Cyanogen Bromide → 5-[4-(Trifluoromethyl)phenyl]-1,3,4-oxadiazol-2-amine

HRID 1023200Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1023200
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:12]=[CH:11][C:6]([C:7]([NH:9][NH2:10])=[O:8])=[CH:5][CH:4]=1.C(=O)(O)[O-].[Na+].[N:20]#[C:21]Br>O1CCOCC1.O>[F:1][C:2]([F:13])([F:14])[C:3]1[CH:12]=[CH:11][C:6]([C:7]2[O:8][C:21]([NH2:20])=[N:10][N:9]=2)=[CH:5][CH:4]=1

Komponenten

6

Edukt 3

HCID 10476Cyanogen BromideHCID 516892Sodium BicarbonateHCID 5206624-(Trifluoromethyl)benzohydrazide

Produkt 1

HCID 52160855-[4-(Trifluoromethyl)phenyl]-1,3,4-oxadiazol-2-amineAusbeute 50 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To a solution of 4-(trifluoromethyl)benzohydrazide (0.5 g, 2.449 mmol) in dioxane (10 mL) and water (2 mL) was added sodium bicarbonate (0.617 g, 7.35 mmol) and cyanic bromide (0.519 g, 4.90 mmol). The reaction was stirred at room temperature for 15 h. The reaction mixture was diluted with water (50 mL), extracted with EtOAc, dried over sodium sulfate, and evaporated to yield 5-(4-(trifluoromethyl)phenyl)-1,3,4-oxadiazol-2-amine (0.28, 50%). 1H NMR: 400 MHz, DMSO-d6: δ 7.43 (s, 2H), 7.91 (d, J=8.40 Hz, 2H), 8.00 (d, J=8.40 Hz, 2H). LCMS: RT 1.55 min. LCMS (ES-API), m/z 230.0 (M+H).

Aufarbeitung

  1. extractionextracted with EtOAc
  2. dry with materialdried over sodium sulfate
  3. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-458df4e5b20243b1b4238d47b11dfe5c
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08722670B2

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