Perchloric Acid → Methyl phenyl-1,3,4-oxadiazole

HRID 1723037ノート

反応式

HRID 1723037 の反応式
Cl(O)(=O)(=O)=O.[C:6]([NH:9][NH:10][C:11](=[O:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)(=O)[CH3:7]>C(OC(=O)C)(=O)C>[CH3:7][C:6]1[O:18][C:11]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)=[N:10][N:9]=1

参加物

4

反応物 2

HCID 24247Perchloric AcidHCID 256983Benzoic acid, 2-acetylhydrazide

生成物 1

HCID 138101Methyl phenyl-1,3,4-oxadiazole収率 32.3%

試薬・触媒・溶媒 1

HCID 7918Acetic Anhydride溶媒

実験手順

60% Perchloric acid (12 ml) was added to a stirred suspension of 1-acetyl-2-benzoyl hydrazine (31 g, 0.174 mole) in acetic anhydride (150 ml) over 45 minutes at 5°±5° C. The solution was brought to ambient temperature over 1 hour, then filtered. The precipitate was dissolved in water (200 ml), solid sodium carbonate added to pH 9 and the product extracted with ethyl acetate. The extract was washed with water, dried over MgSO4 and concentrated to an oil. Chromatography gave 2-methyl-5-phenyl-1,3,4-oxadiazole as a gum (9 g, 30%). This was reacted with ethanolamine following the procedure of Preparation (a) above to give the title compound as an oil (5 g).

後処理

  1. filtrationfiltered
  2. dissolutionThe precipitate was dissolved in water (200 ml)
  3. additionsolid sodium carbonate added to pH 9
  4. extractionthe product extracted with ethyl acetate
  5. washThe extract was washed with water
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated to an oil

出典と根拠

ORDレコード
ord-195099c2eeaf498e9aebcb1597e29488
出典データセット
uspto-grants-1989_08
特許番号
US04859686

反応ノート

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