Document Type
Thesis
Date of Award
6-30-1960
Degree Name
Master of Science in Chemical Engineering - (M.S.)
Department
Chemical Engineering
First Advisor
Saul I. Kreps
Second Advisor
James A. Bradley
Third Advisor
Michael Frederick
Abstract
The acetylation of 5-chloropyridine-2,3-diamino with chloroacetyl-chloride to yield 5-chloropyridine-2,3-dichlo-roacetamide and the subsequent ring closure form 6-chloro-2-chloromethyl-3H-imidazo-(b)pyridine has been studied in detail. The method of experimentation utilized statistically designed mathematical experiments.
The yield of 5-chloropyridine-2,3-dichloroacetamido is dependent upon the excess of the reactants and temperature, while time is not a significant factor. An important contribution to the study was obtained by extracting the product with solvents and discovering that the ring closed material 6-chloro-2-chloromethyl-3H-imidazo-(b)pyridine yields in quantity during the diacetylation reaction.
The ring closure of 5-chloro-2,3-dichloroacetamidopyridine is markedly temperature dependent. Time has little effect on the reaction yield. The analysis of regression of the statistically designed experiment resulted in an equation for yield in terms of the reaction time and temperature. It was determined experimentally that reaction temperature of 100°C. resulted in a tar-like polymer instead of the cyclized product, 6-chloro-2-chloromethyl-3H-imidazo-(b)pyridine.
The surface response contour curves were plotted and the optimum conditions for the cyclization reaction determined. The recommended optimum reaction conditions are:
a. Temperature - 75°C
b. Time - 2 hours
c. Yield - 68 theoretical
Recommended Citation
Naiman, Edward Aloysius, "The synthesis and cyclization of 5-chloro-2, 3-dichloroacetamidopyridine" (1960). Theses. 3021.
https://digitalcommons.njit.edu/theses/3021
