반응 #1747854

반응 방정식

3,7-dibromo-10-methylphenothiazine

phenylboronic acid

potassium carbonate

→

10-Methyl-3,7-diphenylphenothiazine

용매

dimethoxyethane

chloroform

water

반응 조건

후처리

1. 1
   기타(75° C.)
2. 2
   여과The precipitate was filtered off with suction
3. 3
   세척washed successively with 125 ml of ethanol and hot water
4. 4
   기타dried at 70° C. under reduced pressure
5. 5
   온도The crude product (2.30 g) was heated
6. 6
   온도under reflux in cyclohexane for two hours
7. 7
   여과After the hot suspension had been filtered
8. 8
   기타the residue was dried
9. 9
   workup.DISSOLUTIONdissolved in 40 ml of methylene chloride
10. 10
    여과filtered through a silica-
11. 11
    workup.ADDITIONgel-filled glass fit
12. 12
    기타After the solvent had been removed
13. 13
    기타were obtained

실험 절차

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.

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