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

HRID 1386345Notes

Reaction equation

HRID 1386345 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][C:2]1=[O:10].[Cl:11][S:12](O)(=[O:14])=[O:13]>>[Cl:11][S:12]([C:6]1[CH:5]=[C:4]2[C:9](=[CH:8][CH:7]=1)[NH:1][C:2](=[O:10])[CH2:3]2)(=[O:14])=[O:13]

Participants

3

Reactant 2

HCID 24638Chlorosulfonic acidHCID 321710Oxindole

Product 1

HCID 49625062-oxo-2,3-dihydro-1H-indole-5-sulfonyl chlorideYield 80.6%

Conditions

Temperature
5 °C

Procedure

Oxindole (2 g, 15 mmol) was added in portions to chlorosulphonic acid (5 ml, 75 mmol) cooled at 5° C. The mixture was stirred at ambient temperature for 10 minutes and then heated at 80° C. for 30 minutes. The mixture was allowed to cool, and then poured onto ice. The precipitate was collected by filtration, washed with water, and dried over phosphorus pentoxide to give 5-chlorosulphonyloxindole (2.8 g, 80%).

Workup

  1. temperatureheated at 80° C. for 30 minutes
  2. temperatureto cool
  3. additionpoured onto ice
  4. filtrationThe precipitate was collected by filtration
  5. washwashed with water
  6. dry with materialdried over phosphorus pentoxide

Sources & evidence

ORD record
ord-ca3c1127212446ecb03b588d8a6b44bf
Source dataset
uspto-grants-2001_07
Patent number
US06265411B1

Reaction notes

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