Reacción #2161222

ord-59880d494367462ea83af81fb78a9989

Ecuación de reacción

[N-]=[N+]=[N-].[Na+]
sodium azide
CCCCCCCCCC=CBr
undecenyl bromide
O
water
CCCCCCCCCC=CN=[N+]=[N-]
undecenyl azide
Rendimiento 60.0%

Reactivos

Ninguno

Condiciones de reacción

Temperatura
80°CELSIUS
Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    workup.WAITThe mixture was left
  2. 2
    Temperaturato cool to ambient temperature
  3. 3
    ExtracciónAn extraction with ethanol (3×100 ml)
  4. 4
    Lavadothe organic phase was then washed with water (3×100 ml)
  5. 5
    Secadodried over sodium sulfate (Na2SO4)
  6. 6
    OtroFinally, the solvent was evaporated off

Procedimiento

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.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US07919046B2uspto-grants-2011_04