Réaction #2028882

Équation de réaction

aldehyde

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

ethyl cyanoacetate

ammonium acetate

acetic acid

→

desired product

Rendement 66.0%

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

Rendement 66.0%

Solvants

benzene

Conditions de réaction

Traitement

1. 1
   TempératureThe solution was heated
2. 2
   Températureat reflux for 18 hours
3. 3
   Températurecooled
4. 4
   Autrepartitioned between water and ethyl acetate
5. 5
   LavageThe organic solution was washed with a saturated aqueous sodium bicarbonate solution, water and brine
6. 6
   AutreThe organic solution was dried
7. 7
   Concentrationconcentrated
8. 8
   AutreThe residue was chromatographed on silica (40% hexane in ethyl acetate)

Mode opératoire

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.

Source