Morpholine → 5-(Morpholinosulfonyl)-2-oxindole

HRID 1057427Notes

Reaction equation

HRID 1057427 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]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1>ClCCl>[N:15]1([S:2]([C:5]2[CH:6]=[C:7]3[C:11](=[CH:12][CH:13]=2)[NH:10][C:9](=[O:14])[CH2:8]3)(=[O:4])=[O:3])[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 49625062-oxo-2,3-dihydro-1H-indole-5-sulfonyl chloride

Product 1

HCID 97957535-(Morpholinosulfonyl)-2-oxindoleYield 74.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A suspension of 2.3 g of 5-chlorosulfonyl-2-oxindole from example O-18 and 2.2 g of morpholine in 50 mL of dichloromethane was stirred at room temperature for 3 hours. The white precipitate was collected by vacuum filtration, washed with ethyl acetate and hexane and dried under vacuum at 40° C. overnight to give 2.1 g (74% yield) of 5-(morpholin-4-sulfonyl)-2-oxindole.

Workup

  1. filtrationThe white precipitate was collected by vacuum filtration
  2. washwashed with ethyl acetate and hexane
  3. customdried under vacuum at 40° C. overnight

Sources & evidence

ORD record
ord-b89c38f9449d4c2c93b90e59a0494b10
Source dataset
uspto-grants-2003_02
Patent number
US06514981B1

Reaction notes

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