ChemicalBook CAS DataBase List 2,4-Thiazolidinedione

2,4-Thiazolidinedione synthesis

9synthesis methods

Product Name:2,4-Thiazolidinedione
CAS Number:2295-31-0
Molecular formula:C3H3NO2S
Molecular Weight:117.13

2,4-Thiazolidinedione can be used as an intermediate for the synthesis of thiazole sensitizers such as pioglitazone and rosiglitazone. Its synthesis method is as follows: 2-Chloroacetic acid and thiourea in water was heated to reflux for 10 h, then collected by filtering over vacuum and washed with a small amount of ice water to give 1,3-thiazolidine-2,4-dione.

556-90-1
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2295-31-0
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Yield:2295-31-0 83%

Reaction Conditions:

with hydrogenchloride;ethanolReflux;

Steps:

B
B) Synthesis of 2,4-thiazolidinedione (V):; 2-Imino-thiazolidin-4-one (IV) (1Og) was hydrolyzed with 2N HCl (40ml) in ethanol (40ml). The mixture was refluxed and the reaction was monitored on TLC. The reaction mixture was cooled and neutralized with, saturated solution of sodium bicarbonate (10%). Upon neutralization the crude product, 2,4-thiazolidinedione (V) separated as solid. The crude product was recrystallized from ethanol: water (40:60) mixture. The product was dried at 60°C. Yield : 83% M. P. : 120-123°C

References:

ELDER PHARMACEUTICALS LTD;SAKHARDANDE, Rajiv WO2010/82212, 2010, A2 Location in patent:Page/Page column 28

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