Thiazolidinedione → 5-(4-[2-(4-Methanesulfonyloxyphenyl)ethoxy]benzylidene)thiazolidine-2,4-dione
Reaktionsgleichung
[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]Komponenten
4
Reaktionsbedingungen
- Temperatur
- 155 °C
Versuchsvorschrift
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.