Ethylenediamine → 3-(1H-imidazol-2-yl)-2-methylpyridine

HRID 72752

Reaction equation

HRID 72752 reaction equation
[CH3:1][C:2]1[C:7]([C:8]#[N:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[CH2:10](N)[CH2:11][NH2:12].[S].[Mn]([O-])(=O)(=O)=O.[K+].[Si](=O)=O>C(O)C.C(#N)C.O.C1(C)C=CC=CC=1>[NH:9]1[CH:10]=[CH:11][N:12]=[C:8]1[C:7]1[C:2]([CH3:1])=[N:3][CH:4]=[CH:5][CH:6]=1

Participants

9

Reactant 4

HCID 3301EthylenediamineHCID 47383082-Methylpyridine-3-carbonitrileHCID 5362487SulfurHCID 23697328Potassium permanganate silicon dioxide

Product 1

HCID 591988423-(1H-imidazol-2-yl)-2-methylpyridine

Reagents, catalysts & solvents 4

HCID 702EthanolSolventHCID 962WaterSolventHCID 1140TolueneSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
120 °C

Procedure

2-Methyl-3-pyridinecarbonitrile 1.05 g, ethylenediamine 5 mL and sulfur 71 mg were mixed, and stirred at 120° C. for 24 hours. Cooling it off to room temperature, toluene and water were added to effect phase separation. The aqueous layer was dried to solid under reduced pressure. Thus obtained crude product was mixed with potassium permanganate/silicon dioxide (carried at a ratio of 2.81 g:3.57 g) 6.38 g and acetonitrile 10 mL at room temperature, and stirred (inducing a rapid exothermic reaction). After the exotherm subsided and the reaction liquid was restored to room temperature, the liquid was diluted with 20 mL of ethanol and filtered through Celite. The solvent was distilled off and the residue was recrystallized from ethyl acetate/methanol (10:1) to provide 1.03 g of the title compound.

Workup

  1. additionwere added to effect phase separation
  2. customThe aqueous layer was dried to solid under reduced pressure
  3. customThus obtained crude product
  4. customa rapid exothermic reaction)
  5. customthe reaction liquid
  6. customwas restored to room temperature
  7. filtrationfiltered through Celite
  8. distillationThe solvent was distilled off
  9. customthe residue was recrystallized from ethyl acetate/methanol (10:1)

Sources & evidence

ORD record
ord-c9acd577965d45f4ba22a52ca2776db2
Source dataset
uspto-grants-2014_09
Patent number
US08829000B2

Linked notes

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