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

HRID 72752

반응식

HRID 72752 반응식
[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

참가 물질

9

반응물 4

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

생성물 1

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

시약·촉매·용매 4

HCID 702Ethanol용매HCID 962Water용매HCID 1140Toluene용매HCID 6342Acetonitrile용매

반응 조건

온도
120 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-c9acd577965d45f4ba22a52ca2776db2
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08829000B2

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