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

HRID 1588763Notes

Reaction equation

HRID 1588763 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 methylene chloride (2×50 ml) and the organic layers were 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 methylene chloride (2×50 ml)
  3. dry with materialthe organic layers were dried (Na2SO4) and solvent
  4. customremoved in vacuo

Sources & evidence

ORD record
ord-351f6a27936e4d21ab80be4fcabd91a2
Source dataset
uspto-grants-1993_06
Patent number
US05223522

Reaction notes

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