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2-[(Phenylmethyl)thio]-3-pyridinecarboxylic acid, also known as 2-(phenylthio)pyridine-3-carboxylic acid, is a heterocyclic organic compound that is commonly used in various applications in the chemical industry.
This compound has been studied extensively and has been found to be an important intermediate in several synthetic routes.
In this article, we will discuss the various synthetic routes of 2-[(Phenylmethyl)thio]-3-pyridinecarboxylic acid in the chemical industry.
Synthetic Route 1: via Thiophene and Pyridine
One of the most common synthetic routes for 2-[(Phenylmethyl)thio]-3-pyridinecarboxylic acid involves the reaction of thiophene and pyridine.
The reaction between thiophene and pyridine can be catalyzed by various reagents, such as sodium hypophosphite, potassium hydroxide, or trimethylsilyl chloride.
The reaction can be conducted under various conditions, such as in the presence of solvents like benzene, acetonitrile, or DMF.
The product can be isolated using conventional methods, such as filtration, washing, and drying.
Synthetic Route 2: via P2S5 and Pyridine
Another synthetic route for 2-[(Phenylmethyl)thio]-3-pyridinecarboxylic acid involves the reaction of P2S5 (diphenyl sulfide) and pyridine.
This reaction can be carried out in the presence of a solvent such as dimethylformamide (DMF), and can be catalyzed by a base such as potassium hydroxide.
The product can be purified by recrystallization, or by using chromatography techniques such as column chromatography or high-performance liquid chromatography (HPLC).
Synthetic Route 3: via Thiopyranyl Chloride and Pyridine
A third synthetic route for 2-[(Phenylmethyl)thio]-3-pyridinecarboxylic acid involves the reaction of thiopyranyl chloride and pyridine.
This reaction can be carried out in the presence of a solvent such as DMF, and can be catalyzed by a base such as pyridine.
The product can be isolated by filtration, washing, and drying.
Synthetic Route 4: via Thiophene-2-carboxaldehyde and Pyridine
A synthetic route for 2-[(Phenylmethyl)thio]-3-pyridinecarboxylic acid also includes thiophene-2-carboxaldehyde and pyridine.
In this process, thiophene-2-carboxaldehyde is first synthesized through a separate reaction, and then reacted with pyridine.
The reaction can be carried out in the presence of a base such as sodium hydroxide, and can be catalyzed by a solvent such as DMSO.
The product can be purified by recrystallization, or by using chromatography techniques such as column chromatography or HPLC.
In each of these synthetic routes, the quality of the starting materials, the reaction conditions, and the purification methods all play a critical role in the generation of a successful synthesis.
The selection of a specific synthetic route will depend on the specific application and the desired properties of the final product.
In the pharmaceutical industry, 2-[(Phenylmethyl)thio]-3-pyridinecarboxylic acid is used as an intermediate in the synthesis of certain drugs.
For example, it can be used as a precursor for the synthesis of bosent