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

HRID 874117노트

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HRID 874117 반응식
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

참가 물질

6

반응물 4

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

생성물 1

HCID 2946154-((2-Hydroxyethyl)amino)benzonitrile수율 72.6%

시약·촉매·용매 1

HCID 962Water용매

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온도
100 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-e9b6d640f69643969562dcd5301ac18a
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08980322B2

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