Chapter 24.8, Problem 16P

Interpretation Introduction

Interpretation:

Using benzene and any other necessary amines how to synthesize sulfathiazole is to be shown.

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.