Water → Diethyl {[di(prop-2-en-1-yl)amino]methyl}phosphonate

HRID 2247147Notes

Reaction equation

HRID 2247147 reaction equation
C(NC[CH2:6][P:7](=[O:14])([O:11][CH2:12][CH3:13])[O:8][CH2:9][CH3:10])C=C.C([N:17]([CH2:20][CH3:21])CC)C.[CH2:22](Br)[CH:23]=[CH2:24].O.[CH2:27](OCC)C>>[CH2:22]([N:17]([CH2:6][P:7](=[O:14])([O:8][CH2:9][CH3:10])[O:11][CH2:12][CH3:13])[CH2:20][CH:21]=[CH2:27])[CH:23]=[CH2:24]

Participants

6

Reactant 5

HCID 962WaterHCID 3283Diethyl EtherHCID 7841Allyl bromideHCID 8471TriethylamineHCID 54407134HCID 54407134, compound

Product 1

HCID 15250413Diethyl {[di(prop-2-en-1-yl)amino]methyl}phosphonateYield 84%

Procedure

0.60 g (2.9 mmole) of diethyl allylaminoethylphosphonate was dissolved in 50 ml dry diethyl ether, and 1.17 g (11.6 mmole) triethylamine was added. After 15 minutes of stirring at room temperature, 1.40 g of allylbromide was added dropwise. The mixture was refluxed during 4 days. 50 ml of water was added to the mixture and was subsequently extracted three times with 50 ml CH2Cl2. The organic layers were combined and dried with MgSO4. After filtering MgSO4 and subsequent evaporation of the solvent, the resulting product was further purified with high vacuum distillation, providing 0,6 gram (2,4 mmole, 84% yield) diethyl diallylaminomethylphosphonate having a boiling point of 65° C. under a reduced pressure of 0.1 mbar. This product was further characterised by the following spectra:

Workup

  1. temperatureThe mixture was refluxed during 4 days
  2. extractionwas subsequently extracted three times with 50 ml CH2Cl2
  3. dry with materialdried with MgSO4
  4. filtrationAfter filtering
  5. customMgSO4 and subsequent evaporation of the solvent
  6. distillationthe resulting product was further purified with high vacuum distillation

Sources & evidence

ORD record
ord-65b695040f704b98bc2c715e950a08c2
Source dataset
uspto-grants-2010_03
Patent number
US07687635B2

Reaction notes

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