Reaction #1747863

Reaction equation

potassium tert-butoxide

10-phenylphenothiazine-3-carbaldehyde

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

→

10-Phenyl-3-(2-{4′-[2-(10-phenylphenothiazin-3-yl)vinyl]biphenyl-4-yl}vinyl)phenothiazine

Solvents

dimethyl sulfoxide

Conditions

Workup

1. 1
   Otherdried over molecular sieve
2. 2
   workup.ADDITIONthe reaction solution was diluted with 200 ml of methanol
3. 3
   workup.STIRRINGstirred for a further 15 min
4. 4
   FiltrationThe precipitate was filtered off
5. 5
   Washwashed with 500 ml of methanol
6. 6
   Otherdried at 35° C. under reduced pressure
7. 7
   OtherThe crude product (5.85 g) was recrystallized in 400 ml of toluene
8. 8
   Otherwere obtained

Procedure

2.73 g (24.1 mmol) of potassium tert-butoxide and then 7.80 g (25.7 mmol) of 10-phenylphenothiazine-3-carbaldehyde were added under nitrogen at room temperature with stirring to a solution of 4.83 g (10.7 mmol) of diethyl[4′-(diethoxyphosphorylmethyl)biphenyl-4-ylmethyl]phosphonate in 80 ml of dimethyl sulfoxide dried over molecular sieve. After stirring at room temperature for four hours, the reaction solution was diluted with 200 ml of methanol and stirred for a further 15 min. The precipitate was filtered off, washed with 500 ml of methanol and dried at 35° C. under reduced pressure. The crude product (5.85 g) was recrystallized in 400 ml of toluene. 3.85 g of yellow solid having a melting point of 278-290° C. were obtained.

Source