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

HRID 24521Notes

Reaction equation

HRID 24521 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 slowly added 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. and stirred an additional 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.
  4. stirringstirred an additional 1 hr
  5. temperaturecooled
  6. washThe precipitate was washed with water
  7. customdried in a vacuum oven

Sources & evidence

ORD record
ord-a70b3c2acf8e4ac7b78bad2dd8829832
Source dataset
uspto-grants-2005_02
Patent number
US06855730B2

Reaction notes

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