Triethyl phosphite → Phosphonic acid, [(formylamino)methyl]-, diethyl ester

HRID 905162Notes

Reaction equation

HRID 905162 reaction equation
O[CH2:2][NH:3][CH:4]=[O:5].[CH2:6]([O:8][P:9]([O:13]CC)[O:10][CH2:11][CH3:12])[CH3:7]>C(O)C>[CH2:6]([O:8][P:9]([CH2:2][NH:3][CH:4]=[O:5])(=[O:13])[O:10][CH2:11][CH3:12])[CH3:7]

Participants

4

Reactant 2

HCID 31215Triethyl phosphite2×HCID 83086Formamide, N-(hydroxymethyl)-

Product 1

HCID 12673118Phosphonic acid, [(formylamino)methyl]-, diethyl ester

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The mole ratio of N-(hydroxymethyl)formamide to triethylphosphite in step (2) of the process of the invention is 1:1. The reaction is conducted in the presence of heat and at a temperature sufficient to cause the reaction to go to completion. The reactants are heated until ethyl alcohol starts to evolve and this occurs at reflux temperature. When triethylphosphite is used, this temperature is approximately 120°-125° C. At this point, the alcohol is distilled off, leaving the product diethyl-N-(formyl)aminomethylphosphonate as the residue.

Workup

  1. temperatureof heat and at a temperature sufficient
  2. customthe reaction
  3. temperatureat reflux temperature
  4. customis approximately 120°-125° C
  5. distillationAt this point, the alcohol is distilled off

Sources & evidence

ORD record
ord-7133614b944b452fbfa4482758121e65
Source dataset
uspto-grants-1983_12
Patent number
US04422982

Reaction notes

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