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

HRID 21610

反応式

HRID 21610 の反応式
C([Li])CCC.[Cl:6][C:7]1[C:8]([S:19]([C:22]2[C:27]([CH3:28])=[CH:26][CH:25]=[CH:24][C:23]=2[CH2:29][CH3:30])(=[O:21])=[O:20])=[N:9][N:10]([C:12](=[O:18])[N:13]([CH2:16][CH3:17])[CH2:14][CH3:15])[CH:11]=1.[CH3:31][S:32]SC.[Cl-].[NH4+]>CCCCCC.O1CCCC1>[Cl:6][C:7]1[C:8]([S:19]([C:22]2[C:27]([CH3:28])=[CH:26][CH:25]=[CH:24][C:23]=2[CH2:29][CH3:30])(=[O:21])=[O:20])=[N:9][N:10]([C:12](=[O:18])[N:13]([CH2:16][CH3:17])[CH2:14][CH3:15])[C:11]=1[S:32][CH3:31]

参加物

7

反応物 4

HCID 12232Dimethyl DisulfideHCID 25517Ammonium ChlorideHCID 199320704-Chloro-1-(diethylcarbamoyl)-3-(2-ethyl-6-methylphenylsulfonyl)pyrazoleHCID 178418339Butyllithium

生成物 1

HCID 199318464-Chloro-1-(diethylcarbamoyl)-3-(2-ethyl-6-methylphenylsulfonyl)-5-methylthiopyrazole収率 35%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8058Hexane溶媒

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.

後処理

  1. customThe resulting reaction mixture
  2. stirringwas stirred for 30 minutes
  3. extractionextracted with diethyl ether
  4. washThe extract was washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated by evaporation under reduced pressure
  7. customThe concentrate was purified by column chromatography through silica gel
  8. washeluted with a 10:1 by volume mixture of hexane and ethyl acetate

出典と根拠

ORDレコード
ord-40bce63c99b742fd8db573663eccc516
出典データセット
uspto-grants-1995_06
特許番号
US05424279

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