Chlorosuccinimide → 2-chloro-6-fluoro-N-hydroxybenzimidoyl chloride

HRID 2047235

Reaktionsgleichung

Reaktionsgleichung von HRID 2047235
[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([F:11])[C:3]=1/[CH:4]=[N:5]/[OH:6].[Cl:12]N1C(=O)CCC1=O>CN(C)C=O>[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([F:11])[C:3]=1[C:4]([Cl:12])=[N:5][OH:6]

Komponenten

4

Edukt 2

HCID 31398ChlorosuccinimideHCID 73293182-Chloro-6-fluorobenzaldehyde oxime

Produkt 1

HCID 713670442-chloro-6-fluoro-N-hydroxybenzimidoyl chlorideAusbeute 697,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of (E)-2-chloro-6-fluorobenzaldehyde oxime (2 g) in 10 mL Dimethylformamide (DMF) at room temperature 0.23 g N-Chlorosuccinimide (NCS) were added. Dry hydrogen chloride was bubbled into the DMF solution until the reaction temperature rise up to 35° C. Then 1.21 g N-chloro-succinimide were added in portions, the temperature was kept at 35-45° C. The reaction mixture was cooled to room temperature and poured into 30 mL ice and extracted with ether. Combined extracts were dried and evaporated to give 2.5 g of 2-chloro-6-fluoro-N-hydroxybenzimidoyl chloride as a yellow oil.

Aufarbeitung

  1. customDry hydrogen chloride was bubbled into the DMF solution until the reaction temperature rise up to 35° C
  2. additionThen 1.21 g N-chloro-succinimide were added in portions
  3. customwas kept at 35-45° C
  4. additionpoured into 30 mL ice
  5. extractionextracted with ether
  6. customCombined extracts were dried
  7. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-eeb1ec58b9d94bbaad975e33a2f8b30a
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08592456B2

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