Thiazolidinedione → HCID 53634277, compound

HRID 1595548Notes

Reaction equation

HRID 1595548 reaction equation
[F:1][C:2]([F:25])([F:24])[S:3]([O:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][O:15][C:16]2[CH:21]=[CH:20][C:19]([CH:22]=O)=[CH:18][CH:17]=2)=[CH:9][CH:8]=1)(=[O:5])=[O:4].[S:26]1[CH2:30][C:29](=[O:31])[NH:28][C:27]1=[O:32].C([O-])(=O)C.[Na+]>O.CC(C)=O>[F:24][C:2]([F:1])([F:25])[S:3]([O:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][O:15][C:16]2[CH:17]=[CH:18][C:19]([CH:22]=[C:30]3[S:26][C:27](=[O:32])[NH:28][C:29]3=[O:31])=[CH:20][CH:21]=2)=[CH:9][CH:8]=1)(=[O:4])=[O:5]

Participants

5

Reactant 3

HCID 5437ThiazolidinedioneHCID 517045Sodium AcetateHCID 21705009HCID 21705009, compound

Product 1

HCID 53634277HCID 53634277, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 18366337Propan-2-one--water (1/1)Solvent

Conditions

Temperature
140 °C

Procedure

7 g (18.7 mmole) of 4-[2-(4-formylphenoxy)ethyl]phenyl trifluoromethanesulfonate, 2.74 g (23.4 mmole) 2,4-thiazolidinedione and 3.8 g (46.8 mmole) sodium acetate were mixed and heated under vacuum to 140° C. when it melted. It was kept at 140° C. for 20 minutes and thereafter taken off the heat, water:acetone (2:1) was added, the formed crystals were filtered off and recrystallization in dichloromethane gave 2.09 g (yield 24%) 5-(4-[2-(4-trifluoromethanesulfonyloxyphenyl)ethoxy]benzylidene)thiazolidine-2,4-dione.

Workup

  1. additionwas added
  2. filtrationthe formed crystals were filtered off
  3. customrecrystallization in dichloromethane

Sources & evidence

ORD record
ord-cce88dc9733c4630be38121761e03c03
Source dataset
uspto-grants-2001_09
Patent number
US06288096B1

Reaction notes

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