反応 #1747864

反応方程式

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

溶媒

methylene chloride

dimethyl sulfoxide

反応条件

後処理

1. 1
   その他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
   ろ過The precipitate was filtered off
5. 5
   洗浄washed with 500 ml of methanol
6. 6
   その他dried at 80° C. under reduced pressure
7. 7
   その他The crude product (5.44 g) was recrystallized in 250 ml of o-dichlorobenzene
8. 8
   ろ過The crystals were filtered off with suction
9. 9
   洗浄washed successively with o-dichlorobenzene and ethanol
10. 10
    ろ過filtered off with suction
11. 11
    その他dried at 80° C. under reduced pressure
12. 12
    その他After solvent residues had been removed in high vacuum (2×10−5 mbar) at 250° C.
13. 13
    その他were obtained

実験手順

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.

出典