Trichloroisocyanuric Acid → 3-Chloro-6-(chloromethyl)pyridazine

HRID 2188632Notes

Reaction equation

HRID 2188632 reaction equation
[Cl:1][C:2]1[N:3]=[N:4][C:5]([CH3:8])=[CH:6][CH:7]=1.[Cl:9]N1C(=O)N(Cl)C(=O)N(Cl)C1=O>C(Cl)(Cl)Cl>[Cl:1][C:2]1[N:3]=[N:4][C:5]([CH2:8][Cl:9])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6909Trichloroisocyanuric AcidHCID 2272543-Chloro-6-methylpyridazine

Product 1

HCID 224986393-Chloro-6-(chloromethyl)pyridazine

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a refluxing solution of 3-chloro-6-methylpyridazine (5.0 g, 39 mmol) in chloroform (75 mL) was added trichloroisocyanuric acid (3.6 g, 16 mmol) portionwise. The solution was allowed to reflux overnight, after which the crude reaction mixture was filtered, washed with 1 M sodium hydroxide (NaOH), and the organic phase was dried over magnesium sulfate. The crude product was concentrated under reduced pressure and purified by silica gel chromatography to furnish 3-chloro-6-chloromethyl-pyridazine (D) as a yellow oil which upon sitting became a brown solid=2.9 g (46%).

Workup

  1. temperatureto reflux overnight
  2. customafter which the crude reaction mixture
  3. filtrationwas filtered
  4. washwashed with 1 M sodium hydroxide (NaOH)
  5. dry with materialthe organic phase was dried over magnesium sulfate
  6. concentrationThe crude product was concentrated under reduced pressure
  7. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-a7436a11508b40b799cdf29d76a132e9
Source dataset
uspto-grants-2012_12
Patent number
US08324209B2

Reaction notes

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