2-(3-Chlorophenyl)thioacetamide synthesis

Yield:834861-72-2 73%

Reaction Conditions:

with hydrogenchloride;O,O-Diethyl hydrogen phosphorodithioate in ethyl acetate at 20;

Steps:

157.157-A

A mixture of (3-chlorophenyl)acetonitrile (10.00 g, 65.97 mmol), 0,0-diethyl dithiophosphate (11.45 mL, 72.56 mmol) and 4M hydrogen chloride-ethyl acetate solution (100 mL) was stirred at room temperature overnight. Water (100 mL) was added thereto in an ice bath, the organic layer was separated, successively washed twice with water (100 mL), twice with 0.2N aqueous sodium hydroxide solution (100 mL), saturated aqueous sodium hydrogen carbonate solution (100 mL) and saturated brine (100 mL), dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was treated with hexane (100 mL) in an ice bath to allow solidification. The solid was collected by filtration, and washed with hexane (50 mL) to give the title compound (8.94 g) as a yellow solid (yield 73%). MS (ESI+) : [M+H]⁺ 185. ¹H NMR (300 MHz, CDCl₃) δ 4.07 (2H, s), 6.64 (1H, brs), 7.13-7.23 (1H, m), 7.28-7.37 (3H, m), 7.41-7.61 (1H, m).

References:

EP2530078,2012,A1 Location in patent:Page/Page column 131