Methanol → 5-(2,4-Dichloro-phenyl)-penta-2,4-dienoic acid [3-(4-chloro-phenyl)-allyl]-amide

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-(2,4-dichloro-phenyl)-penta-2,4-dienoyl chloride (62.5 mmol) in 300 mL CH2Cl2 at 0° C. was added Et3N (13.0 mL) followed by DMAP (i.e., 4-diaminomethylpyridine) (760 mg). To this was added a solution of 3-(4-chloro-phenyl)-allylamine (10.5 g) in 30 mL CH2Cl2. The mixture was stirred at 0° C. for 1 hr. Then 2 mL of MeOH was added, and the solution was stirred for 10 min. The solution was then diluted with aq. NaHCO3 and extracted with EtOAc. Filtration of solids and concentration of EtOAc layers provided a combined yield of 24.6 g of 5-(2,4-dichloro-phenyl)-penta-2,4-dienoic acid [3-(4-chloro-phenyl)-allyl]-amide. MS: m/e 392.2 (MH+)

Provenance & Evidence