반응 #792161

반응 방정식

hexachloroethane

N-dimethylsulfamoylpyrazole

n-butyllithium

→

title product

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

용매

tetrahydrofuran

hexane

tetrahydrofuran

반응 조건

후처리

1. 1
   workup.ADDITIONUpon completion of the addition the reaction mixture
2. 2
   온도was maintained at ˜78° C. for an additional 45 minutes
3. 3
   온도The reaction mixture was maintained for an hour at ˜78° C.
4. 4
   온도warmed to ˜20° C.
5. 5
   기타quenched with water (1 L)
6. 6
   추출The reaction mixture was extracted with methylene chloride (4×500 mL)
7. 7
   건조the organic extracts were dried over magnesium sulfate
8. 8
   농축concentrated
9. 9
   기타The crude product was further purified by chromatography on silica gel

실험 절차

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).

출처