Reaction #927273

Reaction equation

N-methyl acetamide

CH3CN CO2

pyridine

cinnamoyl chloride

→

N-cinnamoyl-N-methyl acetamide

Solvents

CH2Cl2

CH2Cl2

Conditions

Workup

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

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.

Source