Method for synthesizing 2-(nitromethylene) imidazolidine by one-pot type

Abstract

The invention provides a method for synthesizing 2-(nitromethylene) imidazolidine by a one-pot type. The method comprises the following steps of adding 1,1-dichloro-2-nitroethylene, fatty alcohol andalkaline into a reaction container, and reacting for 1 to 4h at low temperature, so as to obtain an intermediate A; adding ethylenediamine into the reaction container, heating to react for 5 to 15h, naturally cooling to normal temperature, and post-treating, so as to obtain the 2-(nitromethylene) imidazolidine. The method has the characteristics that the obtaining of the raw materials is easy, thereaction process is short, the reaction activity is good, the operation conditions are moderate, the technology is green and environment-friendly, and the production cost is lower; the yield rate andpurity of a product are higher, the technology is environment-friendly, the operation steps are simple, the usage amount of equipment is small, the utilization rate of the equipment is high, and thelike; the method is favorable for large-scale industrialized production.

Description

technical field [0001] The invention relates to a method for synthesizing a fine chemical intermediate, in particular to a method for synthesizing 2-(nitromethylene) imidazolidine in one pot. Background technique [0002] 2-(Nitromethylene) imidazolidine is an important fine chemical intermediate, which is mainly used as an important synthetic raw material for the insecticides piclopyrid and cyclopyrid. Wherein, the molecular formula of the 2-(nitromethylene) imidazolidine is: C 4 h 7 N 3 o 2 , its English name is: 2-(nitromethylene)imidazolidine; its CAS number is: 13623-98-8; its structural formula is as follows: [0003] [0004] In the prior art, a series of synthetic methods of 2-(nitromethylene) imidazolidines have been reported; however, the related synthetic methods reported in many documents, when used as industrial production techniques, have complicated technological process, poor operability, and products The yield is low and the production cost is high. ...

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Problems solved by technology

[0004] In the prior art, a series of synthetic methods of 2-(nitromethylene) imidazolidines have been reported; however, the related synthetic methods reported in many documents, when used as industrial production techniques, have complicated technological process, poor operability, and products Low yield and high production cost

For example, a document in Journal of Medicinal Chemistry, 2012, 55 (1), 465-474 reported that 2-(nitromethylene ) the preparation technology of imidazolidine, yet, this reaction process needs to be stirred overnight under ethanol reflux condition, and reaction process generates colorless poisonous gas methyl mercaptan, therefore, this preparation technology is not suitable for large-scale industrial production

As another example, Chinese patent application CN103524489A discloses a synthesis process of 2-chloro-5-((2-(nitromethylene)imidazolin-1-yl)methyl)pyridine. Nitrification is separated to obtain dichloronitroethylene, and then reacted with ethylenediamine to generate 2-(nitromethylene) imidazolidine, the yield is only 57%, and it is necessary to separate the irritating dichloronitroethylene; , the synthesis process used in this Chinese patent application requires adding 1,1-dichloro-2-nitroethylene dropwise to sodium methoxide for reaction, and isolating 1,1-dimethoxy-2-nitroethylene , then heated to reflux with ethylenediamine for 24 hours to synthesize 2-(nitromethylene) imidazolidine, the separation total yield of the product obtained is only 18%, as seen, the overall yield of the synthesis process is too low and the process The operation is more complicated, therefore, it is not suitable for large-scale industrial production

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