Sodium Hydroxide → 3-(2-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)-benzoic acid

HRID 2099452Notes

Reaction equation

HRID 2099452 reaction equation
[CH3:1][C:2]1[N:3]([C:7]2[CH:8]=C([CH:12]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:14]=2)C#N)[CH:4]=[CH:5][N:6]=1.[OH-:19].[Na+].[O:21]1[CH2:26][CH2:25]OCC1>>[CH3:1][C:2]1[N:3]([C:7]2[CH:8]=[C:25]([CH:12]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:14]=2)[C:26]([OH:21])=[O:19])[CH:4]=[CH:5][N:6]=1

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 312751,4-DioxaneHCID 672146433-(2-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)-benzonitrile

Product 1

HCID 672143253-(2-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)-benzoic acid

Conditions

Temperature
95 °C

Procedure

A solution of 3-(2-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)-benzonitrile (Example 91a; 16.7 g, 66 mmol) in dioxane (300 mL) is added to an aqueous solution of sodium hydroxide (275 mL of 1 M) and the mixture is heated at 95° C. for 18 h. The solvent is evaporated off under reduced pressure and the residue is neutralised with hydrochloric acid (1 M) and extracted with butanol (2×250 mL). The solvent is evaporated of under reduced pressure to give the title compound. 1H-NMR (400 MHz, DMSO-d6, δ): 7.17 (s, 1H); 8.03 (s, 1H); 8.12 (s, 1H); 8.35 (s, 1H); 8.41 (s, 1H); 8.53 (s, 1H); 13.90 (br., 1H).

Workup

  1. customThe solvent is evaporated off under reduced pressure
  2. extractionextracted with butanol (2×250 mL)
  3. customThe solvent is evaporated of under reduced pressure

Sources & evidence

ORD record
ord-a3b94597515044f29593aa9d8f51a0d5
Source dataset
uspto-grants-2009_08
Patent number
US07569566B2

Reaction notes

Loading…