Benzaldehyde → 1,4-Dimethyl-2,3-diphenyl-1,4,2lambda~5~-diazaphospholidine-2,5-dione

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Reaction Steps

A solution of 0.3 mole each of bis(chloropropyl) phenylphosphonite, 1,3-dimethylurea, and benzaldehyde in 100g of toluene is warmed at 105°-110° for 1.5 hr, giving a light yellow reaction mixture in which about half of the phosphorus detectable by nmr had a chemical shift at -25.9 ppm. Stripping to 107°/0.5mm followed by dilution with ether and filtration gives 14.8g of white solid: mp 132°-138° (141.5°-143.5° from tetrahydrofuran-ether); 31P nmr -25.6 ppm; 1H nmr δ 7.3 and 7.6 (m, 10, aryl), 4.6 (d, 1, J = 6Hz, CH), 2.9 (d, 3, J = 8Hz, CH3NP), 2.8 (s, 3, CH3NCH) (phosphorus decoupling converted both doublets to singlets); mass spectrum (70 eV) m/e(rel intensity) 300(27) (molecular ion), 243(67), 228(35), 166(15), 124(30), 118(100), 77(38), 60(15).

Provenance & Evidence