Dimethylamine → Phosphonic acid, P,P'-ethenylidenebis-, P,P,P',P'-tetrakis(1-methylethyl) ester

HRID 620137

Reaction equation

HRID 620137 reaction equation
[CH2:1]([P:12](=[O:21])([O:17][CH:18]([CH3:20])[CH3:19])[O:13][CH:14]([CH3:16])[CH3:15])[P:2](=[O:11])([O:7][CH:8]([CH3:10])[CH3:9])[O:3][CH:4]([CH3:6])[CH3:5].C=O.[CH3:24]NC>CO>[C:1]([P:2](=[O:11])([O:7][CH:8]([CH3:9])[CH3:10])[O:3][CH:4]([CH3:6])[CH3:5])([P:12](=[O:21])([O:13][CH:14]([CH3:16])[CH3:15])[O:17][CH:18]([CH3:20])[CH3:19])=[CH2:24]

Participants

5

Reactant 3

HCID 674DimethylamineHCID 712FormaldehydeHCID 74266Tetraisopropyl methylenediphosphonate

Product 1

HCID 4488726Phosphonic acid, P,P'-ethenylidenebis-, P,P,P',P'-tetrakis(1-methylethyl) esterYield 24.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

11.95 g (34.7 mmol) of tetraisopropyl methylenebisphosphonate, 5.2 g (173.5 mmol) of paraformaldehyde and 2.54 g (34.7 mmol) of dimethylamine are combined with the same reactants and at the same conditions as described above in Example I. This mixture is then refluxed for 117 hours. After the methanol has been eliminated as described above in Example I, 3.0 g of tetraisopropyl ethenylidenebisphosphonate is produced as a clear liquid.

Workup

  1. temperatureThis mixture is then refluxed for 117 hours

Sources & evidence

ORD record
ord-0de123eb8d014e9995f2781281d67cdd
Source dataset
uspto-grants-1989_04
Patent number
US04820698

Linked notes

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