Ethyl orthoformate → 3-(4-Nitrophenyl)-1,2,4-oxadiazole

HRID 1665618Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1665618
[CH:1](OCC)(OCC)OCC.[OH:11][NH:12][C:13](=[NH:23])[C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=1>C1COCC1>[N+:20]([C:17]1[CH:16]=[CH:15][C:14]([C:13]2[N:23]=[CH:1][O:11][N:12]=2)=[CH:19][CH:18]=1)([O-:22])=[O:21]

Komponenten

4

Edukt 2

HCID 31214Ethyl orthoformateHCID 178513348HCID 178513348, Verbindung

Produkt 1

HCID 27982883-(4-Nitrophenyl)-1,2,4-oxadiazoleAusbeute 55 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Triethyl orthoformate (2.93 g, 19.8 mmol) was added to a stirred solution of N-hydroxy-4-nitro-benzamidine (1.2 g, 6.6 mmol) in THF (15 mL). The mixture was cooled to 0° C. and boron triflouride dimethyl ether (900 mg, 7.9 mmol) was added drop wise. The mixture was maintained at room temperature for three hours. The volatiles were evaporated and the residue was washed with ether and dried to afford 650 mg (55%) of 3-(4-nitro-phenyl)-[1,2,4]oxadiazole.

Aufarbeitung

  1. temperatureThe mixture was maintained at room temperature for three hours
  2. customThe volatiles were evaporated
  3. washthe residue was washed with ether
  4. customdried

Quellen und Nachweise

ORD-Eintrag
ord-f152925894374548be7a82e0028f655e
Quelldatensatz
uspto-grants-2011_10
Patentnummer
US08039463B2

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