Acetonitrile → P-((Acetylamino)methyl)phosphonic acid

HRID 443780Notes

Reaction equation

HRID 443780 reaction equation
[P:1]([OH:4])([OH:3])[OH:2].O1C[CH2:9][CH2:8][O:7]O1.P(Cl)(Cl)Cl.[C:15](#[N:17])C>>[C:8]([NH:17][CH2:15][P:1]([OH:4])(=[O:3])[OH:2])(=[O:7])[CH3:9]

Participants

5

Reactant 4

HCID 6342AcetonitrileHCID 24387Phosphorus trichlorideHCID 107909Phosphorous acidHCID 19593658CID 19593658

Product 1

HCID 3017080P-((Acetylamino)methyl)phosphonic acid

Procedure

82 g of aqueous phosphorous acid and 32 g of trioxane are dissolved in 200 cc of acetonitrile. 5 cc of phosphorus trichloride are added to said solution. The resulting mixture is heated to boiling under reflux for about two hours. A highly viscous oil separates as a result of the reaction. Unreacted acetonitrile is distilled off. The residue is dissolved in a small amount of water. Addition of acetone precipitates therefrom a white crystalline product which is filtered off and dried at 60° C. in a water jet vacuum. About 100 g of N-acetylaminomethane phosphonic acid are obtained. By thin layer chromatographic investigation of the filtrate it was found that, in addition to phosphorous acid, the solution still contained some additional N-acetylaminomethane phosphonic acid and also another phosphonic acid which apparently is N-acetylimino-bis-methane phosphonic acid.

Workup

  1. temperatureThe resulting mixture is heated
  2. temperatureunder reflux for about two hours
  3. customA highly viscous oil separates as a result of the reaction
  4. distillationUnreacted acetonitrile is distilled off
  5. dissolutionThe residue is dissolved in a small amount of water
  6. additionAddition of acetone
  7. customprecipitates
  8. filtrationa white crystalline product which is filtered off
  9. dry with materialdried at 60° C. in a water jet vacuum

Sources & evidence

ORD record
ord-955ff3aa99dc40ecb93407d9cf0d9938
Source dataset
uspto-grants-1981_04
Patent number
US04261929

Reaction notes

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