4-Toluenesulfonyl chloride → HCID 59473789, compound

Participants

Reaction Steps

To a solution of 1-(5-bromo-1-methyl-2-oxo-1,2-dihydro-pyridin-3-yl)-3-(2-hydroxy-ethyl)-thiourea (306 mg, 1 mmol) in tetrahydrofuran (8 mL) was added aqueous 2N sodium hydroxide (1.25 mL, 2.5 mmol). With vigorous stirring a solution of para-toluene sulfonyl chloride (210 mg, 1.1 mmol) in tetrahydrofuran (4 mL) was added via drop-wise addition over 2 minutes. The material was stirred for 1 hour and then the solvent and volatiles were removed on the rotary evaporator. The remainder was taken up in ethyl acetate (25 mL) and water (15 mL) and shaken in a separatory funnel. The organic phase was collected and the aqueous phase was back extracted with ethyl acetate (2×20 mL). The organic phases were combined, dried over magnesium sulfate, filtered and stripped. The crude was purifed by preparative TLC, eluted with 7% methanol in methylene chloride to provide the desired product as a light green-grey solid (243 mg). (M+H)+=272/274 m/e.

Provenance & Evidence