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

HRID 1172066ノート

反応式

HRID 1172066 の反応式
C(=O)([O-])[O-].[K+].[K+].[Cl:7][C:8]1[NH:12][N:11]=[C:10]([C:13]([F:16])([F:15])[F:14])[C:9]=1[CH2:17][S:18][C:19]1[CH2:23][C:22]([CH3:25])([CH3:24])[O:21][N:20]=1.Cl[CH:27]([F:29])[F:28].O>CN(C)C=O>[Cl:7][C:8]1[N:12]([CH:27]([F:29])[F:28])[N:11]=[C:10]([C:13]([F:15])([F:14])[F:16])[C:9]=1[CH2:17][S:18][C:19]1[CH2:23][C:22]([CH3:25])([CH3:24])[O:21][N:20]=1.[Cl:7][C:8]1[C:9]([CH2:17][S:18][C:19]2[CH2:23][C:22]([CH3:25])([CH3:24])[O:21][N:20]=2)=[C:10]([C:13]([F:15])([F:14])[F:16])[N:11]([CH:27]([F:29])[F:28])[N:12]=1

参加物

7

反応物 4

HCID 962WaterHCID 6372ChlorodifluoromethaneHCID 11430Potassium CarbonateHCID 178427280HCID 178427280、化合物

生成物 2

HCID 178628493-(5-chloro-1-difluoromethyl-3-trifluoromethyl-1H-pyrazol-4-ylmethylthio)-5,5-dimethyl-2-isoxazoline収率 25.8%HCID 178628663-(3-chloro-1-difluoromethyl-5-trifluoromethyl-1H-pyrazol-4-ylmethylthio)-5,5-dimethyl-2-isoxazoline収率 20.2%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
135 °C

実験手順

3.1 g (22.5 mmoles) of anhydrous potassium carbonate was added to a solution of 2.3 g (7.3 mmoles) of 3-(5-chloro-3-trifluoromethyl-1H-pyrazol-4-ylmethylthio)-5,5-dimethyl-2-isoxazoline dissolved in 50 ml of N,N-dimethylformamide. Thereinto was blown chlorodifluoromethane. The resulting mixture was stirred at 130 to 140° C. for 3 hours to give rise to a reaction. After confirmation of the completion of the reaction, the reaction mixture was pored into water, followed by extraction with ethyl acetate. The resulting organic layer was washed with water and 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 0.69 g (yield: 25.8%) of 3-(5-chloro-1-difluoromethyl-3-trifluoromethyl-1H-pyrazol-4-ylmethylthio)-5,5-dimethyl-2-isoxazoline as light yellow crystals (melting point: 41.0 to 42.0° C.) and 0.54 g (yield: 20.2%) of 3-(3-chloro-1-difluoromethyl-5-trifluoromethyl-1H-pyrazol-4-ylmethylthio)-5,5-dimethyl-2-isoxazoline as a white powder (melting point: 89.0 to 90.0° C.).

後処理

  1. customto give rise
  2. customto a reaction
  3. customAfter confirmation of the completion of the reaction
  4. extractionfollowed by extraction with ethyl acetate
  5. washThe resulting organic layer was washed with water
  6. dry with materialan aqueous sodium chloride solution and then dried over anhydrous magnesium sulfate
  7. distillationThe resulting solution was subjected to vacuum distillation
  8. customto remove the solvent
  9. 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-ebc76da087694144bab300f8e838ef08
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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