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ChemicalBook CAS DataBase List 2,4-Thiazolidinedione, 5-[(4-hydroxyphenyl)methylene]-

2,4-Thiazolidinedione, 5-[(4-hydroxyphenyl)methylene]- synthesis

3synthesis methods
-

Yield:103788-60-9 95.5%

Reaction Conditions:

with piperidine;acetic acid in toluene at 80;Dean-Stark;

Steps:

61.1 Preparation of Reaction Intermediate

First, Compounds 61a to 75a (5-(4-hydroxy-ben- zylidene)thiazolidine-2,4-dione), which are reactants used for synthesizing Compounds 61 to 75, were synthesized according to the following scheme.1 g (8.19 mmol) of 4-hydroxy-benzaldehyde and0.959 g (8.19 mmol) of 2,4-thiazolidinedione were placed in a round flask equipped with a Dean-Stark trap, and then dissolved in 20 ml of toluene, which is a reaction solvent, and then, 0.404 ml (4.09 mmol) of piperidine and 0.234 ml (4.09 mmol) of acetic acid were added thereto, followed by the reaction at a temperature of 80° C. for 18 hours or more. The completion of the reaction was confirmed by TLC, and the resulting precipitate was recrystallized and then filteredunder reduced pressure to obtain a pure solid.Yield: 95.5%1H NMR (300 MHz, DMSO-d6) 0 12.46 (s, 1H),o 10.32 (s, 1H), 0 7.69 (s, 1H), 0 7.46 (d, J=8.43 Hz, 2H),o 6.92 (d, J=8.43 Hz, 2H)

References:

US2019/16695,2019,A1 Location in patent:Paragraph 0386; 0387; 0389; 0390