Water → 2-phenyl-1H-imidazole-4-carboxylic acid

HRID 1712922Notes

Reaction equation

HRID 1712922 reaction equation
[C:1]1([C:7]2[NH:8][C:9]([C:12](F)(F)F)=[CH:10][N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-:16].[Na+].[OH2:18]>>[C:1]1([C:7]2[NH:8][C:9]([C:12]([OH:18])=[O:16])=[CH:10][N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 3

HCID 962Water2×HCID 14798Sodium HydroxideHCID 6113582-Phenyl-4-(trifluoromethyl)-1H-imidazole

Product 1

HCID 27381392-phenyl-1H-imidazole-4-carboxylic acid

Conditions

Temperature
95 °C

Procedure

A mixture of 2-phenyl-5-(trifluoromethyl)-1H-imidazole (47.1 mmol) and NaOH (63.8 mmol) in water (20 mL) was allowed to stir at 95° C. overnight. The reaction mixture was allowed to cool to rt and was diluted with water and extracted with DCM. The pH of the aqueous solution was adjusted to pH=7 with 1N HCl and the solution was extracted again with DCM. The aqueous solution was concentrated to give 2-phenyl-1H-imidazole-5-carboxylic acid as a white solid which was used without further purification.

Workup

  1. temperatureto cool to rt
  2. extractionextracted with DCM
  3. extractionthe solution was extracted again with DCM
  4. concentrationThe aqueous solution was concentrated

Sources & evidence

ORD record
ord-1f2a91bde39a41638db267a412a24f83
Source dataset
uspto-grants-2010_09
Patent number
US07795249B2

Reaction notes

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