Studies on s-Triazines. VII. A New Method of Preparing 2-Methyl-4,6-bis(trichloromethyl)-s-triazine

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During the liquid-phase chlorination of CH3CN, a trimerization reaction occurred to yield four s-triazine derivatives, 2-methyl-4,6-bis(trichloromethyl)-s-triazine (I), 2-chloromethyl-4,6-bis(trichloromethyl)-s-triazine (II), 2-dichloromethyl-4,6-bis(trichloromethyl)-s-triazine (III), and 2,4,6-tris(trichloromethyl)-s-triazine (IV). The structure of each s-triazine derivative has been assigned on the basis of the results of elemental analysis and the spectral (particularly Mass and NMR) data after each derivative had been separated in a pure form using the gas-liquid chromatographic (GLC) method. The product composition was seen to depend upon the rate of the chrorination of CH3CN and the presence of a catalyst. The s-triazine I was shown to be the precursor of the s-triazines II and III; the pathways for the formation of the s-triazine IV were also investigated. Then, the selective cotrimerization of CH3CN with its chlorinated compounds was investigated; this yielded the s-triazine I, a useful intermediate of pesticides and resines. The reaction was found to provide a new method of preparing s-triazine I.
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