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The Synthetic Routes of 3-Bromo-N-(2-Hydroxyethyl)Benzene-sulphonamide: A Comprehensive Overview in the Chemical Industry
3-Bromo-N-(2-hydroxyethyl)benzene-sulphonamide, commonly referred to as BENSULL, is an organic compound that has gained significant attention in the scientific community due to its unique chemical properties and diverse range of applications.
Its synthesis has been the subject of extensive research in the field of organic chemistry, and there are several synthetic routes available for the production of this compound.
In this article, we will provide a comprehensive overview of the various synthetic routes that are currently used in the chemical industry to produce 3-bromo-N-(2-hydroxyethyl)benzene-sulphonamide.
We will also discuss the advantages and disadvantages of each route and their impact on the final product's quality and cost.
- Direct Synthesis
The direct synthesis of BENSULL involves the reaction of 2-hydroxyethylbenzene with malononitrile and sodium hydroxide in the presence of a solvent such as tetrahydrofuran.
The reaction proceeds through a series of steps, including SN2 reaction, forming an intermediate, and elimination of the solvent to yield the desired product.
Advantages:
- Simple and straightforward reaction pathway.
- High yield of product.
- Can be carried out with readily available reagents.
Disadvantages:
- The use of tetrahydrofuran as a solvent leads to the production of a large amount of waste.
- The use of concentrated sodium hydroxide can be hazardous.
- Intermediate Synthesis
The intermediate synthesis of BENSULL involves the synthesis of an intermediate product and its subsequent reduction to yield the desired product.
One of the most common intermediates used in the synthesis of BENSULL is 2-chloro-6-nitro-benzene-1,4-dioxane.
The intermediate is then reduced using hydrazine to yield the desired product.
Advantages:
- The intermediate synthesis route can be modified to produce other derivatives of BENSULL, increasing the versatility of the process.
- The reduction step using hydrazine is relatively mild, and the product can be easily purified.
Disadvantages:
- The intermediate synthesis route requires the use of additional reactants and purification steps, increasing the cost and complexity of the process.
- The use of 2-chloro-6-nitro-benzene-1,4-dioxane can lead to the production of waste and the need for proper disposal.
- Reductive Amination
The reductive amination route involves the reaction of an amine with a carbonyl compound in the presence of a reducing agent such as lithium aluminum hydride (LAH) or hydrogen in a solvent such as dimethylformamide (DMF).
The reaction proceeds through a series of steps, including the formation of an imine, the reduction of the imine to the amine, and the reaction of the amine with the carbonyl compound to yield the desired product.
Advantages:
- The reductive amination route is a versatile and widely used method for the synthesis of organic compounds.
- The use of LAH or hydrogen as reducing agents can simplify the purification process.
Disadvantages:
- The use of LAH or hydrogen can be hazardous and requires the use of proper safety precautions.
- The use of DMF as a solvent can lead to the production of waste and the need for proper disposal.
Conclusion
In summary, the synthetic routes for the production of 3-