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

HRID 1158254Notes

Reaction equation

HRID 1158254 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]>>[O:10]=[C:2]1[CH2:3][C:4]2[C:9](=[CH:8][CH:7]=[C:6]([S:12]([Cl:11])(=[O:14])=[O:13])[CH:5]=2)[NH:1]1

Participants

3

Reactant 2

HCID 24638Chlorosulfonic acidHCID 321710Oxindole

Product 1

HCID 49625062-oxo-2,3-dihydro-1H-indole-5-sulfonyl chlorideYield 70%

Procedure

1,3-Dihydro-indol-2-one 13 (4.43 g, 33.3 mmol) was added slowly to cold chlorosulfonic acid (9 ml, 135 mmol). The reaction temperature was maintained below 30° C. during the addition. After the addition, the reaction mixture was stirred for 2 h at room temperature, then heated to 68° C. for 1 h, cooled and poured into ice water. The precipitate was washed with water and dried under vacuum to give 2-oxo-2,3-dihydro-1H-indole-5-sulfonyl chloride 14 (5.4 g, 70%). MS m/z 229 [MH]+. 1H NMR, CD3CN 8.91 (S, 1H), 7.90-7.95 (m, 2H), 7.04 (d, J=0.11, 1H), 3.57 (S,1H).

Workup

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

Sources & evidence

ORD record
ord-60f8b22a319c4eb8922ace2baafcb132
Source dataset
uspto-grants-2010_10
Patent number
US07807845B2

Reaction notes

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