반응 #1747864

반응 방정식

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

용매

methylene chloride

dimethyl sulfoxide

반응 조건

후처리

1. 1
   기타dried 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
   여과The precipitate was filtered off
5. 5
   세척washed with 500 ml of methanol
6. 6
   기타dried at 80° C. under reduced pressure
7. 7
   기타The crude product (5.44 g) was recrystallized in 250 ml of o-dichlorobenzene
8. 8
   여과The crystals were filtered off with suction
9. 9
   세척washed successively with o-dichlorobenzene and ethanol
10. 10
    여과filtered off with suction
11. 11
    기타dried at 80° C. under reduced pressure
12. 12
    기타After solvent residues had been removed in high vacuum (2×10−5 mbar) at 250° C.
13. 13
    기타were obtained

실험 절차

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.

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