反应详情

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.

1. customwas formed
2. filtrationThe solution was filtered
3. washwashing the solid with THF
4. additionadding the washings to the solution
5. customevaporated
6. customgiving a residue which
7. washthis then washed with CH2Cl2 (2×100 ml)
8. extractionextracted into CH2Cl2 (3×200 m)
9. dry with materialdried (Na2SO4)
10. filtrationfiltered
11. customevaporated
12. customgiving a very viscous oil which