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

HRID 1805264

Reaction equation

HRID 1805264 reaction equation
[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]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 73293182-Chloro-6-fluorobenzaldehyde oxime

Product 1

HCID 713670442-chloro-6-fluoro-N-hydroxybenzimidoyl chlorideYield 697.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-99962c7171a640b1972812f1a7ea7583
Source dataset
uspto-grants-2013_01
Patent number
US08354436B2

Linked notes

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