Pseudothiohydantoin

white to yellowish fine needles or powder

Thiourea (1.52g, 0.02mol) was added to 10mL 95percent ethanol. It was stirred at reflux for 10min, Slowly added dropwise ethyl chloroacetate (2.16mL, 0.02mol) then reflux for 3h. Cooling to room temperature, it was then filtered. Washed with a small amount of ethanol. Dried to give a white solid 2.51g, 92percent yield.In a clean 50 mL single-necked flask, add 0.05 mol of thiourea, 25.0 mL mass concentration of 95percent ethanol, Reflux stirring about 20min, so that thiourea all dissolved in 10min after the drop out of 0.05 mol ethyl chloroacetate, and then stirring reflux reaction 3h, A large amount of white fine crystals appeared in the resulting reaction solution, and the reaction solution was cooled to room temperature, followed by suction filtration and washing with a small amount of ethanol, finally drying, A solution of 2-imino-1, 3-thiazolidin-4-one (7.40 g) as a white solid in 92percent yield, m.p. 222-224 °C.A) Synthesis of 2-imino-4-thiazolidinone (IV):; 2Og (0.263mol) of thiourea (III) was added in 100ml round bottom flask, equipped with condenser, containing 50 ml ethanol. The mixture was gently refluxed. To this mixture 32.22g (0.263 mol) of ethylchloroacetate (II) was slowly added over a period of 30min. The mixture was refluxed and monitored on TLC. The reaction mixture was allowed to cool to room temperature. The hydrochloride salt of 2-imino- thiazolidin-4-one or pseudothiohydantoin was filtered from the solution. This salt was added to water and neutralized with solution of sodium acetate, which precipitates, 2-imino-4-thiazolidinone (TV) on cooling. The product was filtered and dried at 60°C. Yield : 86percent M. P. : 254-259°CA solution of 239 (0.76 g, 10 mmoi), ethyl 2-chioroacetate (2.1 rnL, 20 mrnol). and sodium acetate in EtOFI (100 mL) is stirred at 60 °c overnight, After cooling to room temperature, the solid is collected to give 1)10 as a white solid (0.65 g, 55percent yield). (MS:[M+HJ 117.2)

Molecular Weight:116.14
XLogP3:-0.3
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Exact Mass:116.00443393
Monoisotopic Mass:116.00443393
Topological Polar Surface Area:80.8
Heavy Atom Count:7
Complexity:131
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes