Methane → 2,3-Dichloro-6-nitrobenzonitrile

HRID 636366

Reaktionsgleichung

Reaktionsgleichung von HRID 636366
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4](Cl)[C:3]=1[Cl:12].[Cu](C#N)[C:14]#[N:15].Cl.C>CN(C=O)C.CO.C1(C)C=CC=CC=1.O>[Cl:12][C:3]1[C:2]([Cl:1])=[CH:7][CH:6]=[C:5]([N+:8]([O-:10])=[O:9])[C:4]=1[C:14]#[N:15]

Komponenten

9

Edukt 4

HCID 297MethaneHCID 313Hydrochloric AcidHCID 286972,3,4-TrichloronitrobenzeneHCID 178418260HCID 178418260, Verbindung

Produkt 1

HCID 27360202,3-Dichloro-6-nitrobenzonitrile

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 1.831 kg of 1,2,3-trichloro-4-nitrobenzene and 0.861 kg of copper cyanide in 1.21 L of DMF is heated to 155° C. for 2 hours, then cooled to room temperature. A solution of 3.24 kg of ferric chloride hexahydrate, 0.806 L of concentrated hydrochloric acid, and 4.87 L of water is added and the solution heated to 65° C. for 20 minutes. The mixture is cooled, stirred with 0.55 kg of charcoal and 4 L of toluene, and filtered. The organic phase is separated and the aqueous phase extracted with toluene. The combined toluene layers are washed with water and 6 N HCl, dried and concentrated to give a slurry. The slurry is dissolved in 1.5 L of methanol, and stored at 5° C. for 24 hours. The nitrile product is collected by filtration, washed with 1.5 L cold methanol and dried at 40° C.

Aufarbeitung

  1. temperaturethe solution heated to 65° C. for 20 minutes
  2. temperatureThe mixture is cooled
  3. filtrationfiltered
  4. customThe organic phase is separated
  5. extractionthe aqueous phase extracted with toluene
  6. washThe combined toluene layers are washed with water and 6 N HCl
  7. customdried
  8. concentrationconcentrated
  9. customto give a slurry
  10. filtrationThe nitrile product is collected by filtration
  11. washwashed with 1.5 L cold methanol
  12. customdried at 40° C.

Quellen und Nachweise

ORD-Eintrag
ord-ac1bbce14889489e8ec6c9fba78fcac6
Quelldatensatz
uspto-grants-2001_02
Patentnummer
US06194420B1

Verknüpfte Notizen

Wird geladen…