Toluene → Benzyl Cyanomethylcarbamate

Participants

Reaction Steps

To a vigorously stirred solution of aminoacetonitrile (20 g; 0.216 mole), NaHCO3 (50 g; 0.595 mole) in water (450 ml) and dioxane (250 ml), 50% benzyl chloroformate in toluene (67.88 ml; 0.475 mole) was added at 0° C. After stirring at room temperature for 16 h, the reaction mixture was extracted with EtOAc. The EtOAc layer was washed with water and dried over anhydrous Na2SO4. Solvent was removed and the dark brown oil was purified by flash chromatography over silica gel with 30-50% EtOAc-PE 60-80° C. Yield, 33 g (80.3%); mp, 42-43° C.; MS (EI): 190 (M+), 145, 130, 117, 108, 91; analysis: C10H10N2O2 requires C, 63.15; H, 5.30; N, 14.73; found: C, 62.95; H, 5.05; N, 14.50%.

Provenance & Evidence