Ammonia → 1-(benzenesulfonyl)-1H-indole-2-sulfonamide

HRID 1904171Notes

Reaction equation

HRID 1904171 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]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 142562991-(Benzenesulfonyl)-1H-indole-2-sulfonyl chloride

Product 1

HCID 142563001-(benzenesulfonyl)-1H-indole-2-sulfonamideYield 97.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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).

Workup

  1. customwas sparged with nitrogen
  2. customto remove excess ammonia
  3. filtrationThe slurry was filtered
  4. customthe filtrate evaporated in vacuo

Sources & evidence

ORD record
ord-e7452656e347409da199a17e75d433f7
Source dataset
uspto-grants-1989_06
Patent number
US04836846

Reaction notes

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