Thionyl Chloride → methyl 3-[4-[(E)-2-[N-(3-pyridylmethyl)carbamoyl]ethenyl]phenyl]propionate

HRID 2227494Notes

Reaction equation

HRID 2227494 reaction equation
[CH3:1][O:2][C:3]([CH2:5][CH2:6][C:7]1[CH:17]=[CH:16][C:10]([CH:11]=[CH:12][C:13]([OH:15])=O)=[CH:9][CH:8]=1)=[O:4].S(Cl)(Cl)=O.[N:22]1[CH:27]=[CH:26][CH:25]=[C:24]([CH2:28][NH2:29])[CH:23]=1>CN(C)C=O.ClCCl.C(OCC)(=O)C>[N:22]1[CH:27]=[CH:26][CH:25]=[C:24]([CH2:28][NH:29][C:13](/[CH:12]=[CH:11]/[C:10]2[CH:9]=[CH:8][C:7]([CH2:6][CH2:5][C:3]([O:2][CH3:1])=[O:4])=[CH:17][CH:16]=2)=[O:15])[CH:23]=1

Participants

7

Reactant 3

HCID 24386Thionyl ChlorideHCID 310183-PyridinemethanamineHCID 538622044-[2-(Methoxycarbonyl)ethyl]cinnamic acid

Product 1

HCID 18473815methyl 3-[4-[(E)-2-[N-(3-pyridylmethyl)carbamoyl]ethenyl]phenyl]propionateYield 86%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of 4-[2-(methoxycarbonyl)ethyl]cinnamic acid (2.38 g), thionyl chloride (0.82 ml) and dimethylformamide (2 drops) in 50 ml dichloromethane was heated at reflux for 30 minutes. After evaporation of dichloromethane and low-boiling components, the residue was dried under reduced pressure to give a solid, which was then dissolved in 20 ml ethyl acetate and stirred with 1.10 g of 3-picolylamine in 20 ml ethyl acetate at room temperature for 30 minutes. After the reaction mixture was washed with saturated aqueous sodium bicarbonate, the resulting aqueous layer was extracted with 40 ml ethyl acetate. The combined organic layers were washed with saturated aqueous sodium carbonate and brine, and then dried over sodium sulfate. The drying agent was filtered off and the solvent was evaporated to give crude crystals (3.23 g), which were then recrystallized from ethyl acetate to provide methyl 3-[4-[(E)-2-[N-(3-pyridylmethyl)carbamoyl]ethenyl]phenyl]propionate (2.82 g, 86%) as colorless plate crystals.

Workup

  1. temperatureat reflux for 30 minutes
  2. customAfter evaporation of dichloromethane and low-boiling components
  3. customthe residue was dried under reduced pressure
  4. customto give a solid, which
  5. washAfter the reaction mixture was washed with saturated aqueous sodium bicarbonate
  6. extractionthe resulting aqueous layer was extracted with 40 ml ethyl acetate
  7. washThe combined organic layers were washed with saturated aqueous sodium carbonate and brine
  8. dry with materialdried over sodium sulfate
  9. filtrationThe drying agent was filtered off
  10. customthe solvent was evaporated
  11. customto give crude crystals (3.23 g), which
  12. customwere then recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-a12d426f312e4d4c87c4b75b0e4c0940
Source dataset
uspto-grants-2002_07
Patent number
US06413995B1

Reaction notes

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