Imidazole.pptx Synthesis, Chemical reaction

Imidazole synthesis, Chemical reaction and medicinal uses

1. Chandigarh College of Pharmacy PHARMACEUTICAL ORGANIC CHEMISTRY III IMIDAZOLE

2. IMIDAZOLE INTRODUCTION :- Imidazole is an organic compound with the formula C 3 N 2 H 4 . It is a white colour less solid that is soluble in water, producing a mildly alkaline solution. In Chemistry it is an aromatic hetero cycle, classified as a diazole and has non-adjacent nitrogen atoms.

3. PROPERTIES PHYSICAL PROPERTIES :- Imidazole is a white or colourless solid. it can show a prisamatic crystal apperence . imidazole is highly soluble in water, ethanol, ethyl ether and chloroform and its soluble in non polar solvents. In water it produces an alkaline solution. Its melting point is 88- 91 o C and its boiling point is 256 o C.

4. PROPERTIES CHEMICAL PROPERTIES :- Imidazole is a 5-Membere rings that show two tautomeric structures due to the positive charge can be located in both of the nitrogen atom, thus the hydrogen binds to the nitrogen atom can be removed easily because the lesser electron density of nitrogen atom has an unshared electron pair in a sp 2 orbital that can accept protons consequently imidazole shows an amproteric behavior . It can act as a weak base or a weak acid.

5. PREPARATION 1. By the action of glyoxal and ammonia .

6. PREPARATION 2. General method of preparation . 3. By Action of ammonia or mixture of HCHO and tartaric acid Di-nitrate and then Heating the corresponding Di- Carboxilic Acid.

7. REACTIONS Imidazole is a weak base but more basic than pyrazole it is a tautomeric substance because position 4 & 5 are equivalent. 1. Alkylation: Imidazole reacts with methyl iodide in KOH solution to form 1- ,ethyl imidazole which when heated strongly converts to 2- methyl imidazole.

8. REACTIONS HYDROGENATION :- - ELECTROPHILIC SUBSTITUTION REACTION: Nitration and Sulphonation takes place at position 4 and 5.

9. BENZIMIDAZOLE :- Benzimidazole is prepared by condensing O - phenyle Di- amine and formic acid.

10. USE OF IMIDAZOLE Use :- .Used as raw material by the pharmaceutical industries for manufacturing anti fungul drugs e.g Clotrimazole , Ketoconazole . Also used as pesticide & insectiside .