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

HRID 530296Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 530296
[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

Komponenten

4

Edukt 2

HCID 10821PhenylacetyleneHCID 78378Azidotrimethylsilane

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

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%).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-ede9eab4eee946bbb339df56a25367e8
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09353082B2

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