Iodoethane → 2-Phenylmethyl-4-propyl-5-ethyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide

Participants

Reaction Steps

Potassium t-butoxide (2 . 3 g, 20.5 mmol) was added to a solution of 2-phenylmethyl-4-propyl-1,2,5-thiadiazolidin-3-one 1, 1-dioxide (5 g, 18.6 mmol) in 100 ml of THF at 0° C. and the mixture was stirred at this temperature for 1 hour. To the mixture was added ethyl iodide (11.64 g, 74.6 mmol) and the resulting mixture was allowed to stir at room temperature for 40 hours. The resulting mixture was diluted with brine, extracted with ethyl acetate (150 ml) and the organic layer was washed with brine. The organic layer was dried, concentrated in vacuo, and the residue was purified by flash chromatography to afford 5.27 g of 2-phenylmethyl-4-propyl-5-ethyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide (Formula XI: R1 =H; R2 =propyl; R3 =ethyl) as an oil.

Provenance & Evidence