4-(2-氯-6-(1H-1,2,4-三唑-1-基)苯甲酰胺基)苯甲酸异丙酯的合成

Synthesis of isopropyl 4-(2-chloro-6-(1H-1,2,4-triazol-1-yl)benzamido)benzoate

[目的]开发具有全新结构的小麦全蚀病抑制剂4-(2-氯-6-(1H-1,2,4-三唑-1-基)苯甲酰胺基)苯甲酸异丙酯的合成路线。[方法]以2-氟-6-氯苯甲酸为原料,通过羧酸的酰胺化以及1,2,4-三唑的选择性取代等过程,更高效地合成4-(2-氯-6-(1H-1,2,4-三唑-1-基)苯甲酰胺基)苯甲酸异丙酯;以4-硝基苯甲酸为原料,通过酯化和还原,合成中间体4-氨基苯甲酸异丙酯。各中间体及产品通过1H NMR、13C NMR、元素分析等手段进行了结构表征和确证。[结果]所开发合成路线具有合成步骤少、中间体及产品分离容易,目标化合物的合成收率达到了62%,含量达到了98%。[结论]该合成路线为4-(2-氯-6-(1H-1,2,4-三唑-1-基)苯甲酰胺基)苯甲酸异丙酯的生理生化实验、田间试验及环境实验等样品的获得提供了有力的技术支持。

[Aims] This study aims to explore a new synthetic route of isopropyl 4-(2-chloro-6-(1 H-1,2,4-triazol-1-yl)benzamido)benzoate as an active compound against Gaeumannomyces graminis var. tritici. [Methods] Using2-chloro-6-fluorobenzoic acid as the starting material, isopropyl 4-(2-chloro-6-(1 H-1,2,4-triazol-1-yl)benzamido)benzoate was synthesized smoothly via amidation of carboxylic acid and the C-F selective substitution with 1,2,4-triazole. An important intermediate isopropyl 4-aminobenzoate was also synthesized by esterification and reduction from4-nitrobenzoic acid. The structures of intermediates and product were characterized and confirmed by1 H NMR,13 C NMR and elemental analysis. [Results] The developed procedure had fewer synthetic steps. The intermediates and products could be isolated easily. The yield of the target compound was up to 62% and the purity was up to 98%.[Conclusions] The results provide a technical support for the physiological and biochemical experiments, field experiments and environmental experiments of isopropyl 4-(2-chloro-6-(1 H-1,2,4-triazol-1-yl) benzoate.