1-Isocyanato-4-methoxybenzene → HCID 14650639, compound

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Reaction Steps

4-Methoxyphenyl isocyanate (1 g) is added at a temperature in the region of 20° C. to a solution, maintained under an argon atmosphere, of (4RS, 5RS)-2,4-diphenyl-5,6-dihydro-4H-1,3-oxazin-5-ol (1.7 g) in 1,2-dichloroethane (20 cc). The solution obtained is stirred under reflux for 4 hours and then concentrated to dryness under reduced pressure (2.7 kPa). The residue is purified by chromatography on silica (0.063-0.2 mm; 40 g) contained in a column 2 cm in diameter, collecting 20-cc fractions. Fractions 2 to 6, eluted with a mixture of ethyl acetate and cyclohexane (3:7 by volume), are combined and concentrated to dryness under reduced pressure (2.7 kPa) at 40° C. After recrystallization in diisopropyl ether, (4RS, 5RS)-5-(4-methoxyphenylcarbamoyloxy)-2,4-diphenyl-5,6-dihydro-4H-1,3-oxazine (0.7 g), m.p. 140° C., is obtained.

Provenance & Evidence