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

HRID 4352

반응식

HRID 4352 반응식
[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

참가 물질

6

반응물 2

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

생성물 1

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

시약·촉매·용매 3

HCID 75056Tetrahexylammonium iodide촉매HCID 241Benzene용매HCID 962Water용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-fdefa7a16d504159aa72430f307694ae
출처 데이터셋
uspto-grants-1988_02
특허 번호
US04725606

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