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

HRID 723736노트

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HRID 723736 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

실험 절차

To a solution of N-(4-chloro-3-trifluoromethylphenyl)-2,2-dimethylpropionamide (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), added 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 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 were washed with brine, dried over MgSO4, filtered and concentrated in vacuo. The residue was chomatographed (silica gel), eluting with CH2Cl2 to afford compound 841B (1.60 g, 67%). MS (ES): m/z=294 [M+1]+.

후처리

  1. additionadded slowly so that the reaction temperature
  2. temperaturewas maintained below 5° C
  3. temperaturewhile maintaining the temperature below 5° C
  4. stirringThe suspension was stirred at 0–5° C. for 1 h
  5. extractionThe aqueous layer was extracted with ether
  6. washthe combined organic layers were washed with brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. washeluting with CH2Cl2

출처 및 근거

ORD 기록
ord-8c4393121f3e40f98edf34f926896ba8
출처 데이터셋
uspto-grants-2006_11
특허 번호
US07141578B2

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