Trichloroisocyanuric Acid → 2-(Chloromethyl)-4,6-dimethylpyridine

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Reaction Steps

A solution of 121.18 g (1 mole) of 2,4,6-collidine in 400 ml of chloroform was heated at reflux while adding in portions 140 g (0.6 mole) of trichloroisocyanuric acid (min. 90% available chlorine) over 4 hours and stirring was continued for another 30 minutes and then cooled and filtered. The filtrate was admixed with 150 ml of 10% HCl to transform the product into the aqueous phase. The decanted acid aqueous phase was mixed with 150 ml of ethyl acetate and was made alkaline with sodium hydroxide. The decanted aqueous phase was extracted with 100 ml of ethyl acetate. The organic phase was dried and evaporated to dryness under reduced pressure to obtain 45 g (28.9%) of 2-chloromethyl-4,6-dimethyl pyridine with a Cl content of 22.78% (theoretical 22.78%) and a boiling point of 64° to 70° C. at 1 mm Hg.

Provenance & Evidence