N-Ethyl-N-benzylaniline → N-benzyl-N-(4-bromophenyl)-N-ethylamine

HRID 432207

反応式

HRID 432207 の反応式
[CH2:1]([N:8]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:9][CH3:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:17]C1C(=O)C(Br)=CC(Br)(Br)C=1>ClCCl>[CH2:1]([N:8]([C:11]1[CH:16]=[CH:15][C:14]([Br:17])=[CH:13][CH:12]=1)[CH2:9][CH3:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

4

反応物 2

HCID 7098N-Ethyl-N-benzylanilineHCID 884332,4,4,6-Tetrabromocyclohexa-2,5-dienone

生成物 1

HCID 22347350N-benzyl-N-(4-bromophenyl)-N-ethylamine収率 76.6%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

N-benzyl-N-phenyl-N-ethylamine (2.25 g, 0.0107 mol) was dissolved in anhydrous dichloromethane (80 mL) and 2,4,4,6-tetrabromocyclohexadiene-1-one (4.36 g, 0.0107 mol) was added in 6 equal portions over a 20 min. period. Stirring was continued at ambient temperature for 20 hours; the organic phase was successively washed with 0.5N solution of sodium hydroxide in water (50 mL), 1N solution of sodium hydroxide in water (50 mL), water (70 mL) and brine (75 mL). The organic phase was dried with magnesium sulfate and concentrated under reduced pressure. The residue was purified by flash chromatography on silica using ethyl acetate/n-heptane (1:99) as mobile phase to yield N-benzyl-N-(4-bromophenyl)-N-ethylamine (2.38 g, 0.0082 mol) as a colorless oil.

後処理

  1. washthe organic phase was successively washed with 0.5N solution of sodium hydroxide in water (50 mL), 1N solution of sodium hydroxide in water (50 mL), water (70 mL) and brine (75 mL)
  2. dry with materialThe organic phase was dried with magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by flash chromatography on silica

出典と根拠

ORDレコード
ord-accf4bcf582142b2b40bfe74ca528ad4
出典データセット
uspto-grants-2003_12
特許番号
US06660744B1

関連ノート

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