Sodium Azide → 3-Azido-3-methylbutan-2-one

HRID 246640Notes

Reaction equation

HRID 246640 reaction equation
Br[C:2]([CH3:7])([CH3:6])[C:3](=[O:5])[CH3:4].[N-:8]=[N+:9]=[N-:10].[Na+]>CC(C)=O.O>[N:8]([C:2]([CH3:7])([CH3:6])[C:3](=[O:5])[CH3:4])=[N+:9]=[N-:10]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 3449113-Bromo-3-methyl-2-butanone

Product 1

HCID 855288823-Azido-3-methylbutan-2-oneYield 65%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

A stirred solution of 3-bromo-3-methylbutan-2-one (1 g, 6.1 mmol) in 50 mL of acetone and 5 mL of water was treated with NaN3 (0.4 g, 6.1 mmol). The reaction mixture was stirred at reflux for 18 hours and then evaporated to dryness. The residue was partitioned between ethyl acetate and water and the organic layer was washed with brine, evaporated to dryness to give 3-azido-3-methylbutan-2-one (0.5 g, 65%) which was used in the next step without further purification. LCMS: No molecular ion observed for desired mass.

Workup

  1. temperatureat reflux for 18 hours
  2. customevaporated to dryness
  3. customThe residue was partitioned between ethyl acetate and water
  4. washthe organic layer was washed with brine
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-92321c88cd82477c825f9b6851969617
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

Loading…