Reaction #2161222

Reaction equation

sodium azide

undecenyl bromide

water

→

undecenyl azide

Yield 60.0%

Solvents

dimethylformamide

Conditions

Workup

1. 1
   workup.WAITThe mixture was left
2. 2
   Temperatureto cool to ambient temperature
3. 3
   ExtractionAn extraction with ethanol (3×100 ml)
4. 4
   Washthe organic phase was then washed with water (3×100 ml)
5. 5
   Dryingdried over sodium sulfate (Na2SO4)
6. 6
   OtherFinally, the solvent was evaporated off

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.

Source