Ammonia → 9-Cyano 10,11-dihydro-11-oxo-dibenzo[b,f]thiepin

HRID 866918Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 866918
Cl[C:2]1[C:7]2[CH2:8][C:9](=[O:17])[C:10]3[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=3[S:12][C:6]=2[CH:5]=[CH:4][CH:3]=1.[Cu](C#N)[C:19]#[N:20].CN1CCCC1=O.N>S([O-])([O-])(=O)=O.[Cu+2].O>[C:19]([C:2]1[C:7]2[CH2:8][C:9](=[O:17])[C:10]3[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=3[S:12][C:6]=2[CH:5]=[CH:4][CH:3]=1)#[N:20]

Komponenten

7

Edukt 4

HCID 222AmmoniaHCID 13387N-methyl-2-pyrrolidoneHCID 8270451-chlorodibenzo[b,f]thiepin-10(11H)-oneHCID 178418260HCID 178418260, Verbindung

Produkt 1

HCID 126870859-Cyano 10,11-dihydro-11-oxo-dibenzo[b,f]thiepinAusbeute 27,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24462Copper SulfateKatalysatorHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
200 °C

Versuchsvorschrift

The mixture of 2.6g of 9-chloro-10,11-dihydro-11-oxo-dibenzo-[b,f]thiepin, 2.0g of copper cyanide, 0.1g of anhydrous copper sulfate and 50ml of N-methyl pyrrolidone was heated with stirring at 200° C overnight in a flask equipped with a tube packed with silica gel. After cooling, to the reaction mixture were added 100ml of conc. aqueous ammonia and 200ml of water, and the resulting mixture was extracted with benzene. The extract was washed with water, diluted hydrochloric acid and then water, which was dried over potassium sulfate and the solvent evaporated therefrom. The residue thus obtained was chromatographed on 200g of silica gel, and eluted with chloroform/methanol (50/1). 0.6g of the starting material was recovered from a first eluate. Recrystallization of the residue of a second eluate from benzene gave 0.7g of 9-cyano 10,11-dihydro-11-oxo-dibenzo[b,f]thiepin as pale yellow prismatic crystals having a melting point of 165°-167° C.

Aufarbeitung

  1. temperaturewas heated
  2. customequipped with a tube
  3. temperatureAfter cooling, to the reaction mixture
  4. extractionthe resulting mixture was extracted with benzene
  5. washThe extract was washed with water, diluted hydrochloric acid
  6. dry with materialwater, which was dried over potassium sulfate
  7. customthe solvent evaporated
  8. customThe residue thus obtained
  9. customwas chromatographed on 200g of silica gel
  10. washeluted with chloroform/methanol (50/1)
  11. custom0.6g of the starting material was recovered from a first eluate
  12. customRecrystallization of the residue of a second eluate from benzene

Quellen und Nachweise

ORD-Eintrag
ord-3d05fa2ffaee460caf237e748256a230
Quelldatensatz
uspto-grants-1978_07
Patentnummer
US04101667

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