Methyl iodide → N-[4-chloro-2-methyl-3-(trifluoromethyl)phenyl]-2,2-dimethylpropanamide

HRID 501552노트

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HRID 501552 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:14])[C:10]([CH3:13])([CH3:12])[CH3:11])=[CH:4][C:3]=1[C:15]([F:18])([F:17])[F:16].[CH2:19]([Li])CCC.IC>C1COCC1.O.CCOCC>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:14])[C:10]([CH3:11])([CH3:12])[CH3:13])=[C:4]([CH3:19])[C:3]=1[C:15]([F:16])([F:17])[F:18]

참가 물질

7

반응물 3

HCID 6328Methyl iodideHCID 715673N-[4-chloro-3-(trifluoromethyl)phenyl]-2,2-dimethylpropanamideHCID 178418339Butyllithium

생성물 1

HCID 21874848N-[4-chloro-2-methyl-3-(trifluoromethyl)phenyl]-2,2-dimethylpropanamide수율 67%

시약·촉매·용매 3

HCID 962Water용매HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매

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온도
2.5 °C

실험 절차

To a solution of compound 18A (2.29 g, 8.19 mmol) in anhydrous THF (25 mL) cooled to 0-5° C. was added a solution of 1.6 M n-butyllithium in hexanes (12.3 mL, 19.7 mmol) slowly, so that the reaction temperature was maintained below 5° C. The solution was stirred at 0-5° C. for 1.5 h. A solution of iodomethane (0.56 mL, 9.01 mmol) in petroleum ether (2 mL) was then added over 20 min while maintaining the temperature below 5° C. The suspension was stirred at 0-5° C. for 1 h and diluted with water and ether. The aqueous layer was extracted with ether and the combined organic layers washed with brine, dried (MgSO4), filtered and concentrated. The residue was chromatographed (silica gel), eluting with CH2Cl2 to afford the title compound (1.60 g, 67%). MS (ES) m/z 294 [M+1]+.

후처리

  1. temperatureso that the reaction temperature was maintained below 5° C
  2. temperaturewhile maintaining the temperature below 5° C
  3. stirringThe suspension was stirred at 0-5° C. for 1 h
  4. extractionThe aqueous layer was extracted with ether
  5. washthe combined organic layers washed with brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was chromatographed (silica gel)
  10. washeluting with CH2Cl2

출처 및 근거

ORD 기록
ord-403ca9c6fae2473cafe5efb704ffb46a
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07772267B2

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