Benzene → Diphenyl alpha-(3,3-diphenylureido)-4-nitrobenzylphosphonate

Participants

Reaction Conditions

Reaction Steps

A mixture of 21.2g (0.1 mole) of 1,1-diphenylurea. 15.1g (0.1 mole) of 4-nitrobenzaldehyde, and 31.0g (0.1 mole) of triphenyl phosphite in 50g of benzene is stirred under nitrogen and warmed at reflux (87°C) for 2 hours to give a light yellow solution: 31P nmr -13.2 (d, J = 23Hz), -127.8 ppm (area ratio 5:1). Most of the benzene is removed at reduced pressure, and ether is stirred into the yellow oil remaining, causing 32g of solid to separate after a few minutes. A portion is recrystallized from acetonitrile to give a white solid: mp 157°-162°; 31P nmr -13.2 ppm (d, J = 24Hz); molecular weight (CHCl3) 565 (calcd 579).

Provenance & Evidence