Ethanolamine → 2-Benzamidoethanol

HRID 50989Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 50989
[CH2:1]([CH2:3][NH2:4])[OH:2].[C:5](Cl)(=[O:12])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>C1COCC1>[OH:2][CH2:1][CH2:3][NH:4][C:5](=[O:12])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Komponenten

4

Edukt 2

HCID 700EthanolamineHCID 7412Benzoyl chloride

Produkt 1

HCID 5695262-BenzamidoethanolAusbeute 99,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of ethanolamine (1.09 g, 17.8 mmol) in THF was added benzoyl chloride (520 mg, 3.60 mmol) dropwise at 0° C. under N2 atmosphere. The reaction mixture was stirred for 10 min and then quenched with 1M HCl. The mixture was then diluted with EtOAc and washed with sat. aq. NaHCO3 and brine. The organic layer was dried over MgSO4, filtered and concentrated in vacuo. The residue was crystalized to give N-(2-hydroxyethyl)benzamide (593 mg, 97%) as a white crystalline solid. 1H NMR (CDCl3, 300 MHz) δ3.41 (s, 1H), 3.49-3.59 (m, 2H), 3.75 (t, 2H, J=5.2 Hz), 7.10 (s, 1H), 7.32-7.38 (m, 2H), 7.42-7.48 (m, 1H), 7.72-7.76 (m, 2H) ppm.

Aufarbeitung

  1. customquenched with 1M HCl
  2. additionThe mixture was then diluted with EtOAc
  3. washwashed with sat. aq. NaHCO3 and brine
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was crystalized

Quellen und Nachweise

ORD-Eintrag
ord-073e531e194c45a2b99c068393de2392
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06713471B1

Notizen zur Reaktion

Wird geladen…