Chlorosulfonic acid → HCID 46739849, compound

HRID 2191509Notes

Reaction equation

HRID 2191509 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].[S:11]([Cl:15])(=O)(=[O:13])[OH:12]>O>[Cl:15][S:11]([C:6]1[CH:7]=[CH:8][C:9]2[C:4](=[CH:3][C:2](=[O:10])[N:1]=2)[CH:5]=1)(=[O:13])=[O:12]

Participants

4

Reactant 2

HCID 24638Chlorosulfonic acidHCID 321710Oxindole

Product 1

HCID 46739849HCID 46739849, compoundYield 65.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1,3-Dihydro-indol-2-one 64a (13.3 g, 100 mmol) was added slowly with chlorosulfuric acid (26.6 ml, 400 mmol) in an ice-water bath. Upon completion of the addition, the reaction mixture was stirred for 1 hour in an ice-water bath, for another 1 hour at room temperature, and heated to 68° C. for 1 hour. The reaction mixture was cooled down to room temperature, added slowly with water (400 ml), stirred and yellow precipitates were formed. After standing for 1 hour at room temperature, the filter cake was washed with water (20 ml×4) and dried to obtain the title compound 5-chlorosulfonyl-indol-2-one 64b (15.0 g, yield 65%) as a yellow solid.

Workup

  1. additionUpon completion of the addition
  2. temperatureheated to 68° C. for 1 hour
  3. temperatureThe reaction mixture was cooled down to room temperature
  4. stirringstirred
  5. customyellow precipitates
  6. customwere formed
  7. waitAfter standing for 1 hour at room temperature
  8. washthe filter cake was washed with water (20 ml×4)
  9. customdried

Sources & evidence

ORD record
ord-ceeafc13bc094e7da889237513cd95f9
Source dataset
uspto-grants-2012_12
Patent number
US08329682B2

Reaction notes

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