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

HRID 1425956Notes

Reaction equation

HRID 1425956 reaction equation
[Cl:1]N1C(=O)N(Cl)C(=O)N(Cl)C1=O.[Cl:13][C:14]1[N:15]=[N:16][C:17]([CH3:20])=[CH:18][CH:19]=1>C(Cl)(Cl)Cl>[Cl:13][C:14]1[N:15]=[N:16][C:17]([CH2:20][Cl:1])=[CH:18][CH:19]=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

Conditions

Temperature
60 °C

Procedure

Trichloroisocyanuric acid (3.62 g) was added to a solution of 3-chloro-6-methyl-pyridazine (5.00 g) in chloroform (130 mL) heated to 60° C. The mixture was stirred at 60° C. for 2 h and then at room temperature overnight. The mixture was filtered over Celite and the filtrate was concentrated. The residue was chromatographed on silica gel (cyclohexane/ethyl acetate 98:2→70:30) to give the title compound as a colorless oil that solidified on standing. Yield: 2.48 g (39% of theory); Mass spectrum (ESI+): m/z=163/165/167 (2 Cl) [M+H]+.

Workup

  1. customat room temperature
  2. customovernight
  3. filtrationThe mixture was filtered over Celite
  4. concentrationthe filtrate was concentrated
  5. customThe residue was chromatographed on silica gel (cyclohexane/ethyl acetate 98:2→70:30)

Sources & evidence

ORD record
ord-854afccc18d74bea8421787466162f0f
Source dataset
uspto-grants-2015_01
Patent number
US08933072B2

Reaction notes

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