Dimethylamine → 2-Oxo-2,3-dihydro-1H-indole-5-sulfonic acid dimethylamide

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Reaction Steps

A suspension of 2.3 g of 5-chlorosulfonyl-2-oxindole in 10 mL of 2M dimethylamine in methanol was stirred at room temperature for 4 hours. The precipitate was collected by vacuum filtration, washed with 5 mL of 1 N sodium hydroxide and 5 mL of 1 N hydrochloric acid and dried under vacuum at 40° C. overnight to give 1.9 g (79% yield) of 5-dimethylaminosulfonyl-2-oxindole. 1H-NMR (300 MHz, DMSO-d6) δ 10.87 (br s, 1H, NH), 7.73 (d, 1H, CH), 7.58 (dd, 1H, CH), 7.02 (d, 1H, CH), 2.59 (s, 3H, CH3), 2.54 (s, 2H, CH2), 2.36 (s, 3H, CH3). MS m/z 241 [M+1].

Provenance & Evidence