tert-Butylsulfinamide, (R)-(+)- → (NZ,R)-N-[(4-bromo-2-chlorophenyl)methylidene]-2-methylpropane-2-sulfinamide

HRID 40280

Reaktionsgleichung

Reaktionsgleichung von HRID 40280
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[C:4]([Cl:10])[CH:3]=1.[CH3:11][C:12]([S@:15]([NH2:17])=[O:16])([CH3:14])[CH3:13]>C(Cl)Cl.S([O-])([O-])(=O)=O.[Cu+2]>[Br:1][C:2]1[CH:9]=[CH:8][C:5](/[CH:6]=[N:17]\[S@@:15]([C:12]([CH3:14])([CH3:13])[CH3:11])=[O:16])=[C:4]([Cl:10])[CH:3]=1

Komponenten

5

Edukt 2

HCID 10964479tert-Butylsulfinamide, (R)-(+)-HCID 141091094-Bromo-2-chlorobenzaldehyde

Produkt 1

HCID 57691068(NZ,R)-N-[(4-bromo-2-chlorophenyl)methylidene]-2-methylpropane-2-sulfinamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24462Copper SulfateKatalysatorHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
37 °C

Versuchsvorschrift

A suspension of 4-bromo-2-chlorobenzaldehyde (1150 mg, 5240 μmol), (r)-(+)-2-methyl-2-propanesulfinamide (1588 mg, 13100 μmol), copper(ii) sulfate (696.4 μl, 15720 μmol) in DCM (10 mL) was stirred at 37° C. for 78 h. Reaction filtered through Celite, and solid washed repeatedly with DCM. Filtrate concentrated then purified on silica (80 g) eluting product with 0>30% of EtOAc/Hex. MS (ESI pos. ion) m/z: 322/324 (MH+). Calc'd exact mass for C11H13BrClNOS: 321/323.

Aufarbeitung

  1. customReaction
  2. filtrationfiltered through Celite, and solid
  3. washwashed repeatedly with DCM
  4. concentrationFiltrate concentrated
  5. customthen purified on silica (80 g)
  6. washeluting product with 0>30% of EtOAc/Hex

Quellen und Nachweise

ORD-Eintrag
ord-4f79440e739e4ef3b2297af9766d349c
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524900B2

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