Benzaldehyde → 1,4-Dimethyl-2-(4-methylphenoxy)-3-phenyl-1,4,2-diazaphospholidin-5-one-2-oxide

HRID 1576283Notes

Reaction equation

HRID 1576283 reaction equation
[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:9][NH:10][C:11]([NH:13][CH3:14])=[O:12].[C:15]1([CH3:39])[CH:20]=[CH:19][C:18]([O:21][P:22](OC2C=CC(C)=CC=2)[O:23]C2C=CC(C)=CC=2)=[CH:17][CH:16]=1>C1C=CC=CC=1>[CH3:9][N:10]1[C:11](=[O:12])[N:13]([CH3:14])[CH:1]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[P:22]1(=[O:23])[O:21][C:18]1[CH:19]=[CH:20][C:15]([CH3:39])=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 7293N,N'-DimethylureaHCID 12106Phosphorous acid, tris(methylphenyl) ester

Product 1

HCID 215012361,4-Dimethyl-2-(4-methylphenoxy)-3-phenyl-1,4,2-diazaphospholidin-5-one-2-oxide

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Benzaldehyde, 0.5 mole, is added dropwise to a solution of 0.5 mole of 1,3-dimethylurea and 0.5 mole of tris(p-tolyl)phosphite in 100 g of benzene as the solution was warmed from 60°-90°. Warming is continued at 90° for 3 hr, giving a reaction mixture having 31P nmr peaks at -24.2 and -21.9 ppm (~6:1 areas). The solvent and most of the by-product p-cresol are removed by stripping to 120°/0.5mm, and the remaining yellow, viscous oil is dissolved in acetone. A solid that separates is recrystallized from acetone to give a white solid: mp 126.5°-128°; 31P nmr -24.2 ppm; 1H nmr δ6.9-7.5 (m, 9, aryl), 4,6 (d, 1, J = 19Hz, PCH), 2.9 (d, 3, J = 8Hz, PNCH3), 2.7 (s, 3, NCH3), 2.3 (s, 3, CH3); ms 330(50) (molecular ion), 273(1), 224(4), 239(6), 223(27), 182(4), 166(100), 118(49), 107(5), 91(17), 77(14), 60(42).

Workup

  1. temperaturewas warmed from 60°-90°
  2. temperatureWarming
  3. customgiving a reaction mixture
  4. customThe solvent and most of the by-product p-cresol are removed
  5. customby stripping to 120°
  6. dissolutionthe remaining yellow, viscous oil is dissolved in acetone
  7. customA solid that separates is recrystallized from acetone
  8. customto give a white solid

Sources & evidence

ORD record
ord-a83329b2a9c348548372fd24d45ba894
Source dataset
uspto-grants-1976_09
Patent number
US03980618

Reaction notes

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