Reacción #1747854

Ecuación de reacción

3,7-dibromo-10-methylphenothiazine

phenylboronic acid

potassium carbonate

→

10-Methyl-3,7-diphenylphenothiazine

Disolventes

dimethoxyethane

chloroform

water

Condiciones de reacción

Tratamiento posterior

1. 1
   Otro(75° C.)
2. 2
   FiltraciónThe precipitate was filtered off with suction
3. 3
   Lavadowashed successively with 125 ml of ethanol and hot water
4. 4
   Otrodried at 70° C. under reduced pressure
5. 5
   TemperaturaThe crude product (2.30 g) was heated
6. 6
   Temperaturaunder reflux in cyclohexane for two hours
7. 7
   FiltraciónAfter the hot suspension had been filtered
8. 8
   Otrothe residue was dried
9. 9
   workup.DISSOLUTIONdissolved in 40 ml of methylene chloride
10. 10
    Filtraciónfiltered through a silica-
11. 11
    workup.ADDITIONgel-filled glass fit
12. 12
    OtroAfter the solvent had been removed
13. 13
    Otrowere obtained

Procedimiento

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.

Fuente