Ammonia → 3,4,5-Trifluorobenzamide

Participants

Reaction Steps

3,4,5-Trifluorobenzoic acid (1.00 g) was dissolved in N,N-dimethylformamide (15 mL), and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (1.31 g) and N-hydroxysuccinimide (785 mg) were added thereto at 0° C. The mixture was stirred at room temperature for 3 hr. 28% Aqueous ammonia solution (2 mL) was added to the mixture at 0° C. and the mixture was stirred at room temperature for 30 min. Water was added to the mixture and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (developing solvent: ethyl acetate-hexane=1:2→3:1) and recrystallized from a mixed solvent of isopropylether and hexane to give the title compound as colorless crystals (yield: 734 mg).

Provenance & Evidence