Hydrochloric Acid → 5-Methoxy-3-methyl-2-(3-trifluoromethoxy-phenyl)-3H-imidazole-4-carboxylic acid

HRID 545365Notes

Reaction equation

HRID 545365 reaction equation
COC1N=C(C2C=CC=C(OC(F)(F)F)C=2)N(C)C=1C=O.C[O:23][C:24]([C:26]1[N:27]([CH3:44])[C:28]([C:33]2[CH:38]=[CH:37][CH:36]=[C:35]([O:39][C:40]([F:43])([F:42])[F:41])[CH:34]=2)=[N:29][C:30]=1[O:31][CH3:32])=[O:25].[Li+].[OH-].Cl>C1COCC1.CO>[CH3:32][O:31][C:30]1[N:29]=[C:28]([C:33]2[CH:38]=[CH:37][CH:36]=[C:35]([O:39][C:40]([F:41])([F:42])[F:43])[CH:34]=2)[N:27]([CH3:44])[C:26]=1[C:24]([OH:25])=[O:23]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 671325565-methoxy-3-methyl-2-(3-trifluoromethoxy-phenyl)-3H-imidazole-4-carboxylic acid methyl esterHCID 866260325-Methoxy-3-methyl-2-(3-trifluoromethoxy-phenyl)-3H-imidazole-4-carbaldehyde

Product 1

HCID 671331715-Methoxy-3-methyl-2-(3-trifluoromethoxy-phenyl)-3H-imidazole-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

A stirred solution of 0.27 g of a mixture of 5-methoxy-3-methyl-2-(3-trifluoromethoxy-phenyl)-3H-imidazole-4-carbaldehyde and 5-methoxy-3-methyl-2-(3-trifluoromethoxy-phenyl)-3H-imidazole-4-carboxylic acid methyl ester (ca. 1:1) in 10 ml of THF/MeOH 1:1 was treated with 0.49 ml (0.5 mmol) of a LiOH solution (1.0 molar in H2O) and the mixture was stirred for 34 days at RT. It was then poured into crashed ice, acidified with HCl (1.0 N) and extracted twice with MeCl2; the organic phases were washed with water, dried over magnesium sulfate, filtered and evaporated. The residue was purified by flash column chromatography (CH2Cl2/MeOH 1:0 to 4:1) to give 0.056 g (ca. 22% over two steps) of the title compound, which has been used without further characterization.

Workup

  1. additionIt was then poured
  2. extractionextracted twice with MeCl2
  3. washthe organic phases were washed with water
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by flash column chromatography (CH2Cl2/MeOH 1:0 to 4:1)

Sources & evidence

ORD record
ord-10cab0aff26f4686a0838e9fd2ee287a
Source dataset
uspto-grants-2011_05
Patent number
US07935707B2

Reaction notes

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