Sodium Iodide → 2-[4-[5-(3-Methylisoxazol-5-yl)pentoxy]phenyl]-1,3,4-oxadiazole

HRID 1722748Notes

Reaction equation

HRID 1722748 reaction equation
[O:1]1[CH:5]=[N:4][N:3]=[C:2]1[C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1.Br[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]1[O:23][N:22]=[C:21]([CH3:24])[CH:20]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>C(#N)C>[CH3:24][C:21]1[CH:20]=[C:19]([CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][O:12][C:9]2[CH:10]=[CH:11][C:6]([C:2]3[O:1][CH:5]=[N:4][N:3]=3)=[CH:7][CH:8]=2)[O:23][N:22]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 7147704-(1,3,4-Oxadiazol-2-yl)phenolHCID 135440465-(5-Bromopentyl)-3-methylisoxazole

Product 1

HCID 148360152-[4-[5-(3-Methylisoxazol-5-yl)pentoxy]phenyl]-1,3,4-oxadiazoleYield 40.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 23.6 g 4-(1,3,4-oxadiazolyl)phenol (U.S. Pat. No. 4,218,458, Example XIX), 35 g 5-(5-bromopentyl)-3-methylisoxazole and 40 g milled potassium carbonate in 1.5 liters acetonitrile under nitrogen was heated to reflux. A catalytic amount of sodium iodide was added and refluxing continued for 4 hrs. The reaction mixture was filtered and concentrated to a solid residue. The latter was dissolved in ethyl acetate and the solution washed with water and saturated sodium chloride solution, dried over magnesium sulfate and concentrate in vacuo. The residue was recrystallized from triethylamine to give 18.5 g 3-methyl-5-{5-[4-(1,3,4-oxadiazol-2-yl)phenoxy]-pentyl}isoxazole, white needles, m.p. 84-86° C.

Workup

  1. temperaturewas heated to reflux
  2. temperaturerefluxing
  3. filtrationThe reaction mixture was filtered
  4. concentrationconcentrated to a solid residue
  5. dissolutionThe latter was dissolved in ethyl acetate
  6. washthe solution washed with water and saturated sodium chloride solution
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrate in vacuo
  9. customThe residue was recrystallized from triethylamine

Sources & evidence

ORD record
ord-a84aa76ed9fa42888abb84de4058316e
Source dataset
uspto-grants-1989_08
Patent number
US04857539

Reaction notes

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