A kind of synthetic method of 1-((3-(5-nitro-2-furyl) allyl) amino)hydantoin

Abstract

A kind of 1-((3-(5-nitro-2-furyl) allylidene) amino) hydantoin synthesis method is to use 5-nitrofuran acrolein, hydrazine hydrate, urea and ethyl chloroacetate As the main raw material, it is prepared through aldehyde-amine condensation and condensation ring-closing reaction. The process is simple, the raw material is easy to obtain, and the use of flammable, explosive, toxic and other chemical solvents is eliminated in the synthesis. The yield is 5 times higher than that of the original process. It has the characteristics of high yield, good purity, low cost, less three wastes, and environmental friendliness.

Description

technical field [0001] The invention relates to a method for synthesizing 1-((3-(5-nitro-2-furyl)allylidene)amino)hydantoin. Background technique [0002] 1-((3-(5-nitro-2-furyl)allylidene)amino)hydantoin, CAS number is [1672-88-4]. The molecular structure is shown in the figure below: [0003] [0004] 1-((3-(5-nitro-2-furyl)allylidene)amino)hydantoin is a class of nitrofuran derivatives, an anti-infective drug, mainly used for urinary tract infections, Its antibacterial properties are similar to those of nitrofurantoin and nitrofurandine. 1-((3-(5-nitro-2-furyl)allylidene)amino)hydantoin has a broad antibacterial spectrum and has antibacterial effects on most Gram-positive and Gram-negative bacteria, such as Staphylococcus aureus , Escherichia coli, Staphylococcus albus and Streptococcus pyogenes. It is clinically used for urinary system infection caused by sensitive bacteria, such as pyelonephritis, urinary tract infection, cystitis and prostatitis, etc. It has an...

AI Technical Summary

Problems solved by technology

[0026] The main disadvantages of this process are: the first is that the equipment requirements are greatly improved, the second is that the stability of the reactive distillation operation is difficult to grasp, and the scale-up of the workshop is difficult. Infectious drugs, high cost

[0028] 1. Using hydrazine hydrate and chloroacetic acid as the reaction raw materials, because the reaction selectivity is very poor, the total yield is too low caused by too many reaction steps;

[0029] 2. Using the condensation of benzylidene semicarbazone and ethyl chloroacetate, the existing process not only cannot satisfy the purity of the product, but also has great difficulties in industrial production;

[0030] 3. Using nitrofurantoin as a reaction raw material, the cost is too high, and the workshop equipment and production requirements are extremely high, so it is difficult to form industrialized production

In the existing technology, there are shortcomings such as too long reaction route, low yield and poor purity. In different reaction steps, toxic and harmful substances such as pyridine and hydrazine hydrate are also involved, as well as flammable, explosive and toxic substances. The use of organic solvents causes a lot of pollution, which not only increases the pressure on recycling work and environmental impact, but also increases production costs

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