Reaction #1747862

Reaction equation

potassium tert-butoxide

10-methyl-5,5-dioxophenothiazine-3-carbaldehyde

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

→

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

Solvents

N-methylpyrrolidone

dimethyl sulfoxide

Conditions

Workup

1. 1
   Otherdried over molecular sieve
2. 2
   workup.ADDITIONthe reaction solution was diluted with 90 ml of methanol
3. 3
   workup.STIRRINGstirred for a further 15 min
4. 4
   FiltrationThe precipitate was filtered off
5. 5
   Washwashed with 220 ml of methanol
6. 6
   Otherdried at 35° C. under reduced pressure
7. 7
   OtherThe crude product (2.50 g) was recrystallized in 58 ml of dimethyl sulfoxide
8. 8
   OtherAfter solvent residues had been removed under high vacuum at 200° C.
9. 9
   Otherwere obtained

Procedure

1.02 g (9.05 mmol) of potassium tert-butoxide and then 2.20 g (8.05 mmol) of 10-methyl-5,5-dioxophenothiazine-3-carbaldehyde (Example 21) were added under nitrogen at room temperature with stirring to a solution of 1.82 g (4.00 mmol) of diethyl[4′-(diethoxyphosphorylmethyl)biphenyl-4-ylmethyl]phosphonate in 41 ml of dimethyl sulfoxide dried over molecular sieve. After stirring at room temperature for four hours, the reaction solution was diluted with 90 ml of methanol and stirred for a further 15 min. The precipitate was filtered off, washed with 220 ml of methanol and dried at 35° C. under reduced pressure. The crude product (2.50 g) was recrystallized in 58 ml of dimethyl sulfoxide. After solvent residues had been removed under high vacuum at 200° C., 1.64 g (59% of theory) of analytically pure yellow solid having a melting point of 360° C. were obtained, whose solution in N-methylpyrrolidone fluoresced at λ=460 nm.

Source