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

HRID 1372433Notes

Reaction equation

HRID 1372433 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].[CH3:15][NH2:16]>O1CCCC1>[CH3:15][NH: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 6329MethylamineHCID 49625062-oxo-2,3-dihydro-1H-indole-5-sulfonyl chloride

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A suspension of 3.38 g of 5-chlorosulfonyl-2-oxindole in 10 mL of 2M methylamine in tetrahydrofuran was stirred at room temperature for 4 hours. 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. 1H-NMR (300 MHz, DMSO-d6) δ 10.87 (br s, 1H, NH), 7.86 (br s, 1H, SO2NH), 7.61 (d, 1H), 7.32 (d, 1H), 6.97 (d, 1H), 2.53 (s, 2H, CH2), 2.36 (s, 3H, NHCH3). MS m/z 226 [M].

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-8171f612da3c41a7b6a1b402df24559e
Source dataset
uspto-grants-2007_01
Patent number
US07157577B2

Reaction notes

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