4-Vinylpyridine → 2-[2-(Pyridin-4-yl)ethyl]-1lambda~6~,2-thiazolidine-1,1-dione

Participants

Reaction Steps

A mixture of 4-vinylpyridine (324 g), isothiazolidine-1,1-dioxide (373 g), and "Triton B" solution (129 ml, 40% w/v in methanol) was heated in D.M.F. at 50°-55° for 7 hours. The reaction mixture was then concentrated under vacuum, water (2.52 liters) was added, and the product was extracted into CH2Cl2 (3×1.87 liters). The combined methylene chloride extracts were washed with water and then evaporated to dryness. The residue was dissolved in ethyl acetate (1.3 liters) at 35° and hexane (0.87 liters) was added over 10 minutes. The resulting crystalline product was granulated at -5 to 0° for 4 hours, filtered, washed with hexane (0.37 liters) and dried in vacuum at 25°, to give 2-[2-(4-pyridyl)ethyl]isothiazolidine-1,1-dioxide (518 g).

Provenance & Evidence