Acetic Acid → 4-(4-methyl-1H-imidazole-1-yl)-3-(trifluoromethyl)benzoic acid

HRID 1441744Notes

Reaction equation

HRID 1441744 reaction equation
[CH3:1][C:2]1[N:3]=[CH:4][N:5]([C:7]2[CH:14]=[CH:13]C(C#N)=[CH:9][C:8]=2[C:15]([F:18])([F:17])[F:16])[CH:6]=1.Cl.[C:20]([OH:23])(=[O:22])[CH3:21]>>[CH3:1][C:2]1[N:3]=[CH:4][N:5]([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:6]=1

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 686771234-(4-methyl-1H-imidazol-1-yl)-3-(trifluoromethyl)-benzonitrile

Product 1

HCID 686786644-(4-methyl-1H-imidazole-1-yl)-3-(trifluoromethyl)benzoic acid

Conditions

Temperature
95 °C

Procedure

A mixture of 4-(4-methyl-1H-imidazol-1-yl)-3-(trifluoromethyl)-benzonitrile (1.01 g, 4 mmol), 6 mL of acetic acid and 3 mL of 12 M 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 ethyl acetate. The organic phase is dried (Na2SO4) and evaporated to yield the title compound as a pale yellow 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 ethyl acetate
  7. dry with materialThe organic phase is dried (Na2SO4)
  8. customevaporated

Sources & evidence

ORD record
ord-76403a98352d43aa901a121e4f79fe8b
Source dataset
uspto-grants-2010_02
Patent number
US07655669B2

Reaction notes

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