Sodium → N-cyclohexyl-N-methyl-4-[3-[(1-methyl-2,4-dioxoimidazolidin-5-ylidene)methyl]-4-nitrophenoxy]butanamide

Participants

Reaction Steps

Sodium (0.079 g, 0.003 g atom) was dissolved in ethanol (20 mL) and diethyl 1-methyl-2,4-dioxoimidazolidine-5-phosphonate (0.86 g, 3.4 mmol) added. After 5 minutes, N-cyclohexyl-4-(3-formyl-4-nitrophenoxy)-N-methylbutanamide (1 g, 2.9 mmol) was added and the mixture stirred at room temperature for 90 minutes. The solvent was evaporated and the residue diluted with water and extracted with dichloromethane to give a foam. Crystallization from hexane/dichloromethane afforded N-cyclohexyl-N-methyl-4-[3-[(1-methyl-2,4-dioxoimidazolidin-5-ylidene)methyl]-4-nitrophenoxy]butanamide (0.96 g, 75%) as a 3:1 mixture of geometrical isomers, m.p. 149°-154° C.

Provenance & Evidence