Dimethylformamide → HCID 67312322, compound

Participants

Reaction Steps

To a solution (20 mL) of 3-(acetyloxy)benzoic acid (18.0 g, 100 mmol) in thionyl chloride was added N,N-dimethylformamide (0.1 mL), and the mixture was stirred at room temperature for 1 hr. Excess reagents were evaporated under reduced pressure, and the obtained residue was dissolved in tetrahydrofuran (50 mL), and 4-(trifluoromethyl)aniline (24.2 g, 150 mmol) and N-ethyl-N-isopropylpropane-2-amine (19.4 g, 150 mmol) were successively added dropwise under ice-cooling. The reaction mixture was stirred at room temperature for 1 hr, poured into water and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (eluent:hexane/ethyl acetate=5:1), and triturated with diethyl ether to give the title compound (27.7 g, 86%) as a pale-yellow solid.

Provenance & Evidence