反応 #792161

反応方程式

hexachloroethane

N-dimethylsulfamoylpyrazole

n-butyllithium

→

title product

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

溶媒

tetrahydrofuran

hexane

tetrahydrofuran

反応条件

後処理

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
   その他quenched with water (1 L)
6. 6
   抽出The reaction mixture was extracted with methylene chloride (4×500 mL)
7. 7
   乾燥the organic extracts were dried over magnesium sulfate
8. 8
   濃縮concentrated
9. 9
   その他The crude product was further purified by chromatography on silica gel

実験手順

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).

出典