Sodium Methoxide → 4-Propyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide

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Reaction Steps

A solution of 2-(aminosulfonylamino)pentanoic acid methyl ester (24.6 g, 0.11 mol) in methanol (150 ml) was added to a solution of sodium methoxide (8.86 g, 0.164 mol) in 150 ml of methanol and the resulting reaction mixture was refluxed for 18 hours. The mixture was cooled, neutralized with BIO-RAD® 50W-X8 H+ ion exchange resin, and filtered. The filtrate was concentrated in vacuo to yield an oil which was crystallized from methanol/hexane to afford 20.73 g (theory) of 4-propyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide (Formula IV: R1 =propyl; R2 =R3 =H).

Provenance & Evidence