4-Chlorophenylurea → Diphenyl{1-[3-(4-chlorophenyl)ureido]butyl}phosphine oxide

Participants

Reaction Steps

A mixture of 0.15 mole each of p-chlorophenylurea, phenyl diphenylphosphinite, and n-butylraldehyde in 150g of toluene is warmed at reflux for 5.5 hr, giving a reaction mixture having a 31P nmr signal only at -36.8 ppm. When the toluene is removed at reduced pressure, the residue solidifies. Recrystallization of a portion from benzene gives a white solid: mp 275°-278° C.; 31P nmr -37.4 ppm; 1H nmr δ9.1 (s, 1, NHC6H4Cl), 6.4-8.1 (m, 15, aryl and CHNH), 5.1 (m, 1, PCH), 0.6-2.0 (m, 7, CH2CH2CH3).

Provenance & Evidence