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

HRID 728991Notes

Reaction equation

HRID 728991 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 toa solid residue. The latter was dissolved in ethyl acetate and the solutionwashed with water and saturated sodium chloride solution, dried over magnesium sulfate and concentrated 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 toa solid residue
  5. dissolutionThe latter was dissolved in ethyl acetate
  6. dry with materialthe solutionwashed with water and saturated sodium chloride solution, dried over magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe residue was recrystallized from triethylamine

Sources & evidence

ORD record
ord-83aa13532bc040c6902ae98dbfdfe7f3
Source dataset
uspto-grants-1991_09
Patent number
US05051437

Reaction notes

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