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Dimethylformamide → HCID 89854217, Verbindung

HRID 931127
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 931127
Br[C:2]1[CH:3]=[C:4]([S:8]([NH:11][CH3:12])(=[O:10])=[O:9])[CH:5]=[N:6][CH:7]=1.[CH3:13][N:14](C)C=O>[C-]#N.[Zn+2].[C-]#N>[C:13]([C:2]1[CH:3]=[C:4]([S:8]([NH:11][CH3:12])(=[O:10])=[O:9])[CH:5]=[N:6][CH:7]=1)#[N:14]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 6228DimethylformamideHCID 467389795-Bromo-N-methylpyridine-3-sulfonamide

Produkt 1

HCID 89854217HCID 89854217, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 11186Zinc cyanide (Zn(CN)2)Katalysator

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a solution of 5-bromo-N-methylpyridine-3-sulfonamide (0.1 g, 0.39 mmol) in N,N-dimethylformamide was added zinc cyanide (0.056 g, 0.47 mmol). The solution was degassed with nitrogen for 10 min, then tetrakis(triphenylphosphine)palladium(0) (30 mg) was added. The reaction mixture was heated to 100° C. for 2 h. The mixture was then diluted with water and extracted with ethyl acetate. The organic layer was dried, filtered, and concentrated under reduced pressure. The crude compound was purified by rinsing with diethyl ether to afford 5-cyano-N-methylpyridine-3-sulfonamide (60 mg) which was used without further purification.

Aufarbeitung

  1. customThe solution was degassed with nitrogen for 10 min
  2. additiontetrakis(triphenylphosphine)palladium(0) (30 mg) was added
  3. additionThe mixture was then diluted with water
  4. extractionextracted with ethyl acetate
  5. customThe organic layer was dried
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe crude compound was purified
  9. washby rinsing with diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-9f254e608b4342e2ab6a2f1954aaf2cc
Quelldatensatz
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09296745B2

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