Abstract
Conditions for alkoxymethylation of 2-aminothiazole with semiformals obtained by the interaction of aliphatic alcohols with formaldehyde were worked out. Alkoxymethylation was performed by means of preliminary preparation of the semiformal of appropriate hydroxylcontaining compounds followed by interaction of semiformal with equimolar amount of 2- aminothiazole. The structure of the obtained compounds was acknowledged by means of IR and NMR 1 H spectroscopy. It was established that the reaction of the alkoxymethylation proceeds in the amino form of the starting 2-aminothiazole to form an appropriate monosubstituted Nalkoxymethyl derivative. As a result of microbiological tests, it was established that these compounds have high bactericidal properties against microorganisms which affect petroleum products and, at a concentration of 0.5%, completely protect both M-8 lubricating oil and diesel fuel from damage by bacteria even in terms of their forced infection. It found that at a concentration of 100 mg/l the obtained compounds protect the CT-3 steel from acid corrosion, moreover N-(isopropoxymethyl)thiazol-2-amine has the greatest protection effect.
Highlights
As it is known that 2-aminothiazole is a reaction centers and can enter into chemical potentially tautomeric compound with several reactions in amino and imino forms [1]: Studies of the effect of the type and position of the substituent on the conformational structure and amino-imine tautomerism, carried out in phases of gas, water and carbon tetrachloride showed that in these phases the amino form is more stable than the imino form and the amino tautomer is the predominant species [2]
Triazine derivatives containing 2-aminothiazole fragments as a substituent are recommended as effective polyfunctional additives to lubricating oils [11]
In the 1H compounds was established by IR and 1H NMR NMR spectra of these substances the following spectroscopy data and their composition signals were observed: a broadened singlet which was characteristic for NH group in the range 2.47-2.86 m.d., and a singlet typical for NCH2O group in the range 5.20-5.25 m.d
Summary
As it is known that 2-aminothiazole is a reaction centers and can enter into chemical potentially tautomeric compound with several reactions in amino and imino forms [1]: Studies of the effect of the type and position of the substituent on the conformational structure and amino-imine tautomerism, carried out in phases of gas, water and carbon tetrachloride showed that in these phases the amino form is more stable than the imino form and the amino tautomer is the predominant species [2]. Anticorrosive and antimicrobial properties of 2-aminothiazole derivatives replaced in the position 4 by methyl, phenyl and naphthyl groups in watered jet fuel were studied [12, 13]. Object of these studies is to synthesize new derivatives of 2-aminothiazole and explore their protective (antimicrobial and anticorrosive) properties.
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