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Practical Synthesis of 1-(7-Chlorobenzothiazol-2-yl)-1-methylethylamine, a Key Synthetic Intermediate for the Production of New Oxazine Herbicide, MI-3069
Masahiko IKEGUCHI, Masahiko SAWAI, Kazuyuki MAEDA and Hiroshi KIKUGAWA
J. Pestic. Sci.
26, 21-27 (2001)
Practical synthetic routes for the preparation of 1-(7-chlorobenzothiazol-2-yl)-1-methylethylamine (VII), a key intermediate of the barnyardgrass-controlling herbicide, 3-[[1-(7-chlorobenzothiazol-2-yl)-1-methyl]ethyl]-2,3-dihydro-6-methyl-5-phenyl-4H-1,3-oxazin-4-one (MI-3069), were investigated. As the result, the intermediate VII was prepared in an excellent overall yield by cyclization of 2-amino-2-methylpropionitrile with 2-amino-6-chlorothiophenol, which was synthesized by hydrogenation of 2-nitro-6-chlorothiophenol derived from 2,3-dichloronitrobenzene. This practical route consisted of shorter steps with relatively cheaper reactants than the reported method.
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