Reacción #75954

Ecuación de reacción

ethyl 2-chloro-3-oxo-3-phenylpropanoate

thiourea

EtOAc

→

ethyl 2-amino-4-phenyl-1,3-thiazole-5-carboxylate

Rendimiento 89.0%

Disolventes

EtOH

—

Hexanes

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturaat reflux overnight
2. 2
   ConcentraciónThe resulting mixture was concentrated in vacuo
3. 3
   Extracciónextracted with CH2Cl2
4. 4
   LavadoThe organic phase was washed with brine
5. 5
   Secadodried over anhydrous sodium sulfate
6. 6
   Concentraciónconcentrated
7. 7
   Otroto afford a yellow solid
8. 8
   Lavadothat was washed with MeOH (3 mL)
9. 9
   Otrodried
10. 10
    Otroto afford the product in 89% yield as a pale yellow solid

Procedimiento

A solution of ethyl 2-chloro-3-oxo-3-phenylpropanoate (9.73 mmol) and thiourea (9.73 mmol) in EtOH (25 mL) was heated at reflux overnight. The resulting mixture was concentrated in vacuo, neutralized with 18M-NH4OH, and extracted with CH2Cl2. The organic phase was washed with brine, dried over anhydrous sodium sulfate, and concentrated to afford a yellow solid that was washed with MeOH (3 mL) and dried to afford the product in 89% yield as a pale yellow solid. MH+=249.1, Rf=0.29 (Hexanes:EtOAc=1:1). MH+=249.1, retention time (LC-MS)=2.37 min.

Fuente