Ammonia → 1-(benzenesulfonyl)-1H-indole-2-sulfonamide
Reaction equation
[C:1]1([S:7]([N:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12]=[C:11]2[S:19](Cl)(=[O:21])=[O:20])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH3:23]>C1COCC1>[C:1]1([S:7]([N:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12]=[C:11]2[S:19]([NH2:23])(=[O:21])=[O:20])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a stirred solution of 10 g (0.0281 mole) of 1-phenylsulfonyl-1H-indole-2-sulfonyl chloride in 150 ml anhydrous THF was added at -78° 4 ml (0.192 mole) of anhydrous ammonia. The resulting slurry was allowed to warm to room temperature over 30 minutes, then was sparged with nitrogen to remove excess ammonia. The slurry was filtered and the filtrate evaporated in vacuo to afford 9.19 g of tan solid, m.p. 199°-200.5°, 1H NMR (CDCl3 /DMSO-d6) δ7.23-7.77 (m, 9H), 8.1-8.28 (m, 3H, C-3 proton and SO2NH2). The infrared spectrum of the product included absorptions at 3400 and 3280 cm-1 (SO2NH2).