Sodium Azide → 3-(Azidomethyl)-5-(furan-2-yl)-1,2-oxazole

HRID 606285Notes

Reaction equation

HRID 606285 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[O:10][N:9]=[C:8]([CH2:11]OS(C)(=O)=O)[CH:7]=1.[N-:17]=[N+:18]=[N-:19].[Na+]>CN(C=O)C>[N:17]([CH2:11][C:8]1[CH:7]=[C:6]([C:2]2[O:1][CH:5]=[CH:4][CH:3]=2)[O:10][N:9]=1)=[N+:18]=[N-:19]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 57696260Methanesulfonic acid 5-furan-2-yl-isoxazol-3-ylmethyl ester

Product 1

HCID 576962103-(Azidomethyl)-5-(furan-2-yl)-1,2-oxazoleYield 86.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2.21 g of methane sulfonic acid 5-furan-2-yl-isoxazol-3-ylmethyl ester in 45 mL of DMF was added 0.61 g of sodium azide. After stirring for 15 hrs, the reaction mixture was concentrated under reduced pressure. The residue was dissolved in methylene chloride and distilled water, and the organic layer was separated. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to afford 1.50 g of 3-azidomethyl-5-furan-2-yl-isoxazole. This concentrate was used in the next step without further purification.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in methylene chloride
  3. distillationdistilled water
  4. customthe organic layer was separated
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7e037c2a58e6426d89ec69b7e09c3a58
Source dataset
uspto-grants-2011_03
Patent number
US07915297B2

Reaction notes

Loading…