Benzaldehyde → HCID 689895, compound

Participants

Reaction Steps

To a solution of t-butyl carbazate (5.62 g, 42.5 mmol) in ethyl acetate (15 mL) was added with stirring benzaldehyde (4.51 g, 42.5 mmol). Crystallization occurred and the resulting slurry was stirred at rt for 45 min. Hexanes (70 mL) was added and the slurry was cooled to 0° C. The slurry was stirred at 0° C. for 60 min, then filtered and rinsed with cold hexanes (20 mL) and dried in vacuo at 40° C. to afford the title compound as a solid (8.34 g, 89.0%): mp 184.1-184.9° C.; 1H NMR (DMSO-d6) δ 10.91 (s, 1H), 7.99 (s, 1H), 7.58 (d, 2H, J=3 Hz), 7.39 (m, 3H), 1.45 (s, 9H); 13C NMR (DMSO-d6) δ 153.0, 143.8, 135.3, 130.0, 129.4, 127.2, 80.1, 28.8; IR (KBr mull) 2983, 1735, 1511, 1157 cm−1; A portion was recrystallized (ethyl acetate) for analysis. Anal. Calcd. For C12H16N2O2: C, 65.43; H, 7.32; N, 12.72. Found: C, 65.16; H, 7.43; N, 12.62.

Provenance & Evidence