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ChemicalBook CAS DataBase List 2-thioxo-3-[4-(trifluoromethyl)phenyl]-1,3-thiazolidin-4-one
57669-54-2

2-thioxo-3-[4-(trifluoromethyl)phenyl]-1,3-thiazolidin-4-one synthesis

5synthesis methods
-

Yield:57669-54-2 54%

Reaction Conditions:

in methanol;water; for 4 h;Reflux;

Steps:

5.1.16. 3-(4-(Trifluoromethyl)phenyl)-2-thioxothiazolidin-4-one (12h)

A solution of 4-(trifluoromethyl)phenyl isothiocyanate (609 mg, 3.0 mmol), 2-mercaptoacetic acid (300 mg, 3.25 mmol) in methanol (10 mL), and water (20 mL) was heated to reflux for 4 h. After cooling to room temperature, the mixture was poured into water, and the solid was filtered out and purified by flash silica column [gradual eluant: EtOAc/petroleum ether, 0-40%] to afford 450 mg of 12h, pale-yellow solid, 54% yield. Mp 140-142 °C; 1H NMR δ ppm 7.82 (d, 2H, J = 8.4 Hz, ArH-2, 6), 7.38 (d, 2H, J = 8.4 Hz, ArH-3, 5), 4.23 (s, 2H, SCH2); MS m/z 276 (M-1, 100).

References:

He, Xiao-Yang;Zou, Peng;Qiu, Jiayin;Hou, Ling;Jiang, Shibo;Liu, Shuwen;Xie, Lan [Bioorganic and Medicinal Chemistry,2011,vol. 19,# 22,p. 6726 - 6734] Location in patent:experimental part