Sodium Hydroxide → Fumaric Acid

Participants

Reaction Steps

To a stirred solution of sodium hydroxide (2.02 g, 0.05 mole) in ethanol (180 ml) at 25° under a blanket of nitrogen, was added 1-[2-(2,4-dichlorophenyl)-2-(ethoxythiocarbonylthio)ethyl]1-H-imidazole hydrogen oxalate* (4.51 g, 0.01 mole). After stirring at 25° for 0.75 hour a solution of 4-chlorobenzyl chloromethyl sulfide (2.07 g, 0.01 mole) in ethanol (2 ml) was added. The mixture was refluxed for twenty hours and concentrated to dryness. The residue was partitioned between diethyl ether and water. The ethereal layer was washed successively with H2O, Na2Co3 -H2O, H2O, brine and dried (Na2SO4). Removal of the ether left the free base (3.3 g) as a viscous brown oil. Treatment of a solution of the free base (3.3 g) in acetonitrile with fumaric acid (0.78 g) provided 2.5 g of the title compound, mp 120°-125°. Recrystallization from ethyl acetate gave colorless crystals, mp 121°-123°, of the analytical sample.

Provenance & Evidence