Potassium Carbonate → 3-(3,5-dichloro-1-ethyl-1H-pyrazol-4-ylmethylthio)-5,5-dimethyl-2-isoxazoline

HRID 1172077ノート

反応式

HRID 1172077 の反応式
[SH-].[Na+].[CH3:3][C:4]1([CH3:14])[O:8][N:7]=[C:6]([S:9]([CH2:12][CH3:13])(=O)=O)[CH2:5]1.C(=O)([O-])[O-].[K+].[K+].C(S([O-])=O)O.[Na+].BrCC1[C:30]([Cl:37])=[N:31][N:32]([CH2:35][CH3:36])[C:33]=1[Cl:34]>CN(C)C=O.O>[Cl:37][C:30]1[C:13]([CH2:12][S:9][C:6]2[CH2:5][C:4]([CH3:14])([CH3:3])[O:8][N:7]=2)=[C:33]([Cl:34])[N:32]([CH2:35][CH3:36])[N:31]=1

参加物

8

反応物 5

HCID 11430Potassium CarbonateHCID 28015Sodium hydrosulfideHCID 178629194-bromomethyl-3,5-dichloro-1-ethyl-1H-pyrazoleHCID 178629235,5-Dimethyl-3-ethylsulfonyl-2-isoxazolineHCID 23689980Sodium Formaldehyde Sulfoxylate

生成物 1

HCID 178629073-(3,5-dichloro-1-ethyl-1H-pyrazol-4-ylmethylthio)-5,5-dimethyl-2-isoxazoline収率 74.2%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

0.6 g of sodium hydrosulfide (purity: 70%, 10.7 mmoles) was added to a solution of 0.7 g (3.7 mmoles) of 5,5-dimethyl-3-ethylsulfonyl-2-isoxazoline dissolved in 30 ml of N,N-dimethylformamide. The mixture was stirred for 1 hour. Thereto were added 0.51 g (3.7 mmoles) of anhydrous potassium carbonate and 0.56 g (3.6 mmoles) of Rongalit. The resulting mixture was stirred for 2 hours. Thereto was added, with ice-cooling, 0.9 g (3.5 mmoles) of 4-bromomethyl-3,5-dichloro-1-ethyl-1H-pyrazole. The resulting mixture was stirred at room temperature for 2 hours to give rise to a reaction. After confirmation of 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 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 0.8 g (yield: 70.8%) of 3-(3,5-dichloro-1-ethyl-1H-pyrazol-4-ylmethylthio)-5,5-dimethyl-2-isoxazoline as a colorless transparent oily substance.

後処理

  1. stirringThe resulting mixture was stirred for 2 hours
  2. additionThereto was added, with ice-
  3. temperaturecooling
  4. stirringThe resulting mixture was stirred at room temperature for 2 hours
  5. customto give rise
  6. customto a reaction
  7. customAfter confirmation of the completion of the reaction
  8. extractionfollowed by extraction with ethyl acetate
  9. washThe resulting organic layer was washed with water
  10. dry with materialan aqueous sodium chloride solution and then dried over anhydrous magnesium sulfate
  11. distillationThe resulting solution was subjected to vacuum distillation
  12. customto remove the solvent
  13. 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-0f9b099aedf947659cd598f218588582
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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