Pyridine → 2-(Phenyldiazenyl)succinonitrile

HRID 522154

Reaktionsgleichung

Reaktionsgleichung von HRID 522154
[C:1]([CH:3]([CH2:9][C:10]#[N:11])C(OCC)=O)#[N:2].N1C=CC=CC=1.F[B-](F)(F)F.[C:23]1([N+:29]#[N:30])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>CO>[C:23]1([N:29]=[N:30][CH:3]([CH2:9][C:10]#[N:11])[C:1]#[N:2])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 5284485Benzenediazonium tetrafluoroborateHCID 10725530Ethyl 2,3-Dicyanopropionate

Produkt 1

HCID 1184560602-(Phenyldiazenyl)succinonitrileAusbeute 28 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A solution of ethyl 2,3-dicyanopropanoate (1.58 g, 10.38 mmol) in methanol (52 mL) and pyridine (2.52 mL, 31.14 mmol) was cooled to 10° C. in an ice bath. Benzenediazonium tetrafluoroborate was added portion-wise over 20 minutes at 10° C. and the reaction stirred at room temperature for 18 hours. The reaction was concentrated in vacuo and partitioned between DCM and water. The organic layer was dried over magnesium sulphate and concentrated in vacuo to afford the title compound (2.8 g, 28%). The crude product was taken on directly to the next step.

Aufarbeitung

  1. concentrationThe reaction was concentrated in vacuo
  2. custompartitioned between DCM and water
  3. dry with materialThe organic layer was dried over magnesium sulphate
  4. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-e04577d859ea4acab1e0bbddfd132a30
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09328096B2

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