Pyridine → 5-Isopropylaminosulfonyl-2-oxindole

HRID 1790977Notes

Reaction equation

HRID 1790977 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].[CH:15]([NH2:18])([CH3:17])[CH3:16].N1C=CC=CC=1>ClCCl>[CH:15]([NH:18][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])([CH3:17])[CH3:16]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6363IsopropylamineHCID 49625062-oxo-2,3-dihydro-1H-indole-5-sulfonyl chloride

Product 1

HCID 219156105-Isopropylaminosulfonyl-2-oxindoleYield 45.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A suspension of 3 g of 5-chlorosulfonyl-2-oxindole, 1.15 g of isopropylamine and 1.2 mL of pyridine in 50 mL of dichloromethane was stirred at room temperature for 4 hours at which time a white solid was present. The precipitate was collected by vacuum filtration. The solids were slurry-washed with hot ethanol, cooled, collected by vacuum filtration and dried under vacuum at 40° C. overnight to give 1.5 g (45% yield) of 5-isopropylaminosulfonyl-2-oxindole.

Workup

  1. filtrationThe precipitate was collected by vacuum filtration
  2. washThe solids were slurry-washed with hot ethanol
  3. temperaturecooled
  4. filtrationcollected by vacuum filtration
  5. customdried under vacuum at 40° C. overnight

Sources & evidence

ORD record
ord-8db5f9b6624f4568a95dc50f93c1c1cd
Source dataset
uspto-grants-2006_07
Patent number
US07071332B2

Reaction notes

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