2-甲氧基-3-(1-甲基-1H-1,2,4-三唑-3-基)苯胺的合成工艺研究

Study on the Synthesis of 2-methoxy-3-(1-methyl-1H-1,2,4-triazole-3-yl)Aniline

目的研究2-甲氧基-3-(1-甲基-1H-1,2,4-三唑-3-基)苯胺的合成工艺。方法以2-羟基-3-硝基苯甲酸甲酯为原料经两步取代得到2-甲氧基-3-硝基苯甲酰胺(3),3与劳森试剂反应制得2-甲氧基-3-硝基苯并硫代酰胺(7),7与碘甲烷反应制得2-甲氧基-3-硝基苯并亚氨基硫代甲酸甲酯(8),8与1-甲基肼甲酸叔丁酯反应制得2-(亚氨基(2-甲氧基-3-硝基苯基)甲基)-1-甲基肼甲酸叔丁酯(9),9经取代,还原得到目标化合物2-甲氧基-3-(1-甲基-1H-1,2,4-三唑-3-基)苯胺。结果目标化合物总收率为45.8%,结构经1H NMR和MS表征确证。结论本合成工艺各步反应条件温和易操作,后处理简单,降低了原料成本,增加了反应稳定性,可为工业化生产提供参考。

Objective To study the synthesis of 2-methoxy-3-(1-methyl-1 H-1,2,4-triazole-3-yl)aniline.Methods 2-Methoxy-3-nitrobenzoate acid methyl ester was used as a raw material to synthesize 2-methoxy-3-nitrobenzamide(3)by two-step substitution,and 3 was reacted with Lawson’s reagent to obtain 2-methoxy-3-nitrobenzothioamide(7),7 reacts with methyl iodide to obtain methyl 2-methoxy-3-nitrobenzoiminothioformate(8),8 and 1-methyl Tert-Butyl hydrazine formate was prepared to give 2-(imino(2-methoxy-3-nitrophenyl)methyl)-1-methyl tert-butyl hydrazine(9),9 was substituted and reduced.The target compound was 2-methoxy-3-(1-methyl-1 H-1,2,4-triazole-3-yl)aniline.Results The total yield of the target compound was 45.8%and the structure was characterized by 1 H NMR and MS.Conclusion The reaction conditions of each step in the synthesis process are mild and easy to operate,the post-treatment is simple,the cost of raw materials is reduced,the reaction stability is increased,and it can provide a reference for industrial production.