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

HRID 1615198Notes

Reaction equation

HRID 1615198 reaction equation
[NH2:1][CH3:2].[O:3]=[C:4]1[CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[C:9]([S:13](Cl)(=[O:15])=[O:14])[CH:10]=2)[NH:5]1>C1COCC1>[CH3:2][NH:1][S:13]([C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][CH:8]=1)[NH:5][C:4](=[O:3])[CH2:12]2)(=[O:15])=[O:14]

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 74%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A dry round-bottom flask was charged with 1 mL of a 2.0 M solution of H2NMe in THF. 2-oxoindoline-5-sulfonyl chloride (100 mg, 0.432 mmol) was then added and the reaction stirred overnight. The solvents were removed and the residue purified by column chromatography (silica gel, 93:7 CH2Cl2/MeOH) to give 73 mg, 74% of a brown solid. 1H NMR (400 MHz, CD3OD) δ 7.73 (d, J=8.8 Hz, 1H), 7.72 (s, 1H), 7.03 (d, J=8.0 Hz, 1H), 3.35 (s, 2H), 2.52 (s, 3H); MS ESI 226.9 [M+H]+, calcd for [C9H10N2O3S+H]+ 227.05.

Workup

  1. customThe solvents were removed
  2. customthe residue purified by column chromatography (silica gel, 93:7 CH2Cl2/MeOH)

Sources & evidence

ORD record
ord-912ea9765371435e9afa9154584152f0
Source dataset
uspto-grants-2014_07
Patent number
US08765748B2

Reaction notes

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