Hydrochloric Acid → HCID 19369069, compound

Participants

Reaction Steps

Sulfuryl chloride (6.2 g, 46 mmol) was added dropwise to a stirred solution of 2,4-diisopropylthiophenol (8.9 g, 46 mmol) in dichloromethane (50 ml) and stirring was continued at room temperature for 2 hrs. Volatiles were removed by rotary evaporation to give an oil. A solution of N-(2-chloro-4-dodecylsulfonylphenyl)-N-[4,5-dihydro-5-oxo-1-(2,4,6-trichlorophenyl)-1H-pyrazol-3-yl]acetamide (29.0 g, 44 mmol) in N,N-dimethylformamide (75 ml) was added to the oil and the mixture was stirred at room temperature for 26 hrs. The solution was poured into 3N hydrochloric acid (750 ml) and the resulting sticky solid was collected by filtration. The solid was dissolved in ethyl acetate (200 ml) and the organic solution was washed with brine (100 ml), dried (MgSO4) and evaporated to an orange glass. The crude material was purified by column chromatography on 63-200 mesh silica gel eluting with 1:4 ethyl acetate/60-80 petroleum ether. Pure product was obtained as a cream colored glass, 11.7 g, 31%. C41H51Cl4N3O4S2Req: C 57.5%,H 6.0%,Cl 16.6%,N 4.9%,S 7.5%; Fd: C 57.1%,H 6.1%,Cl 16.4%,N 4.8%,S 7.2%

Provenance & Evidence