Реакция #1747859

Уравнение реакции

methanol

potassium tert-butoxide

10-methylphenothiazine-3,7-dicarbaldehyde

diethyl benzhydrylphosphonate

→

3,7-Bis(2,2-diphenylvinyl)-10-methylphenothiazine

Растворители

dimethyl sulfoxide

Условия реакции

Обработка

1. 1
   Другоеprepared analogously to Example 13 in U.S
2. 2
   Другоеrose from 25 to 43° C
3. 3
   workup.STIRRINGstirred for 15 min
4. 4
   Фильтрацияfiltered through a black band
5. 5
   Фильтрацияfilter
6. 6
   ПромывкаThe residue was washed with 300 ml of methanol
7. 7
   Другоеdried at 80° C. under reduced pressure
8. 8
   workup.DISSOLUTIONThe crude product (4.7 g) was dissolved in 150 ml of methylene chloride
9. 9
   Другоеpurified on silica gel
10. 10
    Другоеrecrystallized from 83 ml of butylglycol
11. 11
    Другоеwere obtained

Методика

3.46 g (30.4 mmol) of potassium tert-butoxide and then 3.60 g (13.4 mmol) of 10-methylphenothiazine-3,7-dicarbaldehyde were added with stirring and at room temperature to a solution of 8.20 g (26.8 mmol) of diethyl benzhydrylphosphonate (prepared analogously to Example 13 in U.S. Pat. No. 5,130,603) in 60 ml of anhydrous dimethyl sulfoxide, in the course of which the temperature rose from 25 to 43° C. After stirring at room temperature for 5 hours, the reaction solution was admixed with 150 ml of methanol, stirred for 15 min and filtered through a black band filter. The residue was washed with 300 ml of methanol and dried at 80° C. under reduced pressure. The crude product (4.7 g) was dissolved in 150 ml of methylene chloride, purified on silica gel and recrystallized from 83 ml of butylglycol. 3.56 g (23% of theory) of greenish microcrystals having a melting point of 233-241° C. were obtained.

Источник