Reaction #2786

ord-1a927144cffe4757b1c0239ad6f9ed5a

Reaction equation

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
Yield 32.0%
CNN=NCCN=NNC
1,2-Bis(methyltriazeno)ethane
Yield 32.0%

Reactants

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

Reagents

None

Conditions

Temperature
50°CELSIUS
Detailed conditions
See reaction.notes.procedure_details.

Workup

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

Procedure

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.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05731301uspto-grants-1998_03