Ethanol, 2-chloro-, 1-(4-methylbenzenesulfonate) → HCID 13768090, compound

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Reaction Steps

A mixture of 5 g of N-methyl-2-(4-hydroxyphenyl)thiazolidine-3-carbothioamide, 4.6 g of 1-chloro-2-tosyloxyethane, 4 g of potassium carbonate and 20 ml of dimethylformamide is stirred at room temperature for 2 days and further stirred at 50° C. for 20 hours. The mixture is concentrated under reduced pressure to remove solvent. Water is added to the residue, and the aqueous mixture is extracted with ethyl acetate. The extract is washed with an aqueous 10% sodium hydroxide solution and water, and dried and then concentrated under reduced pressure to remove solvent. The residue is purified by silica gel chromatography (solvent, ethyl acetate:chloroform=2:8), and the resultant product is recrystallized from ethanol. 3.07 g of N-methyl-2-[4-(2-chloroethyloxy)phenyl]thiazolidine-3-carbothioamide are obtained. Yield: 51.9%.

Provenance & Evidence