Dimethylamine → 2-Oxo-2,3-dihydro-1H-indole-5-sulfonic acid dimethylamide

HRID 1372434Notes

Reaction equation

HRID 1372434 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][NH:16][CH3:17]>CO>[CH3:15][N:16]([CH3:17])[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 674DimethylamineHCID 49625062-oxo-2,3-dihydro-1H-indole-5-sulfonyl chloride

Product 1

HCID 98161852-Oxo-2,3-dihydro-1H-indole-5-sulfonic acid dimethylamideYield 79%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A suspension of 2.3 g of 5-chlorosulfonyl-2-oxindole in 10 mL of 2M dimethylamine in methanol was stirred at room temperature for 4 hours. The precipitate was collected by vacuum filtration, washed with 5 mL of 1 N sodium hydroxide and 5 mL of 1 N hydrochloric acid and dried under vacuum at 40° C. overnight to give 1.9 g (79% yield) of 5-dimethylaminosulfonyl-2-oxindole. 1H-NMR (300 MHz, DMSO-d6) δ 10.87 (br s, 1H, NH), 7.73 (d, 1H, CH), 7.58 (dd, 1H, CH), 7.02 (d, 1H, CH), 2.59 (s, 3H, CH3), 2.54 (s, 2H, CH2), 2.36 (s, 3H, CH3). MS m/z 241 [M+1].

Workup

  1. filtrationThe precipitate was collected by vacuum filtration
  2. washwashed with 5 mL of 1 N sodium hydroxide and 5 mL of 1 N hydrochloric acid
  3. customdried under vacuum at 40° C. overnight

Sources & evidence

ORD record
ord-70ca8e5b591546b6a0b74e0e5dc2dd77
Source dataset
uspto-grants-2007_01
Patent number
US07157577B2

Reaction notes

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