Potassium Carbonate → 3-(1-tert-butyl-5-chloro-3-trifluoromethyl-1H-pyrazol-4-ylmethylthio)-5,5-dimethyl-2-isoxazoline

HRID 1172064노트

반응식

HRID 1172064 반응식
[SH-].[Na+].[CH3:3][C:4]1([CH3:13])[O:8][N:7]=[C:6]([S:9]([CH3:12])(=O)=O)[CH2:5]1.C(=O)([O-])[O-].[K+].[K+].C(S([O-])=O)O.[Na+].BrC[C:28]1[C:29]([C:38]([F:41])([F:40])[F:39])=[N:30][N:31]([C:34]([CH3:37])([CH3:36])[CH3:35])[C:32]=1[Cl:33]>CN(C)C=O.O>[C:34]([N:31]1[C:32]([Cl:33])=[C:28]([CH2:12][S:9][C:6]2[CH2:5][C:4]([CH3:13])([CH3:3])[O:8][N:7]=2)[C:29]([C:38]([F:39])([F:41])[F:40])=[N:30]1)([CH3:37])([CH3:35])[CH3:36]

참가 물질

8

반응물 5

HCID 11430Potassium CarbonateHCID 28015Sodium hydrosulfideHCID 121376563-Methylsulfonyl-5,5-dimethyl-2-isoxazolineHCID 178628684-bromomethyl-1-tert-butyl-5-chloro-3-trifluoromethyl-1H-pyrazoleHCID 23689980Sodium Formaldehyde Sulfoxylate

생성물 1

HCID 178628593-(1-tert-butyl-5-chloro-3-trifluoromethyl-1H-pyrazol-4-ylmethylthio)-5,5-dimethyl-2-isoxazoline수율 57.1%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

21.8 g of sodium hydrosulfide (purity: 70%, 272.5 mmoles) was added to a solution of 24.1 g (136.0 mmoles) of 5,5-dimethyl-3-methylsulfonyl-2-isoxazoline dissolved in 200 ml of N,N-dimethylformamide. The mixture was stirred for 1 hour. Thereto were added 18.8 g (136.2 mmoles) of anhydrous potassium carbonate and 21.0 g (136.2 mmoles) of Rongalit. The resulting mixture was stirred for 2 hours. Thereto was added, with ice-cooling, 40 g (125 mmoles) of 4-bromomethyl-1-tert-butyl-5-chloro-3-trifluoromethyl-1H-pyrazole. The resulting mixture was stirred at room temperature for 2 hours 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 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 23.0 g (yield: 57.1%) of 3-(1-tert-butyl-5-chloro-3-trifluoromethyl-1H-pyrazol-4-ylmethylthio)-5,5-dimethyl-2-isoxazoline as light pink crystals (melting point: 79.0 to 81.0° C.).

후처리

  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 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)

출처 및 근거

ORD 기록
ord-f268e1f87de645bba2b07833f61fbbeb
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07833939B2

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