反応 #2186224

反応方程式

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

収率 70.0%

溶媒

dioxane

dioxane

反応条件

後処理

1. 1
   温度was heated
2. 2
   温度to reflux
3. 3
   温度heated
4. 4
   温度under reflux for 6 hours
5. 5
   抽出extracted with dichloromethane
6. 6
   乾燥the organic phase dried over magnesium sulfate
7. 7
   その他evaporated
8. 8
   その他The resulting gum was triturated with pentane

実験手順

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).

出典