Acetoacetic Acid → HCID 20337187, compound

HRID 1706216Notes

Reaction equation

HRID 1706216 reaction equation
[C:1](O[C:5](=[O:7])C)(=[O:3])C.[OH:8][NH:9][CH2:10][CH2:11][CH2:12][P:13](=[O:16])([OH:15])[OH:14].CC(CC(O)=O)=O.[CH2:24]([NH:31][CH2:32][CH2:33][NH:34][CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>O.C(O)=O>[CH:5]([N:9]([CH2:10][CH2:11][CH2:12][P:13](=[O:14])([OH:16])[OH:15])[OH:8])=[O:7].[CH:1]([N:9]([CH2:10][CH2:11][CH2:12][P:13](=[O:15])([OH:14])[OH:16])[OH:8])=[O:3].[CH2:24]([NH:31][CH2:32][CH2:33][NH:34][CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

7

Reactant 4

HCID 96Acetoacetic AcidHCID 7918Acetic AnhydrideHCID 8793BenzathineHCID 3421703-(Hydroxyamino)propylphosphonic acid

Product 1

HCID 20337187HCID 20337187, compound

Reagents, catalysts & solvents 2

HCID 284Formic AcidSolventHCID 962WaterSolvent4×

Procedure

formic acid (2 ml.) was added dropwise to acetic anhydride (2.45 ml.) at ambient temperature with stirring. After the stirring was continued at the same temperature for 30 minutes, 3-(N-hydroxyamino)propylphosphonic acid (3.10 g.) was added to the mixture. The reaction mixture was stirred at ambient temperature for an hour and then concentrated under reduced pressure to give an oily residue, which was dissolved in water (25 ml.). To the aqueous solution was added dropwise a solution of diacetic acid salts of N,N'-dibenzylethylenediamine (3.60 g.) in water (15 ml.) under ice-cooling and with stirring. The resultant mixture was concentrated under reduced pressure to give an oily residue, which was dissolved in water (30 ml.). The aqueous solution was concentrated under reduced pressure to give an oily residue, which was dissolved in water (30 ml.). The aqueous solution was concentrated under reduced pressure to give an oily residue, which was crystallized with a mixture of methanol (30 ml.) and ethanol (40 ml.). The crystals were separated by filtration, washed with ethanol (20 ml.) and then dried to give crystals (3.34 g.). The same crystals (1.00 g.) were recovered from the filtrate and the washings by concentrating them under reduced pressure to a volume of 40 ml. and allowing the concentrate to stand overnight at 4° C. A part (3 g.) of the combined crystals, as obtained above, was recrystallized from a mixture of water and ethanol (1:6) (40 ml.) to give N,N'-dibenzylethylenediamine bis[3-(N-formyl-N-hydroxyamino)propylphosphonate] (2.60 g.) in the form of needles. M.P. 155°-157° C. (dec.)

Workup

  1. stirringThe reaction mixture was stirred at ambient temperature for an hour
  2. concentrationconcentrated under reduced pressure
  3. customto give an oily residue, which
  4. temperaturecooling
  5. stirringwith stirring
  6. concentrationThe resultant mixture was concentrated under reduced pressure
  7. customto give an oily residue, which
  8. concentrationThe aqueous solution was concentrated under reduced pressure
  9. customto give an oily residue, which
  10. concentrationThe aqueous solution was concentrated under reduced pressure
  11. customto give an oily residue, which
  12. customwas crystallized with a mixture of methanol (30 ml.) and ethanol (40 ml.)
  13. customThe crystals were separated by filtration
  14. washwashed with ethanol (20 ml.)
  15. customdried
  16. customto give crystals (3.34 g.)
  17. customThe same crystals (1.00 g.) were recovered from the filtrate
  18. concentrationthe washings by concentrating them under reduced pressure to a volume of 40 ml
  19. concentrationconcentrate
  20. waitto stand overnight at 4° C
  21. customA part (3 g.) of the combined crystals, as obtained above,
  22. customwas recrystallized from a mixture of water and ethanol (1:6) (40 ml.)

Sources & evidence

ORD record
ord-ee32e7f22b504cc2bda9a118e03779de
Source dataset
uspto-grants-1980_06
Patent number
US04206156

Reaction notes

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