Practical synthesis of 1-(7-chlorobenzothiazol-2-yl)-1-methylethylamine, a key synthetic intermediate for the production of new oxazine herbicide, MI-3069

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....

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Bibliographic Details
Published in:Journal of Pesticide Science 2001/02/20, Vol.26(1), pp.21-27
Main Authors: Ikeguchi, M. (Ishihara Sangyo Kaisha Ltd., Kusatsu, Shiga (Japan)), Sawaki, M, Maeda, K, Kikugawa, H
Format: Article
Language:English
Subjects:
2-(7-chlorobenzothiazol-2-yl)-1-methylethylamine
Applied sciences
Biological and medical sciences
Chemical control
Chemical industry and chemicals
CHEMICAL SYNTHESIS
ECHINOCHLOA FRUMENTACEA
Exact sciences and technology
Fundamental and applied biological sciences. Psychology
herbicide
HERBICIDES
Industrial chemicals
MI-3069
NEW PRODUCTS
Organic industry
oxazinone
Parasitic plants. Weeds
Phytopathology. Animal pests. Plant and forest protection
PROCESSING
THIAZOLES
Weeds
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Summary: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.
ISSN:0385-1559
1348-589X
1349-0923
DOI:10.1584/jpestics.26.21