P-Cresol → 5-p-Tolyloxy-thiophene-2-carbonitrile

HRID 77915

反応式

HRID 77915 の反応式
[N+]([C:4]1[S:8][C:7]([C:9]#[N:10])=[CH:6][CH:5]=1)([O-])=O.[CH:11]1[C:16]([OH:17])=[CH:15][CH:14]=[C:13]([CH3:18])[CH:12]=1.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[C:13]1([CH3:18])[CH:12]=[CH:11][C:16]([O:17][C:4]2[S:8][C:7]([C:9]#[N:10])=[CH:6][CH:5]=2)=[CH:15][CH:14]=1

参加物

5

反応物 3

HCID 2879P-CresolHCID 11430Potassium CarbonateHCID 5192945-Nitrothiophene-2-carbonitrile

生成物 1

HCID 231303655-p-Tolyloxy-thiophene-2-carbonitrile収率 78.9%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
60 °C

実験手順

To a dimethyl sulfoxide (100 mL) solution of 5-nitro-2-thiophenecarbonitrile (6.30 g, 40.9 mmol) were added p-cresol (8.85 g, 81.8 mmol) and potassium carbonate (11.3 g, 81.8 mmol) under nitrogen atmosphere, which was stirred for 5 hours at 60° C. The reaction solution was cooled to room temperature, and extracted with ethyl acetate after addition of water. The organic layer was washed with saturated aqueous sodium chloride, and the solvent was evaporated under a reduced pressure. The residue was purified by NH silica gel column chromatography (ethyl acetate:heptane=1:3→2:1) to obtain the title compound (6.95 g, 78.9%).

後処理

  1. temperatureThe reaction solution was cooled to room temperature
  2. extractionextracted with ethyl acetate
  3. additionafter addition of water
  4. washThe organic layer was washed with saturated aqueous sodium chloride
  5. customthe solvent was evaporated under a reduced pressure
  6. customThe residue was purified by NH silica gel column chromatography (ethyl acetate:heptane=1:3→2:1)

出典と根拠

ORDレコード
ord-76c8cc069daa43d38db074f6750cd495
出典データセット
uspto-grants-2014_09
特許番号
US08841327B2

関連ノート

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