Sodium Hydroxide → 3-Cyclopropyl-5-methyl-2-(4-trifluoromethoxy-phenyl)-3H-imidazole-4-carboxylic acid

HRID 545339Notes

Reaction equation

HRID 545339 reaction equation
C([O:3][C:4]([C:6]1[N:7]([CH:23]2[CH2:25][CH2:24]2)[C:8]([C:12]2[CH:17]=[CH:16][C:15]([O:18][C:19]([F:22])([F:21])[F:20])=[CH:14][CH:13]=2)=[N:9][C:10]=1[CH3:11])=[O:5])C.[OH-].[Na+]>CCO>[CH:23]1([N:7]2[C:6]([C:4]([OH:5])=[O:3])=[C:10]([CH3:11])[N:9]=[C:8]2[C:12]2[CH:17]=[CH:16][C:15]([O:18][C:19]([F:22])([F:21])[F:20])=[CH:14][CH:13]=2)[CH2:25][CH2:24]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 671330023-Cyclopropyl-5-methyl-2-(4-trifluoromethoxy-phenyl)-3H-imidazole-4-carboxylic acid ethyl ester

Product 1

HCID 671331923-Cyclopropyl-5-methyl-2-(4-trifluoromethoxy-phenyl)-3H-imidazole-4-carboxylic acidYield 62%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 0.1 g (0.3 mmol) of 3-cyclopropyl-5-methyl-2-(4-trifluoromethoxy-phenyl)-3H-imidazole-4-carboxylic acid ethyl ester in 3 ml of EtOH was added 61 microliters of 6 M sodium hydroxide solution (0.4 mmol) and the mixture heated to reflux for 6 h. The solvent was then evaporated, 1M hydrochloric acid solution was added and the resulting precipitate was isolated by filtration, affording 0.06 g (62%) of the title compound as a white solid. MS: 327.1 (MH+).

Workup

  1. temperaturethe mixture heated
  2. temperatureto reflux for 6 h
  3. customThe solvent was then evaporated
  4. addition1M hydrochloric acid solution was added
  5. customthe resulting precipitate was isolated by filtration

Sources & evidence

ORD record
ord-94c8cc2942c84541ba77829e6b34c43d
Source dataset
uspto-grants-2011_05
Patent number
US07935707B2

Reaction notes

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