The Synthetic Routes of 4-(5-CHLORO-2-THIENYL)-1,3-THIAZOL-2-AMINE

4-(5-Chloro-2-thienylt)-1,3-thiazol-2-amine is an important compound in the chemical industry, and it has various applications in different fields.
The synthetic routes for this compound are many, and the choice of a specific route depends on the availability of starting materials, the desired yield, and the cost of the synthesis.
In this article, we will discuss the different synthetic routes for 4-(5-chloro-2-thienylt)-1,3-thiazol-2-amine and their applications in the chemical industry.

Route 1: via 2-Amino-5-chlorothiophene-3-carboxaldehyde
2-Amino-5-chlorothiophene-3-carboxaldehyde is a versatile intermediate that can be used to synthesize 4-(5-chloro-2-thienylt)-1,3-thiazol-2-amine through a series of chemical reactions.
The synthesis of 2-amino-5-chlorothiophene-3-carboxaldehyde involves the reaction of 2-mercapto-5-chlorothiophene-3-carboxylic acid with ammonia, followed by hydrolysis of the resulting intermediate (Scheme 1).

Scheme 1: Synthesis of 2-amino-5-chlorothiophene-3-carboxaldehyde

The carboxaldehyde can be further converted to the desired thiazole amine by treatment with an appropriate amine, such as N,N-dimethylamine or N,N-diethylamine, in the presence of a base, such as sodium hydroxide or potassium hydroxide (Scheme 2).

Scheme 2: Synthesis of 4-(5-chloro-2-thienylt)-1,3-thiazol-2-amine via 2-amino-5-chlorothiophene-3-carboxaldehyde

Route 2: via 4-(5-chloro-2-thienyl)-1,3-oxazolidin-2-one
4-(5-Chloro-2-thienyl)-1,3-oxazolidin-2-one is another intermediate that can be used to synthesize 4-(5-chloro-2-thienylt)-1,3-thiazol-2-amine.
The synthesis of 4-(5-chloro-2-thienyl)-1,3-oxazolidin-2-one involves the reaction of 2-mercapto-5-chlorothiophene-3-carboxylic acid with 2-amino-1,3-oxazolidine in the presence of a condensing agent, such as dicyclohexylcarbodiimide (DCC) or hydroxybenzotriazole (HBT), and a solvent, such as dichloromethane or chloroform (Scheme 3).

Scheme 3: Synthesis of 4-(5-chloro-2-thienyl)-1,3-oxazolidin-2-one

The oxazolidinone can be converted to the desired thiazole amine by treatment with an appropriate amine, such as N,N-dimethylamine or N,N-diethylamine, in the presence of a base, such as sodium hydroxide or potassium hydroxide, and then hydrolysis of the resulting intermediate (Scheme 4).

Scheme 4: Synthesis of 4-(5-chloro-2-thienylt)-1,3-thiazol-2-amine via 4-(5-chloro-2-thienyl)-1,3-oxazolidin-2-one

Route 3: via 2-Chloro-5-methylthiophene-3-carboxylic acid
2-Chloro-5-methylthiophene-3-carboxylic acid can be used to synthesize 4-(5-chloro-2-thienylt)-1,3-thiazol-2-amine through a series of chemical