Azide → Dimethyl 2-azidononanedioate

HRID 371378Notes

Reaction equation

HRID 371378 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-4e8d13433170482a9249a7721e8ecc51
Source dataset
uspto-grants-1985_07
Patent number
US04532138

Reaction notes

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