Hexane → 3-(3-Benzyloxy-benzyl)-1,2,4-triazole

HRID 902606

Reaktionsgleichung

Reaktionsgleichung von HRID 902606
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH2:15][C:16]#[N:17])[CH:12]=[CH:13][CH:14]=1)C1C=CC=CC=1.[CH:18]([NH:20][NH2:21])=O.C(=O)([O-])[O-].[K+].[K+].[CH3:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33]>CO>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:12]=[CH:13][CH:14]=1)[CH2:15][C:16]1[N:17]=[CH:18][NH:20][N:21]=1)[C:30]1[CH:29]=[CH:28][CH:33]=[CH:32][CH:31]=1

Komponenten

6

Edukt 4

HCID 8058HexaneHCID 11430Potassium CarbonateHCID 12229HydrazinecarboxaldehydeHCID 5198313-Benzyloxyphenylacetonitrile

Produkt 1

HCID 1784203933-(3-Benzyloxy-benzyl)-1,2,4-triazoleAusbeute 30 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a stirring solution of 3-benzyloxyphenylacetonitrile (5.0 g, 0.022 mole) in methanol (100 mL) was added formic hydrazide (2.69 g, 0.060 mole) and solid potassium carbonate (9.9 g, 0.027 mole). The reaction was heated at reflux and stirred overnight. The mixture was cooled to RT, filtered, and the filtrate was concentrated. The crude product was purified by column chromatography over silica gel (silica gel 60, EM Science) using 75% ethyl acetate:hexane as eluent to afford 1.8 g (30% yield) of the title compound as an oil: MS (ESI) 266.0 (M+H+).

Aufarbeitung

  1. temperatureThe reaction was heated
  2. temperatureat reflux
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated
  5. customThe crude product was purified by column chromatography over silica gel (silica gel 60, EM Science)

Quellen und Nachweise

ORD-Eintrag
ord-d6d702fabbfb4a7ea1cf73e72427808a
Quelldatensatz
uspto-grants-2008_04
Patentnummer
US07365085B2

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