Russian Journal of Applied Chemistry, 2010, Vol. 83, No. 11, pp. 1973−1977.
Pleiades Publishing, Ltd., 2010.
Original Russian Text © E.G. Mamedbeili, I.A. Dzhafarov, K.A. Kochetkov, T.G. Kyazimova, Kh.I. Gasanov, O.B. Gadzhieva, 2010, published in Zhurnal
Prikladnoi Khimii, 2010, Vol. 83, No. 11, pp. 1841−1845.
AND INDUSTRIAL ORGANIC CHEMISTRY
Aminomethoxy Derivatives of Benzylsulfanylheptane
E. G. Mamedbeili, I. A. Dzhafarov, K. A. Kochetkov, T. G. Kyazimova,
Kh. I. Gasanov, and O. B. Gadzhieva
Azerbaijani Pedagogical University, Baku, Azerbaijan
Institute of Petrochemical Processes, National Academy of Sciences of Azerbaijan, Baku, Azerbaijan
Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Moscow, Russia
Received March 1, 2010
Abstract—Synthesis and structure of new aminomethoxy derivatives of 1-benzylsulfanylheptane by the Mannich
condensation of 1-benzylsulfanylheptan-2-ol, formaldehyde, and secondary amines were studied.
Organic compounds containing various functional
groups and heteroatoms, such as sulfur and nitrogen (or
both together), are widely used as effective biologically
active substances and pharmaceutical preparations, as
well as additives improving the quality of oils and fuels
[1–3]. A directed synthesis of these compounds used in
various chemical industries is a rather topical task not
only for development of synthetic organic chemistry,
but also for applied research. In this context, syntheses
of new compounds of this kind from accessible raw
materials by improved methods continue to attract
researchers’ attention [4–6]. The Mannich reaction is
an important and promising way to obtain sulfur- and
nitrogen-containing compounds [7–9].
In continuation of previous studies concerned with
nitrogen-containing alkyl(aryl) sulfanyl alkanes [10–
14], we report here results obtained in synthesis of
aminomethoxy derivatives of 1-benzyl sulfanyl heptane
and analysis of their properties. For this purpose, we ﬁ rst
synthesized the previously unknown sulfur-containing
secondary alcohol, 1-benzyl sulfanyl heptan-2-ol (III)
SH + Br
+ NaBr + H
by reacting benzylthiol (I) with 1-bromoheptan-2-ol (II)
by Scheme 1.
The secondary thioalcohol (III) was synthesized by
reacting equimolar amounts of the starting components
I and II in an alkaline medium (40% aqueous solution
of NaOH) at a temperature of 50–60°C in the course of
3–4 h. The yield of the target product was 72%.
Further, we used the Mannich condensation of
1-benzyl sulfanyl heptan-2-ol (III) with formaldehyde
in the presence of secondary amines (IV)–(VIII) to
obtain amino derivatives of 1-benzyl sulfanyl heptane,
(IX)–(XIII), by Scheme 2.
Aminomethoxy derivatives of 1-benzyl sulfanyl
heptane, (IX)–(XIII), were synthesized at 50–60°C
in the course of 3–4 h at the equimolar ratio between
the starting components. In this case, the yield of the
reaction products was 72–78%.
The thus synthesized 1-benzyl sulfanyl heptan-
2-ol (III) and its amino derivatives (IX)–(XIII) are
transparent liquids with characteristic odors. They are
insoluble in water, but can be well dissolved in ethanol,