5-CHLORO-2-MERCAPTOANILINE HYDROCHLORIDE synthesis

Yield:-

Reaction Conditions:

with hydrogenchloride;tin in ethanol;water;

Steps:

112

Concentrated hydrochloric acid (125 mL) was slowly (overnight, 15 hours) added to a well-stirred suspension of the trisulfide (37.7 g) described above and tin (Aldrich, 88 g, 737 mmol) in 95% ethanol (200 mL). After filtration of the hot solution, the filtrate was allowed to stand at room temperature overnight to precipitate the crude product. The precipitate was collected by filtration, washed with 1:1 ethanol/concentrated HCl. Recrystalization from 1:1 MeOH/concentrated HCl gave compound 112 (13.8 g) as white needles. ¹H NMR (DMSO-d₆) δ 6.96 (d, J=8.3 Hz, 1H), 6.86 (d, J=2.3 Hz, 1H), 6.50 (dd, J=8.3, 2.3 Hz, 1H).

References:

US2005/250820,2005,A1 Location in patent:Page/Page column 55