反应 #1747855

反应方程式

3,7-dibromo-10-methylphenothiazine

1-naphthylboronic acid

potassium carbonate

methanol

→

10-methyl-3,7-bis(1-naphthyl)phenothiazine

溶剂

dimethoxyethane

water

chloroform

反应条件

后处理

1. 1
   过滤filtered
2. 2
   洗涤The residue was washed with 470 ml of ethanol and hot water
3. 3
   其他dried at 70° C. under reduced pressure
4. 4
   workup.DISSOLUTIONThe solid was dissolved in 100 ml of methylene chloride
5. 5
   过滤filtered through silica gel
6. 6
   其他After the solvent had been removed under reduced pressure
7. 7
   其他a tacky mass was obtained which
8. 8
   其他crystallized
9. 9
   workup.STIRRINGwith stirring overnight
10. 10
    过滤The crystals were filtered off with suction
11. 11
    洗涤washed with 300 ml of methanol
12. 12
    其他dried at 40° C. under reduced pressure
13. 13
    其他were obtained
14. 14
    其他The crude product was recrystallized twice from ethyl acetate
15. 15
    其他were obtained

实验过程

9.30 g (25.1 mmol) of 3,7-dibromo-10-methylphenothiazine, 9.50 g (55.2 mmol) of 1-naphthylboronic acid, 0.407 g (0.50 mmol) of bis(triphenylphosphane)palladium dichloride and 3.80 g (27.5 mmol) of potassium carbonate were heated to boiling under reflux under nitrogen for 5 hours in 204 ml of dimethoxyethane and 101 ml of water. The reaction mixture was cooled to room temperature, stirred further overnight and then filtered. The residue was washed with 470 ml of ethanol and hot water, and dried at 70° C. under reduced pressure. The solid was dissolved in 100 ml of methylene chloride and filtered through silica gel. After the solvent had been removed under reduced pressure, a tacky mass was obtained which, after 200 ml of methanol had been added, crystallized with stirring overnight. The crystals were filtered off with suction, washed with 300 ml of methanol and dried at 40° C. under reduced pressure. 10.33 g of light yellow microcrystals having a melting point of 185-190° C. were obtained. The crude product was recrystallized twice from ethyl acetate. 5.71 g (49% of theory) of analytically pure, almost colorless microcrystals having a melting point of 191-194° C. were obtained, whose solution in chloroform fluoresced at λ=468 nm.

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