Chloromethyl phenyl sulphide → 2-Phenylthiomethyl-4-(3-methyl-3-chlorobutyl)-5-methyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide

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Reaction Conditions

Reaction Steps

A mixture of 4-(3-methyl-3-chlorobutyl)-5-methyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide (2.5 g, 9.81 mmol), phenylthiomethyl chloride (2.18 g, 13.74 mmol) and tetrabutylammonium bromide (0.369 g, 1.145 mmol) suspended in 150 ml of DMF was heated at 100° C. for 18 hours. After adding additional TBAB (0.369 g), the mixture was stirred at 95° C. for 4 hours, cooled, and poured into ice/water. The reaction mixture was extracted with ethyl acetate and the organic layer was washed with water and brine, and dried over sodium sulfate. The organic layer was concentrated in vacuo and the residue was purified by silica column chromatography (15% ethyl acetate in hexane) to afford 1.396 g (39%) of 2-phenylthiomethyl-4- (3-methyl-3-chlorobutyl) -5-methyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide (Formula VI: R1 =H; R2 =(CH2)2C(Cl) (CH3)2 ; R3 =CH3) as a solid.

Provenance & Evidence