Triethylamine → 5-(4-trifluoromethoxyphenyl)-3H-[1,3,4]oxadiazol-2-one

HRID 856038

Reaktionsgleichung

Reaktionsgleichung von HRID 856038
C(N(CC)CC)C.[C:8](N1C=CN=C1)(N1C=CN=C1)=[O:9].[F:20][C:21]([F:34])([F:33])[O:22][C:23]1[CH:32]=[CH:31][C:26]([C:27]([NH:29][NH2:30])=[O:28])=[CH:25][CH:24]=1>C1COCC1>[F:20][C:21]([F:33])([F:34])[O:22][C:23]1[CH:32]=[CH:31][C:26]([C:27]2[O:28][C:8](=[O:9])[NH:30][N:29]=2)=[CH:25][CH:24]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 27772304-(Trifluoromethoxy)benzoic acid hydrazide

Produkt 1

HCID 230813495-(4-trifluoromethoxyphenyl)-3H-[1,3,4]oxadiazol-2-oneAusbeute 94,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Triethylamine (3.52 ml, 25.28 mmol) and 1,1′-carbonyldiimidazole (4.84 g, 29.87 mmol) were added to a solution of 4-trifluoromethoxybenzoic hydrazide (5.06 g, 22.98 mmol) in THF (150 ml) while cooling in an ice-bath and the mixture was stirred at room temperature for 2 hours. The reaction mixture was concentrated under reduced pressure, to which water was added. The mixture was extracted with ethyl acetate, and the extract was dried over magnesium sulfate and then concentrated under reduced pressure to afford 5-(4-trifluoromethoxyphenyl)-3H-[1,3,4]oxadiazol-2-one (5.34 g, yield 94%) as a colorless crystalline powder.

Aufarbeitung

  1. temperaturewhile cooling in an ice-bath
  2. concentrationThe reaction mixture was concentrated under reduced pressure, to which water
  3. additionwas added
  4. extractionThe mixture was extracted with ethyl acetate
  5. dry with materialthe extract was dried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-b7344eb8b5604348905737af6d806895
Quelldatensatz
uspto-grants-2007_08
Patentnummer
US07262212B2

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