Oxindole → N-methyl-2-oxoindoline-5-sulfonamide

HRID 1057425Notes

Reaction equation

HRID 1057425 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].[NH:15]1C2C(=CC=CC=2)C[C:16]1=O>CN.O1CCCC1>[CH3:16][NH: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 321710OxindoleHCID 49625062-oxo-2,3-dihydro-1H-indole-5-sulfonyl chloride

Product 1

HCID 10176909N-methyl-2-oxoindoline-5-sulfonamideYield 88%

Reagents, catalysts & solvents 2

HCID 6329MethylamineSolventHCID 8028TetrahydrofuranSolvent

Procedure

A suspension of 3.38 g of 5-chlorosulfonyl-2-oxindole from the oxindole O-17 in 10 mL of 2 M methylamine in tetrahydrofuran was stirred at room temperature for 4 hours at which time a white solid was present. The precipitate was collected by vacuum filtration, washed twice with 5 mL of water each time and dried under vacuum at 40° C. overnight to give 3.0 g (88% yield) of 5-methylaminosulfonyl-2-oxindole.

Workup

  1. filtrationThe precipitate was collected by vacuum filtration
  2. washwashed twice with 5 mL of water each time
  3. customdried under vacuum at 40° C. overnight

Sources & evidence

ORD record
ord-69f20c9c243c4dfa8a2e68887509dc3a
Source dataset
uspto-grants-2003_02
Patent number
US06514981B1

Reaction notes

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