1.2.3- Triazine, 4,6-dimethyl-, chlorination

Azomethine group (>C=N-) containing compounds cyolane, cytrolane, chlordimerform, drazoxolon s-Triazines atrazine Chlorinated compounds 2,4-D (2,4-dichlorphenoxyacetic acid), propachlor (2-chloro-A/-2-propylacetanilide), pentachlorophenol, picloram (4-amino-3,5,6-trichloropicolinic acid), hexachlorocyclohexane Nitro-group-containing compounds metaphos (o,o-dimethyl-o-(4-nitrophenyl) thiophosphate, parathion, paraoxon... 

Alkyl groups attached to the triazine ring are quite prone to halogena-tion [77CCC2182 84MI7 89H(29)2253 90H(31)1933], A 70% yield of 6-dichloromethyl-5-trichloromethyl-2-phenyl-l, 2,4-triazine was obtained when 5,6-dimethyl-2-phenyl-l,2,4-triazine was heated at 90°C with chlorine dissolved in an acetic acid-acetic anhydride-sodium acetate mixture [90H(31)1933]. Thionyl chloride similarly chlorinated 58 in the fused saturated ring [89H(29)2253] (Scheme 53). 

The only direct replacement of a proton by a substituent is the halogenation of 1,2,3-triazines I.79-106 Best results (67%) were obtained in the reaction of 4,6-dimethyl-l,2,4-triazine (1, R1 = R2 = Me) with bromine lower yields were obtained with chlorine and the interhalogens. No halogenation was observed with iodine. The unsubstituted (1, R1 = R2 = H) and 4-methyl-... 

N,N-dialkylimidoyl derivatives are also converted by high-temperature chlorination into carbonimidoyl dichlorides C ). For example, 4-dimethyl-amino-2,6-dichloro-l,3,5-triazine (XXXVII) reacts with chlorine via two pathways to yield the traizinylcarbonimidoyl dichloride XXXVIII and chloroform, or cyanuric chloride (XXXIX) and trichloromethylcarbon-imidoyl dichloride (" ). 

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