Hydroxyamine hydrochloride → 2,3-Dichloro-N-{2-[formyl(Hydroxy)amino]ethyl}benzamide

HRID 23813

Reaktionsgleichung

Reaktionsgleichung von HRID 23813
[Cl:1][C:2]1[C:13]([Cl:14])=[CH:12][CH:11]=[CH:10][C:3]=1[C:4]([NH:6][CH2:7][CH:8]=O)=[O:5].Cl.[NH2:16][OH:17].[C:18]([O-:21])(=O)C.[Na+]>CO>[Cl:1][C:2]1[C:13]([Cl:14])=[CH:12][CH:11]=[CH:10][C:3]=1[C:4]([NH:6][CH2:7][CH2:8][N:16]([CH:18]=[O:21])[OH:17])=[O:5]

Komponenten

5

Edukt 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 121339042,3-dichloro-N-(2-oxo-ethyl)-benzamide

Produkt 1

HCID 98384882,3-Dichloro-N-{2-[formyl(Hydroxy)amino]ethyl}benzamideAusbeute 96 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of 2,3-dichloro-N-(2-oxo-ethyl)-benzamide (33 g, 0.14 mol) in MeOH (500 mL) was added hydroxylamine hydrochloride (20 g, 0.28 mol) and sodium acetate (23.6 g, 0.28 mol). The mixture was stirred 1.5 h and the MeOH was removed in vacuo. The residue was partioned between saturated NaHCO3 (200 mL) and dichloromethane/MeOH (9:1; 100 mL). The aqueous layer was extracted (4×100 mL) with dichloromethane/MeOH (9:1). The combined organic extracts were washed with brine (50 mL), were dried (Na2SO4) and were concentrated to provide the title compound (34.3 g, 96%) as a 1:1 mixture of cis and trans isomers as a clear, pale brown oil. 1H NMR (400 MHz, CD3OD): δ 7.66 (m, 1H); 7.45 (m, 3H); 6.78 (t, j=4.1 Hz, 0.5H); 4.30 (d, j=4.1 Hz, 1H); 4.12 (d, j=5.3 Hz, 1H).

Aufarbeitung

  1. customthe MeOH was removed in vacuo
  2. extractionThe aqueous layer was extracted (4×100 mL) with dichloromethane/MeOH (9:1)
  3. washThe combined organic extracts were washed with brine (50 mL)
  4. dry with materialwere dried (Na2SO4)
  5. concentrationwere concentrated

Quellen und Nachweise

ORD-Eintrag
ord-7dd96b6db9174f8eb3739fca06e77bee
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06852882B2

Verknüpfte Notizen

Wird geladen…