Reacción #2028882

Ecuación de reacción

aldehyde

4-[3-formyl-5-phenyl-1H-pyrazol-1-yl]benzenesulfonamide

ethyl cyanoacetate

ammonium acetate

acetic acid

→

desired product

Rendimiento 66.0%

Ethyl 3-[1-[4-(aminosulfonyl)phenyl]-5-phenyl-1H-pyrazol-3-yl]-2-cyano-2-propenoate

Rendimiento 66.0%

Disolventes

benzene

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe solution was heated
2. 2
   Temperaturaat reflux for 18 hours
3. 3
   Temperaturacooled
4. 4
   Otropartitioned between water and ethyl acetate
5. 5
   LavadoThe organic solution was washed with a saturated aqueous sodium bicarbonate solution, water and brine
6. 6
   OtroThe organic solution was dried
7. 7
   Concentraciónconcentrated
8. 8
   OtroThe residue was chromatographed on silica (40% hexane in ethyl acetate)

Procedimiento

To a solution of the aldehyde from Step 1 (1.2 g, 3.6 mmol) in benzene (18 mL) was added ethyl cyanoacetate (0.38 mL, 3.6 mmol), ammonium acetate (50 mg, 0.7 mmol) and glacial acetic acid (0.17 mL, 2.8 mmol). The solution was heated at reflux for 18 hours, cooled, and partitioned between water and ethyl acetate. The organic solution was washed with a saturated aqueous sodium bicarbonate solution, water and brine. The organic solution was dried and concentrated. The residue was chromatographed on silica (40% hexane in ethyl acetate) to give the desired product (1.0 g, 66%): Anal. calc'd for C21H18N4O4S: C, 59.82; H, 4.30; N, 13.22. Found: C, 59.70; H, 4.29; N, 13.26.

Fuente