反应 #1747864

反应方程式

potassium tert-butoxide

10-phenyl-5,5-dioxophenothiazine-3-carbaldehyde

10-Phenyl-5,5-dioxophenothiazine-3-carbaldehyde

diethyl[4′-(diethoxyphosphorylmethyl)biphenyl-4-ylmethyl]phosphonate

→

10-Phenyl-3-(2-{4′-[2-(10-phenyl-5,5-dioxophenothiazin-3-yl)vinyl]-biphenyl-4-yl}vinyl)phenothiazine 5,5-dioxide

溶剂

methylene chloride

dimethyl sulfoxide

反应条件

后处理

1. 1
   其他dried over molecular sieve
2. 2
   workup.ADDITIONthe reaction solution was diluted with 200 ml of methanol
3. 3
   workup.STIRRINGstirred for a further 1 h
4. 4
   过滤The precipitate was filtered off
5. 5
   洗涤washed with 500 ml of methanol
6. 6
   其他dried at 80° C. under reduced pressure
7. 7
   其他The crude product (5.44 g) was recrystallized in 250 ml of o-dichlorobenzene
8. 8
   过滤The crystals were filtered off with suction
9. 9
   洗涤washed successively with o-dichlorobenzene and ethanol
10. 10
    过滤filtered off with suction
11. 11
    其他dried at 80° C. under reduced pressure
12. 12
    其他After solvent residues had been removed in high vacuum (2×10−5 mbar) at 250° C.
13. 13
    其他were obtained

实验过程

2.28 g (19.9 mmol) of potassium tert-butoxide and then 5.90 g (17.6 mmol) of 10-phenyl-5,5-dioxophenothiazine-3-carbaldehyde (Example 21) were added under nitrogen at room temperature with stirring to a solution of 4.00 g (8.80 mmol) of diethyl[4′-(diethoxyphosphorylmethyl)biphenyl-4-ylmethyl]phosphonate in 45 ml of dimethyl sulfoxide dried over molecular sieve. After stirring at room temperature for 72 h, the reaction solution was diluted with 200 ml of methanol and stirred for a further 1 h. The precipitate was filtered off, washed with 500 ml of methanol and dried at 80° C. under reduced pressure. The crude product (5.44 g) was recrystallized in 250 ml of o-dichlorobenzene. The crystals were filtered off with suction, washed successively with o-dichlorobenzene and ethanol, filtered off with suction and dried at 80° C. under reduced pressure. After solvent residues had been removed in high vacuum (2×10−5 mbar) at 250° C., 4.35 g (60% of theory) of yellow microcrystals having a melting point of 392° C. were obtained, whose solution in methylene chloride fluoresced at λ=456 nm.

来源