Cyclohexylamine → HCID 15730054, compound

A solution of ethyl 2-mercaptoacetate (12 g) and cyclohexylamine (29.7 g) in ethanol (50 ml) was allowed to stand at ambient temperature for 72 hours, and was then refluxed for 6 hours. The solvent was evaporated and the residue dissolved in ethyl acetate (200 ml). The solution was washed sequentially with 2M HCl (3×50 ml), water (2×50 ml) and brine (50 ml), and the solvent removed in vacuo. The crude product was purified by chromatography on silica (eluting with dichloromethane/methanol 99:1 v/v) to give N-cyclohexyl-2-mercaptoacetamide as low-melting tan crystals, NMR: 1.0-2.0 (complex, 11H, cyclohexyl-CH2 and SH), 3.2(d,2H, CH2), 3.6-3.9(m,1H, cyclohexyl --CH), 6.4-6.9 (broad d,1H, NH); m/e 174 (M+H)+.

1. temperaturewas then refluxed for 6 hours
2. customThe solvent was evaporated
3. dissolutionthe residue dissolved in ethyl acetate (200 ml)
4. washThe solution was washed sequentially with 2M HCl (3×50 ml), water (2×50 ml) and brine (50 ml)
5. customthe solvent removed in vacuo
6. customThe crude product was purified by chromatography on silica (eluting with dichloromethane/methanol 99:1 v/v)

ORD record

ord-b51b6235b8e6413d835a2e299f7990a6

Source dataset

uspto-grants-1993_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05270311