ethyl 2-butyl-6-methyl-1-[[2'-(1H-tetrazol-5-yl)biphenyl-4-yl]methyl]benzimidazole-7-carboxylate → 2-Butyl-6-methyl-1-[[2'-(1H-tetrazol-5-yl)biphenyl-4-yl]methyl]benzimidazole-7-carboxylic acid

HRID 1655478Notes

Reaction equation

HRID 1655478 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:33]([O:35]CC)=[O:34])=[C:29]([CH3:32])[CH:30]=[CH:31][C:7]=2[N:6]=1)[CH2:2][CH2:3][CH3:4]>[OH-].[Na+].C(O)C>[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:33]([OH:35])=[O:34])=[C:29]([CH3:32])[CH:30]=[CH:31][C:7]=2[N:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 1

HCID 178441462ethyl 2-butyl-6-methyl-1-[[2'-(1H-tetrazol-5-yl)biphenyl-4-yl]methyl]benzimidazole-7-carboxylate

Product 1

HCID 1784414602-Butyl-6-methyl-1-[[2'-(1H-tetrazol-5-yl)biphenyl-4-yl]methyl]benzimidazole-7-carboxylic acidYield 42.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A mixture of ethyl 2-butyl-6-methyl-1-[[2'-(1H-tetrazol-5-yl)biphenyl-4-yl]methyl]benzimidazole-7-carboxylate (0.55 g) in 5N aqueous sodium hydroxide (5 ml) and ethanol (10 ml) was heated for 100 hours under reflux. The reaction mixture was concentrated to dryness and then was dissolved in water, and the solution was made acidic with conc. HCl. Precipitates separated out were collected by filtration and washed with a mixture of dichloromethane and methanol. The precipitates were dissolved in saturated aqueous sodium bicarbonate. After removal of insoluble materials by filtration, the filtrate was made acidic with conc. HCl. Precipitates then separated out were collected by filtration and crystallized from dimethylformamide --H2O to afford colorless crystals (0.22 g, 42%), m.p. 298-299° C.

Workup

  1. temperaturewas heated for 100 hours
  2. temperatureunder reflux
  3. concentrationThe reaction mixture was concentrated to dryness
  4. dissolutionwas dissolved in water
  5. customPrecipitates
  6. customseparated out
  7. filtrationwere collected by filtration
  8. washwashed with a mixture of dichloromethane and methanol
  9. dissolutionThe precipitates were dissolved in saturated aqueous sodium bicarbonate
  10. customAfter removal of insoluble materials
  11. filtrationby filtration
  12. customPrecipitates
  13. customthen separated out
  14. filtrationwere collected by filtration
  15. customcrystallized from dimethylformamide

Sources & evidence

ORD record
ord-e057f314ecd34cd786f7a913b58bdc69
Source dataset
uspto-grants-1993_10
Patent number
US05250554

Reaction notes

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