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

HRID 428147

Reaction equation

HRID 428147 reaction equation
[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]

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 776396trans-3-(3-Pyridyl)acrylic acidHCID 14446612HCID 14446612, compound

Product 1

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

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

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%).

Workup

  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)

Sources & evidence

ORD record
ord-882e318f99a64b5b911b33cb022ceb3c
Source dataset
uspto-grants-2001_11
Patent number
US06313153B1

Linked notes

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