Propionitrile → 3-Chloro-5-(trifluoromethyl)pyridine-2-carbonitrile

HRID 47880

Reaktionsgleichung

Reaktionsgleichung von HRID 47880
[C:1](#[N:4])CC.Cl[C:6]1[C:11]([Cl:12])=[CH:10][C:9]([C:13]([F:16])([F:15])[F:14])=[CH:8][N:7]=1.[C-]#N.[Na+]>CN(C)C1C=CN=CC=1.O>[Cl:12][C:11]1[C:6]([C:1]#[N:4])=[N:7][CH:8]=[C:9]([C:13]([F:16])([F:15])[F:14])[CH:10]=1

Komponenten

6

Edukt 3

HCID 7854PropionitrileHCID 8929Sodium CyanideHCID 1122342,3-Dichloro-5-(trifluoromethyl)pyridine

Produkt 1

HCID 14733743-Chloro-5-(trifluoromethyl)pyridine-2-carbonitrileAusbeute 73 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 962WaterLösungsmittel2×

Reaktionsbedingungen

Temperatur
15 °C

Versuchsvorschrift

Propionitrile (656 ml), 2,3-dichloro-5-trifluoromethylpyridine (87.5 g) and 4-dimethylaminopyridine (52 g) were heated at reflux for 5 hours under nitrogen. The mixture was cooled and a solution of sodium cyanide (30 g) in water (110 ml) added at 15° C. After stirring at 15° C. for 5 hours the reaction was complete and water (250 ml) added to dissolve the inorganic salts. The organic phase was washed with water followed by extraction with 2N HCl to remove 4-dimethylaminopyridine. Propionitrile was removed by vacuum distillation at 40° C. to give the product, 3-chloro-2-cyano-5-trifluoromethylpyridine in 73 to 84% yield.

Aufarbeitung

  1. temperatureat reflux for 5 hours under nitrogen
  2. temperatureThe mixture was cooled
  3. dissolutionto dissolve the inorganic salts
  4. washThe organic phase was washed with water
  5. extractionfollowed by extraction with 2N HCl
  6. customto remove 4-dimethylaminopyridine
  7. customPropionitrile was removed by vacuum distillation at 40° C.

Quellen und Nachweise

ORD-Eintrag
ord-2759955b5a064331b73b1134fed2a2e3
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06699993B1

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