4-Isopropylaniline → 4-Isopropyl-N-(2,2-diethoxyethyl)aniline

HRID 751009

反応式

HRID 751009 の反応式
[CH:1]([C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[CH:6][CH:5]=1)([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:18][CH:19]([O:23][CH2:24][CH3:25])[O:20][CH2:21][CH3:22]>CN(C=O)C>[CH:1]([C:4]1[CH:10]=[CH:9][C:7]([NH:8][CH2:18][CH:19]([O:23][CH2:24][CH3:25])[O:20][CH2:21][CH3:22])=[CH:6][CH:5]=1)([CH3:3])[CH3:2]

参加物

5

反応物 3

HCID 74644-Isopropylaniline2 回HCID 11430Potassium CarbonateHCID 74852Ethane, 2-bromo-1,1-diethoxy-

生成物 1

HCID 196009444-Isopropyl-N-(2,2-diethoxyethyl)aniline

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a mixture of 4-isopropylaniline (4.05 g, 30.0 mmol) and potassium carbonate (6.21 g, 45 mmol) in DMF (100 mL) at room temperature was added 2-bromo-1,1-diethoxyethane (6.50 g, 33.0 mmol). The mixture was then stirred at 80-90° C. until all of the 4-isopropylaniline was consumed (24 h). The solvent was removed in vacuo and the residue was treated with dichloromethane (150 mL), washed with water and brine, dried over anhydrous MgSO4, and then concentrated. Chromatography (silica gel, hexanes:ethyl acetate, 9:1) of the crude product, furnished the pure intermediate, N-(4-isopropylphenyl)-2,2-diethoxyethylamine, as a colorless oil (5.71 g, 75.8%). 1H NMR (CDCl3, 300 MHz) δ (ppm) 1.18-1.32(m, 12H), 2.75-2.91 (m, 1H), 3.24 (d, 2H), 3.52-3.62 (m, 2H), 3.67-3.79 (m, 2H), 3.87 (s, br, 1H), 4.70 (t, 1H), 6.60 (d, 2H), 7.05 (d, 2H).

後処理

  1. customwas consumed (24 h)
  2. customThe solvent was removed in vacuo
  3. additionthe residue was treated with dichloromethane (150 mL)
  4. washwashed with water and brine
  5. dry with materialdried over anhydrous MgSO4
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-0bfe98708e7c44049c4ca424b2c2f5dc
出典データセット
uspto-grants-2008_07
特許番号
US07405233B2

関連ノート

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