Sodium Cyanide → 3-Chloro-5-(trifluoromethyl)pyridine-2-carbonitrile

HRID 47881

Reaktionsgleichung

Reaktionsgleichung von HRID 47881
[C-:1]#[N:2].[Na+].[Cl:4][C:5]1[C:6](F)=[N:7][CH:8]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:10]=1>O.C(#N)CC.CN(C)C1C=CN=CC=1>[Cl:4][C:5]1[C:6]([C:1]#[N:2])=[N:7][CH:8]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:10]=1

Komponenten

6

Edukt 2

HCID 8929Sodium CyanideHCID 12680753-Chloro-2-fluoro-5-(trifluoromethyl)pyridine

Produkt 1

HCID 14733743-Chloro-5-(trifluoromethyl)pyridine-2-carbonitrileAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 962WaterLösungsmittelHCID 7854PropionitrileLösungsmittel

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

A reactor was charged with a solution of sodium cyanide (73.5 g) in water (150 ml), propionitrile (500 ml), 4-dimethylaminopyridine (16 g), and 3-chloro-2-fluoro-5-trifluoromethylpyridine (149.3 g) added over 30 minutes. After stirring for 5 hours at 20° C., the upper organic phase was separated off and washed with water. The lower aqueous layer was extracted with propionitrile, the two organic layers combined and solvent distilled off under vacuum at 45° C. to give an 83% yield of 3-chloro-2-cyano-5-trifluoromethylpyridine.

Aufarbeitung

  1. additionadded over 30 minutes
  2. customthe upper organic phase was separated off
  3. washwashed with water
  4. extractionThe lower aqueous layer was extracted with propionitrile
  5. distillationsolvent distilled off under vacuum at 45° C.

Quellen und Nachweise

ORD-Eintrag
ord-25f66ee5310c437fb8f594e64e59f8fe
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06699993B1

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