Chlorosuccinimide → Alpha-chlorobenzaldoxime

HRID 2219298

Reaktionsgleichung

Reaktionsgleichung von HRID 2219298
[CH:1](=[N:8]/[OH:9])/[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:10]N1C(=O)CCC1=O>CN(C=O)C>[OH:9]/[N:8]=[C:1](\[Cl:10])/[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

4

Edukt 2

HCID 31398ChlorosuccinimideHCID 5324470Syn-benzaldehyde oxime

Produkt 1

HCID 5706359Alpha-chlorobenzaldoximeAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of (E)- and/or (Z)-benzaldehyde-oxime (5.27 g, 44 mmol) in DMF (44 mL) was added N-chlorosuccinimide (5.81 g, 44 mmol) portionwise over 1 h, keeping the temperature below 35° C. The reaction mixture was stirred at room temperature overnight. The mixture was then poured onto ice-water, and extracted with ethyl acetate. The combined organic layers were then washed with water and brine, dried over sodium sulphate and evaporated to afford the title compound (5.91 g, 87%) which was obtained as a light yellow solid. MS m/e (EI): 155.0 [M].

Aufarbeitung

  1. customthe temperature below 35° C
  2. additionThe mixture was then poured onto ice-water
  3. extractionextracted with ethyl acetate
  4. washThe combined organic layers were then washed with water and brine
  5. dry with materialdried over sodium sulphate
  6. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-d7ffc38c69cb4108bb7f9423e7f8b582
Quelldatensatz
uspto-grants-2008_08
Patentnummer
US07414061B2

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