Phenylacetylene → 4-(4-phenyl-1H-1,2,3-triazol-1-yl)pyridine

HRID 1401372Notes

Reaction equation

HRID 1401372 reaction equation
[N:1]([C:4]1[CH:9]=[CH:8][N:7]=[CH:6][CH:5]=1)=[N+:2]=[N-:3].[C:10]1([C:16]#[CH:17])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.O=C1O[C@H]([C@H](CO)O)C([O-])=C1O.[Na+]>S([O-])([O-])(=O)=O.[Cu+2].O.CC(C)=O>[C:10]1([C:16]2[N:3]=[N:2][N:1]([C:4]3[CH:9]=[CH:8][N:7]=[CH:6][CH:5]=3)[CH:17]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 3

HCID 10821PhenylacetyleneHCID 113324494-AzidopyridineHCID 23667548Sodium Ascorbate

Product 1

HCID 1023234934-(4-phenyl-1H-1,2,3-triazol-1-yl)pyridine

Reagents, catalysts & solvents 2

HCID 24462Copper SulfateCatalystHCID 18366337Propan-2-one--water (1/1)Solvent

Procedure

Approximately equimolar amounts of 4-azidopyridine and phenylacetylene (4.12 ml, 41.8 mmol) were added into a 250 mL round-bottom flask with 50 mL mixture of water/acetone. Copper (II) sulfate and sodium L-ascorbate were added to this solution and the reaction was stirred at room temperature for 24 hours. The solution was filtered and concentrated. Ethyl acetate (200 ml) was added to the concentrated solution. The organic layer was washed twice with 25 mL water, dried with MgSO4, filtered, concentrated and dried in vacuo, producing 4-(4-phenyl-1H-1,2,3-triazol-1-yl)pyridine.

Workup

  1. filtrationThe solution was filtered
  2. concentrationconcentrated
  3. additionEthyl acetate (200 ml) was added to the concentrated solution
  4. washThe organic layer was washed twice with 25 mL water
  5. dry with materialdried with MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customdried in vacuo

Sources & evidence

ORD record
ord-06f9e4861c7b43b489a1f59c84c5fbeb
Source dataset
uspto-grants-2014_12
Patent number
US08907105B1

Reaction notes

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