Dimethylformamide → 2,1,3-Benzoxadiazole-5-carbonitrile

HRID 1425853Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1425853
[CH2:1]1[CH:5]2[CH:6]([C:8]3ON=C(N)[N:9]=3)C[N:3]([CH2:4]2)[CH2:2]1.[C:14]([Cu])#[N:15].CN(C=[O:21])C>O>[N:15]1[O:21][N:9]=[C:8]2[CH:6]=[C:5]([C:4]#[N:3])[CH:1]=[CH:2][C:14]=12

Komponenten

5

Edukt 3

HCID 6228DimethylformamideHCID 1639383-(3-Amino-1,2,4-oxadiazol-5-yl)-1-azabicyclo(2.2.1)heptaneHCID 178418546HCID 178418546, Verbindung

Produkt 1

HCID 27354522,1,3-Benzoxadiazole-5-carbonitrileAusbeute 48 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

To a stirred solution of 5-bromobenzo[c][1, 2, and 5]oxadiazole (2.0 g, 10.050 mmol) in DMF (50 mL) was added CuCN (1.79 g, 230.10 mmol) at RT under an inert atmosphere. The reaction mixture was then heated at 140° C. for 24 h., cooled to RT, diluted with water (10 mL) and stirred for 10 min. The precipitated solid was filtered off and the filtrate was concentrated in vacuo to obtain the crude product. The crude material was purified via silica gel column chromatography to afford benzo[c][1,2,5]oxadiazole-5-carbonitrile (0.7 g, 48%) as a yellow solid.

Aufarbeitung

  1. temperaturecooled to RT
  2. filtrationThe precipitated solid was filtered off
  3. concentrationthe filtrate was concentrated in vacuo
  4. customto obtain the crude product
  5. customThe crude material was purified via silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-145f2a7e145a44388c9eada1b6bc3624
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08933074B2

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