Sodium Azide → 2-Azido-1-(naphthalen-1-yl)ethan-1-one

HRID 2073717Notes

Reaction equation

HRID 2073717 reaction equation
Br[CH2:2][C:3]([C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[CH:7][CH:6]=1)=[O:4].[N-:15]=[N+:16]=[N-:17].[Na+]>CC(C)=O>[N:15]([CH2:2][C:3]([C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[CH:7][CH:6]=1)=[O:4])=[N+:16]=[N-:17]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 38305132-Bromo-1-(1-naphthalenyl)ethanone

Product 1

HCID 150572332-Azido-1-(naphthalen-1-yl)ethan-1-one

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Combine 24.9 g (0.1 mol) of 2-bromo-1-(naphthalen-1-yl)ethanone and 24 g (0.37 mol) of sodium azide in 200 mL of 60% aqueous acetone. Heat the mixture at reflux for about 18 to 36 hr and follow the progress of the reaction by thin-layer chromatography on silica gel. At the completion of the reaction, distill off the acetone and add 25 mL of water. Extract the aqueous mixture with three 100 mL portions of diethyl ether. Dry the organic extracts over anhydrous sodium sulfate. Filter the drying agent and remove the solvent in vacuo to obtain the title compound.

Workup

  1. temperatureHeat the mixture
  2. temperatureat reflux for about 18 to 36 hr
  3. customthe progress of the reaction by thin-layer chromatography on silica gel
  4. customAt the completion of the reaction
  5. distillationdistill off the acetone
  6. additionadd 25 mL of water
  7. extractionExtract the aqueous mixture with three 100 mL portions of diethyl ether
  8. dry with materialDry the organic extracts over anhydrous sodium sulfate
  9. filtrationFilter the drying agent
  10. customremove the solvent in vacuo

Sources & evidence

ORD record
ord-9647317a42d64364b8fc9d9f55554efb
Source dataset
uspto-grants-1990_04
Patent number
US04920116

Reaction notes

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