Toluene → HCID 15042230, compound

Participants

Reaction Steps

A slurry of 15.9 g (0.036 mole) of 1-(diphenylmethyl)-3-(3-chlorophenoxy)azetidine ethanedioate in 200 ml of water was treated with 10 g of potassium carbonate and 500 ml of toluene. This mixture was heated while stirring until the emulsion which had formed cleared and formed two clear phases. The toluene phase was separated, washed with hot water and concentrated in vacuo. The residue was dissolved in 50 ml of methlene chloride and added dropwise to a stirred mixture of 4 g (0.04 mole) of phosgene and 5.5 g (0.04 mole) of potassium carbonate in 50 ml of methylene chloride under nitrogen. After 2 hr the reaction mixture was treated with ice water to destroy the excess phosgene and dissolve the inorganic salts. The methylene chloride solution was separated, dried over magnesium sulfate and concentrated in vacuo to yield 13 g of residue. A sample was crystallized by cooling to -78° C. and was used to seed the residue which formed a semi-solid paste. Trituration of the paste with petroleum ether yielded 3.5 g (66.5%) of white powder upon filtration. Recrystallization from petroleum ether yielded 0.6 g of white crystalline product, mp 64°-65° C.

Provenance & Evidence