Methanesulfonyl chloride → 3-bromo-5-nitro-4-(4-methoxy-3-(6-oxo-3(1H)-pyridazinylmethyl)phenoxy)benzaldehyde

HRID 1165628

Reaktionsgleichung

Reaktionsgleichung von HRID 1165628
CS(Cl)(=O)=O.[Br:6][C:7]1[CH:8]=[C:9]([CH:12]=[C:13]([N+:16]([O-:18])=[O:17])[C:14]=1[OH:15])[CH:10]=[O:11].[CH3:19][O:20][C:21]1[CH:26]=[CH:25][C:24](O)=[CH:23][C:22]=1[CH2:28][C:29]1[CH:34]=[CH:33][C:32](=[O:35])[NH:31][N:30]=1>N1C=CC=CC=1>[Br:6][C:7]1[CH:8]=[C:9]([CH:12]=[C:13]([N+:16]([O-:18])=[O:17])[C:14]=1[O:15][C:24]1[CH:25]=[CH:26][C:21]([O:20][CH3:19])=[C:22]([CH2:28][C:29]2[CH:34]=[CH:33][C:32](=[O:35])[NH:31][N:30]=2)[CH:23]=1)[CH:10]=[O:11]

Komponenten

5

Edukt 3

HCID 31297Methanesulfonyl chlorideHCID 14943783-Bromo-4-hydroxy-5-nitrobenzaldehydeHCID 143331384-methoxy-3-(6-oxo-3(1H)-pyridazinylmethyl)phenol

Produkt 1

HCID 146735223-bromo-5-nitro-4-(4-methoxy-3-(6-oxo-3(1H)-pyridazinylmethyl)phenoxy)benzaldehydeAusbeute 40 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel2×

Versuchsvorschrift

Methane sulphonyl chloride (3.6 g) was added to a solution of 3-bromo-4-hydroxy-5-nitrobenzaldehyde (7.7 g) in dry pyridine (100 ml), and the mixture heated at reflux for 10 min. A solution of 4-methoxy-3-(6-oxo-3(1H)pyridazinylmethyl)phenol (prepared as in Example 44(a)) (6.6 g) in dry pyridine (50 ml) was then added and the resultant dark mixture heated at reflux for 1.5 hours, then allowed to cool to room temperature. The solvent was then evaporated and the residue dissolved in dichloromethane (150 ml), washed with aqueous 2N hydrochloride acid (100 ml), water (100 ml), aqueous saturated sodium bicarbonate solution (2×100 ml) and water (4×100 ml), then dried and evaporated to dryness. The orange residue was dissolved in IMS, treated with charcoal and filtered. On addition of water (200 ml) and cooling a precipitate was formed which was filtered off and dried. This solid was recrystallised from ethyl acetate/petroleum spirit to give 3-bromo-5 -nitro-4-(4- methoxy-3-(6-oxo-3(1H)-pyridazinylmethyl)phenoxy)benzaldehyde (5.2 g, 40%) as a yellow solid, m.p. 188°-190°.

Aufarbeitung

  1. temperaturethe mixture heated
  2. temperatureat reflux for 10 min
  3. temperaturethe resultant dark mixture heated
  4. temperatureat reflux for 1.5 hours
  5. customThe solvent was then evaporated
  6. dissolutionthe residue dissolved in dichloromethane (150 ml)
  7. washwashed with aqueous 2N hydrochloride acid (100 ml), water (100 ml), aqueous saturated sodium bicarbonate solution (2×100 ml) and water (4×100 ml)
  8. customdried
  9. customevaporated to dryness
  10. dissolutionThe orange residue was dissolved in IMS
  11. additiontreated with charcoal
  12. filtrationfiltered
  13. additionOn addition of water (200 ml)
  14. temperaturecooling a precipitate
  15. customwas formed which
  16. filtrationwas filtered off
  17. customdried
  18. customThis solid was recrystallised from ethyl acetate/petroleum spirit

Quellen und Nachweise

ORD-Eintrag
ord-740b4c8211134dac854fbd4e95ce24ba
Quelldatensatz
uspto-grants-1990_03
Patentnummer
US04910305

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