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

HRID 1722748ノート

反応式

HRID 1722748 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-a84aa76ed9fa42888abb84de4058316e
出典データセット
uspto-grants-1989_08
特許番号
US04857539

反応ノート

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