Thioxanthone → HCID 12392817, Verbindung

HRID 393260

Reaktionsgleichung

Reaktionsgleichung von HRID 393260
[CH:1]1[C:14]2[CH:13](O)[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[S:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.O=S(Cl)Cl.[C:20]([Cu])#[N:21].C1C2CC3C(=CC=CC=3)SC=2C=CC=1.C1C2C(=O)C3C(=CC=CC=3)SC=2C=CC=1>CCOCC.C1C=CC=CC=1>[CH:1]1[C:14]2[CH:13]([C:20]#[N:21])[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[S:6][C:5]=2[CH:4]=[CH:3][CH:2]=1

Komponenten

8

Edukt 5

HCID 10295ThioxanthoneHCID 24386Thionyl ChlorideHCID 67495ThioxantheneHCID 51541709H-thioxanthen-9-olHCID 178418546HCID 178418546, Verbindung

Produkt 1

HCID 12392817HCID 12392817, VerbindungAusbeute 59 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 241BenzeneLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Reaktionsbedingungen

Temperatur
2.5 °C

Versuchsvorschrift

A suspension of 9H-Thioxanthen-9-ol [32] (2.14 g, 9.98 mmol) in anhydrous Et2O (20 mL) under N2 and SOCl2 (0.8 mL, 11.48 mmol) was added with caution via syringe with stirring at 0-5° C. The alcohol dissolved before a white solid began to separate. After stirring (1 hr.) at room temperature, the solvent was removed under reduced pressure and C6H6 (10 mL) was added and solvent removed to dryness again. All manipulations were performed with rigorous exclusion of air. Anhydrous C6H6 (20 mL) and CuCN powder (1.79 g, 19.97 mmol) were added and the suspension was stirred at reflux (4 hr.).The reaction mixture was filtered while hot and the residue was washed with hot C6H6 (50 mL). The filterate was evaporated to give a crystalline residue containing thioxanthene and thioxanthen-9-one as well as the desired nitrile. One recrystallizations from hexane removed thioxanthene and one recrystallizations from 2-propanol removed most of the thioxanthen-9one to provide 1.3 g (59%) of the pure nitrile, mp. 97-98° C.

Aufarbeitung

  1. customto separate
  2. stirringAfter stirring (1 hr.) at room temperature
  3. customthe solvent was removed under reduced pressure and C6H6 (10 mL)
  4. additionwas added
  5. customsolvent removed to dryness again
  6. stirringthe suspension was stirred
  7. temperatureat reflux (4 hr
  8. filtration).The reaction mixture was filtered while hot and the residue
  9. washwas washed with hot C6H6 (50 mL)
  10. customThe filterate was evaporated
  11. customto give a crystalline residue
  12. customOne recrystallizations from hexane
  13. customremoved
  14. customthioxanthene and one recrystallizations from 2-propanol
  15. customremoved most of the thioxanthen-9one

Quellen und Nachweise

ORD-Eintrag
ord-539b33e1ea4f428da25253c40e791f30
Quelldatensatz
uspto-grants-2004_10
Patentnummer
US06806283B2

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