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

HRID 1172063노트

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HRID 1172063 반응식
[CH3:1][NH:2][CH3:3].[CH3:4][C:5]1([CH3:28])[O:9][N:8]=[C:7]([S:10][CH2:11][C:12]2[C:13]([C:24]([F:27])([F:26])[F:25])=[N:14][N:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:16]=2F)[CH2:6]1.O>CN(C)C=O>[CH3:4][C:5]1([CH3:28])[O:9][N:8]=[C:7]([S:10][CH2:11][C:12]2[C:13]([C:24]([F:27])([F:26])[F:25])=[N:14][N:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:16]=2[N:2]([CH3:3])[CH3:1])[CH2:6]1

참가 물질

5

반응물 3

HCID 674Dimethylamine2회HCID 962WaterHCID 178628915,5-dimethyl-3-(5-fluoro-1-phenyl-3-trifluoromethyl-1H-pyrazol-4-ylmethylthio)-2-isoxazoline

생성물 1

HCID 178628635,5-dimethyl-3-(5-dimethylamino-1-phenyl-3-trifluoromethyl-1H-pyrazol-4-ylmethylthio)-2-isoxazoline수율 80.6%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
100 °C

실험 절차

0.8 g (6.7 mmoles) of a 40% aqueous dimethylamine solution was added to a solution of 0.5 g (1.3 mmoles) of 5,5-dimethyl-3-(5-fluoro-1-phenyl-3-trifluoromethyl-1H-pyrazol-4-ylmethylthio)-2-isoxazoline dissolved in 10 ml of N,N-dimethylformamide. The mixture was stirred at 100° C. for 9 hours in a sealed tube. Thereto was added 3.0 g (26.6 mmoles) of a 40% aqueous dimethylamine solution, and the resulting mixture was stirred for 9 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 an aqueous sodium chloride solution and then dried over anhydrous sodium 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 0.4 g (yield: 80.6%) of 5,5-dimethyl-3-(5-dimethylamino-1-phenyl-3-trifluoromethyl-1H-pyrazol-4-ylmethylthio)-2-isoxazoline.

후처리

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

출처 및 근거

ORD 기록
ord-62da2cc3136747bab5f05a797b86c133
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07833939B2

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