Chlorosuccinimide → 3-fluoro-N-hydroxybenzene-1-carbonimidoyl chloride

HRID 83201

Reaktionsgleichung

Reaktionsgleichung von HRID 83201
[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)/[CH:5]=[N:6]\[OH:7].[Cl:11]N1C(=O)CCC1=O>CN(C=O)C>[OH:7]/[N:6]=[C:5](\[Cl:11])/[C:4]1[CH:8]=[CH:9][CH:10]=[C:2]([F:1])[CH:3]=1

Komponenten

4

Edukt 2

HCID 31398ChlorosuccinimideHCID 5582750(E)-N-[(3-Fluorophenyl)methylidene]hydroxylamine

Produkt 1

HCID 142213383-fluoro-N-hydroxybenzene-1-carbonimidoyl chlorideAusbeute 73 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of (E)- and/or (Z)-3-fluoro-benzaldehyde oxime (6.9 g, 50 mmol) in DMF (50 mL) was added N-chlorosuccinimide (6.6 g, 50 mmol) portionwise over 1 h, keeping the temperature below 35° C. The reaction mixture was stirred at room temperature for 1 h. 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 sulfate and evaporated to afford the title compound (6.3 g, 73%) which was obtained as an off white solid. MS m/e (EI): 173.1 [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 sulfate
  6. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-91e8c48a772f4e2392986e130f39e660
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846719B2

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