Chlorosuccinimide → 4-Chloro-N-hydroxybenzimidoyl chloride

HRID 1911649Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1911649
[Cl:1][C:2]1[CH:10]=[CH:9][C:5](/[CH:6]=[N:7]\[OH:8])=[CH:4][CH:3]=1.[Cl:11]N1C(=O)CCC1=O>CN(C=O)C>[OH:8]/[N:7]=[C:6](\[Cl:11])/[C:5]1[CH:9]=[CH:10][C:2]([Cl:1])=[CH:3][CH:4]=1

Komponenten

4

Edukt 2

HCID 31398ChlorosuccinimideHCID 5354056anti-p-Chlorobenzaldoxime

Produkt 1

HCID 72718654-Chloro-N-hydroxybenzimidoyl chlorideAusbeute 86,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of (E)- and/or (Z)-4-chloro-benzaldehyde oxime (27.0 g, 173 mmol) in DMF (173 mL) was added N-chlorosuccinimide (22.8 g, 173 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 (28.4 g, 86%) which was obtained as a light yellow solid. MS: m/e=189.1 [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-95d443c3c76c4799a3bbce96a955578f
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08604062B2

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