Реакция #1747854

Уравнение реакции

3,7-dibromo-10-methylphenothiazine

phenylboronic acid

potassium carbonate

→

10-Methyl-3,7-diphenylphenothiazine

Растворители

dimethoxyethane

chloroform

water

Условия реакции

Обработка

1. 1
   Другое(75° C.)
2. 2
   ФильтрацияThe precipitate was filtered off with suction
3. 3
   Промывкаwashed successively with 125 ml of ethanol and hot water
4. 4
   Другоеdried at 70° C. under reduced pressure
5. 5
   ТемператураThe crude product (2.30 g) was heated
6. 6
   Температураunder reflux in cyclohexane for two hours
7. 7
   ФильтрацияAfter the hot suspension had been filtered
8. 8
   Другоеthe residue was dried
9. 9
   workup.DISSOLUTIONdissolved in 40 ml of methylene chloride
10. 10
    Фильтрацияfiltered through a silica-
11. 11
    workup.ADDITIONgel-filled glass fit
12. 12
    ДругоеAfter the solvent had been removed
13. 13
    Другоеwere obtained

Методика

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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