Hydrochloric Acid → HCID 19966768, compound

Participants

Reaction Steps

A round-bottomed flask (300 cc) equipped with a dropping funnel was charged with 5-(1-methyl-2-propynyloxy)-4-chloro-2-fluorophenyl isocyanate (10.0 g, 41.7 mmol) and triethylamine (1.0 mL), as well as isopropyl ether (40 mL) and diethyl ether (50 mL) and methacrolein cyanohydrin (4.86 g, 50.0 mmol) was dropwise added slowly with stirring under cooling in an ice-water bath. After the addition, the mixture was heated to room temperature and stirred for an additional 12 h. After completion of the reaction, the reaction mixture was poured into 1N HCl (50 mL) and extraction was conducted with ethyl acetate (50 mL×3). The organic layer was dried with magnesium sulfate and the solvent was subsequently distilled off under vacuum to yield a crude product, which was purified by silica gel column chromatography (eluting solvents: ethyl acetate/hexane=1/5). The separated product of interest in turn was recrystallized from ether/hexane to give 3-[5-(1-methyl-2-propynyloxy)-4-chloro-2-fluorophenyl]-4-imino-5-isopropylideneoxazolidine-2-one (compound 5) as a white crystal (7.37 g; yield, 52.4%).

Provenance & Evidence