3,4-Dichlorobenzaldehyde → HCID 2692515, compound

Participants

Reaction Steps

To a solution of t-butyl carbazate (4.99 g, 37.76 mmol) in ethyl acetate (10 mL) was added with vigorous stirring a solution of 3,4-dichlorobenzaldehyde (6.77 g, 38.6 mmol) in ethyl acetate (10 mL) followed by hexanes (40 mL). Crystallization occurred and the resulting slurry was stirred at rt for 15 min, then cooled to 0° C. and held at that temperature for 45 min. The solids were filtered, rinsed with cold hexanes and dried in vacuo at 60° C. to afford the title compound as a solid (10.10 g, 92.4%): mp 173.8-174.4° C. (dec); 1H NMR (DMSO-d6) δ 11.16 (br s, 1 H), 7.79 (s, 1 H), 7.62 (d, 1 H, J=1.8 Hz), 7.57 (d, 1 H, J=8.5 Hz), 7.55 (m, 1 H), 1.44 (s, 9 H); 13C NMR (DMSO-d6) δ 152.9, 141.1, 136.1, 132.3, 132.1, 131.6, 128.6, 127.0, 80.4, 28.7; IR (KBr mull) 3358, 3010, 2983, 1736, 1508, 1475 cm−1. A portion was recrystallized (ethyl acetate) for analysis. Anal. Calcd. for C12H14Cl2N2O2: C, 49.84; H, 4.88; Cl, 24.52; N, 9.69. Found: C, 49.59; H, 4.71; Cl, 24.43; N, 9.57.

Provenance & Evidence