2,6-Dichloroaniline → HCID 19814841, Verbindung

HRID 465886Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 465886
[Cl:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([Cl:9])[C:3]=1[NH2:4].[H-].[Na+].[H][H].F[C:15]1[CH:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:18]=[C:17]([CH3:25])[N:16]=1>CS(C)=O>[Cl:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([Cl:9])[C:3]=1[NH:4][C:15]1[CH:20]=[C:19]([C:21]([F:22])([F:24])[F:23])[CH:18]=[C:17]([CH3:25])[N:16]=1

Komponenten

6

Edukt 4

HCID 118462,6-DichloroanilineHCID 24758Sodium hydrideHCID 198148432-Fluoro-6-methyl-4-(trifluoromethyl)pyridineHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 19814841HCID 19814841, VerbindungAusbeute 54,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel3×

Versuchsvorschrift

4.0 g (0.025 mol) of 2,6-dichloroaniline in 20 ml of dimethyl sulfoxide are added dropwise at 15°-20° C. to 1.2 g (0.05 mol) of sodium hydride in 20 ml of dimethyl sulfoxide. After hydrogen has ceased to evolve, 4.5 g (0.025 mol) of 2-fluoro-4-trifluoromethyl-6-methylpyridine in 10 ml of dimethyl sulfoxide are added dropwise, whereupon the temperature rises to 30° C. The reaction mixture is stirred for 2 hours at room temperature and then ice-water is added. After extraction with diethyl ether, the ether phase is dried over sodium sulfate and concentrated by evaporation. The residue is chromatographed over silica gel with ethyl acetate/hexane (1:3), affording 4.4 g (54.8%) of the title compound of formula ##STR28## in the form of crystals which melt at 108° C. (compound 2.033).

Aufarbeitung

  1. customrises to 30° C
  2. extractionAfter extraction with diethyl ether
  3. dry with materialthe ether phase is dried over sodium sulfate
  4. concentrationconcentrated by evaporation
  5. customThe residue is chromatographed over silica gel with ethyl acetate/hexane (1:3)

Quellen und Nachweise

ORD-Eintrag
ord-833367caa6a54dd9aab923705ea4bf1d
Quelldatensatz
uspto-grants-1992_10
Patentnummer
US05154751

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