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

HRID 751072ノート

反応式

HRID 751072 の反応式
[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]

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
2.5 °C

実験手順

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]+.

後処理

  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

出典と根拠

ORDレコード
ord-dbd1348a9375478fb789dfbb824cf7b4
出典データセット
uspto-grants-2008_07
特許番号
US07405234B2

反応ノート

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