Triethylamine → Benzenesulfonamide, 2-nitro-N-(tetrahydro-2H-thiopyran-4-yl)-

Participants

Reaction Conditions

Reaction Steps

To a suspension of tetrahydro-2H-thiopyran-4-amine hydrochloride (80.0 g) in THF (800 mL) were added triethylamine (239 mL) and 2-nitrobenzenesulfonyl chloride (126.9 g) under ice-cooling at an inside temperature of 2-24° C., and the mixture was stirred at room temperature for 23 hr. The reaction solution was partitioned and extracted with ethyl acetate and water, and the organic layer was washed with water and saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure to the extent crystals do not precipitate and purified by silica gel column chromatography [eluent; hexane:ethyl acetate=50:50 (volume ratio)]. The obtained solid was washed with ethanol-diisopropyl ether (1:4), and dried under reduced pressure to give the title compound (145.6 g, yield 92%) as a pale-green solid.

Provenance & Evidence