申请人:Awano Hirokazu
公开号:US20050143581A1
公开(公告)日:2005-06-30
An alkoxybenzamide represented by the general formula (3):
(wherein R1, R2, R3, R4, and R5 independently indicate a hydrogen atom, an alkyl group having one to six carbon atoms, or an alkoxy group having one to six carbon atoms; if R3 indicates a hydrogen atom or an alkyl group having one to six carbon atoms, R1 indicates an alkoxy group having one to six carbon atoms and R4 indicates an alkyl or alkoxy group having one to six carbon atoms; two adjacent substituents may be coupled with a cross-linking group to form a ring; R6 indicates a heteroaromatic ring; and A indicates an oxygen atom or a sulfur atom) is produced by reacting an alkoxybenzene represented by the general formula (1):
(wherein R1, R2, R3, R4, and R5 are defined above) with an isocyanate represented by the general formula (2):
(wherein R6 and A are defined above; and n indicates 1 or 2) in the presence of a Lewis acid. Among isocyanates represented by the general formula (2) is a thiazolyl isocyanate represented by the general formula (5):
(wherein R1 indicates a hydrogen atom, a saturated or unsaturated alkyl group having one to six carbon atoms, a haloalkyl group having one to six carbon atoms, an alkoxy group having one to six carbon atoms, an alkoxycarbonyl group, or an acyl group; R2 indicates a hydrogen atom, a halogen atom, a saturated or unsaturated alkyl group having one to six carbon atoms, a haloalkyl group having one to six carbon atoms, an alkoxycarbonyl group having one to six carbon atoms, an acyl group, or a substituted or unsubstituted phenyl group; both R1 and R2 do not indicate a hydrogen atom; and n indicates 1 or 2). This thiazolyl isocyanate is produced from two precursors: an aminothiazole and a carbonyl halide. The present invention can provide a method for producing a high yield of alkoxybenzamide with fewer steps, and can also provide thiazolyl isocyanates, which are useful in the production of ureas, carbamates, and aromatic amides having a thiazole ring.
通式(3)表示的烷氧基苯甲酰胺:(其中R1、R2、R3、R4和R5独立地表示氢原子、具有1至6个碳原子的烷基或具有1至6个碳原子的烷氧基;如果R3表示氢原子或具有1至6个碳原子的烷基,则R1表示具有1至6个碳原子的烷氧基,R4表示具有1至6个碳原子的烷基或烷氧基;两个相邻的取代基可以与交联基耦合形成环;R6表示杂环芳烃环;A表示氧原子或硫原子),通过在路易斯酸的存在下将通式(1)表示的烷氧基苯与通式(2)表示的异氰酸酯反应而制得:(其中R1、R2、R3、R4、R5、R6和A的定义如上;n表示1或2)。通式(2)表示的异氰酸酯中包括通式(5)表示的噻唑基异氰酸酯:(其中R1表示氢原子、具有1至6个碳原子的饱和或不饱和烷基、具有1至6个碳原子的卤代烷基、具有1至6个碳原子的烷氧基、烷氧羰基、或酰基;R2表示氢原子、卤素原子、具有1至6个碳原子的饱和或不饱和烷基、具有1至6个碳原子的卤代烷基、具有1至6个碳原子的烷氧羰基、酰基或取代或未取代的苯基;R1和R2均不表示氢原子;n表示1或2)。该噻唑基异氰酸酯由两个前体物质产生:氨基噻唑和羰基卤化物。本发明可以提供一种生产高产率烷氧基苯甲酰胺的方法,步骤更少,也可以提供噻唑基异氰酸酯,其在尿素、氨基甲酸酯和带有噻唑环的芳香酰胺的生产中有用。