Sodium Azide → 11-Azidoundecan-1-ol

HRID 1895841Notes

Reaction equation

HRID 1895841 reaction equation
Br[CH:2]([OH:13])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[N-:14]=[N+:15]=[N-:16].[Na+]>CN(C=O)C>[N:14]([CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][OH:13])=[N+:15]=[N-:16]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 220339541-Bromoundecan-1-ol

Product 1

HCID 7133999411-Azidoundecan-1-olYield 107.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a 250 mL round-bottom dry flask was added anhydrous DMF (60 mL), 11 bromo-1-undecanol (10 g, 39.8 mmol) and NaN3 (2.85 g, 43.8 mmol). The solution was stirred with a magnetic bar for 24 hours at ambient temperature and quenched with DI water (60 mL). The solution was extracted with CH2Cl2 (3×40 mL), re-extracted with DI water (2×50 mL), dried with sodium sulfate overnight, and filtered. After the removal of the solvent by a rotoevaporator, a clear, colorless liquid (9.1 g, 93.4%) was obtained.

Workup

  1. customquenched with DI water (60 mL)
  2. extractionThe solution was extracted with CH2Cl2 (3×40 mL)
  3. extractionre-extracted with DI water (2×50 mL)
  4. dry with materialdried with sodium sulfate overnight
  5. filtrationfiltered
  6. customAfter the removal of the solvent by a rotoevaporator

Sources & evidence

ORD record
ord-b0bf7db14d5e42bca5048f61140ae30c
Source dataset
uspto-grants-2013_08
Patent number
US08518473B2

Reaction notes

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