Thiazolidinedione → 5-(4-[2-(4-Methanesulfonyloxyphenyl)ethoxy]benzylidene)thiazolidine-2,4-dione

HRID 1595493Notes

Reaction equation

HRID 1595493 reaction equation
[CH3:1][S:2]([O:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13][O:14][C:15]2[CH:20]=[CH:19][C:18]([CH:21]=O)=[CH:17][CH:16]=2)=[CH:8][CH:7]=1)(=[O:4])=[O:3].[S:23]1[CH2:27][C:26](=[O:28])[NH:25][C:24]1=[O:29].C([O-])(=O)C.[Na+]>>[CH3:1][S:2]([O:5][C:6]1[CH:7]=[CH:8][C:9]([CH2:12][CH2:13][O:14][C:15]2[CH:16]=[CH:17][C:18]([CH:21]=[C:27]3[S:23][C:24](=[O:29])[NH:25][C:26]3=[O:28])=[CH:19][CH:20]=2)=[CH:10][CH:11]=1)(=[O:3])=[O:4]

Participants

4

Reactant 3

HCID 5437ThiazolidinedioneHCID 517045Sodium AcetateHCID 114159454-[2-(4-Formylphenoxy)ethyl]phenyl methanesulfonate

Product 1

HCID 536855295-(4-[2-(4-Methanesulfonyloxyphenyl)ethoxy]benzylidene)thiazolidine-2,4-dioneYield 84.7%

Conditions

Temperature
155 °C

Procedure

1.5 g (4.7 mmole) 4-[2-(4-formylphenoxy)ethyl]phenyl methanesulfonate, 0.68 g (5.8 mmole) 2,4-thiazolidinedione and 0.96 g (11.8 mmole) sodium acetate were mixed and heated under vacuum to 155° C. The reaction mixture melted and was removed from the heat after 15 minutes. Water/acetone (2:1) was added and the mixture was stirred for 1 h. Filtration gave 1.67 g (yield 83%) of 5-(4-[2-(4-methanesulfonyloxyphenyl)-ethoxy]benzylidene)thiazolidine-2,4-dione as yellow crystals.

Workup

  1. customwas removed from the
  2. temperatureheat after 15 minutes
  3. additionWater/acetone (2:1) was added
  4. filtrationFiltration

Sources & evidence

ORD record
ord-304504b011df4600a4035edf734b21e9
Source dataset
uspto-grants-2001_09
Patent number
US06288096B1

Reaction notes

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