Benzoyl Peroxide → HCID 22615271, compound

HRID 842708

Reaction equation

HRID 842708 reaction equation
C1C(=O)N([Cl:8])C(=O)C1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.[Cl:27][C:28]1[C:33]([C:34]#[N:35])=[CH:32][CH:31]=[C:30]([CH3:36])[N:29]=1>C1C=CC=CC=1>[Cl:27][C:28]1[C:33]([C:34]#[N:35])=[CH:32][CH:31]=[C:30]([CH2:36][Cl:8])[N:29]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 31398ChlorosuccinimideHCID 5204002-Chloro-6-methylpyridine-3-carbonitrile

Product 1

HCID 22615271HCID 22615271, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

NCS (1.44 g, 10.8 mmol) and benzoyl peroxide (238 mg, 0.98 mmol) were added to a stirred solution of 2-chloro-3-cyano-6-methyl-pyridine (750 mg, 4.92 mmol) in benzene (35 mL) and the mixture was heated to reflux. After 4 h, the mixture was cooled and filtered. The filtrate was diluted with ethyl acetate and was washed with sodium metabisulfite solution, water and brine, dried (Na2SO4) and evaporated in vacuo. The residue was purified by chromatography on silica (chloroform) to give the title compound:

Workup

  1. temperaturethe mixture was heated to reflux
  2. temperaturethe mixture was cooled
  3. filtrationfiltered
  4. additionThe filtrate was diluted with ethyl acetate
  5. washwas washed with sodium metabisulfite solution, water and brine
  6. dry with materialdried (Na2SO4)
  7. customevaporated in vacuo
  8. customThe residue was purified by chromatography on silica (chloroform)

Sources & evidence

ORD record
ord-770e2c5221a6477481db72971c6ebf26
Source dataset
uspto-grants-2002_04
Patent number
US06376499B1

Linked notes

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