3,4-dihydro-2H-pyran → 4,5-dibromo-2-{4-[(tetrahydropyranyl)oxy]phenyl}-2H-pyridazin-3-one

HRID 15048Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 15048
C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.[O:18]1[CH:23]=[CH:22][CH2:21][CH2:20][CH2:19]1.[Br:24][C:25]1[C:26](=[O:39])[N:27]([C:32]2[CH:37]=[CH:36][C:35]([OH:38])=[CH:34][CH:33]=2)[N:28]=[CH:29][C:30]=1[Br:31]>ClCCl>[Br:24][C:25]1[C:26](=[O:39])[N:27]([C:32]2[CH:33]=[CH:34][C:35]([O:38][CH:23]3[CH2:22][CH2:21][CH2:20][CH2:19][O:18]3)=[CH:36][CH:37]=2)[N:28]=[CH:29][C:30]=1[Br:31]

Komponenten

5

Edukt 3

HCID 80803,4-dihydro-2H-pyranHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 684287654,5-dibromo-2-(4-hydroxyphenyl)-2H-pyridazin-3-one

Produkt 1

HCID 684288614,5-dibromo-2-{4-[(tetrahydropyranyl)oxy]phenyl}-2H-pyridazin-3-oneAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A catalytic amount of pyridinium p-toluenesulfonate and 3,4-dihydro-2H-pyrane (0.8 mL, 8.89 mmols) were added to a dichloromethane (30 mL) solution of 4,5-dibromo-2-(4-hydroxyphenyl)-2H-pyridazin-3-one (1.03 g, 2.98 mmols), and stirred at room temperature for 2 hours, washed with saturated aqueous sodium bicarbonate solution and saturated brine, and dried over anhydrous potassium carbonate. Concentrating the solvent under reduced pressure, the resulting residue was crystallized from mixed solvent of ethyl acetate and hexane to provide the title compound (1.1 g, 86%).

Aufarbeitung

  1. washwashed with saturated aqueous sodium bicarbonate solution and saturated brine
  2. dry with materialdried over anhydrous potassium carbonate
  3. concentrationConcentrating the solvent under reduced pressure
  4. customthe resulting residue was crystallized
  5. additionfrom mixed solvent of ethyl acetate and hexane

Quellen und Nachweise

ORD-Eintrag
ord-2d12e7bdf6a04c519d5deb44ecdd7cfa
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07732456B2

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