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

HRID 346205Notes

Reaction equation

HRID 346205 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-f91e5ce27abd4ecea07d11d7b04d89e3
Source dataset
uspto-grants-1991_10
Patent number
US05061717

Reaction notes

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