Phenylacetylene → 1-Benzyl-4-phenyl-1,2,3-triazole

HRID 64497

Reaction equation

HRID 64497 reaction equation
[C:1]1([C:7]#[CH:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:9]([N:16]=[N+:17]=[N-:18])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>ClCCl>[CH2:9]([N:16]1[CH:8]=[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[N:18]=[N:17]1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 10821PhenylacetyleneHCID 12152Benzyl azide

Product 1

HCID 113108941-Benzyl-4-phenyl-1,2,3-triazoleYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Phenylacetylene (103 mg, 1.0 mmol, 1.0 eq.) and benzyl azide (133 mg, 1.0 mmol, 1.0 eq.) were dissolved in an air-tight lockable vial with a septum in 10 mL dry dichloromethane. The Cu complex (catalytic or stoichiometric amounts) shown below was added, the vial sealed and the reaction stirred at room temperature for 2 days. For the removal of the catalyst complex the reaction mixture was put in 50 mL methanol and stirred for 20 min. The complex was removed by filtering and the filtrate was concentrated. Removal of the solvent and drying of the product in high vacuum resulted in the compound 1-benzyl-4-phenyl-1H-1,2,3-triazole as light yellow solid with 95% yield (245 mg, 0.95 mmol). The identity of the product was proven by NMR-spectroscopy, infrared spectroscopy and high-resolution mass spectroscopy.

Workup

  1. additionbelow was added
  2. customthe vial sealed
  3. customFor the removal of the catalyst complex the reaction mixture
  4. stirringstirred for 20 min
  5. customThe complex was removed
  6. filtrationby filtering
  7. concentrationthe filtrate was concentrated
  8. customRemoval of the solvent
  9. customdrying of the product in high vacuum

Sources & evidence

ORD record
ord-501c5620fdde4b33b511a2d682e2a9d3
Source dataset
uspto-grants-2016_09
Patent number
US09447245B2

Linked notes

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