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

HRID 723736ノート

反応式

HRID 723736 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

実験手順

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]+.

後処理

  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

出典と根拠

ORDレコード
ord-8c4393121f3e40f98edf34f926896ba8
出典データセット
uspto-grants-2006_11
特許番号
US07141578B2

反応ノート

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