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

Participants

Reaction Steps

A solution of 2-(aminosulfonylamino)pentanoic acid methyl ester (24.6 g; 0.117 retool) in methanol (150 ml) was added to a solution of sodium methoxide (8.86 g, from 3.77 g of Na) 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 4-propyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide (Formula IV: R1 =H; R2 =propyl; R3 =H).

Provenance & Evidence