Furfural → HCID 178420175, Verbindung

HRID 589291Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 589291
[CH:1]1[CH:5]=[C:4]([CH:6]=[O:7])[O:3][CH:2]=1.O[N:9]=[C:10]([NH2:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>N1CCCCC1.C1(C)C=CC=CC=1>[O:3]1[CH:2]=[CH:1][CH:5]=[C:4]1[CH:6]1[O:7][N:9]=[C:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[NH:17]1

Komponenten

5

Edukt 2

HCID 7362FurfuralHCID 69186N'-Hydroxybenzenecarboximidamide

Produkt 1

HCID 178420175HCID 178420175, VerbindungAusbeute 43,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8082PiperidineKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

A mixture of 2-furfural (1.0 mL, 1.17 g, 12.2 mmol, 1.5 equivalents), N′-hydroxybenzimidamide (1.11 g, 8.1 mmol) and one drop of piperidine in toluene (100 mL) was heated to reflux for 18 hours in a SOXHLETT apparatus that was charged with SILCARBON 3 Angstrom molecular sieve (8 g). The reaction mixture was allowed to cool to room temperature, and the solvent was removed in vacuo. After purification by automated column chromatography on an ISCO COMPANION apparatus (SiO2, gradient heptane/ethyl acetate), the 5-(furan-2-yl)-3-phenyl-4,5-dihydro-1,2,4-oxadiazole product (745 mg, 3.5 mmol) was obtained as a brown oil that solidified to a tan solid upon standing. The overall reaction yield was approximately 43%. LC-MS [M+H] 215 (C12H10N2O2+H, expected 215.07].

Aufarbeitung

  1. temperaturewas heated
  2. temperatureto reflux for 18 hours in a SOXHLETT apparatus that
  3. additionwas charged with SILCARBON 3 Angstrom molecular sieve (8 g)
  4. customthe solvent was removed in vacuo
  5. customAfter purification by automated column chromatography on an ISCO COMPANION apparatus (SiO2, gradient heptane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-13b71fcdc0e74ce5a651b1bb185fc890
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09232800B2

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