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

HRID 21610

반응식

HRID 21610 반응식
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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8058Hexane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-40bce63c99b742fd8db573663eccc516
출처 데이터셋
uspto-grants-1995_06
특허 번호
US05424279

연결된 노트

불러오는 중…