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

HRID 544631Notes

Reaction equation

HRID 544631 reaction equation
[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

Participants

6

Reactant 3

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

Product 1

HCID 133169663-[5-(2-Chloro-4-methoxyphenoxy)pentyl]-5-methylisoxazoleYield 48.7%

Reagents, catalysts & solvents 2

HCID 4875Potassium IodideCatalystHCID 6342AcetonitrileSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-97e24da81c744afcb15b6d315bf05c77
Source dataset
uspto-grants-1984_05
Patent number
US04451476

Reaction notes

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