3-Ethoxy-2-propenoyl chloride → 3-ethoxy-N-[4-(2-methyl-1H-imidazol-1-yl)phenyl]acrylamide

Participants

Reaction Conditions

Reaction Steps

4-(2-methyl-1H-imidazol-1-yl)aniline (40.7 g, 232 mmol; RN: 74852-81-6, Maybridge, J. Med. Chem., 48(6), 1729-1744; 2005) was dissolved in dry pyridine (290 mL), 3-ethoxyacryloyl chloride (36.1 g, 268 mmol) was then added dropwise at 0°/−10° C. The resulting mixture was stirred at 0° C. for 2 hours and at r.t. overnight. The reaction mixture was quenched with 100 mL of water, and pyridine was distilled i.v., the residue was taken up with water and the pH was adjusted to pH=10, by adding K2CO3, the resulting suspension was extracted with AcOEt and concentrated. The resulting solid was stirred with hexane and filtered to afford the title product (58 g; 92%). C15H17N3O2, MW: 271.32.

Provenance & Evidence