반응 #2186224

반응 방정식

potassium hydrogensulfate

sodium hydride

1-(2,6-dichloro-4-trifluoromethylphenyl)-5-hydroxy-4-trifluoromethylthio-1H-pyrazole-3-carbonitrile

diethyl sulfate

→

1-(2,6-dichloro-4-trifluoromethylphenyl)-5-ethoxy-4-trifluoromethylthio-1 H-pyrazole-3-carbonitrile

수율 70.0%

용매

dioxane

dioxane

반응 조건

후처리

1. 1
   온도was heated
2. 2
   온도to reflux
3. 3
   온도heated
4. 4
   온도under reflux for 6 hours
5. 5
   추출extracted with dichloromethane
6. 6
   건조the organic phase dried over magnesium sulfate
7. 7
   기타evaporated
8. 8
   기타The resulting gum was triturated with pentane

실험 절차

To a stirred suspension of sodium hydride (0.41 g, 60%, 10.3 mmol) in dioxane (150 ml) was added a solution of 1-(2,6-dichloro-4-trifluoromethylphenyl)-5-hydroxy-4-trifluoromethylthio-1H-pyrazole-3-carbonitrile (4.00 g, 8.53 mmol) in dioxane (50 ml). After gas evolution had ceased the mixture was heated to reflux and diethyl sulfate (1.25 ml, 9.47 mmol) added, and then heated under reflux for 6 hours. The cooled mixture was acidified with aqueous potassium hydrogensulfate (5%), extracted with dichloromethane, and the organic phase dried over magnesium sulfate and evaporated. The resulting gum was triturated with pentane to give 1-(2,6-dichloro-4-trifluoromethylphenyl)-5-ethoxy-4-trifluoromethylthio-1 H-pyrazole-3-carbonitrile (2.68 g, yield 70 %) as off-white crystals, mp 106° C., 1H NMR (CDCl3): 1.36 (t, 3H, CH3), 4.71 (q, 2H, OCH2), and 7.76 (s, 2H, Ar—H).

출처