tert-Butylsulfinamide, (R)-(+)- → (NE)-N-[(2-chloro-3-fluorophenyl)methylidene]-2-methylpropane-2-sulfinamide

HRID 80534

Reaktionsgleichung

Reaktionsgleichung von HRID 80534
[Cl:1][C:2]1[C:9]([F:10])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=O.[CH3:11][C:12]([S@:15]([NH2:17])=[O:16])([CH3:14])[CH3:13]>ClCCl.CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[Cl:1][C:2]1[C:9]([F:10])=[CH:8][CH:7]=[CH:6][C:3]=1/[CH:4]=[N:17]/[S:15]([C:12]([CH3:14])([CH3:13])[CH3:11])=[O:16]

Komponenten

5

Edukt 2

HCID 10964479tert-Butylsulfinamide, (R)-(+)-HCID 149449052-Chloro-3-fluorobenzaldehyde

Produkt 1

HCID 88924234(NE)-N-[(2-chloro-3-fluorophenyl)methylidene]-2-methylpropane-2-sulfinamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11026Titanium isopropoxideKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

2-Chloro-3-fluorobenzaldehyde (2.5 g) and (R)-(+)-2-methyl-2-propanesulfinamide were dissolved in dichloromethane (50 ml), and then titanium(IV) isopropoxide (23.6 ml) was added. The mixture was heated for three hours under reflux, then poured onto ice (150 g) and stirred vigorously for ten minutes. The mixture was filtered through kieselguhr and the filtrate was extracted with dichloromethane (3×50 ml). The organic phase was dried (Na2SO4), filtered and concentrated under reduced pressure. The product (4 g) was used further without further purification.

Aufarbeitung

  1. temperatureThe mixture was heated for three hours
  2. temperatureunder reflux
  3. additionpoured onto ice (150 g)
  4. filtrationThe mixture was filtered through kieselguhr
  5. extractionthe filtrate was extracted with dichloromethane (3×50 ml)
  6. dry with materialThe organic phase was dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe product (4 g) was used further without further purification

Quellen und Nachweise

ORD-Eintrag
ord-77f803d76031470495a65644be01caf6
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846666B2

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