Pyridine → 2-oxo-2,3-dihydro-1H-indole-5-sulfonic acid (2-methoxy-ethyl)-amide

HRID 49115Notes

Reaction equation

HRID 49115 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][O:16][CH2:17][CH2:18][NH2:19].N1C=CC=CC=1>ClCCl>[CH3:15][O:16][CH2:17][CH2:18][NH:19][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 3

HCID 1049PyridineHCID 80182-MethoxyethylamineHCID 49625062-oxo-2,3-dihydro-1H-indole-5-sulfonyl chloride

Product 1

HCID 607092942-oxo-2,3-dihydro-1H-indole-5-sulfonic acid (2-methoxy-ethyl)-amideYield 33%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 5-chlorosulfonyl-2-oxindole (5 g), 2-methoxyethylamine (2.25 mL) and pyridine (7 mL) in dichloromethane (30 mL) was stirred at room temperature for 4 hours. The reaction was concentrated and dichloromethane (15 mL) was added. The precipitate was filtered, washed with dichloromethane and dried to give 1.9 g (33%) of 2-oxo-2,3-dihydro-1H-indole-5-sulfonic acid (2-methoxy-ethyl)-amide.

Workup

  1. concentrationThe reaction was concentrated
  2. additiondichloromethane (15 mL) was added
  3. filtrationThe precipitate was filtered
  4. washwashed with dichloromethane
  5. customdried

Sources & evidence

ORD record
ord-4217565339e54bb891fa7bb79ac92e43
Source dataset
uspto-grants-2004_03
Patent number
US06706709B2

Reaction notes

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