Acetic Acid → 4-(2-Methyl-1H-imidazol-1-yl)-3-(trifluoromethyl)-benzoic acid

HRID 1441743Notes

Reaction equation

HRID 1441743 reaction equation
[CH3:1][C:2]1[N:3]([C:7]2[CH:14]=[CH:13]C(C#N)=[CH:9][C:8]=2[C:15]([F:18])([F:17])[F:16])[CH:4]=[CH:5][N:6]=1.Cl.[C:20]([OH:23])(=[O:22])[CH3:21]>>[CH3:1][C:2]1[N:3]([C:7]2[CH:14]=[CH:13][C:21]([C:20]([OH:23])=[O:22])=[CH:9][C:8]=2[C:15]([F:18])([F:16])[F:17])[CH:4]=[CH:5][N:6]=1

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 686779374-(2-Methyl-1H-imidazol-1-yl)-3-(trifluoromethyl)-benzonitrile

Product 1

HCID 686779654-(2-Methyl-1H-imidazol-1-yl)-3-(trifluoromethyl)-benzoic acid

Conditions

Temperature
95 °C

Procedure

A mixture of 4-(2-methyl-1H-imidazol-1-yl)-3-(trifluoromethyl)-benzonitrile (1.01 g, 4 mmol), 6 mL of acetic acid and 3 mL of 12M hydrochloric acid (37%) is shaken for 16 hours at 95° C. After cooling, the reaction mixture is evaporated to dryness under reduced pressure. The resulting residue is evaporated twice with toluene, dissolved in water and the pH is adjusted to ˜5-6 by dropwise addition of 1M sodium hydroxide solution. The aqueous phase is extracted twice with n-butanol and the organic phase evaporated to yield the title compound as a beige solid.

Workup

  1. temperatureAfter cooling
  2. customthe reaction mixture is evaporated to dryness under reduced pressure
  3. customThe resulting residue is evaporated twice with toluene
  4. dissolutiondissolved in water
  5. additionthe pH is adjusted to ˜5-6 by dropwise addition of 1M sodium hydroxide solution
  6. extractionThe aqueous phase is extracted twice with n-butanol
  7. customthe organic phase evaporated

Sources & evidence

ORD record
ord-f00b2ccadb0540a6bcd110800afd9bef
Source dataset
uspto-grants-2010_02
Patent number
US07655669B2

Reaction notes

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