Chlorosuccinimide → 5-bromo-N-hydroxy-pyridine-2-carboximidoyl chloride

HRID 459011Notes

Reaction equation

HRID 459011 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]=[N:9][OH:10])=[N:6][CH:7]=1.[Cl:11]N1C(=O)CCC1=O>CN(C=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([Cl:11])=[N:9][OH:10])=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 1363756105-Bromopyridine-2-carbaldehyde oxime

Product 1

HCID 1363851125-bromo-N-hydroxy-pyridine-2-carboximidoyl chlorideYield 94.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-Bromopyridine-2-carbaldehyde oxime (49.5 g, 246.3 mmol) was dissolved in DMF (150 ml) followed by addition of N-chlorosuccinimide (39.5 g, 295.5 mmol). HCl gas was then bubbled in the solution for 20 seconds to initiate the reaction, which was then allowed to stir for 1 hr. The reaction was poured into distilled water (1 L) and the precipitate was collected by vacuum filtration. The filter cake was washed with distilled water (2×500 ml) and then dried overnight in a vacuum oven at 60° C. (−30 inches Hg) to yield the product as a white powder (55 g).

Workup

  1. customHCl gas was then bubbled in the solution for 20 seconds
  2. customthe reaction, which
  3. additionThe reaction was poured
  4. distillationinto distilled water (1 L)
  5. filtrationthe precipitate was collected by vacuum filtration
  6. washThe filter cake was washed with distilled water (2×500 ml)
  7. customdried overnight in a vacuum oven at 60° C. (−30 inches Hg)

Sources & evidence

ORD record
ord-5a05e44e0801433ab2e585f365eba3f5
Source dataset
uspto-grants-2007_03
Patent number
US07192974B2

Reaction notes

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