Sodium Azide → Methyl 11-azidoundecanoate

HRID 2112436Notes

Reaction equation

HRID 2112436 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].Br[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([O:18][CH3:19])=[O:17]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C)C=O.O>[N:1]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([O:18][CH3:19])=[O:17])=[N+:2]=[N-:3]

Participants

6

Reactant 2

HCID 33557Sodium AzideHCID 223913Methyl 11-bromoundecanoate

Product 1

HCID 57642038Methyl 11-azidoundecanoate

Reagents, catalysts & solvents 3

HCID 67553Tetrabutylammonium IodideCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

Sodium azide (4.66 g, 72 mmol) and tetrabutylammonium iodide (66 mg, 0.18 mmol) were successively added to a solution of methyl 11-bromoundecanoate (commercially available at Aldrich, 5.00 g, 17.9 mmol) in N,N-dimethylformamide (50 ml). The reaction mixture was heated to 60° C. for 16 h and cooled to room temperature. It was diluted with water (200 ml) and extracted with ethyl acetate (200 ml). The aqueous phase was washed with water (2×200 ml). The organic phase was dried over sodium sulphate. The solvent was removed in vacuo to give 4.28 g of methyl 11-azidoundecanoate.

Workup

  1. temperaturecooled to room temperature
  2. extractionextracted with ethyl acetate (200 ml)
  3. washThe aqueous phase was washed with water (2×200 ml)
  4. dry with materialThe organic phase was dried over sodium sulphate
  5. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-6719aa14373240dd98cef39096183230
Source dataset
uspto-grants-2009_04
Patent number
US07524813B2

Reaction notes

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