Sodium Azide → (2-Azido-ethoxy)methyl-phosphonic acid-diethylester

HRID 353420Notes

Reaction equation

HRID 353420 reaction equation
[CH2:1]([O:3][P:4]([CH2:9][O:10][CH2:11][CH2:12]Cl)(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2].[N-:14]=[N+:15]=[N-:16].[Na+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[CH2:1]([O:3][P:4]([CH2:9][O:10][CH2:11][CH2:12][N:14]=[N+:15]=[N-:16])(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 10014096Diethyl ((2-chloroethoxy)methyl)phosphonate

Product 1

HCID 10037145(2-Azido-ethoxy)methyl-phosphonic acid-diethylester

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 1140TolueneSolvent

Procedure

0.02 mol (2-chloroethoxy)methyl-phosphonic acid diethylester, 3 mmol tetrabutylammoniumbromide and 2.5 g sodiumazide are boiled in 50 ml toluol under reflux for 4 h. After cooling-off it is washed for three times with 25 ml water respectively. The watery phase may be extracted with toluol. The combined toluol phases are dried over sodiumsulfate and the solvent is removed in the vacuum. A yellow oil remains.

Workup

  1. temperatureunder reflux for 4 h
  2. washAfter cooling-off it is washed for three times with 25 ml water respectively
  3. extractionThe watery phase may be extracted with toluol
  4. dry with materialThe combined toluol phases are dried over sodiumsulfate
  5. customthe solvent is removed in the vacuum

Sources & evidence

ORD record
ord-a3b9080ec2d24822b33cf252aa890ae6
Source dataset
uspto-grants-2004_06
Patent number
US06753324B2

Reaction notes

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