Chlorosuccinimide → HCID 72255376, compound

HRID 2423489Notes

Reaction equation

HRID 2423489 reaction equation
[Cl:1][C:2]1[C:7]([CH:8]=[N:9][OH:10])=[C:6]([Cl:11])[CH:5]=[CH:4][N:3]=1.[Cl:12]N1C(=O)CCC1=O>CN(C=O)C>[Cl:1][C:2]1[C:7]([C:8]([Cl:12])=[N:9][OH:10])=[C:6]([Cl:11])[CH:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 72488567HCID 72488567, compound

Product 1

HCID 72255376HCID 72255376, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
64 °C

Procedure

A solution of 2,4-dichloro-3-pyridinecarbaldehyde oxime (1.88 g, 9.9 mmol) in DMF (7.9 mL) was stirred as N-chlorosuccinimide (1.32 g, 9.9 mmol) was added. The solution was stirred in a 64° C. oil bath for 1 hour then allowed to cool to room temperature. The solution was poured onto ice. The solution was extracted with ether and the organic layer was washed with brine, dried with MgSO4, filtered and concentrated to yield 2,4-dichloro-N-hydroxy-3-pyridinecarboximidoyl chloride (1.94 g, 87%). 1H NMR (400 MHz, DMSO-d6): δ 12.89 (s, 1H), 8.52 (d, J=5 Hz, 1H), 7.81 (d, J=5 Hz, 1H).

Workup

  1. additionwas added
  2. temperatureto cool to room temperature
  3. additionThe solution was poured onto ice
  4. extractionThe solution was extracted with ether
  5. washthe organic layer was washed with brine
  6. dry with materialdried with MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-0ae1874739c54d9890583589b1d96af0
Source dataset
uspto-grants-2011_06
Patent number
US07960552B2

Reaction notes

Loading…