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

Participants

Reaction Steps

A solution of N-(aminosulfonyl)-2-propyl-DL-alanine methyl ester (10.66 g; 47.53 mmol) in methanol (100 ml) was added in one portion to a solution of sodium methoxide (prepared from 2.0 g of Na in 100 ml of dry methanol under nitrogen) and the resulting reaction mixture was stirred for 15 hours. The mixture was neutralized with BIO-RAD® 50W-X8 H+ ion exchange resin with stirring (20 minutes), and filtered. The filtrate was concentrated in vacuo to yield an oil which was dried in vacuo (4 hours) to afford 8.96 g (98%) of 4-methyl-4-propyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide (Formula IV: R1 =propyl;R2 =CH3 ; R3 =H).

Provenance & Evidence