Potassium Carbonate → 3-[5-(2-Chloro-4-methoxyphenoxy)pentyl]-5-methylisoxazole

HRID 544631Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 544631
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[OH:10].Br[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]1[CH:21]=[C:20]([CH3:22])[O:19][N:18]=1.C(=O)([O-])[O-].[K+].[K+]>[I-].[K+].C(#N)C>[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[O:10][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]1[CH:21]=[C:20]([CH3:22])[O:19][N:18]=1

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 874592-Chloro-4-methoxyphenolHCID 133169783-(5-Bromopentyl)-5-methylisoxazole

Produkt 1

HCID 133169663-[5-(2-Chloro-4-methoxyphenoxy)pentyl]-5-methylisoxazoleAusbeute 48,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 4875Potassium IodideKatalysatorHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A mixture of 5.5 g (0.0345 mole) of 2-chloro-4-methoxyphenol, 8.0 g (0.0345 mole) of 3-(5-bromopentyl)-5-methylisoxazole (Example 40i), 6 g of potassium carbonate, 0.1 g of potassium iodide and 75 ml of acetonitrile was heated at reflux for 24 hours. The reaction mixture was filtered, concentrated in vacuo, dissolved in 50 ml of methylene dichloride, filtered and again concentrated. The residue was distilled at 135°-200° C.(0.2 mm) and then redistilled, collecting the fraction boiling at 170°-190° C.(0.05 mm). The product crystallized and was recrystallized from ether--pentane to give 5.2 g of 3-[5-(2-chloro-4-methoxyphenoxy)pentyl]-5-methylisoxazole, m.p. 45°-47° C.; MIC vs. rhinovirus Type 2=0.7 μg/ml; and vs. polio-2 virus=1.4 μg/ml.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux for 24 hours
  3. filtrationThe reaction mixture was filtered
  4. concentrationconcentrated in vacuo
  5. dissolutiondissolved in 50 ml of methylene dichloride
  6. filtrationfiltered
  7. concentrationagain concentrated
  8. distillationThe residue was distilled at 135°-200° C.(0.2 mm)
  9. distillationredistilled
  10. customcollecting the fraction boiling at 170°-190° C.(0.05 mm)
  11. customThe product crystallized
  12. customwas recrystallized from ether

Quellen und Nachweise

ORD-Eintrag
ord-97e24da81c744afcb15b6d315bf05c77
Quelldatensatz
uspto-grants-1984_05
Patentnummer
US04451476

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