Ethanethiol → Benzenesulfonamide

Participants

Reaction Conditions

Reaction Steps

To a solution of NaH (0.025 g, 1.03 mmol) in tetrahydrofuran (2 mL) was added ethanethiol (0.096 g, 1.54 mmol), followed by 4-chloro-N-[2,5-dichlorophenyl]-N-[(R)-1-methyl-4-bromobutyl]benzenesulfonamide (0.500 g 1.03 mmol) under nitrogen at 0° C. The reaction was stirred overnight at 22° C. The mixture was quenched with H2° (3 mL), extracted with ethyl ether (2×10 mL), dried over Na2SO4, and filtered. The organic solvent was concentrated under reduced pressure. Silica gel chromatography (1:9, ethyl acetate:hexanes) afforded 0.460 g of 4-chloro-N-[2,5-dichlorophenyl}-N-[4-(ethylthio)]-1-(R)-methylbutyl]benzenesulfonamide as a yellow oil in 59% yield. LC/MS 466.

Provenance & Evidence