反应 #792161

反应方程式

hexachloroethane

N-dimethylsulfamoylpyrazole

n-butyllithium

→

title product

3-Chloro-N,N-dimethyl-1H-pyrazole-1-sulfonamide

溶剂

tetrahydrofuran

hexane

tetrahydrofuran

反应条件

后处理

1. 1
   workup.ADDITIONUpon completion of the addition the reaction mixture
2. 2
   温度was maintained at ˜78° C. for an additional 45 minutes
3. 3
   温度The reaction mixture was maintained for an hour at ˜78° C.
4. 4
   温度warmed to ˜20° C.
5. 5
   其他quenched with water (1 L)
6. 6
   萃取The reaction mixture was extracted with methylene chloride (4×500 mL)
7. 7
   干燥the organic extracts were dried over magnesium sulfate
8. 8
   浓缩concentrated
9. 9
   其他The crude product was further purified by chromatography on silica gel

实验过程

To a solution of N-dimethylsulfamoylpyrazole (188.0 g, 1.07 mol) in dry tetrahydrofuran (1500 mL) at ˜78° C. was added dropwise a solution of 2.5 M n-butyllithium (472 mL, 1.18 mol) in hexane while maintaining the temperature below ˜65° C. Upon completion of the addition the reaction mixture was maintained at ˜78° C. for an additional 45 minutes, after which time a solution of hexachloroethane (279 g, 1.18 mol) in tetrahydrofuran (120 mL) was added dropwise. The reaction mixture was maintained for an hour at ˜78° C., warmed to ˜20° C. and then quenched with water (1 L). The reaction mixture was extracted with methylene chloride (4×500 mL); the organic extracts were dried over magnesium sulfate and concentrated. The crude product was further purified by chromatography on silica gel using methylene chloride as eluent to afford the title product compound as a yellow oil (160 g).

来源