Azide → Dimethyl 2-azidononanedioate

HRID 647799Notes

Reaction equation

HRID 647799 reaction equation
[N-:1]=[N+:2]=[N-:3].Br[CH:5]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([O:18][CH3:19])=[O:17])[C:6]([O:8][CH3:9])=[O:7]>C(#N)C>[N:1]([CH:15]([CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:5][C:6]([O:8][CH3:9])=[O:7])[C:16]([O:18][CH3:19])=[O:17])=[N+:2]=[N-:3]

Participants

4

Reactant 2

HCID 33558AzideHCID 12760707Dimethyl 2-bromononanedioate

Product 1

HCID 13251059Dimethyl 2-azidononanedioateYield 99.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Soldium azide (4.87 g, 75 mmol) was added to a solution of dimethyl 2-bromoazelate (5.9 g, 20 mmol) prepared according to Auguston, M, et al; Acta Chim. Acad. Sci. Hung; 46: 85 (1965) in acetonitrile, and the mixture was heated at reflux temperature for 4 h. The solvent was removed in vacuo, dichloromethane (80 ml) was added to the residue, and the mixture was washed with water. The organic phase was dried over sodium sulfate and the solvent was removed in vacuo to give the title compound as an oil (5.1 g, 98% yield).

Workup

  1. customprepared
  2. temperatureat reflux temperature for 4 h
  3. customThe solvent was removed in vacuo, dichloromethane (80 ml)
  4. additionwas added to the residue
  5. washthe mixture was washed with water
  6. dry with materialThe organic phase was dried over sodium sulfate
  7. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-a055d5ae61cd45bdaabc3536ba573099
Source dataset
uspto-grants-1983_10
Patent number
US04410526

Reaction notes

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