tert-Butylsulfinamide, (S)-(-)- → (NE,S)-N-[(4-chloro-3,5-dimethylphenyl)methylidene]-2-methylpropane-2-sulfinamide

HRID 1629734Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1629734
[Cl:1][C:2]1[C:9]([CH3:10])=[CH:8][C:5]([CH:6]=O)=[CH:4][C:3]=1[CH3:11].[CH3:12][C:13]([S@@:16]([NH2:18])=[O:17])([CH3:15])[CH3:14]>C1(C)C=CC=CC=1.CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[Cl:1][C:2]1[C:9]([CH3:10])=[CH:8][C:5](/[CH:6]=[N:18]/[S@:16]([C:13]([CH3:15])([CH3:14])[CH3:12])=[O:17])=[CH:4][C:3]=1[CH3:11]

Komponenten

5

Edukt 2

HCID 11355477tert-Butylsulfinamide, (S)-(-)-HCID 222596964-Chloro-3,5-dimethylbenzaldehyde

Produkt 1

HCID 58374474(NE,S)-N-[(4-chloro-3,5-dimethylphenyl)methylidene]-2-methylpropane-2-sulfinamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11026Titanium isopropoxideKatalysatorHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

A solution of 4-chloro-3,5-dimethyl-benzaldehyde (2 g, 11.86 mmol) and (S)-2-methylpropane-2-sulfinamide (1.58 g, 13.05 mmol) in toluene (35 mL) was treated with titanium(IV) isopropoxide (5.27 mL, 17.79 mmol). The mixture was stirred at 50° C. for 24 hours. It was then quenched with 10% sodium bicarbonate solution (50 mL) and extracted twice with EtOAc. The organic layers were washed with water and brine, dried over sodium sulfate, filtered and concentrated. The crude was purified by chromatography on silica gel (cyclohexane/EtOAc).

Aufarbeitung

  1. customIt was then quenched with 10% sodium bicarbonate solution (50 mL)
  2. extractionextracted twice with EtOAc
  3. washThe organic layers were washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude was purified by chromatography on silica gel (cyclohexane/EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-df4e142fd0454214bc944c15e0f05826
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08791100B2

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