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2-(3-Nitro-phenyl)-imidazo[1,2-a]pyrimidine is an important intermediate in the synthesis of various pharmaceuticals and agrochemicals.
Its synthesis can be achieved through several methods, but synthetic routes play a crucial role in determining the efficiency, cost-effectiveness, and scalability of the synthesis process.
In this article, we will discuss the synthetic routes of 2-(3-nitro-phenyl)-imidazo[1,2-a]pyrimidine.
Route 1: via Nitration of Phenyl-substituted Imidazo[1,2-a]pyrimidine
The first synthetic route for 2-(3-nitro-phenyl)-imidazo[1,2-a]pyrimidine involves the nitration of a phenyl-substituted imidazo[1,2-a]pyrimidine.
The reaction is carried out in the presence of a nitrating agent such as nitric acid or a nitrate salt, and a solvent such as acetonitrile or dichloromethane.
The reaction conditions include heating the mixture at a temperature between 50-80°C for a period between 1-24 hours.
The advantages of this route include ease of operation, low cost, and high yield.
However, the reaction can be highly exothermic and requires careful temperature control to avoid unwanted side reactions.
Route 2: via Hydrazoation of Phenyl-substituted Imidazo[1,2-a]pyrimidine
The second synthetic route for 2-(3-nitro-phenyl)-imidazo[1,2-a]pyrimidine involves the hydrazoation of a phenyl-substituted imidazo[1,2-a]pyrimidine.
The reaction is carried out in the presence of a hydrazone such as sodium hydrazone or a nitrite, and a solvent such as ethanol or methanol.
The reaction conditions include heating the mixture at a temperature between 50-80°C for a period between 1-24 hours.
The advantages of this route include ease of operation, high yield, and the ability to use mild reaction conditions.
However, the reaction requires specialized reagents and may not be scalable for industrial applications.
Route 3: via Halogenation of Phenyl-substituted Imidazo[1,2-a]pyrimidine
The third synthetic route for 2-(3-nitro-phenyl)-imidazo[1,2-a]pyrimidine involves the halogenation of a phenyl-substituted imidazo[1,2-a]pyrimidine.
The reaction is carried out in the presence of a halogen such as chlorine or bromine, and a solvent such as dichloromethane or chloroform.
The reaction conditions include heating the mixture at a temperature between 50-80°C for a period between 1-24 hours.
The advantages of this route include the ability to use a variety of halogens to introduce the nitro group, and the ability to modify the substitution position on the imidazo[1,2-a]pyrimidine ring.
However, the reaction requires careful handling of the reagents and may not be suitable for industrial-scale synthesis.
In conclusion, the synthetic routes of 2-(3-nitro-phenyl)-imidazo[1,2-a]pyrimidine involve nitration, hydrazoation, and halogenation of phenyl-substituted imidazo[1,2-a]pyrimidines.
Each route has its own advantages and disadvantages, and the choice of route depends on the desired product yield, cost, and