Russian Journal of Applied Chemistry, 2010, Vol. 83, No. 5, pp. 854−857.
Pleiades Publishing, Ltd., 2010.
Original Russian Text
I.A. Dzhafarov, E.G. Mamedbeili, T.G. Kyazimova, Kh.I. Gasanov, E.I. Suleimanova, 2010, published in Zhurnal Prikladnoi Khimii,
2010, Vol. 83, No. 5, pp. 801−804.
AND INDUSTRIAL ORGANIC CHEMISTRY
Synthesis and Properties of Aminomethyloxy Derivatives
I. A. Dzhafarov, E. G. Mamedbeili, T. G. Kyazimova,
Kh. I. Gasanov, and E. I. Suleimanova
Azerbaijan Pedagogical University, Baku, Azerbaijan
Institute of Petrochemical Processes, National Academy of Sciences of Azerbaijan, Baku, Azerbaijan
Received November 10, 2009
Abstract—New 2-aminomethyloxy derivatives of 1-(propylsulfanyl)pentane were prepared by condensation of
1-(propylsulfanyl)pentan-2-ol with formaldehyde and secondary amines. The starting 1-(propylsulfanyl)pentan-
2-ol was synthesized by the reaction of 1-propanethiol with 1-bromopentan-2-ol. The structures of the products
were proved by elemental analysis, IR and
H NMR spectroscopy, and mass spectrometry. The compounds were
tested as antimicrobial additives to lubricating oils and as antiseptics against bacteria and fungi.
Organic compounds containing sulfur and nitrogen
are widely used as antioxidant, corrosion-protecting,
and antimicrobial additives to fuels and lubricating oils
. They are also biologically active substances and are
components of drugs [2–4]. Preparation of new series
of such compounds from available raw materials and
improvement of general procedures for their synthesis
is a topical problem [5, 6].
The Mannich reaction is an important route to sulfur-
and nitrogen-containing compounds. Proceeding with
studies in the ﬁ eld of nitrogen- and sulfur-containing
compounds [7–10], in this study we synthesized new
2-aminomethyloxy derivatives of 1-(propylsulfanyl)
pentane and examined their properties. To this end, we
ﬁ rst prepared previously unknown sulfur-containing
secondary aliphatic alcohol III by the reaction of
1-propanethiol I with 1-bromopentan-2-ol II (Scheme 1).
The reaction was performed at equimolar ratio of the
reactants in an alkaline medium (40% NaOH solution
in water) at 50–60°С for 3–4 h. The yield of the target
product III was 66%.
Then, by Mannich condensation of alcohol III with
formaldehyde in the presence of secondary amines IV–
VIII, we prepared new 2-aminomethyloxy derivatives
of 1-(propylsulfanyl)pentane IX–XIII (Scheme 2).
Synthesis of IX–XIII by the Mannich reaction was
performed at 40–55°С for 3–4 h at equimolar ratio of the
reactants; the yield was 72–76%.
Alcohol III and its amino derivatives IX–XIII
are transparent liquids with a strong odor. They are
insoluble in water and readily soluble in organic
solvents (ethanol, acetone, benzene, CCl
, etc.). The
physicochemical characteristics, elemental analyses, and
+ NaBr + H