Reaktion #79514

Reaktionsgleichung

3-[(2-aminophenyl)thio]-2-n-octyloxy-7H-benzo[de]anthracene-7-one

Hydrochloric acid

HCl

sodium nitrite

DMF

NaNO2

→

6-n-Octyloxy-14H-anthra(2,1,9 mna)thioxanthene-14-one

Lösungsmittel

H2O

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeInto a 2 liter three-necked round bottom flask, equipped with a mechanical stirrer
2. 2
   Sonstigeplaced into an ice bath
3. 3
   Sonstigedid not exceed 20° C
4. 4
   Temperaturthe reaction was cooled to 0° C.
5. 5
   Sonstigedid not rise above 5° C
6. 6
   Temperaturthe reaction was heated
7. 7
   Sonstigeat 15° C.
8. 8
   workup.WAITThe reaction mass was held at 100° C. for 1.5 hours
9. 9
   Temperaturcooled
10. 10
    Filtrationthe red colored precipitate was filtered
11. 11
    Waschenwashed with water
12. 12
    SonstigeTm=205-208° C.

Vorschrift

Into a 2 liter three-necked round bottom flask, equipped with a mechanical stirrer and a thermometer, containing 77 g 3-[(2-aminophenyl)thio]-2-n-octyloxy-7H-benzo[de]anthracene-7-one (0.16M), placed into an ice bath, was added 1100 ml of DMF. The mixture was cooled to 10° C. while stirring. 35% Hydrochloric acid (247 ml) was added portionwise, ensuring that the reaction temperature did not exceed 20° C. After the HCl addition was complete, the reaction was cooled to 0° C. and a solution of 14.0 g (0.2M) NaNO2 in 78 ml of H2O was added portionwise, making sure that the reaction temperature did not rise above 5° C. The reaction mixture was held at 5° C. for an additional 1 hour after the completion of the sodium nitrite addition. Then, during the addition of 5.2 g copper sulfate catalyst, the reaction was heated, and at 15° C., nitrogen bubbles began to evolve. The reaction mass was held at 100° C. for 1.5 hours, cooled and the red colored precipitate was filtered and washed with water, then ethanol. The yield=66.89 g (90%); Tm=205-208° C.

Quelle