Triethylamine → 2-(4-chloro-2-nitrobenzoyl)-2-cyano-N-ethyl-N-methylacetamide

Participants

Reaction Steps

2-cyano-N-ethyl-N-methylacetamide (5.56 g; 0.044 mol) and triethylamine (13.36 g; 0.132 mol) were dissolved in dry THF (100 ml) under dry nitrogen, and 4-chloro-2-nitrobenzoyl chloride (9.68 g; 0.044 mol) in dry THF (100 ml) added dropwise over 45 min. The mixture was stirred at room temperature under dry nitrogen for 18 hours, during which time a precipitate was formed. The solution was filtered, washing the solid with THF and adding the washings to the solution, and evaporated, giving a residue which was treated with 2M sodium hydroxide solution (200 ml), and this then washed with CH2Cl2 (2×100 ml). The aqueous solution was acidified to pH 1 with concentrated hydrochloric acid, and extracted into CH2Cl2 (3×200 m). The extracts were combined, dried (Na2SO4), filtered and evaporated, giving a very viscous oil which solidified. Trituration with ether (20 ml) gave 2-(4-chloro-2-nitrobenzoyl)-2-cyano-N-ethyl-N-methylacetamide (6.10 g; 45%) as a solid, m.p. 95°-98° C., (Found, C: 49.60; H: 3.87; N: 13.25; Cl: 12.28. C13H12ClN3O4 requires C: 50.40; H: 3.88; N: 13.57; Cl: 11.47%, d (CDCl3); 60 MHz) 1.3 (3H, t, J=7, Hz), 3.2 (3H, s), 3.7 (2H, q, J=7 Hz), 7.4-7.55 (1H, d, J=8 Hz), 7.6-7.8 (1H, dd, J=8, 2 Hz), 8.1 (1H, d, J=2 Hz) and 16.4 (1H, br, s), vmax (nujol) 2200, 1590 (shoulder) and 1500.

Provenance & Evidence