Principle Synthesis mechanism and identifiacation of sulphanilamide

Sulfanilamide is an organic sulfur compound structurally similar to p-aminobenzoic acid (PABA) with antibacterial property. Basically, it is aniline derivative with sulphonamide group which is treated as antibacterial drug'.

1. Topic: SULPHANILAMIDE Subject: Medicinal Chemistry III (Practical) DEPARTMENT OF PHARAMACEUTICAL SCIENCES DR. HARISINGH GOUR VISHWAVIDYALAYA (A Central University), Sagar (MP) Presented by KARTIK JATARIYA B.PHARM DOPS

2. Sulphanilamide

3. TABLE OF CONTENTS 01 INTRODUCTION 02 SYNTHESIS 03 METHODOLOGY 04 I DENTIFICATION

4. INTRODUCTION 01

5. INTRODUCTION Sulfanilamide is an organic sulfur compound structurally similar to p-aminobenzoic acid (PABA) with antibacterial property. Basically, it is aniline derivative with sulphonamide group which is treated as antibacterial drug'.

6. 3D STRUCTURE 2D STRUCTURE STRUCTURE 4-Aminobenzene sulfonamide

7. BACKGROUND DISCOVERY Sulfanilamide was first prepared in 1908 by the Austrian chemist Paul Josef Jakob Gelmo (1879–1961) It was patented in 1909. HISTORY In World War II, Soldiers were used Powdered sulphanilamide to reduce infection rates and contributed to a dramatic reduction in mortality rates compared to previous wars. USES As a antibacterial agent ( wound infection) As a antifungal agent (vaginal yeast infection) ToXICITY Alergic reaction/ Liver problems/ Blood problems

8. PRINCIPLE Sulphanilamide can be prepared by taking acetanilide and treating it with excess of chlorosulphonic acid, which gives p-acetamido-benzene sulphonyl chloride which readily converted into corresponding p-acetamido benzene sulphonamide upon reaction with ammonia or ammonium carbonate. The acetamido groups can easily undergo acid catalyzed hydrolysis reaction toform p-aminobenzene sulphonamide (Sulphanilamide)"

9. AIM To prepare sulphanilamide from acetanilide.

10. REQUIREMENTS APPARATUS Round-bottom flask Reflux Condenser Beaker Burchner funnel Measuring cylinder Filter paper CHEMICALS Chlorosulphonic acid Conc. Ammonia Dil. Sulphuric acid Sodium bicarbonate Conc. Hydrochloric acid.

11. SYNTHESIS 02

12. REACTION SCHEME

13. MECHANISM

14. METHODOLOGY 03

15. 01 02 03 Prepare p-acetamido-benzene-sulphonyl chloride Prepare p-amino-benzene-sulphonamide Prepare p-acetamido-benzene-sulphonamide PROCEDURE

16. Prepare p-acetamido-benzene-sulphonyl chloride Place 5 gm of dry acetanilide into a three necked flaskequipped with a condenser, add 16 ml of chlorosulfonic acid slowly in small portions. Shake the flask well and heat theflask on a water bath for 1 hr . Cool and pour this oily mixtureas a thin stream with stirring into 100 gm of crushed ice. Rinse with water and broke the ice lumps and stir the mixture for several minutes. Filter it at the pump, wash it with cold waterand drain well.

17. Prepare p-acetamido-benzene-sulphonamide Transfer the crude product obtained above into a round bottomflask . Add a mixture of 15ml of ammonia and 15ml of water. Mix the contents of the flask thoroughly with swirling. Heat the mixture for 15 mins (below boiling point.). The sulphonyl chloride is converted into corresponding sulfonamide. Cool on ice, add dil. sulphuric acid until the mixture was just acidic to congo red paper. Collected the product in a buchner funnel

18. Prepare p-amino-benzene-sulphonamide Transfer the crude product into 500ml flask and add 5ml of conc. HCl, 10ml of water. Boil the mixture gently under  refluxfor 10-30 minutes. Cool the mixture to room temperature (should not show any solid) to this add 3gm of charcoal, heat the mixture to boil. Place the filtrate in beaker and continuously add 4gm of solid sodium bicarbonate. Test the filtrate with litmus paper until neutral. Cool it in ice bath and filter the precipitate. Recrystallize from water or alcohol.

19. IDENTIFICATION 04

20. FORMULA – C6H6N2O2S IDENTIFICATION On addition of solution of copper sulphate to a solution of the alkaline salts of sulphonilamide , coloured precipitate or solution obtained. MOL WEIGHT – 172.2 g /mol PHYSICAL STATE – White to brown crystalline powder. MELTING POINT – 163-164 degree celcius . SOLUBILITY IN WATER – 5 g/l at 25 degree celcius .

21. THANKS