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A technology of dichlorodiphenylamine and dichloroaniline, which is applied in the field of chemical drug synthesis, can solve the problems of difficult control of intermediates, high production costs, and many wastes, achieve high unit active sites, reduce reaction costs, and reduce usage Effect
Inactive Publication Date: 2019-08-27
郸城县盛斐生物科技有限公司
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Problems solved by technology
Among the three synthetic routes, the intermediates of the 2,6-dichlorophenol synthetic route are not easy to control, and the yield of 2,6-dichlorodiphenylamine is low; the process of the cyclohexanone synthetic route is complicated, there are many wastes and serious pollution; bromine The benzene route will be exchanged to some extent due to the chlorine-bromine atoms in the reaction process, resulting in the contamination of 2,6-dichlorodiphenylamine by bromine, which is difficult to go out, resulting in the preparation of 2,6-dichlorodiphenylamine The quality of the product is difficult to control, the product yield is low, and the purity is low. In addition, bromobenzene is expensive, resulting in high production costs of 2,6-dichlorodiphenylamine
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Embodiment 1
[0026] A preparation method for 2,6-dichlorodiphenylamine, comprising the following steps:
[0027] (1) Add 2,6-dichloroaniline (100g, 0.617mol) and N,N-dimethylformamide (600ml) into the reaction flask, stir and dissolve, then add chlorobenzene (347.25g, 3.085mol) , Potassium Phosphate (261.929g, 1.234mol) and catalyst (0.031mol), stir and heat up to 130 ℃, insulation reaction 20h; Journal of Organic Chemistry 2011,76,2296-2300) prepared by the method described.
[0028] (2) After the reaction mixture obtained in step (1) is cooled to 80°C, heat filter with diatomaceous earth, collect the filtrate, wash the filter cake with hot water at 50°C, collect the lotion, combine the filtrate and the lotion, and distill under reduced pressure to remove water, Chlorobenzene and N,N-dimethylformamide to obtain a crude product; the crude product was dissolved in dichloromethane, added water to separate layers, distilled from dichloromethane to recover the solvent, and distilled under red...
Embodiment 2
[0030] The content of Example 2 is basically the same as that of Example 1, except that the catalyst is nano-copper oxide particles, and the nano-copper oxide is purchased from Aldrich.
Embodiment 3
[0032] The content of embodiment 3 is basically the same as embodiment 1, and its difference is: catalyst is nano cuprous oxide coating copper particle, and described cuprous oxide coating nano copper particle is according to document (Chemical Communication 2004,778-779 ) prepared by the method recorded.
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Abstract
The invention belongs to the technical field of chemical drug synthesis and specifically relates to a preparation method of 2, 6-dichlorodiphenylamine. The preparation method of the 2, 6-dichlorodiphenylamine comprises the following steps: (1) adding 2, 6-dichlorodiphenylamine and a polar aprotic solvent into a reaction bottle; after the 6-dichlorodiphenylamine and the polar aprotic solvent are stirred and dissolved, adding chlorobenzene, alkali and a catalyst to an obtained mixture; stirring and heating the mixture to 120-160 degrees centigrade; and preserving the heat of the mixture for reaction for 2-4 h, wherein the catalyst is nanometer copper oxide or nanometer copper iodide; and (2) cooling a reaction mixture obtained in the step (1) to 50-90 degrees centigrade; filtering the cooledreaction mixture; carrying out reduced pressure distillation on a filter liquor to obtain a crude product; and purifying the crude product to obtain the 2, 6-dichlorodiphenylamine. The preparation method of the 2, 6-dichlorodiphenylamine, provided by the invention, has the advantages that the catalytic efficiency of the catalyst is high, the usage of the catalyst is less, the selectivity of a reaction solvent is good, the reaction solvent is easy to recover, the raw material cost is low, the yield of a prepared product is high, the purity is high, the quality is high, and the preparation method of the 2, 6-dichlorodiphenylamine is easy to realize industrial production and application.
Description
technical field [0001] The invention belongs to the technical field of chemical medicine synthesis, and in particular relates to a preparation method of 2,6-dichlorodiphenylamine. Background technique [0002] 2,6-Dichlorodiphenylamine is a key intermediate in the synthesis of diclofenac sodium, a potent non-steroidal anti-inflammatory, antipyretic and analgesic drug. The synthetic route of 2,6-dichlorodiphenylamine reported in existing literature mainly consists of following three kinds: (1) 2,6-dichlorophenol synthetic route: this route is to be raw material with 2,6-dichlorophenol and aniline 2,6-dichlorodiphenylamine is obtained through acylation, condensation, and heavy water hydrolysis; (2) Synthesis route of cyclohexanone: This route uses cyclohexanone as the starting material, and organophosphorus compound catalyzes chlorination to generate 2, 2,6,6-tetrachlorocyclohexanone, and then condense with aniline to generate the corresponding Schiff base, and then remove hy...
Claims
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