Sodium Bicarbonate → (E)-N-[2-(3,4-dimethoxyphenyl)-2-(methylthio)ethyl]-3-(3-pyridyl)-2-propenamide

HRID 428147

反応式

HRID 428147 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]([S:14][CH3:15])[CH2:12][NH2:13])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[N:16]1[CH:21]=[CH:20][CH:19]=[C:18](/[CH:22]=[CH:23]/[C:24](O)=[O:25])[CH:17]=1.C(=O)(O)[O-].[Na+]>CN(C)C=O.C(N(CC)CC)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]([S:14][CH3:15])[CH2:12][NH:13][C:24](=[O:25])/[CH:23]=[CH:22]/[C:18]2[CH:17]=[N:16][CH:21]=[CH:20][CH:19]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

参加物

6

反応物 3

HCID 516892Sodium BicarbonateHCID 776396trans-3-(3-Pyridyl)acrylic acidHCID 14446612HCID 14446612、化合物

生成物 1

HCID 20701371(E)-N-[2-(3,4-dimethoxyphenyl)-2-(methylthio)ethyl]-3-(3-pyridyl)-2-propenamide収率 52.3%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8471Triethylamine溶媒

実験手順

To a solution of the crude oily 2-(3,4-dimethoxy-phenyl) -2-(methylthio)ethylamine (0.96 g) and trans-3-(3-pyridyl) acrylic acid (0.63 g, 4.2 mmol) in dimethylformamide (10 ml), diethylphosphoric cyanide (0.69 ml) and triethylamine (1.17 ml) were sequentially added under ice-cooling and stirred for 10 minutes under ice-cooling. Aqueous sodium bicarbonate solution was added to the reaction mixture and extracted with ethyl acetate. The organic layers were combined, washed with water and aqueous saturated sodium chloride solution and dried over magnesium sulfate. The solvent was distilled out under reduced pressure and the residue was purified by silica gel column chromatography (hexane: chloroform:ethanol=8:2:1) to yield the titled compound (788 mg, 47%).

後処理

  1. temperaturecooling
  2. temperaturecooling
  3. extractionextracted with ethyl acetate
  4. washwashed with water and aqueous saturated sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. distillationThe solvent was distilled out under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (hexane: chloroform:ethanol=8:2:1)

出典と根拠

ORDレコード
ord-882e318f99a64b5b911b33cb022ceb3c
出典データセット
uspto-grants-2001_11
特許番号
US06313153B1

関連ノート

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