Benzyl Bromide → 2-Phenylmethyl-4-propyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide

Participants

Reaction Conditions

Reaction Steps

To a mixture of 4-methyl-4-propyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide (8.25 g, 42.92 mmol) in 80 ml of dry DMF was added phenylmethyl bromide (8.08 g, 47.21 mmol) and tetrabutylammonium bromide (2.08 g, 6.64 mmol) in one portion. The resulting mixture was heated at 120° C. for 8 hours and then stirred at room temperature overnight. The mixture was cooled, poured over ice-water (400 ml), and the mixture was extracted with ethyl acetate (2×250 ml). The organic layer was washed with water and brine, dried over sodium sulfate, and concentrated in vacuo. The brown residual oil was purified by flash chromatography (silica gel; 25% ethyl acetate in hexane) to afford 9.34 g (77.1%) of 2-phenylmethyl-4-methyl-4-propyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide (Formula IX: R1 =propyl; R2 =CH3) as an oil.

Provenance & Evidence