Ammonium Hydroxide → 2-Oxoindoline-5-sulfonamide

HRID 1372432Notes

Reaction equation

HRID 1372432 reaction equation
Cl[S:2]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9](=[O:14])[CH2:8]2)(=[O:4])=[O:3].[OH-].[NH4+:16]>C(O)C>[NH2:16][S:2]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9](=[O:14])[CH2:8]2)(=[O:4])=[O:3]

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 49625062-oxo-2,3-dihydro-1H-indole-5-sulfonyl chloride

Product 1

HCID 101982322-Oxoindoline-5-sulfonamideYield 20%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5-Chlorosulfonyl-2-oxindole (2.1 g) was added to 10 mL of ammonium hydroxide in 10 mL of ethanol and stirred at room temperature overnight. The mixture was concentrated and the solid collected by vacuum filtration to give 0.4 g (20% yield) of 5-aminosulfonyl-2-oxindole as an off-white solid. 1H-NMR (360 MHz, dimethylsulfoxide-d6) δ 10.67 (s, 1H, NH), 7.63–7.66 (m, 2H), 7.13 (s, 2H, 5-SO2NH2), 6.91 (d, 1H), 3.56 (s, 2H, CH2). MS m/z 211 [M−1]+.

Workup

  1. concentrationThe mixture was concentrated
  2. filtrationthe solid collected by vacuum filtration

Sources & evidence

ORD record
ord-820e258d26b343b19419057ae04c2e81
Source dataset
uspto-grants-2007_01
Patent number
US07157577B2

Reaction notes

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