Sodium Methoxide → 4-(3-Methyl-3-chlorobutyl)-5-methyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide

Participants

Reaction Steps

A solution of N-(aminosulfonyl)-2-(3-methyl-3-chlorobutyl) sarcosine methyl ester (14.5 g, 50.56 mmol) in methanol (150 ml) was added to a solution of sodium methoxide (Na=2.4 g) in 150 ml of ice-cold methanol. The resulting reaction mixture was stirred at room temperature under nitrogen for 1.5 hours, and the mixture was treated with 25 g of ion-exchange resin (BIO-RAD® 50W- x8 H+) for 40 minutes and filtered. The filtrate was concentrated in vacuo to afford 12.54 g (97.4%) of 4-(3-methyl-3-chlorobutyl)-5-methyl-1,2,5-thiadiazolidin-3-one 1,1 -dioxide (Formula IV: R1 =H; R2 =(CH2)2C(Cl) (CH3)2 ; R3 =CH3) as a solid.

Provenance & Evidence