Toluene → 5-(4-[2-(4-Methanesulfonylphenyl)ethoxy]benzylidene)thiazolidine-2,4-dione

HRID 1595538Notes

Reaction equation

HRID 1595538 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][O:13][C:14]2[CH:19]=[CH:18][C:17]([CH:20]=O)=[CH:16][CH:15]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].[S:22]1[CH2:26][C:25](=[O:27])[NH:24][C:23]1=[O:28].C1(C)C=CC=CC=1>N1CCCCC1.C(O)(=O)C.O>[CH3:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([CH2:11][CH2:12][O:13][C:14]2[CH:15]=[CH:16][C:17]([CH:20]=[C:26]3[S:22][C:23](=[O:28])[NH:24][C:25]3=[O:27])=[CH:18][CH:19]=2)=[CH:9][CH:10]=1)(=[O:3])=[O:4]

Participants

7

Reactant 3

HCID 1140TolueneHCID 5437ThiazolidinedioneHCID 217049634-[2-(4-Formylphenoxy)ethyl]phenyl methyl sulfone

Product 1

HCID 543455175-(4-[2-(4-Methanesulfonylphenyl)ethoxy]benzylidene)thiazolidine-2,4-dioneYield 67.6%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 8082PiperidineCatalystHCID 962WaterSolvent

Procedure

1 g (3.3 mmole) 4-[2-(4-formylphenoxy)ethyl]phenyl methyl sulfone, 0.96 g (8.2 mmole) 2,4-thiazolidinedione, 5 drops of piperidine, 6 drops of acetic acid and toluene were refluxed with water separation in a Dean-Stark apparatus for 1 hour. The heat was removed and the yellow precipitate was filtered off. A slurry of the precipitate and dichloromethane:methanol (95:5) was refluxed. The product was collected by filtration giving 0.9 g (yield 67.6%) of 5-(4-[2-(4-methanesulfonylphenyl)ethoxy]benzylidene)thiazolidine-2,4-dione.

Workup

  1. customThe heat was removed
  2. filtrationthe yellow precipitate was filtered off
  3. temperatureA slurry of the precipitate and dichloromethane:methanol (95:5) was refluxed
  4. filtrationThe product was collected by filtration

Sources & evidence

ORD record
ord-d1a0c8a2773b448bbc9306080b54afe4
Source dataset
uspto-grants-2001_09
Patent number
US06288096B1

Reaction notes

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