Reaktion #1747854

Reaktionsgleichung

3,7-dibromo-10-methylphenothiazine

phenylboronic acid

potassium carbonate

→

10-Methyl-3,7-diphenylphenothiazine

Lösungsmittel

dimethoxyethane

chloroform

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstige(75° C.)
2. 2
   FiltrationThe precipitate was filtered off with suction
3. 3
   Waschenwashed successively with 125 ml of ethanol and hot water
4. 4
   Sonstigedried at 70° C. under reduced pressure
5. 5
   TemperaturThe crude product (2.30 g) was heated
6. 6
   Temperaturunder reflux in cyclohexane for two hours
7. 7
   FiltrationAfter the hot suspension had been filtered
8. 8
   Sonstigethe residue was dried
9. 9
   workup.DISSOLUTIONdissolved in 40 ml of methylene chloride
10. 10
    Filtrationfiltered through a silica-
11. 11
    workup.ADDITIONgel-filled glass fit
12. 12
    SonstigeAfter the solvent had been removed
13. 13
    Sonstigewere obtained

Vorschrift

2.50 g (6.7 mmol) of 3,7-dibromo-10-methylphenothiazine (C. Bodea and M. Terdic, Acad. Rep. Rom. 1962, 13, 81-87), 1.85 g (14.9 mmol) of 98% phenylboronic acid, 0.11 g (0.14 mmol) of bis(triphenylphosphine)palladium dichloride and 1.03 g (7.4 mmol) of potassium carbonate were heated to boiling (75° C.) under reflux under nitrogen for 5 hours in 55 ml of dimethoxyethane and 28 ml of water. The reaction mixture was cooled to room temperature and stirred further overnight. The precipitate was filtered off with suction, washed successively with 125 ml of ethanol and hot water and dried at 70° C. under reduced pressure. The crude product (2.30 g) was heated to boiling under reflux in cyclohexane for two hours. After the hot suspension had been filtered, the residue was dried, dissolved in 40 ml of methylene chloride and filtered through a silica-gel-filled glass fit. After the solvent had been removed, 1.05 g (43% of theory) of light yellow, analytically pure solid having a melting point of 239-241° C. were obtained, whose solution in chloroform fluoresced at λ=464 nm.

Quelle