Thiazolidinedione → 5-(4-[2-(4-Methanesulfonylaminophenyl)ethoxy]benzylidene)thiazolidine-2,4-dione
Reaction equation
[CH:1]([C:3]1[CH:22]=[CH:21][C:6]([O:7][CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([NH:16][S:17]([CH3:20])(=[O:19])=[O:18])=[CH:12][CH:11]=2)=[CH:5][CH:4]=1)=O.[S:23]1[CH2:27][C:26](=[O:28])[NH:25][C:24]1=[O:29].C([O-])(=O)C.[Na+]>O.CC(C)=O>[CH3:20][S:17]([NH:16][C:13]1[CH:14]=[CH:15][C:10]([CH2:9][CH2:8][O:7][C:6]2[CH:21]=[CH:22][C:3]([CH:1]=[C:27]3[S:23][C:24](=[O:29])[NH:25][C:26]3=[O:28])=[CH:4][CH:5]=2)=[CH:11][CH:12]=1)(=[O:19])=[O:18]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 140 °C
Procedure
1.6 g (5 mmole) N-{4-[2-(4-formylphenoxy)ethyl]phenyl}methanesulfonamide, 0.73 g (6.25 mmole) 2,4-thiazolidinedione and 1.025 g (12.5 mmole) sodium acetate were mixed and heated to 140° C. on an oil bath under vacuum (it melted at 130° C.). It was kept at 140° C. for 20 minutes and thereafter taken off the heat. When the temperature was low enough water:acetone (2:1) was added to dissolve the reaction product. Acetone was evaporated in vacuo, acetic acid was added and the obtained crystals were filtered off and recrystallized in dichloromethane to give 0.83 g (yield 40%) of 5-(4-[2-(4-methanesulfonylamino-phenyl)ethoxy]benzylidene)thiazolidine-2,4-dione.
Workup
- additionwas added
- dissolutionto dissolve the reaction product
- customAcetone was evaporated in vacuo, acetic acid
- additionwas added
- filtrationthe obtained crystals were filtered off
- customrecrystallized in dichloromethane
Sources & evidence
- ORD record
- ord-e579b35d72b446908cbc71d33aa59962
- Source dataset
- uspto-grants-2001_09
- Patent number
- US06288096B1
Reaction notes
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