Interpretation:
Using benzene and any other necessary
Concept introduction:
The steps involved in the synthesis of sulfathiazole from benzene are i) Nitration of benzene ii) Reduction of nitrobenzene iii) Acetylation of the amino group iv) Chlorosulfonation of the anilide v) Treatment with 2-aminothiazole vi) Hydrolysis of the anilide to an amine.
To Show:
How to synthesize sulfathiazole starting from benzene and using any other necessary amines.
Answer:
The synthesis of sulfathiazole starting from benzene and using any other necessary amines is given below.
Explanation:
Nitration of benzene with Conc. HNO3 and Conc. H2SO4 yields nitrobenzene which on reduction with H2/Pt in ethanol gives aniline. Acetylation of aniline with acetic anhydride produces acetanilide. Chlorosulfonation of acetanilide leads to the formation of a p-chlorosulfonate as anilide group is orthp and para directing. Treatment of chlorosulfonate with 2-aminothiazole yields N-acetylsulfothiazole. Hydrolysis of N-acetylsulfothiazole yields sulfathiazole.
Conclusion:
The synthesis of sulfathiazole starting from benzene and using 2-aminothiazole is given below.
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Chapter 24 Solutions
Organic Chemistry
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- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning