N-methyl-2-pyrrolidone → 2-Trifluoromethyl-9-cyano-10,11-dihydrodibenzo[b,f]thiepin

HRID 866930Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 866930
[F:1][C:2]([F:20])([F:19])[C:3]1[CH:18]=[CH:17][C:6]2[S:7][C:8]3[CH:15]=[CH:14][CH:13]=[C:12](Cl)[C:9]=3[CH2:10][CH2:11][C:5]=2[CH:4]=1.[Cu](C#N)[C:22]#[N:23].CN1CCCC1=O.O.N>S([O-])([O-])(=O)=O.[Cu+2].O>[F:1][C:2]([F:20])([F:19])[C:3]1[CH:18]=[CH:17][C:6]2[S:7][C:8]3[CH:15]=[CH:14][CH:13]=[C:12]([C:22]#[N:23])[C:9]=3[CH2:10][CH2:11][C:5]=2[CH:4]=1

Komponenten

7

Edukt 4

HCID 13387N-methyl-2-pyrrolidoneHCID 126871202-Trifluoromethyl-9-chloro-10,11-dihydrodibenzo[b,f]thiepinHCID 12896473Azane;hydrateHCID 178418260HCID 178418260, Verbindung

Produkt 1

HCID 126871222-Trifluoromethyl-9-cyano-10,11-dihydrodibenzo[b,f]thiepinAusbeute 14,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24462Copper SulfateKatalysatorHCID 962WaterLösungsmittel

Versuchsvorschrift

The mixture of 450mg of 2-trifluoromethyl-9-chloro-10,11-dihydrodibenzo[b,f]thiepin, 0.4g of copper cyanide, 0.05g of anhydrous copper sulfate and 10ml of N-methylpyrrolidone was stirred at 180° to 210° C for 18.5 hrs. while preventing the moisture. A ter cooling, to the mixture was added 2.5ml of conc. ammonia water and 35ml of water and the resulting mixture was filtered with the use of celite. The thus obtained solution was extracted with benzene and the extract was washed with water and dried over anhydrous sodium sulfate. The solvent was evaporated to obtain 0.3g of a brown oily substance, which was chromatographed on a silica gel, eluted with n-hexane, and there was obtained 64mg of the desired product. This was recrystallized from n-hexane to afford 2-trifluoromethyl-9-cyano-10,11-dihydrodibenzo-[b,f]thiepin having a melting point of 113° to 114.5° C as colorless crystals.

Aufarbeitung

  1. temperatureA ter cooling, to the mixture
  2. filtrationthe resulting mixture was filtered with the use of celite
  3. extractionThe thus obtained solution was extracted with benzene
  4. washthe extract was washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was evaporated
  7. customto obtain 0.3g of a brown oily substance, which
  8. customwas chromatographed on a silica gel
  9. washeluted with n-hexane

Quellen und Nachweise

ORD-Eintrag
ord-733c04bf11f445a1a1c130fbd8cb70f2
Quelldatensatz
uspto-grants-1978_07
Patentnummer
US04101667

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