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

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Reaction Steps

A mixture of 2-chloromethyl-4-propyl-5-methyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide (1 g; 4.16 mmol), diethyl phosphate (Formula III: A=B=Et) (0.96 g, 6.63 mmol), tetrabutylammonium bromide (94 mg, 0.29 mmol) and triethylamine (0.63 g, 6.23 mmol) in methylene chloride (20 ml) was allowed to reflux for 24 hours. After adding an additional tetrabutylammonium bromide, the mixture was refluxed for an additional 48 hours, and then cooled. The mixture was purified by silica gel flash chromatography (ethyl acetate/hexane) to afford 0.98 g (66%) of 2-(diethoxyphosphinyloxymethyl)-4-propyl-5-methyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide (Formula I: A=B=Et; R1 =H; R2 =propyl; R3 =CH3) as an oil.

Provenance & Evidence