反応 #49888

反応方程式

methyl disulfide

butyllithium

4-chloro-1-(diethylcarbamoyl)-3-(2-ethyl-6-methylphenylsulfonyl)pyrazole

ammonium chloride

→

title compound

収率 35.0%

4-Chloro-1-(diethylcarbamoyl)-3-(2-ethyl-6-methylphenylsulfonyl)-5-methylthiopyrazole

収率 35.0%

溶媒

hexane

tetrahydrofuran

反応条件

後処理

1. 1
   その他The resulting reaction mixture
2. 2
   workup.STIRRINGwas stirred for 30 minutes
3. 3
   抽出extracted with diethyl ether
4. 4
   洗浄The extract was washed with water
5. 5
   乾燥dried over anhydrous sodium sulfate
6. 6
   濃縮concentrated by evaporation under reduced pressure
7. 7
   その他The concentrate was purified by column chromatography through silica gel
8. 8
   洗浄eluted with a 10:1 by volume mixture of hexane and ethyl acetate

実験手順

0.11 ml of a 1.49M solution of butyllithium in hexane was added, at -78° C. and under an atmosphere of nitrogen, to a solution of 59 mg of 4-chloro-1-(diethylcarbamoyl)-3-(2-ethyl-6-methylphenylsulfonyl)pyrazole (prepared as described in Example 18) in 2 ml of dry tetrahydrofuran, and the resulting mixture was stirred for 30 minutes, after which 15 μl of methyl disulfide were added. The resulting reaction mixture was stirred for 30 minutes, and then mixed with an aqueous solution of ammonium chloride and extracted with diethyl ether. The extract was washed with water, dried over anhydrous sodium sulfate and concentrated by evaporation under reduced pressure. The concentrate was purified by column chromatography through silica gel, eluted with a 10:1 by volume mixture of hexane and ethyl acetate, to afford 28 mg (yield 35%) of the title compound as an oil.

出典