Acetic Anhydride → Sodium hydrogen {3-[acetyl(hydroxy)amino]propyl}phosphonate

HRID 1840260Notes

Reaction equation

HRID 1840260 reaction equation
[OH:1][NH:2][CH2:3][CH2:4][CH2:5][P:6](=[O:9])([OH:8])[OH:7].[C:10](OC(=O)C)(=[O:12])[CH3:11].[OH-].[Na+:18]>O>[Na+:18].[C:10]([N:2]([OH:1])[CH2:3][CH2:4][CH2:5][P:6](=[O:8])([OH:7])[O-:9])(=[O:12])[CH3:11]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 14798Sodium HydroxideHCID 3421703-(Hydroxyamino)propylphosphonic acid

Product 1

HCID 23665714Sodium hydrogen {3-[acetyl(hydroxy)amino]propyl}phosphonate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A suspension of 3.8 g (0.02 mol) 3-(N-hydroxyamino)-propylphosphonic acid is introduced into 20 ml water and 4.51 g (0.044 mol) acetic anhydride are added drop by drop at room temperature. After the solution has been stirred for 1.5 hours at room temperature a pH of 2.5 is adjusted with 0.2 n NaOH, the solution is concentrated in the entire diaphragm pump vacuum, taken up twice in 40 ml water in each case, which are again removed by concentration and the oil is washed twice with 30 ml ether in each case, taken up in 50 ml water and a pH of 6.5 is adjusted with 1.6 g NaHCO3. After removal of volatile constituents under vacuum, 20 ml n-butanol are added to remove the residual water and are also removed under reduced pressure. The oil is boiled up twice with isopropanol, the isopropanol phase is discarded and the remaining glassy resin is pulverised with a spatula to a yellow solid (5.65 g). In order to recrystallise it, it is taken up in only a little methanol, filtered from the undissolved component and acetone is added dropwise to the filtrate. A first filtering results in 1 g product with a melting point of 175° C. Recrystallisation as described above is carried out again for further purification. (DE-A-27 33 658)

Workup

  1. additionare added drop by drop at room temperature
  2. concentrationthe solution is concentrated in the entire diaphragm pump vacuum
  3. customare again removed by concentration
  4. washthe oil is washed twice with 30 ml ether in each case
  5. customAfter removal of volatile constituents under vacuum, 20 ml n-butanol
  6. additionare added
  7. customto remove the residual water
  8. customare also removed under reduced pressure
  9. customIn order to recrystallise it, it
  10. filtrationfiltered from the undissolved component and acetone
  11. additionis added dropwise to the filtrate
  12. filtrationA first filtering

Sources & evidence

ORD record
ord-e7d89ac9ec8c4d7eb827995b3211a125
Source dataset
uspto-grants-2004_01
Patent number
US06680308B1

Reaction notes

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