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

HRID 4352

Reaction equation

HRID 4352 reaction equation
[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

Participants

6

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 75056Tetrahexylammonium iodideCatalystHCID 241BenzeneSolventHCID 962WaterSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-fdefa7a16d504159aa72430f307694ae
Source dataset
uspto-grants-1988_02
Patent number
US04725606

Linked notes

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