5-(Benzenesulfanyl)-thiazolidine-2,4-dione → 5-(Benzenesulfonyl)-thiazolidine-2,4-dione

HRID 1451816Notes

Reaction equation

HRID 1451816 reaction equation
C1C=CC(S[CH:8]2[S:14][C:12](=[O:13])[NH:11][C:9]2=[O:10])=CC=1.C[C:16]1[CH:21]=[CH:20][CH:19]=[C:18](SC2SC(=O)NC2=O)[CH:17]=1.O[O:31][S:32]([O-:34])=O.[K+]>CO.O>[C:16]1([S:32]([CH:8]2[S:14][C:12](=[O:13])[NH:11][C:9]2=[O:10])(=[O:34])=[O:31])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 3

HCID 104893885-(Benzenesulfanyl)-thiazolidine-2,4-dioneHCID 10610046HCID 10610046, compoundHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 105390745-(Benzenesulfonyl)-thiazolidine-2,4-dioneYield 73%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

A solution of 5-(benzenesulfanyl)-thiazolidine-2,4-dione, [(III), Example 6, 10.0 g, 41.8 mmol] in methanol (105 mL) was added to a mechanically stirred suspension of oxone (51.4 g, 83.6 mmol) in water (210 mL) at 0° C. The suspension was immediately warmed to room temperature. After 3.5 h, the reaction was diluted with water (1.5 L) and the solid was filtered. The solid was washed with water and dried in vacuo to provide the title compound as a white solid (8.31 g, 73%): mp 130°-133° C.: NMR (CDCL3): δ8.07 (s, 1H, NH), 7.98 (d, J=7.2 Hz, 2H, ArH) 7.78 (t, J=7.5 Hz, 1H, ArH), 7.67 (t, J=8.1 Hz, 2H, ArH), 5.44 (s, 1H CH); MS(EI): 225 (MI, 24%), 182 (18%), 153 (12%), 110 (100%).

Workup

  1. filtrationthe solid was filtered
  2. washThe solid was washed with water
  3. customdried in vacuo

Sources & evidence

ORD record
ord-33404c03a5154e36984dc89f8a075a6c
Source dataset
uspto-grants-1997_02
Patent number
US05605918

Reaction notes

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