Methylhydrazine sulfate → N-methyl-3-(4-(trifluoromethoxy)phenyl)-1,2,4-oxadiazole-5-carbohydrazide

HRID 517563Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 517563
[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](OCC)=[O:16])[O:12][N:11]=2)=[CH:6][CH:5]=1.S(O)(O)(=O)=O.[CH3:27][NH:28][NH2:29]>CCO>[CH3:27][NH:28][NH:29][C:15]([C:13]1[O:12][N:11]=[C:10]([C:7]2[CH:8]=[CH:9][C:4]([O:3][C:2]([F:21])([F:20])[F:1])=[CH:5][CH:6]=2)[N:14]=1)=[O:16].[CH3:27][N:28]([C:15]([C:13]1[O:12][N:11]=[C:10]([C:7]2[CH:8]=[CH:9][C:4]([O:3][C:2]([F:21])([F:20])[F:1])=[CH:5][CH:6]=2)[N:14]=1)=[O:16])[NH2:29]

Komponenten

5

Edukt 2

HCID 165286Methylhydrazine sulfateHCID 86711474Ethyl 3-[4-(trifluoromethoxy)phenyl]-1,2,4-oxadiazole-5-carboxylate

Produkt 2

HCID 86711504N'-methyl-3-(4-(trifluoromethoxy)phenyl)-1,2,4-oxadiazole-5-carbohydrazideAusbeute 32 %HCID 89979634N-methyl-3-(4-(trifluoromethoxy)phenyl)-1,2,4-oxadiazole-5-carbohydrazideAusbeute 34 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of ethyl 3-(4-(trifluoromethoxy)phenyl)-1,2,4-oxadiazole-5-carboxylate (3.5 g, 11.5 mmol) in EtOH (25 mL), methylhydrazine sulfate salt (2.5 g, 17.2 mmol) and TEA (7.5 mL) were added at RT. The mixture was stirred at RT overnight, concentrated and purified by Combiflash reverse phase chromatography (50%˜60% MeCN/H2O containing 0.01% TFA) to give N′-methyl-3-(4-(trifluoromethoxy)phenyl)-1,2,4-oxadiazole-5-carbohydrazide (1.1 g, 32%) and N-methyl-3-(4-(trifluoromethoxy)phenyl)-1,2,4-oxadiazole-5-carbohydrazide as white solids (1.2 g, 34%). MS (ES+) C11H9F3N4O3 requires: 302, found: 303[M+H]+.

Aufarbeitung

  1. concentrationconcentrated
  2. custompurified by Combiflash reverse phase chromatography (50%˜60% MeCN/H2O containing 0.01% TFA)

Quellen und Nachweise

ORD-Eintrag
ord-9545778d774343e0852d7c46f9624628
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09115120B2

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