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

HRID 1364592Notes

Reaction equation

HRID 1364592 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:15]=[C:7]1[CH2:8][C:9]2[C:14](=[CH:13][CH:12]=[C:11]([S:2]([Cl:1])(=[O:5])=[O:3])[CH:10]=2)[NH:6]1

Participants

3

Reactant 2

HCID 24638Chlorosulfonic acidHCID 321710Oxindole

Product 1

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

Procedure

To a solution of chlorosulfonic acid (25 mL, 37.5 mmol) at 0° C. was slowly added oxindole over 40 min. The resulting solution was stirred at RT for 1.5 h and then heated to 50° C. for 10 min until gas evolution ceased. After cooling to RT, the reaction mixture was carefully poured onto ice. A white precipitate was formed which was filtered, washed with ice-water and dried under HV. Yield: 14.35 g (82%). LC/MS (10-99%): M/Z: M+ (obs)=232; tR=2.24 min.

Workup

  1. customat 0° C.
  2. customover 40 min
  3. temperatureheated to 50° C. for 10 min until gas evolution
  4. temperatureAfter cooling to RT
  5. additionthe reaction mixture was carefully poured onto ice
  6. customA white precipitate was formed which
  7. filtrationwas filtered
  8. washwashed with ice-water
  9. customdried under HV

Sources & evidence

ORD record
ord-cd4471b4ec67447c91b4723546e98887
Source dataset
uspto-grants-2011_02
Patent number
US07888384B2

Reaction notes

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