Реакция #2028882

Уравнение реакции

aldehyde

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

ethyl cyanoacetate

ammonium acetate

acetic acid

→

desired product

Выход 66.0%

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

Выход 66.0%

Растворители

benzene

Условия реакции

Обработка

1. 1
   ТемператураThe solution was heated
2. 2
   Температураat reflux for 18 hours
3. 3
   Температураcooled
4. 4
   Другоеpartitioned between water and ethyl acetate
5. 5
   ПромывкаThe organic solution was washed with a saturated aqueous sodium bicarbonate solution, water and brine
6. 6
   ДругоеThe organic solution was dried
7. 7
   Концентрированиеconcentrated
8. 8
   ДругоеThe residue was chromatographed on silica (40% hexane in ethyl acetate)

Методика

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.

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