Potassium Carbonate → N'-benzyl-3-(4-(trifluoromethoxy)phenyl)-1,2,4-oxadiazole-5-carbohydrazide

HRID 1475193Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1475193
[F:1][C:2]([F:21])([F:20])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:14]=[C:13]([C:15]([O:17]CC)=O)[O:12][N:11]=2)=[CH:6][CH:5]=1.C([O-])([O-])=O.[K+].[K+].Cl.Cl.[CH2:30]([NH:37][NH2:38])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>C1COCC1>[CH2:30]([NH:37][NH:38][C:15]([C:13]1[O:12][N:11]=[C:10]([C:7]2[CH:6]=[CH:5][C:4]([O:3][C:2]([F:1])([F:20])[F:21])=[CH:9][CH:8]=2)[N:14]=1)=[O:17])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 146540Benzylhydrazine dihydrochlorideHCID 86711474Ethyl 3-[4-(trifluoromethoxy)phenyl]-1,2,4-oxadiazole-5-carboxylate2×

Produkt 1

HCID 86711886N'-benzyl-3-(4-(trifluoromethoxy)phenyl)-1,2,4-oxadiazole-5-carbohydrazideAusbeute 40,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

To a suspension of ethyl 3-(4-(trifluoromethoxy)phenyl)-1,2,4-oxadiazole-5-carboxylate (Intermediate A) (1.0 g, 3.3 mmol) and K2CO3 (1.1 g, 13 mmol) in THF (17 mL) was added benzylhydrazine dihydrochloride (780 mg, 5.0 mmol). The mixture was heated to 70° C. for 3 h. The mixture was cooled to RT, filtered (Celite), and concentrated under reduced pressure. The crude oil was purified by Biotage (5% EtOAc/Hexane—60% EtOAc) to provide a white solid (500 mg, 40%): MS (ES+) C17H13F3N4O3 requires: 378. found: 379 [M+H]+.

Aufarbeitung

  1. temperatureThe mixture was cooled to RT
  2. filtrationfiltered (Celite)
  3. concentrationconcentrated under reduced pressure
  4. customThe crude oil was purified by Biotage (5% EtOAc/Hexane—60% EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-25e832fad5c34ebe81454731e4c91f05
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US09018380B2

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