3-Chloropropanesulphonyl chloride → N-{5-[3-(1,1-dioxido-2-isothiazolidinyl)phenyl]-2,3-dihydro-1H-inden-2-yl}-2-propanesulfonamide

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Reaction Steps

A mixture of N-[5-(3-aminophenyl)-2,3-dihydro-1H-inden-2-yl]-2-propanesulfonamide (100 mg, 0.30 mmol), and diisopropylethylamine (79 mg, 0.61 mmol), in dry dimethylformamide (2 ml) was treated with 3-chloropropanesulfonyl chloride (54 mg, 0.30 mmol) and stirred at room temperature for 1 h. Sodium hydride (60% dispersion in oil, 15 mg, 0.38 mmol) was added and the mixture stirred at 60° C. for 0.5 h. The reaction mix was cooled then partitioned between dichloromethane and 0.5M hydrochloric acid, and the organic layer was evaporated under reduced pressure to give a brown oil which was purified by column chromatography on a 5 g isolute silica sep-pak column eluting from 0-50% ethyl acetate in 40-60° C. petroleum ether to give the title compound as a yellow oil (12 mg, 9%).

Provenance & Evidence