Benzyl Chloride → HCID 44295815, compound

Participants

Reaction Steps

A mixture of 2-[3-(5-chloro-2-methylphenyl)-thioureido]-acetamide (20.6 g), benzyl chloride (25.0 g), and ethanol (350 mL) was heated at reflux for 2.5 hours. The insolubles were removed by filtration and discarded. The filtrate was concentrated to one-half volume. Diethyl ether (300 mL) was added. The precipitated solid was separated by filtration and discarded. The filtrate was evaporated to dryness. The residue was dissolved in chloroform (300 mL) and washed with water. The organic phase was dried over anhydrous MgSO4, decolorized on carbon then evaporated to dryness. The residue was triturated with diethyl ether to give the title compound (14.2 g) as an off-white solid, m.p. 140°-142° C. Anal. Calcd. for. C17H15Cl N2O S: C, 61.72; H, 4.57; N, 8.47. Found: C, 61.62; H, 4.39; N, 8.37. Mass spectrum (EI, M.+) m/z 330/332. 1H-NMR (DMSO-d6 ; 400 MHz) δ7.46 (m, 1 H), 7.42 (m, 2 H), 7.38 (d, 2 H), 7.22-7.32 (m, 3 H), 4.31-4.48 (m, 4 H), and 2.06 ppm (s, 3 H).

Provenance & Evidence