tert-Butylsulfinamide, (S)-(-)- → (NE,S)-N-[[1-(4-chlorophenyl)imidazol-4-yl]methylidene]-2-methylpropane-2-sulfinamide

HRID 57430

Reaktionsgleichung

[C:1]([S@@:5]([NH2:7])=[O:6])([CH3:4])([CH3:3])[CH3:2].[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]2[CH:19]=[C:18]([CH:20]=O)[N:17]=[CH:16]2)=[CH:11][CH:10]=1.CCOC(C)=O.CCCCCCC>ClCCCl.[O-]S([O-])(=O)=O.[Cu+2]>[Cl:8][C:9]1[CH:10]=[CH:11][C:12]([N:15]2[CH:19]=[C:18](/[CH:20]=[N:7]/[S@:5]([C:1]([CH3:4])([CH3:3])[CH3:2])=[O:6])[N:17]=[CH:16]2)=[CH:13][CH:14]=1

Komponenten

Reaktionsbedingungen

Temperatur: 60 °C

Versuchsvorschrift

To a suspension of (S)-(−)tert-Butanesulfinamide (2.35 g, 19.4 mmol) and 1-(4-chlorophenyl)-1H-imidazole-4-carbaldehyde (4 g, 19.4 mmol) in DCE (39 mL) was added CuSO4 (4.63 g, 29.0 mmol). The reaction mixture was heated at 60° C. for 18 hours in a oil bath. A dark brown suspension resulted. The reaction mixture was then cooled to room temperature, filtered through a pad of celite, rinsed with DCM. The solution was then concentrated onto silica gel. Silica gel column chromatography (EtOAc/Heptane 0 to 100%) provided (S,E)-N-((1-(4-chlorophenyl)-1H-imidazol-4-yl)methylene)-2-methylpropane-2-sulfinamide (1.69 g, 5.45 mmol, 28.2% yield) as a light brown solid. LCMS m/z 310.0 (M+H)+, Rt 0.75 min.

Aufarbeitung

customA dark brown suspension resulted
temperatureThe reaction mixture was then cooled to room temperature
filtrationfiltered through a pad of celite
washrinsed with DCM
concentrationThe solution was then concentrated onto silica gel

Quellen und Nachweise

ORD-Eintrag: ord-a02c78eb5d294e7cb5773fcd0cb41ece
Quelldatensatz: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09434719B2

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