Chloromethyl phenyl sulphide → 2-phenylthiomethyl-tetrahydropyrrolo[1,2-b]1,2,5-thiadiazol-3(2H)-one 1,1-dioxide

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Reaction Steps

To a mixture of tetrahydropyrrolo[1,2-b]1,2,5-thiadiazol-3(2H)-one 1,1-dioxide (5.0 g, 28.4 mmol) suspended in 150 ml of toluene was added phenylthiomethyl chloride (6.76 g, 42.6 mmol) and tetrabutylammonium bromide (0.91 g). The resulting mixture was refluxed for 6 hours, cooled, filtered, and the filtrate was concentrated in vacuo. The residue was purified by flash column chromatography (25%-30% ethyl acetate in hexane) to afford 5.58 g (66%) of 2-phenylthiomethyl-tetrahydropyrrolo[1,2-b]1,2,5-thiadiazol-3 (2H)-one 1,1-dioxide (Formula VI: R1 =H; R2 and R3 together =-(CH2 )3 -) as a solid, m.p. 90.5°-91.5° C.

Provenance & Evidence