Yield:261951-90-0 71%

Reaction Conditions:

Stage #1: 2-methyl-4-(trifluoromethoxy)benzoic acidwith thionyl chloride;N,N-dimethyl-formamide for 0.5 h;
Stage #2: with ammonia in water at 60; for 1 h;

Steps:

4A

Example 4A2-Methyl-4-(trifluoromethoxy)benzamide; 795 mg (3.61 mmol) of 2-methyl-4-(trifluoromethoxy)benzoic acid are heated under reflux with 4 ml (54.8 mmol) of thionyl chloride and one drop of DMF for 30 minutes. After cooling, the reaction solution is introduced slowly dropwise into an ice-cooled concentrated aqueous ammonia solution. The resulting precipitate is collected by suction filtration, taken up in 30 ml of water and stirred at 60° C. for 1 h. The mixture is allowed to cool and the solid is collected by filtration and dried under vacuum. Yield 562 mg (71% of theory).LC-MS (method 2): R_t=1.61 min.MS (ESI⁺): m/z=220 (M+H)^{+ 1}H NMR (400 MHz, DMSO-d₆): δ=7.79 (bs, 1H), 7.42-7.50 (m, 2H), 7.19-7.28 (m, 2H), 2.39 (s, 3H).

References:

US2009/181996,2009,A1 Location in patent:Page/Page column 10