反応 #1747872

反応方程式

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

溶媒

chloroform

反応条件

後処理

1. 1
   乾燥3,984,399, 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
   ろ過The precipitate was filtered off
5. 5
   洗浄washed with 100 ml of methanol
6. 6
   workup.STIRRINGstirred up again in 300 ml of methanol
7. 7
   ろ過filtered again
8. 8
   その他dried at 35° C. under reduced pressure
9. 9
   その他The crude product (2.90 g) was recrystallized twice from dimethylformamide and once from chlorobenzene
10. 10
    ろ過The crystals were filtered off with suction
11. 11
    洗浄washed successively with chlorobenzene and ethanol
12. 12
    ろ過filtered off with suction
13. 13
    その他dried at 80° C. under reduced pressure
14. 14
    その他After the removal of solvent residues under high vacuum (2×10−5 mbar) at 250° C.
15. 15
    その他were obtained

実験手順

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.

出典