Tetrahydrofuran → HCID 178504718, compound

Participants

Reaction Steps

N-(3-Chloro-1H-indazol-5-yl)-2-methylsulfonylbenzenesulfonamide can be obtained in the following way: a solution of 0.36 g of 2-methylsulfonylbenzenesulfonyl chloride and of 3.6 ml of tetrahydrofuran is added dropwise to a solution, cooled to 0° C., of 0.22 g of 5-amino-3-chloro-1H-indazole, of 15 ml of tetrahydrofuran and of 0.37 ml of triethylamine. After reacting for 30 minutes at a temperature in the region of 0° C. and 18 hours at a temperature in the region of 20° C., 30 ml of distilled water are added to the reaction medium. The medium is extracted with 30 ml and 15 ml of ethyl acetate. The organic phase is subsequently dried over magnesium sulfate, filtered and concentrated by evaporation under reduced pressure. The residue thus obtained is purified by chromatography on a silica column with a dichloromethane/methanol (99/1 by volume) mixture as eluent. The solid thus obtained is recrystallized from 45 ml of isopropanol. After drying under reduced pressure at 60° C., 0.05 g of N-(3-chloro-1H-indazol-5-yl)-2-methylsulfonylbenzenesulfonamide is thus obtained in the form of a white solid melting above 260° C. (analysis C14H12ClN3O4S2 % calculated C, 43.58; H, 3.13; Cl, 9.19; N, 10.89; O, 16.59; S, 16.62. % found C, 43.72; H, 2.88; Cl, 7.94; N, 10.63; S, 16.80).

Provenance & Evidence