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

HRID 1441741Notes

Reaction equation

HRID 1441741 reaction equation
[N:1]1([C:6]2[CH:13]=[CH:12]C(C#N)=[CH:8][C:7]=2[C:14]([F:17])([F:16])[F:15])[CH:5]=[CH:4][N:3]=[CH:2]1.Cl.[C:19]([OH:22])(=[O:21])[CH3:20]>>[N:1]1([C:6]2[CH:13]=[CH:12][C:20]([C:19]([OH:22])=[O:21])=[CH:8][C:7]=2[C:14]([F:15])([F:16])[F:17])[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 666336134-(1H-Imidazol-1-yl)-3-(trifluoromethyl)-benzonitrile

Product 1

HCID 686790764-(1H-Imidazol-1-yl)-3-(trifluoromethyl)-benzoic acid

Conditions

Temperature
95 °C

Procedure

A mixture of 4-(1H-imidazol-1-yl)-3-(trifluoromethyl)-benzonitrile (1.99 g, 8.4 mmol), 12 mL of acetic acid and 6 mL of 12M hydrochloric acid (37%) is shaken for 16 hours at 95° C. After cooling down the reaction mixture is evaporated under reduced pressure. The resulting residue is dissolved in water and the pH is adjusted to ˜5-6 by dropwise addition of 1M sodium hydroxide solution. The precipitate is filtered off, washed with water and dried in vacuo to afford the title compound as a solid.

Workup

  1. temperatureAfter cooling down the reaction mixture
  2. customis evaporated under reduced pressure
  3. dissolutionThe resulting residue is dissolved in water
  4. additionthe pH is adjusted to ˜5-6 by dropwise addition of 1M sodium hydroxide solution
  5. filtrationThe precipitate is filtered off
  6. washwashed with water
  7. customdried in vacuo

Sources & evidence

ORD record
ord-554ef0e8b4eb424185c520198cb56065
Source dataset
uspto-grants-2010_02
Patent number
US07655669B2

Reaction notes

Loading…