Water → 5,5-dimethyl-3-(5-fluoro-1-phenyl-3-trifluoromethyl-1H-pyrazol-4-ylmethylthio)-2-isoxazoline

HRID 1172061ノート

反応式

HRID 1172061 の反応式
O.[SH-].[Na+].[CH3:4][C:5]1([CH3:14])[O:9][N:8]=[C:7]([S:10]([CH3:13])(=O)=O)[CH2:6]1.BrC[C:17]1[C:18]([C:29]([F:32])([F:31])[F:30])=[N:19][N:20]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:21]=1[F:22].O>CN(C)C=O>[CH3:4][C:5]1([CH3:14])[O:9][N:8]=[C:7]([S:10][CH2:13][C:17]2[C:18]([C:29]([F:32])([F:31])[F:30])=[N:19][N:20]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:21]=2[F:22])[CH2:6]1

参加物

6

反応物 4

HCID 962WaterHCID 121376563-Methylsulfonyl-5,5-dimethyl-2-isoxazolineHCID 16211346Sodium hydrosulfide hydrateHCID 178629274-bromomethyl-5-fluoro-1-phenyl-3-trifluoromethyl-1H-pyrazole

生成物 1

HCID 178628915,5-dimethyl-3-(5-fluoro-1-phenyl-3-trifluoromethyl-1H-pyrazol-4-ylmethylthio)-2-isoxazoline収率 37.4%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

9.3 g of sodium hydrosulfide hydrate (purity: 70%, 116.3 mmoles) was added to a solution of 18.7 g (105.7 mmoles) of 5,5-dimethyl-3-methylsulfonyl-2-isoxazoline (present compound No. 2-1) dissolved in 300 ml of N,N-dimethylformamide. The mixture was stirred for 2 hours. The reaction system was ice-cooled. Thereto was added a solution of 30.3 g (93.8 mmoles) of 4-bromomethyl-5-fluoro-1-phenyl-3-trifluoromethyl-1H-pyrazole dissolved in 200 ml of N,N-dimethylformamide. The mixture was stirred at 0° C. for 30 minutes to give rise to a reaction. After the completion of the reaction, the reaction mixture was poured into water, followed by extraction with ethyl acetate. The resulting organic layer was washed with an aqueous sodium chloride solution and then dried over anhydrous magnesium sulfate. The resulting solution was subjected to vacuum distillation to remove the solvent contained therein. The residue was purified by silica gel column chromatography (developing solvent: hexane-ethyl acetate mixed solvent) to obtain 13.11 g (yield: 37.4%) of 5,5-dimethyl-3-(5-fluoro-1-phenyl-3-trifluoromethyl-1H-pyrazol-4-ylmethylthio)-2-isoxazoline as a yellow oily substance.

後処理

  1. temperaturecooled
  2. stirringThe mixture was stirred at 0° C. for 30 minutes
  3. customto give rise
  4. customto a reaction
  5. customAfter the completion of the reaction
  6. extractionfollowed by extraction with ethyl acetate
  7. washThe resulting organic layer was washed with an aqueous sodium chloride solution
  8. dry with materialdried over anhydrous magnesium sulfate
  9. distillationThe resulting solution was subjected to vacuum distillation
  10. customto remove the solvent
  11. customThe residue was purified by silica gel column chromatography (developing solvent: hexane-ethyl acetate mixed solvent)

出典と根拠

ORDレコード
ord-4488180082844ce68abca14b7a64878e
出典データセット
uspto-grants-2010_11
特許番号
US07833939B2

反応ノート

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