Reaktion #85694

ord-40195af71a4d44e48151dbcb19645063

Reaktionsgleichung

O=Cc1cc(-c2ccc(Cl)cc2)on1
5-(4-chlorophenyl)isoxazole-3-carbaldehyde
CC(C)(C)[S@](N)=O
(R)-2-methylpropane-2-sulfinamide
CC(C)(C)[S@@](=O)/N=C/c1cc(-c2ccc(Cl)cc2)on1
(R,E)-N-((5-(4-chlorophenyl)isoxazol-3-yl)methylene)-2-methylpropane-2-sulfinamide

Lösungsmittel

Reaktionsbedingungen

Temperatur
55°CELSIUS
Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    TemperaturThe reaction was then cooled to room temperature
  2. 2
    Filtrationfiltered through a pad of celite
  3. 3
    Waschento wash through
  4. 4
    EinengenThe filtrate was concentrated in vacuo

Vorschrift

A suspension of 5-(4-chlorophenyl)isoxazole-3-carbaldehyde (2.00 g, 9.63 mmol), (R)-2-methylpropane-2-sulfinamide (1.28 g, 10.6 mmol, 1.1 equiv) and anhydrous copper(II) sulfate (2.31 g, 14.5 mmol, 1.5 equiv) in 1,2-dichloroethane (19 mL) was heated at 55° C. for 2-18 hours. The reaction was then cooled to room temperature and filtered through a pad of celite, using 1,2-dichloroethane to wash through. The filtrate was concentrated in vacuo to give crude (R,E)-N-((5-(4-chlorophenyl)isoxazol-3-yl)methylene)-2-methylpropane-2-sulfinamide as a green solid, which was used without further purification. MS m/z 311.0 (M+H)+; Rt-1.11 min.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US09434719B2uspto-grants-2016_09