2-[3-(Trifluoromethyl)phenyl]ethanethioamide, 3-(2-Amino-2-thioxoethyl)benzotrifluoride synthesis

Yield:952182-78-4 92%

Reaction Conditions:

with hydrogenchloride;O,O-Diethyl hydrogen phosphorodithioate in ethyl acetate at 20;Product distribution / selectivity;

Steps:

19.19-A

A mixture of [3-(trifluoromethyl)phenyl]acetonitrile (25 g, 135 mmol), O,O-diethyl dithiophosphate (27.5 mL, 148 mmol) and 4M hydrogen chloride-ethyl acetate solution (500 mL) was stirred at room temperature overnight. Water (200 mL) was added thereto in an ice bath, and the organic layer was separated, successively washed twice with water (200 mL), twice with 0.2N aqueous sodium hydroxide solution (200 mL), saturated aqueous sodium hydrogen carbonate solution (200 mL) and saturated brine (200 mL), dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified by basic silica gel column chromatography [eluent: hexane-ethyl acetate (2:1)] to give the title compound (27 g) as a pale-yellow oil (yield 92%). MS (ESI+): [M+H]⁺ 219. ¹H NMR (300 MHz, CDCl₃) δ 4.14 (2H, s), 6.63 (1H, brs), 7.45-7.66 (4H, m). * The peak of one proton was not observed.

References:

EP2530078,2012,A1 Location in patent:Page/Page column 83