Water → Undecenyl azide

HRID 2074040Notes

Reaction equation

HRID 2074040 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].[CH:5](Br)=[CH:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15].O>CN(C)C=O>[CH:5]([N:1]=[N+:2]=[N-:3])=[CH:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15]

Participants

5

Reactant 3

HCID 962WaterHCID 33557Sodium AzideHCID 537492951-Bromoundec-1-ene

Product 1

HCID 86632940Undecenyl azideYield 60%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To do this, sodium azide (2.781 g, 43 mmol) was dissolved in 170 ml of dimethylformamide (DMF). 5 ml of undecenyl bromide (36 mmol) were added, with stirring, to the reaction medium, which was subsequently heated at 80° C. for 24 hours. The mixture was left to cool to ambient temperature, and then 100 ml of water were added portionwise. An extraction with ethanol (3×100 ml) was subsequently carried out, and the organic phase was then washed with water (3×100 ml) and dried over sodium sulfate (Na2SO4). Finally, the solvent was evaporated off and 2.58 g of undecenyl azide (20.3 mmol; yield 60%) were isolated in the form of a pale yellow-colored transparent oil.

Workup

  1. waitThe mixture was left
  2. temperatureto cool to ambient temperature
  3. extractionAn extraction with ethanol (3×100 ml)
  4. washthe organic phase was then washed with water (3×100 ml)
  5. dry with materialdried over sodium sulfate (Na2SO4)
  6. customFinally, the solvent was evaporated off

Sources & evidence

ORD record
ord-59880d494367462ea83af81fb78a9989
Source dataset
uspto-grants-2011_04
Patent number
US07919046B2

Reaction notes

Loading…