Water → 4-[3-(1-Benzylimidazol-2-yl)prop-1-en-1-yl]-2-(4-fluorophenyl)benzoic acid

HRID 1019049Notes

Reaction equation

HRID 1019049 reaction equation
[CH2:1]([N:8]1[CH:12]=[CH:11][N:10]=[C:9]1[CH2:13][CH:14]=[CH:15][C:16]1[CH:25]=[CH:24][C:19]([C:20]([O:22]C)=[O:21])=[C:18]([C:26]2[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=2)[CH:17]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].O>CO>[CH2:1]([N:8]1[CH:12]=[CH:11][N:10]=[C:9]1[CH2:13][CH:14]=[CH:15][C:16]1[CH:25]=[CH:24][C:19]([C:20]([OH:22])=[O:21])=[C:18]([C:26]2[CH:27]=[CH:28][C:29]([F:32])=[CH:30][CH:31]=2)[CH:17]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 53719705Methyl 4-[3-(1-benzylimidazol-2-yl)prop-1-en-1-yl]-2-(4-fluorophenyl)benzoate

Product 1

HCID 544808904-[3-(1-Benzylimidazol-2-yl)prop-1-en-1-yl]-2-(4-fluorophenyl)benzoic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of methyl 4-[3-(1-benzylimidazol-2-yl)prop-1-en-1-yl]-2-(4-fluorophenyl)benzoate (3 g; 7 mmol), sodium hydroxide (0.8 g; 20 mmol) and distilled water (5 ml) in methanol (50 ml) was refluxed for 4 hours. After evaporation to dryness and acidification to pH 6 with 6N HCl, the resulting solid was triturated with water and ether to give 4-[3-(1-benzylimidazol-2-yl)prop-1-en-1-yl]-2-(4-fluorophenyl)benzoic acid as a mixture of E and Z isomers.

Workup

  1. temperaturewas refluxed for 4 hours
  2. customAfter evaporation to dryness and acidification to pH 6 with 6N HCl
  3. customthe resulting solid was triturated with water and ether

Sources & evidence

ORD record
ord-643ab88c626a4cf185af458ed8774371
Source dataset
uspto-grants-2002_11
Patent number
US06486156B1

Reaction notes

Loading…