Acetone → [(cyclopropylamino)-phosphonomethyl]phosphonic acid

HRID 1073688Notes

Reaction equation

HRID 1073688 reaction equation
[CH:1]1([NH:4][CH:5]([P:14](=[O:21])([O:18]CC)[O:15]CC)[P:6](=[O:13])([O:10]CC)[O:7]CC)[CH2:3][CH2:2]1.CO.CC(C)=O>C(O)(=O)C.Br>[CH:1]1([NH:4][CH:5]([P:14](=[O:15])([OH:18])[OH:21])[P:6](=[O:7])([OH:13])[OH:10])[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 180AcetoneHCID 887MethanolHCID 14853330HCID 14853330, compound

Product 1

HCID 406069[(cyclopropylamino)-phosphonomethyl]phosphonic acidYield 48.7%

Reagents, catalysts & solvents 1

HCID 21893785Acetic Acid Mixture with Hydrobromic AcidSolvent

Conditions

Temperature
45 °C

Procedure

1.28 g of tetraethyl (cyclopropylamino)methylenebis(phosphonate) was dissolved in 13 ml of 25% hydrogen bromide acetic acid solution and the mixture was stirred at 45° C. for 2 hours. The reaction solution was concentrated under reduced pressure, and 20 ml of purified water was added to the residue. Then, the mixture was again concentrated under reduced pressure. The oily product thus obtained was solidified by methanol and acetone and subjected to the filtration. The solid was washed with acetone to give 0.42 g of (cyclopropylamino)methylenebis(phosphonic acid) as a white solid.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure, and 20 ml of purified water
  2. additionwas added to the residue
  3. concentrationThen, the mixture was again concentrated under reduced pressure
  4. customThe oily product thus obtained
  5. filtrationsubjected to the filtration
  6. washThe solid was washed with acetone

Sources & evidence

ORD record
ord-be195b5494ed430d98f34a90afad90cd
Source dataset
uspto-grants-1990_11
Patent number
US04970335

Reaction notes

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