Potassium Carbonate → O-2-naphthyl N-methyl-N-(6-methyl-2-pyridyl)thiocarbamate

HRID 1731289

反応式

HRID 1731289 の反応式
[CH3:1][C:2]1[N:7]=[C:6]([NH:8][CH3:9])[CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=[CH:18][C:17]=1[O:26][C:27](Cl)=[S:28]>CC(C)=O>[CH3:9][N:8]([C:6]1[CH:5]=[CH:4][CH:3]=[C:2]([CH3:1])[N:7]=1)[C:27](=[S:28])[O:26][C:17]1[CH:18]=[CH:19][C:20]2[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:16]=1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 82681O-2-Naphthyl chlorothioformateHCID 3839092N,6-dimethylpyridin-2-amine

生成物 1

HCID 13387378O-2-naphthyl N-methyl-N-(6-methyl-2-pyridyl)thiocarbamate収率 85.1%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒2 回

実験手順

To a mixture of 1.22 g of 6-methyl-2-methylaminopyridine and 1.38 g of anhydrous potassium carbonate in 20 ml of acetone was added dropwise 2.23 g of 2-naphthylchlorothioformate in 20 ml of acetone under agitation at room temperature. The reaction mixture was stirred overnight at room temperature and inorganic salts were removed by filtration. After acetone was removed by distillation under a reduced pressure, the residue was purified by the column chromatography (silica gel, developed with ethyl acetate/benzene=1/9 (V/V), to obtain 2.62 g of O-2-naphthyl N-methyl-N-(6-methyl-2-pyridyl)thiocarbamate as a solid in a yield of 85%. A portion of the product was recrystallized from ethanol to give colorless crystals having a melting point of 149.5° C.-150.5° C. Elemental analysis of the crystals is given below.

後処理

  1. custominorganic salts were removed by filtration
  2. customAfter acetone was removed by distillation under a reduced pressure
  3. customthe residue was purified by the column chromatography (silica gel

出典と根拠

ORDレコード
ord-7c37c20bfd6a4903b34100695eea24c5
出典データセット
uspto-grants-1986_11
特許番号
US04621090

関連ノート

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