Sodium Azide → Dimethyl 2-azidononanedioate

HRID 2413187Notes

Reaction equation

HRID 2413187 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].Br[CH:6]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([O:19][CH3:20])=[O:18])[C:7]([O:9][CH3:10])=[O:8]>C(#N)C>[N:1]([CH:16]([CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:6][C:7]([O:9][CH3:10])=[O:8])[C:17]([O:19][CH3:20])=[O:18])=[N+:2]=[N-:3]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 12760707Dimethyl 2-bromononanedioate

Product 1

HCID 13251059Dimethyl 2-azidononanedioate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Sodium 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.

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-4e1af700cedd4d7d96a9020ec0793f5a
Source dataset
uspto-grants-1985_01
Patent number
US04496577

Reaction notes

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