Hydroxylamine HCl → HCID 86759069, Verbindung

HRID 1358156Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1358156
[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=O)[CH2:10][CH2:11][CH3:12])=[CH:5][CH:4]=1.[Cl-].[OH:15][NH3+:16].C([O-])(=O)C.[Na+]>C(O)C.O>[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=[N:16][OH:15])[CH2:10][CH2:11][CH3:12])=[CH:5][CH:4]=1

Komponenten

6

Edukt 3

HCID 21645Hydroxylamine HClHCID 517045Sodium AcetateHCID 18183644HCID 18183644, Verbindung

Produkt 1

HCID 86759069HCID 86759069, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

9.72 g (50 mmol) of 1-(4-Methylsulfanyl-phenyl)-butane-1-one is dissolved in hot ethanol. Then a solution of hydroxylammonium chloride (3.58 g, 51.5 mmol) and sodium acetate (7.0 g, 85 mmol) in 20 ml of water is added, and the reaction solution is stirred at 100° C. for 4 hrs. After cooling and concentrating, water is added. The crude product is extracted with ethyl acetate, washed with brine, dried over MgSO4, and concentrated. The residue is purified by column chromatography on silica gel with ethyl acetate-hexane (20:80) as an eluent. The structure is confirmed by the 1H-NMR spectrum (CDCl3). δ[ppm]: 0.98 (t, 3H), 1.54-1.64 (m, 2H), 2.50 (s, 3H), 2.76 (t, 2H), 7.24 (d, 2H), 7.54 (d, 2H), 7.98 (s, 1H).

Aufarbeitung

  1. temperatureAfter cooling
  2. concentrationconcentrating
  3. additionwater is added
  4. extractionThe crude product is extracted with ethyl acetate
  5. washwashed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated
  8. customThe residue is purified by column chromatography on silica gel with ethyl acetate-hexane (20:80) as an eluent

Quellen und Nachweise

ORD-Eintrag
ord-9c3a7e05a2914a8592ad8ebf384207b8
Quelldatensatz
uspto-grants-2003_07
Patentnummer
US06596445B1

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