Reaction #67989

Reaction equation

methyl 3-oxo-3-(1,3-thiazol-2-yl)propionate

m-anisidine

→

N-(3-methoxyphenyl)-3-oxo-3-(1,3-thiazol-2-yl)propaneamide

Solvents

xylene

Conditions

Workup

1. 1
   workup.ADDITIONwas added
2. 2
   Temperatureunder reflux
3. 3
   Temperatureby heating
4. 4
   OtherThe solvent was removed under reduced pressure, and water and ethyl acetate
5. 5
   workup.ADDITIONwere added
6. 6
   OtherThe organic layer was separated
7. 7
   Extractionthe aqueous layer was extracted with ethyl acetate
8. 8
   Washthe resultant solution was washed with an aqueous saturated sodium chloride solution
9. 9
   Dryingdried over anhydrous magnesium sulfate
10. 10
    Otherthe solvent was removed under reduced pressure

Procedure

To 30 mL of a xylene solution containing 2.3 g of methyl 3-oxo-3-(1,3-thiazol-2-yl)propionate, 1.4 mL of m-anisidine was added. The reaction mixture was stirred for 6 hours under reflux by heating. The solvent was removed under reduced pressure, and water and ethyl acetate were added thereto. The organic layer was separated, and the aqueous layer was extracted with ethyl acetate. The organic layer and the extract were combined, the resultant solution was washed with an aqueous saturated sodium chloride solution and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure to obtain 3.3 g of a brown oily substance, N-(3-methoxyphenyl)-3-oxo-3-(1,3-thiazol-2-yl)propaneamide.

Source