Formic Acid → HCID 86736770, compound

HRID 1706218Notes

Reaction equation

HRID 1706218 reaction equation
[CH:1]([OH:3])=O.C(O[C:8](=[O:10])C)(=O)C.[OH:11][NH:12][CH2:13][CH2:14][CH2:15][P:16](=[O:19])([OH:18])[OH:17].[CH2:20]([NH2:23])[CH2:21][NH2:22]>O.C(O)C>[CH:8]([N:12]([CH2:13][CH2:14][CH2:15][P:16]1(=[O:18])[O:17][N:23]2[O:18][P:16]([CH2:15][CH2:14][CH2:13][N:12]([CH:1]=[O:3])[OH:11])(=[O:17])[O:19][N:22]([CH2:21][CH2:20]2)[O:19]1)[OH:11])=[O:10]

Participants

7

Reactant 4

HCID 284Formic AcidHCID 3301EthylenediamineHCID 7918Acetic AnhydrideHCID 3421703-(Hydroxyamino)propylphosphonic acid

Product 1

HCID 86736770HCID 86736770, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

Formic acid (2.0 ml.) was added dropwise to acetic anhydride (2.45 g.) 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 for an hour and concentrated under reduced pressure to give a residue, which was dissolved in water (25 ml.). To the aqueous solution was added ethylenediamine (0.60 g.). The mixture was concentrated under reduced pressure to give a residue, which was dissolved in water. The aqueous solution was concentrated under reduced pressure to give a residue, and to the residue was added ethanol (30 ml.) to give crystals. The crystals were separated by filtration and washed twice with ethanol (10 ml.) to give crystalline ethylenediamine bis[3-(N-formyl-N-hydroxyamino)propylphosphonate] (3.95 g.), a part (3 g.) of which was recrystallized from 90% aqueous methanol to give needles (1 g.) of the same object compound. M.p. 112°-118° C.

Workup

  1. stirringThe reaction mixture was stirred for an hour
  2. concentrationconcentrated under reduced pressure
  3. customto give a residue, which
  4. concentrationThe mixture was concentrated under reduced pressure
  5. customto give a residue, which
  6. concentrationThe aqueous solution was concentrated under reduced pressure
  7. customto give a residue
  8. customto give crystals
  9. customThe crystals were separated by filtration
  10. washwashed twice with ethanol (10 ml.)

Sources & evidence

ORD record
ord-f208ebca4b5a4da99f5be29224d1d7af
Source dataset
uspto-grants-1980_06
Patent number
US04206156

Reaction notes

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