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

HRID 1658546Notes

Reaction equation

HRID 1658546 reaction equation
[C:1]1([P:7]([O:13]CCCCl)OCCCCl)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:18][NH:19][C:20]([NH:22][CH3:23])=[O:21].[CH:24](=O)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>C1(C)C=CC=CC=1>[CH3:18][N:19]1[C:20](=[O:21])[N:22]([CH3:23])[CH:24]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[P:7]1(=[O:13])[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 7293N,N'-DimethylureaHCID 54440617HCID 54440617, compound

Product 1

HCID 215012371,4-Dimethyl-2,3-diphenyl-1,4,2lambda~5~-diazaphospholidine-2,5-dione

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

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).

Sources & evidence

ORD record
ord-e5a392de7f774eb9b0ba568855b056f9
Source dataset
uspto-grants-1976_06
Patent number
US03965127

Reaction notes

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