m-Tolyl isocyanate → HCID 15670989, compound

Participants

Reaction Conditions

Reaction Steps

3-Methylphenyl isocyanate (1.07 g) is added at a temperature in the region of 20° C. to a solution of tert-butyl 2-[2-amino-N-(2-anilinophenyl)acetamido]acetate (2.6 g) in anhydrous tetrahydrofuran (20 cc). The solution obtained is stirred for 2 hours at a temperature in the region of 20° C. and then concentrated to dryness under reduced pressure (2.7 kPa) at 40° C. The residual oil is purified by chromatography on silica (0.063-0.2 mm) (150 g) contained in a column 2 cm in diameter [eluent: cyclohexane/ethyl acetate (50:50 by volume)], collecting 20-cc fractions. The fractions containing only the desired product are combined and concentrated to dryness under reduced pressure (2.7 kPa) at 40° C. After recrystallisation in ethyl acetate, tert-butyl 2-{N-(2-anilinophenyl)-2-[3-(3-methylphenyl)ureido]acetamido}acetate (1.15 g), m.p. 180° C., is obtained.

Provenance & Evidence