Diethyl Ether → HCID 53986966, compound

Participants

Reaction Steps

Sodium (0.386 g, 0.017 g, atom) was dissolved in ethanol (70 mL) and diethyl 2,4-dioxoimidazolidine-5-phosphonate (3.96 g, 17 mmol) added. After 1 hour, a solution of 2-nitro-5-[4-(phenylsulfonyl)butoxy]benzaldehyde (4.70 g, 13 mmol) (prepared by alkylating 5-hydroxy-2-nitrobenzaldehyde with 4-phenylsulfonylbutyl bromide) in ethanol and chloroform was added. After 20 minutes, the solvent was evaporated and the residue extracted with chloroform to give a foamy solid which was dissolved in acetontirile. Diethyl ether was added to the point of precipitate nd the mixture allowed to stand overnight. A solid (0.86 g) was collected and further purified gy crystallication from acetonitrile-diethyl ether to give 5-[[2-nitro-5-[4-(phenylsulfonyl)butoxy]phenyl]methylene]-2,4-imidazolidinedione (0.5 g). Concentration of the combined mother liquors afforded 4.1 g of material that was used without further purification. Yield (4.6 g, 61%). Crystallized material had m.p. 150°-152° C.

Provenance & Evidence