
  10. customRecrystallization from ethanol afforded colorless prisms (310 mg), m.p. 195°-196° C.

Sources & evidence

ORD record
ord-ef83849b699d4a54b3768273bc74a68a
Source dataset
uspto-grants-1992_07
Patent number
US05128356

Reaction notes

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