Trichloromethanethiol → HCID 18411445, compound

Participants

Reaction Steps

To an ice-cooled solution of 2-(3-chlorophenyl)-2-(tetrahydropyran-2-yloxy)acetamidine hydrochloride (12.0 g, 39.51 mmol) in dichloromethane (20 mL) and sodium hydroxide (9.49 g, 0.237 mol, dissolved in 60 mL water) was added a solution of perchloromethyl mercaptan (9.18 g, 49.46 mmol) in dichloromethane (50 mL) over a period of 35 min. The reaction mixture was stirred at ice-cold temperature for a further 1 h and the organic layer was collected, dried (sodium sulfate), filtered and concentrated in vacuo. Purification by column chromatography on silica gel using a mixture of hexane and ethyl acetate (94/6) afforded the title compound as a light yellow oil (8.4 g, 61.5%). 1H-NMR (CDCl3) δ7.56 (d, J=6.9 Hz, 1H, Ar--H), 7.39-7.44 (m, 1H, Ar--H), 7.28-7.32 (m, 2H, Ar--H),6.08 and 6.03 (s, 0.5H each, α-H), 4.84 and 4.72 (t, J=3.1Hz, 0.5H each, OCHO), 3.49-3.92 (m, 2H, OCH2), 1.55-1.94 (m, 6H, 3CH2).

Provenance & Evidence