تفاعل #1747872

معادلة التفاعل

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

المذيبات

chloroform

ظروف التفاعل

المعالجة

1. 1
   تجفيف3,984,399, 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
   ترشيحThe precipitate was filtered off
5. 5
   غسيلwashed with 100 ml of methanol
6. 6
   workup.STIRRINGstirred up again in 300 ml of methanol
7. 7
   ترشيحfiltered again
8. 8
   أخرىdried at 35° C. under reduced pressure
9. 9
   أخرىThe crude product (2.90 g) was recrystallized twice from dimethylformamide and once from chlorobenzene
10. 10
    ترشيحThe crystals were filtered off with suction
11. 11
    غسيلwashed successively with chlorobenzene and ethanol
12. 12
    ترشيحfiltered off with suction
13. 13
    أخرىdried at 80° C. under reduced pressure
14. 14
    أخرىAfter the removal of solvent residues under high vacuum (2×10−5 mbar) at 250° C.
15. 15
    أخرىwere obtained

الإجراء التجريبي

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.

المصدر