Reaktion #1747872

Reaktionsgleichung

potassium tert-butoxide

10-mesityl-5,5-dioxophenothiazine-3-carbaldehyde

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

→

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

Lösungsmittel

chloroform

Reaktionsbedingungen

Aufarbeitung

1. 1
   Trocknen3,984,399, example 2, column 29, lines 58-66) in 40 ml of dimethyl sulfoxide which has been dried over a 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
   FiltrationThe precipitate was filtered off
5. 5
   Waschenwashed with 100 ml of methanol
6. 6
   workup.STIRRINGstirred up again in 300 ml of methanol
7. 7
   Filtrationfiltered again
8. 8
   Sonstigedried at 35° C. under reduced pressure
9. 9
   SonstigeThe crude product (2.90 g) was recrystallized twice from dimethylformamide and once from chlorobenzene
10. 10
    FiltrationThe crystals were filtered off with suction
11. 11
    Waschenwashed successively with chlorobenzene and ethanol
12. 12
    Filtrationfiltered off with suction
13. 13
    Sonstigedried at 80° C. under reduced pressure
14. 14
    SonstigeAfter the removal of solvent residues under high vacuum (2×10−5 mbar) at 250° C.
15. 15
    Sonstigewere obtained

Vorschrift

0.93 g (8.1 mmol) of potassium tert-butoxide and then 2.70 g (7.16 mmol) of 10-mesityl-5,5-dioxophenothiazine-3-carbaldehyde (example 35b) were added at room temperature with stirring under nitrogen to a solution of 1.63 g (3.58 mmol) of diethyl[4′-(diethoxyphosphorylmethyl)biphenyl-4-ylmethyl]phosphonate (U.S. Pat. No. 3,984,399, example 2, column 29, lines 58-66) in 40 ml of dimethyl sulfoxide which has been dried over a molecular sieve. After stirring at room temperature for 4 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 100 ml of methanol, stirred up again in 300 ml of methanol, filtered again and dried at 35° C. under reduced pressure. The crude product (2.90 g) was recrystallized twice from dimethylformamide and once from chlorobenzene. The crystals were filtered off with suction, washed successively with chlorobenzene and ethanol, filtered off with suction and dried at 80° C. under reduced pressure. After the removal of solvent residues under high vacuum (2×10−5 mbar) at 250° C., 0.98 g (30% of theory) of analytically pure luminous yellow microcrystals having an m.p. of >350° C. were obtained, whose solution in chloroform fluoresced at λ=456, 485 (S), 522 (S) nm.

Quelle