Ammonia → 2-Oxoindoline-5-sulfonamide

HRID 1386346Notes

Reaction equation

HRID 1386346 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].[NH3:15]>C(O)C.C(Cl)Cl>[NH2:15][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

5

Reactant 2

HCID 222AmmoniaHCID 49625062-oxo-2,3-dihydro-1H-indole-5-sulfonyl chloride

Product 1

HCID 101982322-Oxoindoline-5-sulfonamideYield 843.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 5-chlorosulphonyloxindole (2 g, 0.86 mmol) in ethanol (30 ml), methylene chloride (150 ml) and 2.8M methanolic ammonia (6.2 ml, 17 mmol) was stirred overnight at ambient temperature. The volatiles were removed by evaporation and the solid residue was purified by column chromatography eluting with methanol/methylene chloride (15/85) to give 5-aminosulphonyloxindole (1.54 g, 84%).

Workup

  1. customThe volatiles were removed by evaporation
  2. customthe solid residue was purified by column chromatography
  3. washeluting with methanol/methylene chloride (15/85)

Sources & evidence

ORD record
ord-2fb8a8534d434293bbaabddb4081ed4f
Source dataset
uspto-grants-2001_07
Patent number
US06265411B1

Reaction notes

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