تفاعل #2028882

معادلة التفاعل

aldehyde

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

ethyl cyanoacetate

ammonium acetate

acetic acid

→

desired product

المردود 66.0%

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

المردود 66.0%

المذيبات

benzene

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةThe solution was heated
2. 2
   درجة الحرارةat reflux for 18 hours
3. 3
   درجة الحرارةcooled
4. 4
   أخرىpartitioned between water and ethyl acetate
5. 5
   غسيلThe organic solution was washed with a saturated aqueous sodium bicarbonate solution, water and brine
6. 6
   أخرىThe organic solution was dried
7. 7
   تركيزconcentrated
8. 8
   أخرىThe residue was chromatographed on silica (40% hexane in ethyl acetate)

الإجراء التجريبي

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.

المصدر