Sodium Azide → 2-Azidocyclohexan-1-one

HRID 541006Notes

Reaction equation

HRID 541006 reaction equation
Br[CH:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C:3]1=[O:8].[N-:9]=[N+:10]=[N-:11].[Na+]>CS(C)=O.O>[N:9]([CH:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C:3]1=[O:8])=[N+:10]=[N-:11]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 117897582-Bromocyclohexanone

Product 1

HCID 108555312-Azidocyclohexan-1-oneYield 92%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

2-Bromocyclohexan-1-one (K. Tanemura, T. Suzuki, Y. Nishida, K. Satsumabayashi, T. Horaguchi, Chem. Commun. 2004, 470-471) (0.55 g, 3.11 mmol) was dissolved in DMSO (3 mL). Sodium azide (1.00 g, 15.5 mmol) was added, and the resulting mixture was stirred for 2 h. The solution was then diluted with water (50 mL) and extracted with diethyl ether (2×20 mL). The organic layers were combined, washed with water (2×20 mL), dried over Na2SO4(s), filtered, and concentrated under reduced pressure. The resulting oil was found to be pure by NMR analysis and was used without further purification (0.40 g, 2.87 mmol, 92% yield).

Workup

  1. extractionextracted with diethyl ether (2×20 mL)
  2. washwashed with water (2×20 mL)
  3. dry with materialdried over Na2SO4(s)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customwas used without further purification (0.40 g, 2.87 mmol, 92% yield)

Sources & evidence

ORD record
ord-f7267f8f3e17468ba0732cfc2b09a684
Source dataset
uspto-grants-2014_10
Patent number
US08871916B2

Reaction notes

Loading…