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

HRID 530296Notes

Reaction equation

HRID 530296 reaction equation
[C:1]1([C:7]#[CH:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N:9]([Si](C)(C)C)=[N+:10]=[N-:11]>C1(C)C=CC=CC=1>[C:1]1([C:7]2[N:9]=[N:10][NH:11][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 10821PhenylacetyleneHCID 78378Azidotrimethylsilane

Product 1

HCID 1784201274-phenyl-1H-1,2,3-triazole

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To a stirred solution of phenylacetylene (1.098 ml, 10 mmol) in abs. toluene (10 ml) was added azidotrimethylsilane (2.65 ml, 20.00 mmol) in one portion. The reaction was heated at 100° C. for 3 days, whereupon was cooled to room temperature and toluene was removed by vacuum. The residue was partitioned between DCM and water. The organic phase was dried over MgSO4 and filtered. After evaporation the crude product was chromatographed in petroleumether:EtOAc=2:1. (Yield: 355 mg, 24%).

Workup

  1. temperaturewhereupon was cooled to room temperature
  2. customtoluene was removed by vacuum
  3. customThe residue was partitioned between DCM and water
  4. dry with materialThe organic phase was dried over MgSO4
  5. filtrationfiltered
  6. customAfter evaporation the crude product
  7. customwas chromatographed in petroleumether

Sources & evidence

ORD record
ord-ede9eab4eee946bbb339df56a25367e8
Source dataset
uspto-grants-2016_05
Patent number
US09353082B2

Reaction notes

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