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

HRID 866935Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 866935
[CH3:1][N:2]1CCCC1=O.[CH3:8][O:9][C:10]1[CH:25]=[CH:24][C:13]2[S:14][C:15]3[CH:22]=[CH:21][CH:20]=[C:19](Cl)[C:16]=3[CH2:17][CH2:18][C:12]=2[CH:11]=1.[Cu](C#N)C#N.O.N>S([O-])([O-])(=O)=O.[Cu+2].C1C=CC=CC=1.O>[CH3:8][O:9][C:10]1[CH:25]=[CH:24][C:13]2[S:14][C:15]3[CH:22]=[CH:21][CH:20]=[C:19]([C:1]#[N:2])[C:16]=3[CH2:17][CH2:18][C:12]=2[CH:11]=1

Komponenten

8

Edukt 4

HCID 13387N-methyl-2-pyrrolidoneHCID 12896473Azane;hydrateHCID 233370502-Methoxy-9-chloro-10,11-dihydrodibenzo[b,f]thiepinHCID 178418260HCID 178418260, Verbindung

Produkt 1

HCID 233370482-Methoxy-9-cyano-10,11-dihydrodibenzo[b,f]thiepinAusbeute 50 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24462Copper SulfateKatalysatorHCID 241BenzeneLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

To 100 ml of N-methylpyrrolidone was added 10.8g of 2-methoxy-9-chloro-10,11-dihydrodibenzo[b,f]thiepin, 10.7g of copper cyanide and 0.4g of anhydrous copper sulfate and the resulting mixture was stirred at 190°-195° C for 15 hours. After cooling, to the mixture was added 28% ammonia water, 200 ml of water and 200 ml of benzene and the resulting mixture was shaked and filtered with celite. The filtrate was extracted with benzene. The extract was washed with saturated sodium chloride solution, dried over anhydrous sodium sulfate and freed of the solvent to obtain 9.0g of light brown cyrstals. This product was chromatographed over silica gel and eluted with benzene, there was obtained 5.4g (50%) of 2-methoxy-9-cyano-10,11-dihydrodibenzo[ b,f]thiepin as colorless prismatic crystals having a melting point of 129°-130° C.

Aufarbeitung

  1. temperatureAfter cooling, to the mixture
  2. filtrationfiltered with celite
  3. extractionThe filtrate was extracted with benzene
  4. washThe extract was washed with saturated sodium chloride solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. customto obtain 9.0g of light brown cyrstals
  7. customThis product was chromatographed over silica gel
  8. washeluted with benzene

Quellen und Nachweise

ORD-Eintrag
ord-4700ad0dff764d38b8e5dd48ae4e6200
Quelldatensatz
uspto-grants-1978_07
Patentnummer
US04101667

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