Potassium Permanganate → 1-Phenyl-1-[4-(4-pyridyl)-2-thiazolyl]methanone

HRID 2309801

反応式

HRID 2309801 の反応式
[CH2:1]([C:8]1[S:9][CH:10]=[C:11]([C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)[N:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Mn]([O-])(=O)(=O)=[O:20].[K+]>C1C=CC=CC=1.O.[I-].C([N+](CCCCCC)(CCCCCC)CCCCCC)CCCCC>[C:2]1([C:1]([C:8]2[S:9][CH:10]=[C:11]([C:13]3[CH:14]=[CH:15][N:16]=[CH:17][CH:18]=3)[N:12]=2)=[O:20])[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

6

反応物 2

HCID 516875Potassium PermanganateHCID 140969524-(2-Benzyl-1,3-thiazol-4-yl)pyridine

生成物 1

HCID 140969581-Phenyl-1-[4-(4-pyridyl)-2-thiazolyl]methanone収率 18.8%

試薬・触媒・溶媒 3

HCID 75056Tetrahexylammonium iodide触媒HCID 241Benzene溶媒HCID 962Water溶媒

実験手順

To a mixture of 2-benzyl-4-(4-pyridyl)thiazole (3.00 g, 0.01 mol) and potassium permanganate (3.16 g, 0.02 mol) in benzene (30 mL) and water (60 mL) was added tetrahexyl ammonium iodide (0.96 g, 0.02 mol). The biphasic mixture was heated at reflux for 15 hours. After cooling the organic layer was separated and concentrated. The residue was taken up in ethyl acetate, filtered through silica gel, concentrated and chromatographed (ethyl acetate/hexane as eluant). Recrystallization from ethyl acetate/hexane afforded 1-phenyl-1-[4-(4-pyridyl)-2-thiazolyl]methanone (0.50 g, 11%). mp. 135°-136° C.

後処理

  1. temperatureThe biphasic mixture was heated
  2. temperatureat reflux for 15 hours
  3. temperatureAfter cooling the organic layer
  4. customwas separated
  5. concentrationconcentrated
  6. filtrationfiltered through silica gel
  7. concentrationconcentrated
  8. customchromatographed (ethyl acetate/hexane as eluant)
  9. customRecrystallization from ethyl acetate/hexane

出典と根拠

ORDレコード
ord-1cb6fdebe7074db480a459f0c84a1e37
出典データセット
uspto-grants-1987_09
特許番号
US04697012

関連ノート

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