Benzaldehyde → N-(diethoxyphosphorylmethyl)-1-phenylmethanimine

HRID 1657992Notes

Reaction equation

HRID 1657992 reaction equation
[NH2:1][CH2:2][P:3](=[O:10])([O:7][CH2:8][CH3:9])[O:4][CH2:5][CH3:6].[CH:11](=O)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C(O)C>[CH:11](=[N:1][CH2:2][P:3](=[O:10])([O:7][CH2:8][CH3:9])[O:4][CH2:5][CH3:6])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 240BenzaldehydeHCID 1596920Diethyl (aminomethyl)phosphonate

Product 1

HCID 2773681N-(diethoxyphosphorylmethyl)-1-phenylmethanimineYield 98.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

Diethyl aminomethylphosphonate (4.03 g., 24.1 mmole) is stirred in an ice bath while benzaldehyde (2.50 ml., 24.5 mMol) is added dropwise over a period of 5 minutes. After having been stirred an additional 15 minutes at 0°C., the mixture is diluted with absolute ethanol (20 ml.) and evaporated in vacuo. The residue is dissolved in dry benzene (20 ml.) and evaporated to give diethyl N-benzylidene-aminomethylphosphonate (6.073 g.) as a pale yellow oil: ir (CCl4) 1639, 1250, 1062, 1037, and 971 cm-1 ; nmr (CDCl3)τ8.68 (t, 6, J=7 Hz, CH3), 5.93 (d of d, 2, J=17.5 Hz and J=1 Hz, CH2), 5.85 (d of q, 4, J=8 Hz and J=7 Hz, CH2CH3), 2.65 (m, 3, ArH), 2.29 (m, 2, ArH), and 1.75 (t of d, 1, J=1 Hz and J=5 Hz, =CH).

Workup

  1. additionis added dropwise over a period of 5 minutes
  2. customevaporated in vacuo
  3. dissolutionThe residue is dissolved in dry benzene (20 ml.)
  4. customevaporated

Sources & evidence

ORD record
ord-d72a4e3530d84ffab32e86f565dc2ba1
Source dataset
uspto-grants-1976_06
Patent number
US03962224

Reaction notes

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