Phosphorus oxychloride → 3-Butyl-6-chloro-4-(4-cyclohexyloxy-phenyl)-pyridazine

HRID 1971901

Reaktionsgleichung

Reaktionsgleichung von HRID 1971901
[CH2:1]([C:5]1[C:6]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH:19]3[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]3)=[CH:14][CH:13]=2)=[CH:7][C:8](=O)[NH:9][N:10]=1)[CH2:2][CH2:3][CH3:4].P(Cl)(Cl)([Cl:27])=O>>[CH2:1]([C:5]1[N:10]=[N:9][C:8]([Cl:27])=[CH:7][C:6]=1[C:12]1[CH:17]=[CH:16][C:15]([O:18][CH:19]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)=[CH:14][CH:13]=1)[CH2:2][CH2:3][CH3:4]

Komponenten

3

Edukt 2

HCID 24813Phosphorus oxychlorideHCID 673752856-butyl-5-(4-cyclohexyloxy-phenyl)-2H-pyridazin-3-one

Produkt 1

HCID 866577793-Butyl-6-chloro-4-(4-cyclohexyloxy-phenyl)-pyridazine

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A suspension of the pyridazin-3-one (58.4 mmol, 19.1 g) in phosphorous oxychloride (292 mmol, 26.7 mL) was heated at 90° C. for 30 min with stirring during which period the starting material was fully consumed as judged by TLC. The reaction mixture was cooled to room temperature and the volatiles were removed in vacuo. The residue was dissolved in ethyl acetate (200 mL), washed with saturated NaHCO3 (3×100 mL), brine (100 mL), dried (Na2SO4) filtered and concentrated under reduced pressure. The residue was purified on a 330 g SiO2 cartridge eluating with 0-10% ethyl acetate in hexanes to afford 3-butyl-6-chloro-4-(4-cyclohexyloxy-phenyl)-pyridazine.

Aufarbeitung

  1. customwas fully consumed
  2. temperatureThe reaction mixture was cooled to room temperature
  3. customthe volatiles were removed in vacuo
  4. dissolutionThe residue was dissolved in ethyl acetate (200 mL)
  5. washwashed with saturated NaHCO3 (3×100 mL), brine (100 mL)
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified on a 330 g SiO2 cartridge eluating with 0-10% ethyl acetate in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-23fe628181d54ddb95272dab9482b79d
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08431575B2

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