Pyridine → N-Acetyl-N-methyl-3-phenylprop-2-enamide

HRID 840091Notes

Reaction equation

HRID 840091 reaction equation
[C:1](Cl)(=[O:10])[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.CC#N.C(=O)=O.N1C=CC=CC=1.[CH3:24][NH:25][C:26](=[O:28])[CH3:27]>C(Cl)Cl>[C:1]([N:25]([CH3:24])[C:26](=[O:28])[CH3:27])(=[O:10])[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 6582N-MethylacetamideHCID 660233-Phenylprop-2-enoyl chlorideHCID 86587134Acetonitrile dry ice

Product 1

HCID 53656868N-Acetyl-N-methyl-3-phenylprop-2-enamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A dry, 3-necked, round-bottomed flask equipped with a mechanical stirrer under an inert atmosphere is charged with 41.6 g (0.25 mol, ) of cinnamoyl chloride (available from Aldrich Chemical Company, Inc. of Milwaukee, Wis.) and 150 mL of CH2Cl2 (available from Aldrich Chemical Company). The stirred, homogeneous solution is cooled to −40° C. (CH3CN/CO2 bath), and 22.0 mL (0.275 mol) of pyridine (available from Aldrich Chemical Company) is added slowly (keeping solution temperature below −30° C.) in one portion. The reaction mixture is stirred for 20 min at which point a precipitate is observed. To the stirred heterogeneous solution is added 19.0 mL (0.25 mol) of N-methyl acetamide (available from Aldrich Chemical Company) in one portion. The resulting reaction mixture is allowed to warm gradually to room temperature and is stirred overnight. The reaction is diluted with 150 mL of CH2Cl2 and extracted twice with 150 mL of 1 N HCl, twice with 0.1 N aqueous NaOH, and twice with water. The organic layer is dried over Na2SO4, and concentrated by rotory evaporation to give the desired N-cinnamoyl-N-methyl acetamide.

Workup

  1. customA dry, 3-necked, round-bottomed flask equipped with a mechanical stirrer under an inert atmosphere
  2. additionis added slowly (keeping solution temperature below −30° C.) in one portion
  3. customThe resulting reaction mixture
  4. stirringis stirred overnight
  5. extractionextracted twice with 150 mL of 1 N HCl, twice with 0.1 N aqueous NaOH
  6. dry with materialThe organic layer is dried over Na2SO4
  7. concentrationconcentrated by rotory evaporation

Sources & evidence

ORD record
ord-a21512adc64f4ff6947d00c93cf0acb0
Source dataset
uspto-grants-2002_04
Patent number
US06365564B1

Reaction notes

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