Sodium Azide → 6-Azidohexan-1-ol

HRID 2423021Notes

Reaction equation

HRID 2423021 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][OH:8].[N-:9]=[N+:10]=[N-:11].[Na+]>C(O)C>[N:9]([CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][OH:8])=[N+:10]=[N-:11]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 779706-Bromo-1-hexanol

Product 1

HCID 110517786-Azidohexan-1-olYield 88%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 6-bromo-1-hexanol (3.6 g, 20 mmol) and sodium azide (2.6 g, 40 mmol) in 95% ethanol (50 mL) was heated with stirring to reflux for 12 hours. The mixture was filtered, and the filtrate concentrated by rotary evaporation. The residue was dissolved in ether (250 mL) and washed three times with water. The ether layer was dried over anhydrous MgSO4, and concentrated by rotary evaporation to give the desired product as a colorless liquid in 88% yield: 1H NMR (CDCl3, 400 MHz): δ (CHCl3 7.26 ppm) 3.65-3.62 (t, J=6.52 Hz, 2H), 3.28-3.24 (t, J=6.88 Hz, 2H), 1.60 (m, 4H), 1.40 (m, 4H); 13C NMR (CDCl3, 100 MHz): δ (ppm) 62.7, 51.3, 32.5, 28.8, 26.5, 25.3.

Workup

  1. temperatureto reflux for 12 hours
  2. filtrationThe mixture was filtered
  3. concentrationthe filtrate concentrated by rotary evaporation
  4. dissolutionThe residue was dissolved in ether (250 mL)
  5. washwashed three times with water
  6. dry with materialThe ether layer was dried over anhydrous MgSO4
  7. concentrationconcentrated by rotary evaporation

Sources & evidence

ORD record
ord-c7aaf6e6ab49444686bc47bac2373a05
Source dataset
uspto-grants-2011_06
Patent number
US07960555B2

Reaction notes

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