Hydrochloric Acid → 4-(1-Imidazolyl)benzoic Acid

HRID 637301Notes

Reaction equation

HRID 637301 reaction equation
F[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8]C)=[O:7])=[CH:4][CH:3]=1.[NH:12]1[CH:16]=[CH:15][N:14]=[CH:13]1.C(=O)([O-])[O-].[K+].[K+].Cl>CS(C)=O.[OH-].[Na+].O>[N:12]1([C:2]2[CH:11]=[CH:10][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=2)[CH:16]=[CH:15][N:14]=[CH:13]1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 795ImidazoleHCID 11430Potassium CarbonateHCID 67878Methyl 4-fluorobenzoate

Product 1

HCID 7365294-(1-Imidazolyl)benzoic Acid

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

Combine methyl 4-fluorobenzoate (1.52 g, 10 mmol), 1H-imidazole (0.82 g, 12 mmol) and potassium carbonate (1.40 g, 10 mmol) in dimethylsulfoxide (7 mL) and heat the mixture with stirring at 120°-130° C. for 5 hours, cool, add water and acid, extract with ether. Adjust the pH of the aqueous layer to 8 with sodium carbonate, extract with ether, dry the extract with sodium sulfate and evaporate. 4-(1H-Imidazol-1-yl)benzoic acid is prepared by refluxing this methyl ester (0.61 g, 3 mmol) in 5 mL of 10% aqueous sodium hydroxide for five minutes; cool, neutralize to pH 6-7 with hydrochloric acid, filter and dry the precipitated acid.

Workup

  1. temperaturecool
  2. extractionextract with ether
  3. extractionextract with ether
  4. customdry the
  5. extractionextract with sodium sulfate
  6. customevaporate
  7. filtrationfilter
  8. customdry the precipitated acid

Sources & evidence

ORD record
ord-7493c448cbab4f6aa6a6dc85736ad7f4
Source dataset
uspto-grants-1985_12
Patent number
US04556665

Reaction notes

Loading…