Dimethyl Sulfoxide → 4-((2-Hydroxyethyl)amino)benzonitrile

HRID 874117ノート

反応式

HRID 874117 の反応式
F[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.[NH2:10][CH2:11][CH2:12][OH:13].C(=O)([O-])[O-].[K+].[K+].CS(C)=O>O>[OH:13][CH2:12][CH2:11][NH:10][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1

参加物

6

反応物 4

HCID 679Dimethyl SulfoxideHCID 700EthanolamineHCID 11430Potassium CarbonateHCID 145174-Fluorobenzonitrile

生成物 1

HCID 2946154-((2-Hydroxyethyl)amino)benzonitrile収率 72.6%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
100 °C

実験手順

A mixture of 4-fluorobenzonitrile (6.06 g), 2-aminoethanol (3.71 g), potassium carbonate (8.29 g) and dimethyl sulfoxide (50 mL) was stirred at 100° C. overnight. Water (200 mL) was added to the reaction mixture and the mixture was extracted with ethyl acetate (200 mL×4). The ethyl acetate layer was washed with saturated brine (100 mL), dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluted with ethyl acetate:hexane=30:70, then 50:50, then 80:20, then ethyl acetate) to give 4-[(2-hydroxyethyl)amino]benzonitrile (5.89 g) as a yellow solid.

後処理

  1. extractionthe mixture was extracted with ethyl acetate (200 mL×4)
  2. washThe ethyl acetate layer was washed with saturated brine (100 mL)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (
  6. washeluted with ethyl acetate

出典と根拠

ORDレコード
ord-e9b6d640f69643969562dcd5301ac18a
出典データセット
uspto-grants-2015_03
特許番号
US08980322B2

反応ノート

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