tert-Butylsulfinamide, (R)-(+)- → (NE,R)-N-[[5-(4-chlorophenyl)-1,2-oxazol-3-yl]methylidene]-2-methylpropane-2-sulfinamide

HRID 57416

Reaktionsgleichung

Reaktionsgleichung von HRID 57416
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][N:11]=[C:10]([CH:13]=O)[CH:9]=2)=[CH:4][CH:3]=1.[CH3:15][C:16]([S@:19]([NH2:21])=[O:20])([CH3:18])[CH3:17]>ClCCCl.S([O-])([O-])(=O)=O.[Cu+2]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][N:11]=[C:10](/[CH:13]=[N:21]/[S@@:19]([C:16]([CH3:18])([CH3:17])[CH3:15])=[O:20])[CH:9]=2)=[CH:4][CH:3]=1

Komponenten

5

Edukt 2

HCID 10964479tert-Butylsulfinamide, (R)-(+)-HCID 162178165-(4-Chlorophenyl)-1,2-oxazole-3-carbaldehyde

Produkt 1

HCID 90415066(NE,R)-N-[[5-(4-chlorophenyl)-1,2-oxazol-3-yl]methylidene]-2-methylpropane-2-sulfinamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24462Copper SulfateKatalysatorHCID 111,2-DichloroethaneLösungsmittel

Reaktionsbedingungen

Temperatur
55 °C

Versuchsvorschrift

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.

Aufarbeitung

  1. temperatureThe reaction was then cooled to room temperature
  2. filtrationfiltered through a pad of celite
  3. washto wash through
  4. concentrationThe filtrate was concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-40195af71a4d44e48151dbcb19645063
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09434719B2

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