반응 #2028882

반응 방정식

aldehyde

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

ethyl cyanoacetate

ammonium acetate

acetic acid

→

desired product

수율 66.0%

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

수율 66.0%

용매

benzene

반응 조건

후처리

1. 1
   온도The solution was heated
2. 2
   온도at reflux for 18 hours
3. 3
   온도cooled
4. 4
   기타partitioned between water and ethyl acetate
5. 5
   세척The organic solution was washed with a saturated aqueous sodium bicarbonate solution, water and brine
6. 6
   기타The organic solution was dried
7. 7
   농축concentrated
8. 8
   기타The residue was chromatographed on silica (40% hexane in ethyl acetate)

실험 절차

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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