Reaction #1747872

Reaction equation

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

Solvents

chloroform

Conditions

Workup

1. 1
   Drying3,984,399, 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
   Washwashed with 100 ml of methanol
6. 6
   workup.STIRRINGstirred up again in 300 ml of methanol
7. 7
   Filtrationfiltered again
8. 8
   Otherdried at 35° C. under reduced pressure
9. 9
   OtherThe 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
    Washwashed successively with chlorobenzene and ethanol
12. 12
    Filtrationfiltered off with suction
13. 13
    Otherdried at 80° C. under reduced pressure
14. 14
    OtherAfter the removal of solvent residues under high vacuum (2×10−5 mbar) at 250° C.
15. 15
    Otherwere obtained

Procedure

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.

Source