Reacción #1957400

Ecuación de reacción

N-[4-(4-ethoxycarbonylphenoxy)-5-fluoro-2-nitrophenyl]glycine ethyl ester

imidazole

→

N-[4-(4-ethoxycarbonylphenoxy)-5-(1H-imidazol-1-yl)-2-nitrophenyl]glycine ethyl ester

Rendimiento 75.0%

Disolventes

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaAfter cooling
2. 2
   Concentraciónthe reaction mixture was concentrated under reduced pressure
3. 3
   workup.DISSOLUTIONThe resulting residue was dissolved in ethyl acetate
4. 4
   LavadoThe resulting solution was washed successively with water and brine
5. 5
   Secadodried over anhydrous sodium sulfate
6. 6
   Concentraciónconcentrated under reduced pressure
7. 7
   OtroThe resulting residue was purified by chromatography on a silica gel column (developing solvent: chloroform+0 to 1% methanol)

Procedimiento

A mixture of 1.78 g (4.39 mmol) of N-[4-(4-ethoxycarbonylphenoxy)-5-fluoro-2-nitrophenyl]glycine ethyl ester, 896 mg of imidazole and 20 ml of DMF was stirred with heating on an oil bath of 70° C. for 12 hours. After cooling, the reaction mixture was concentrated under reduced pressure. The resulting residue was dissolved in ethyl acetate. The resulting solution was washed successively with water and brine, dried over anhydrous sodium sulfate and then, concentrated under reduced pressure. The resulting residue was purified by chromatography on a silica gel column (developing solvent: chloroform+0 to 1% methanol) to give 1.49 g (75%) of N-[4-(4-ethoxycarbonylphenoxy)-5-(1H-imidazol-1-yl)-2-nitrophenyl]glycine ethyl ester.

Fuente