Sodium Azide → HCID 86678260, compound

HRID 2204948Notes

Reaction equation

HRID 2204948 reaction equation
Br[CH2:2][CH2:3][O:4][CH2:5][CH2:6][P:7](=[O:14])([O:11][CH2:12][CH3:13])[O:8][CH2:9][CH3:10].[N-:15]=[N+:16]=[N-:17].[Na+]>CCO.O>[N:15]([CH2:2][CH2:3][O:4][CH2:5][CH2:6][P:7](=[O:14])([O:11][CH2:12][CH3:13])[O:8][CH2:9][CH3:10])=[N+:16]=[N-:17]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 15260324HCID 15260324, compound

Product 1

HCID 86678260HCID 86678260, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

To a solution of diethyl 2-(2-bromoethoxy)ethylphosphonate (1 eq) in EtOH (0.3 M) was added sodium azide (5 eq) in water (2 M). The reaction mixture was heated at reflux overnight. The mixture was then diluted with water, extracted with ethyl acetate. The organic layer was washed with 5% citric acid, saturated NaHCO3, water and brine, dried over anhydrous Na2SO4, and concentrated en vaccuo. The crude material was purified by flash chromatography on a COMBIFLASH® system (ISCO) using 80-100% EtOAc/Hex to give the product as colorless oil.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux overnight
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with 5% citric acid, saturated NaHCO3, water and brine
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated en vaccuo
  7. customThe crude material was purified by flash chromatography on a COMBIFLASH® system (ISCO)

Sources & evidence

ORD record
ord-04ac9a3295184546b11aea4ef30fb44c
Source dataset
uspto-grants-2016_06
Patent number
US09365506B2

Reaction notes

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