Chlorosulfonic acid → 4-[(2,4-Dioxo-1,3-thiazolidin-5-yl)methyl]benzene-1-sulfonyl chloride

HRID 1729053Notes

Reaction equation

HRID 1729053 reaction equation
[Cl:1][S:2]([OH:5])(=O)=[O:3].[CH2:6]([CH:13]1[S:17][C:16](=[O:18])[NH:15][C:14]1=[O:19])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>>[S:17]1[CH:13]([CH2:6][C:7]2[CH:12]=[CH:11][C:10]([S:2]([Cl:1])(=[O:5])=[O:3])=[CH:9][CH:8]=2)[C:14](=[O:19])[NH:15][C:16]1=[O:18]

Participants

3

Reactant 2

HCID 24638Chlorosulfonic acidHCID 31570135-Benzyl-1,3-thiazolidine-2,4-dione

Product 1

HCID 156164324-[(2,4-Dioxo-1,3-thiazolidin-5-yl)methyl]benzene-1-sulfonyl chloride

Procedure

Chlorosulfonic acid (5 mL) was cooled to 0° C. and the 5-benzyl-2,4-thiazolidinedione prepared above (9.6 mmol, 2.0 g) was added portionwise. The reaction mixture was stirred at room temperature for 0.5 hour and poured into ice (25 g). The solution was extracted with methylenechloride (2×50 mL), the organic layers were combined and dried (Na2SO4), and solvent removed in vacuo to afford title product which was used without further purification.

Workup

  1. additionwas added portionwise
  2. extractionThe solution was extracted with methylenechloride (2×50 mL)
  3. dry with materialdried (Na2SO4), and solvent
  4. customremoved in vacuo

Sources & evidence

ORD record
ord-dda1f4175e564f67b86462107eadf389
Source dataset
uspto-grants-1994_07
Patent number
US05330998

Reaction notes

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