Acetamide → HCID 88694378, compound

HRID 615831Notes

Reaction equation

HRID 615831 reaction equation
C([NH2:4])(=[O:3])C.[OH:5][P:6]([OH:8])[OH:7].[C:9]([O:12]C(=O)C)(=[O:11])[CH3:10].O.C(O)(=O)C=O.C1OC1C>CO>[OH2:3].[NH2:4][O:5][P:6]([CH2:10][C:9]([OH:12])=[O:11])([OH:8])=[O:7]

Participants

7

Reactant 5

HCID 178AcetamideHCID 6378Propylene OxideHCID 7918Acetic AnhydrideHCID 107909Phosphorous acidHCID 15620607Glyoxylic acid, monohydrate

Product 1

HCID 88694378HCID 88694378, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
45 °C

Procedure

A solution of 11.8 parts by weight of acetamide, 16.4 parts by weight of orthophosphorus acid in 40 parts by volume of acetic anhydride are heated with stirring to 45° C. To this solution is added, portionwise, 22.2 parts by weight of glyoxylic acid hydrate over 15 minutes. The reaction temperature increases to 80° C., during the addition and this temperature is maintained by external heating for a further 3 hours. The acetic anhydride is removed by distillation, in vacuo, and the viscous residue dissolved in 100 parts by volume concentrated hydrochloric acid. This solution is heated to reflux for 4 hours, then evaporated to dryness to give a brown crystalline solid, which on dissolution in 600 parts by volume of 60% aqueous methanol, followed by addition of propylene oxide, gives 9.3 parts by weight of 2-aminophosphono-acetic acid monohydrate melting at 195° C. with decomposition and having the following elemental analysis by weight:

Workup

  1. additionTo this solution is added
  2. temperatureThe reaction temperature increases to 80° C., during the addition
  3. temperaturethis temperature is maintained
  4. temperatureby external heating for a further 3 hours
  5. customThe acetic anhydride is removed by distillation, in vacuo
  6. dissolutionthe viscous residue dissolved in 100 parts by volume concentrated hydrochloric acid
  7. temperatureThis solution is heated
  8. temperatureto reflux for 4 hours
  9. customevaporated to dryness
  10. customto give a brown crystalline solid, which

Sources & evidence

ORD record
ord-bf3d54176fb1470d9ed8af35e85b650f
Source dataset
uspto-grants-1985_02
Patent number
US04501667

Reaction notes

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