Triethylamine → 2-(Diethoxyphosphinyloxymethyl)-4-propyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide

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Reaction Steps

2-Chloromethyl-4-propyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide (1 g; 4.42 mmol) was added to a solution of diethyl phosphate (Formula III: A=B=Et) (1.02 g; 6.62 mmol) in methylene chloride (5 ml) containing triethylamine (0.67 g; 6.63 mmol), and the mixture was allowed to reflux for 24 hours and then cooled. The mixture was concentrated in vacuo and the residue purified by silica gel flash chromatography (50% ethyl acetate/hexane) to afford 0.54 g (35%) of 2-(diethoxyphosphinyloxymethyl)-4-propyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide (Formula I: R1 =H; R2=propyl; R3 =H; A=B=Et) as an oil.

Provenance & Evidence