Ethanolamine → 2-(2-Hydroxyethylamino)-1-(4-nitrophenyl)ethanol

HRID 387229

Reaktionsgleichung

Reaktionsgleichung von HRID 387229
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]2[CH2:12][O:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH2:13]([CH2:15][NH2:16])[OH:14]>>[OH:14][CH2:13][CH2:15][NH:16][CH2:12][CH:10]([C:7]1[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1)[OH:11]

Komponenten

3

Edukt 2

HCID 700EthanolamineHCID 922282-(4-Nitrophenyl)oxirane

Produkt 1

HCID 671197212-(2-Hydroxyethylamino)-1-(4-nitrophenyl)ethanolAusbeute 60 %

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

The mixture of 2-(4-nitro-phenyl)-oxirane (24.1 g, 0.15 mol) in ethanolamine (500 mL) was stirred at 40° C. for 2 h, then room temperature for 18 h. The reaction was partitioned between ethyl acetate (200 mL) and water (200 mL) and the aqueous layer was extracted with ethyl acetate (4×100 mL). The combined organic layers were dried over sodium sulfate, filtered and evaporated. The residue was triturated with acetonitrile and collected to give the title compound (19.80 g, 0.09 mmol, 60%) as a white solid. ESMS m/z 227 (M+H)+;

Aufarbeitung

  1. waitroom temperature for 18 h
  2. customThe reaction was partitioned between ethyl acetate (200 mL) and water (200 mL)
  3. extractionthe aqueous layer was extracted with ethyl acetate (4×100 mL)
  4. dry with materialThe combined organic layers were dried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was triturated with acetonitrile
  8. customcollected

Quellen und Nachweise

ORD-Eintrag
ord-8d11bdcb02f448218f1a3e5efe0cc5e6
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08372970B2

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