Chlorosulfonic acid → 2-oxo-2,3-dihydro-1H-indole-5-sulfonyl chloride

HRID 24309Notes

Reaction equation

HRID 24309 reaction equation
[Cl:1][S:2]([OH:5])(=O)=[O:3].[NH:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:8][C:7]1=[O:15]>O>[Cl:1][S:2]([C:11]1[CH:10]=[C:9]2[C:14](=[CH:13][CH:12]=1)[NH:6][C:7](=[O:15])[CH2:8]2)(=[O:5])=[O:3]

Participants

4

Reactant 2

HCID 24638Chlorosulfonic acidHCID 321710Oxindole

Product 1

HCID 49625062-oxo-2,3-dihydro-1H-indole-5-sulfonyl chlorideYield 50%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a 100 mL flask charged with 27 mL of chlorosulfonic acid was added slowly 13.3 g of 2-oxindole. The reaction temperature was maintained below 30° C. during the addition. After the addition, the reaction mixture was stirred at room temperature for 1.5 hr, heated to 68° C. for 1 hr, cooled, and poured into water. The precipitate was washed with water and dried in a vacuum-oven to give 11.0 g of 5-chlorosulfonyl-2-oxindole (50% yield) which was used without further purification.

Workup

  1. temperatureThe reaction temperature was maintained below 30° C. during the addition
  2. additionAfter the addition
  3. temperatureheated to 68° C. for 1 hr
  4. temperaturecooled
  5. washThe precipitate was washed with water
  6. customdried in a vacuum-oven

Sources & evidence

ORD record
ord-f36e2b997e6f4097a76a275feda80ec2
Source dataset
uspto-grants-2005_02
Patent number
US06855730B2

Reaction notes

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