反応 #2028882

反応方程式

aldehyde

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

ethyl cyanoacetate

ammonium acetate

acetic acid

→

desired product

収率 66.0%

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

収率 66.0%

溶媒

benzene

反応条件

後処理

1. 1
   温度The solution was heated
2. 2
   温度at reflux for 18 hours
3. 3
   温度cooled
4. 4
   その他partitioned between water and ethyl acetate
5. 5
   洗浄The organic solution was washed with a saturated aqueous sodium bicarbonate solution, water and brine
6. 6
   その他The organic solution was dried
7. 7
   濃縮concentrated
8. 8
   その他The residue was chromatographed on silica (40% hexane in ethyl acetate)

実験手順

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.

出典