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

HRID 72752

反応式

HRID 72752 の反応式
[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

参加物

9

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 702Ethanol溶媒HCID 962Water溶媒HCID 1140Toluene溶媒HCID 6342Acetonitrile溶媒

反応条件

温度
120 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-c9acd577965d45f4ba22a52ca2776db2
出典データセット
uspto-grants-2014_09
特許番号
US08829000B2

関連ノート

読み込み中…