Water → N-[2-(2,4-dichloro-phenyl)-1-methylethyl]-2-trifluoromethylbenzamide

HRID 389173ノート

反応式

HRID 389173 の反応式
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH2:9][CH:10]([NH2:12])[CH3:11].C(N(CC)CC)C.[F:20][C:21]([F:32])([F:31])[C:22]1[CH:30]=[CH:29][CH:28]=[CH:27][C:23]=1[C:24](Cl)=[O:25].O>O1CCCC1>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH2:9][CH:10]([NH:12][C:24](=[O:25])[C:23]1[CH:27]=[CH:28][CH:29]=[CH:30][C:22]=1[C:21]([F:20])([F:31])[F:32])[CH3:11]

参加物

6

反応物 4

HCID 962WaterHCID 8471TriethylamineHCID 675612-(Trifluoromethyl)benzoyl chlorideHCID 30411751-(2,4-Dichlorophenyl)propan-2-amine

生成物 1

HCID 67223276N-[2-(2,4-dichloro-phenyl)-1-methylethyl]-2-trifluoromethylbenzamide収率 28%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of crude [2-(2,4-dichlorophenyl)-1-methylethyl]amine (about 0.8 g, 3.9 mmol) and triethylamine (0.6 g, 5.9 mmol) in tetrahydrofuran (20 ml) was slowly added dropwise 2-trifluoromethylbenzoyl chloride (0.8 g, 3.8 mmol) at room temperature. After stirring at room temperature for 0.5 hr, water was added and the mixture was extracted with ethyl acetate. The organic layer was washed with 0.5N hydrochloric acid, saturated aqueous sodium hydrogen carbonate, and saturated brine, dried over anhydrous magnesium sulfate, and concentrated. The residue was purified by silica gel column chromatography and recrystallized from a mixed solvent of acetone/n-hexane to give a desired compound (white solid, yield; 0.4 g, 27%).

後処理

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with 0.5N hydrochloric acid, saturated aqueous sodium hydrogen carbonate, and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography
  6. customrecrystallized from a mixed solvent of acetone/n-hexane

出典と根拠

ORDレコード
ord-ed43c68206b34ce2885e2c589be96686
出典データセット
uspto-grants-2013_02
特許番号
US08378114B2

反応ノート

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