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

HRID 2166464노트

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HRID 2166464 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

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 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.

후처리

  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. concentrationconcentrated in vacuo
  9. customThe residue was recrystallized from triethylamine

출처 및 근거

ORD 기록
ord-668c78cad45749e99119100decd8eb54
출처 데이터셋
uspto-grants-1990_07
특허 번호
US04945164

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