摘要：脒类化合物在农药和医药上用途很广，因此脒类化合物的合成也受到了很多有机合成专家的关注，发展简便温和制备脒的方法是我们不断努力的方向。本文是以对氯硝基苯和对叔丁基苯酚为原料，在碳酸钾的存在下，制备了中间体（I）4-硝基-4’-叔丁基二苯醚，然后将中间体（I）与氯化铵和还原Fe粉在乙醇和水的混合溶剂下，发生还原反应得到中间体（Ⅱ）对叔丁基苯氧基苯胺，将中间体（Ⅱ）溶于甲酸反应，得到中间体（Ⅲ）对叔丁基苯氧基甲酰苯胺，最后将中间体（Ⅲ）先与三乙胺反应10分钟后，再逐滴滴入三氯氧磷反应一段时间后，加入二乙胺反应得到该目标化合物。本文主要探讨了反应温度、催化剂用量、原料摩尔比、反应时间对目标化合物合成的影响，得到最佳条件：反应温度为100度，10%的氧化亚铜催化剂，原料的摩尔比为1：1.6，反应时间为4h。在此条件下，目标化合物的收率达80%以上，并通过1HNMR对所合成的新化合物进行结构确认和表征。24573
毕业论文关键词：4-硝基-4’-叔丁基二苯醚；对叔丁基苯氧基苯胺；对叔丁基苯氧基甲酰苯胺；N,N-二乙基对叔丁基苯氧基苯甲脒 ；合成；
synthesis of N,N-diethyltertbutylphenoxy benzamidine
Abtract: Amidine compounds are very useful in both pesticides and pharmaceuticals, so the synthesis of amidine compounds has also been a concern of many experts in organic synthesis, developing simple and gentle method for synthesis amidines is the direction of our continuous efforts.In this article,we use p-chloronitrobenzene and p-tert-butylphenol as a raw material in the presence of potassium carbonate to get the intermediate (I) 4 - nitro-4'-t-butyl diphenylether, and then the intermediate (I) reacts with Fe powder and ammonium chloride in a mixed solvent of ethanol and water to give the intermediate (Ⅱ) 4-tert-butylphenoxy-phenylamine, then the intermediate (Ⅱ) dissolve in formic acid to give the intermediate (Ⅲ) 4-tert-butyl-phenoxy-phenylformamide, finally， intermediate (Ⅲ) first reacts with triethylamine for 10 minutes and then added phosphorus oxychloride drop by drop ,and then reacts with diethylamine immediately to give the aimed compound. In addition, this article make a research about the effect that the change of reaction temperature, amount of catalyst, the molar ratio and reaction time will have on the synthesis of amdine compound.The best condition is that reaction temperature is 100, 10% catalyst, the molar ratio is 1:1.6,and react for 4h.Under this condition, We can achieve product with yield of 80%,and the amdine compound’s structure and characterization have been comfirmed by 1HNMR.
Key words: 4-nitro-4'-tbutyldiphenylether; 4-tert-butylphenoxy-phenylamine; 4-tert-butyl-phenoxy-phenylformamide; N,N-diethyltertbutylphenoxy benzamidine; synthesis
目 录
1.前言1
1.1脒类化合物的简介•1
1.2脒类化合物的用途•1
1.3 脒类化合物的前景•2
1.4 国内外脒类化合物的合成方法•2
1.4.1二取代脒的合成方法3
1.4.2脒的其它合成方法8
1.5 本课题的研究意义与研究内容•9
1.5.1研究意义9
1.5.2 研究内容10
1.6 合成思路10
1.6.1合成路线•10
1.7方案论证•11
2 实验部分•12
2.1 仪器与试剂12
2.1.1 仪器•12
2.1.2 试剂•12
2.2 实验过程论述12
2.2.1 4-硝基-4’-叔丁基二苯醚的制备13
2.2.2 对叔丁基苯氧基苯胺的制备•13
2.2.3对叔丁基苯氧基甲酰苯胺的合成•13
2.2.4 目标化合物的制备•14
3. 结果与讨论•16
3.1关于4-硝基-4’-叔丁基二苯醚的合成16 N,N-二乙基对叔丁基苯氧基苯甲脒的合成:http://www.751com.cn/yixue/lunwen_18132.html