N-[(2-methoxyphenyl)methyl]-4,5-dihydro-1,3-oxazol-2-amine

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Commercially available 2-chloroethylisocyanate (3.10 mL, 36.45 mmol) was added slowly to a solution of 2-methoxybenzylamine (5.00 mL, 36.45 mmol) in dichloromethane (60 mL) at room temperature. The resulting reaction mixture was stirred for 30 minutes and the intermediate product thus formed was filtered and washed with hexane, and then suspended in water (150 mL). This suspension was heated to reflux and stirred at refluxing for 2 hours, then cooled to room temperature. The reaction mixture was extracted with ethyl acetate, and the aqueous phase was basified with ammonium hydroxide to pH=14. The basified aqueous phase was then extracted with ethyl ether (50 mL) 3 times and the combined organic phases were dried with magnesium sulfate. Concentration gave 5.10 g of N-(2-methoxybenzyl)-4,5-dihydrooxazol-2-amine. Spectroscopic data: 1H NMR (300 MHz, CDCl3) δ=3.80 (t, 2H, J=10.1 Hz), 3.85 (s, 3H), 4.26 (t, 2H, J=10.1 Hz), 4.38 (s, 2H), 6.83-6.95 (m, 2H), 7.20-7.32 (m, 2H). The resulting reaction mixture the intermediate product thus formed was filtered washed with hexane This suspension was heated to reflux stirred at refluxing for 2 hours The reaction mixture was extracted with ethyl acetate The basified aqueous phase was then extracted with ethyl ether (50 mL) 3 times the combined organic phases were dried with magnesium sulfate Concentration