ChemicalBook CAS DataBase List (S)-4-BENZYL-1,3-THIAZOLIDINE-2-THIONE

(S)-4-BENZYL-1,3-THIAZOLIDINE-2-THIONE synthesis

7synthesis methods

Product Name:(S)-4-BENZYL-1,3-THIAZOLIDINE-2-THIONE
CAS Number:171877-39-7
Molecular formula:C10H11NS2
Molecular Weight:209.33

3182-95-4 Synthesis

3182-95-4
462 suppliers
$5.00/5g

140-89-6
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$12.00/5g

171877-39-7
108 suppliers
$26.00/100mg

Yield: 83%

Reaction Conditions:

in ethanol at 100; for 24 h;Inert atmosphere;Sealed tube;

Steps:

General procedure for preparation of 1,3-thiazolidine-2-thiones (2)
General procedure: To the mixture of vicinal amino alcohol (1, 1.0 mmol, 1.0 equiv.) in absolute ethanol (2.0 mmol),potassium ethylxanthate (5.0 mmol, 5.0 equiv.) was added quickly. After flushed with N2 for 5 mins,the suspension was sealed and heated in an oil bath at 100 °C for 24 hr. The it was cooled down toroom temperature, the mixture was transferred to a 50 mL-round bottom flask, and evaporated underreduced pressure to remove alcohol. Then water (10 mL) was added to the slurry and extracted withethyl acetate (30 mL*3). Combined organic phase was washed with brine (30 mL) and dried overanhydrous Na2SO4. After concentration, the crude product was obtained. Then it was applied onsilica gel for flash chromatography to afford corresponding 1,3-thiazolidine-2-thione (2). For somecases, 1,3-oxazolidine-2-thione (3) was obtained as side product.

References:

Lu, Zheng;Yang, Yong-Qing;Xiong, Weixiang [Synlett,2019,vol. 30,# 6,p. 713 - 716] Location in patent:supporting information