Reacción #2786

ord-1a927144cffe4757b1c0239ad6f9ed5a

Ecuación de reacción

BrCCBr
1,2-dibromoethane
[N-]=[N+]=[N-].[Na+]
sodium azide
CN(C)C=O
DMF
[Li][CH3]
MeLi
[N-]=[N+]=[N-]
azide
→
CNN=NCCN=NNC
off-white solid
Rendimiento 32.0%
CNN=NCCN=NNC
1,2-Bis(methyltriazeno)ethane
Rendimiento 32.0%

Reactantes

BrCCBr
1,2-dibromoethane
[N-]=[N+]=[N-].[Na+]
sodium azide
CN(C)C=O
DMF
—
solution
[Li][CH3]
MeLi
[N-]=[N+]=[N-]
azide

Reactivos

Ninguno

Condiciones de reacción

Temperatura
50°CELSIUS
Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Otrois not evaporated down totally
  2. 2
    workup.WAITAfter 3 hr the reaction is worked up
  3. 3
    Otrois obtained
  4. 4
    OtroCrystallization from ether/petroleum ether

Procedimiento

A flask is charged with 5.0 g (27 mmole) of 1,2-dibromoethane, 3.8 g (58 mmole) of sodium azide, and 50 ml of DMF. The mixture is heated at 50° C. with stirring under argon overnight. The mixture is worked up as described above, except that the azide solution is not evaporated down totally. When about 30 ml of solution remains the mixture is treated with 45 ml of a 1.3M solution of MeLi (58 mmole) as above. After 3 hr the reaction is worked up as described above, and a yellow solid is obtained. Crystallization from ether/petroleum ether affords 1.23 g (32% yield) of an off-white solid, mp 64°-6° C. Mass spectra (FAB) Calc (M+H) 145.1201, Found 145.1220±0.0015.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US05731301uspto-grants-1998_03