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Russian Journal of Applied Chemistry, Vol. 75, No. 4, 2002, p. 672. Translated from Zhurnal Prikladnoi Khimii, Vol. 75, No. 4, 2002,
Original Russian Text Copyright + 2002 by Aronova, Ginak.
Solid-Phase Synthesis of Triethylammonium Salt
E. B. Aronova and A. I. Ginak
St. Petersburg State Technological Institute, St. Petersburg, Russia
Received December 23, 2001; in final form, January 2002
Abstract-A procedure was developed for solid-phase synthesis of triethylammonium salt of 4-oxothiazol-
3-R-Substituted 4-oxothiazolidinethiones are natu-
ral biologically active substances. They are plant
growth stimulants  and metabolites of amino acid
synthesis in cells ; their synthetic analogs exhibit
a wide spectrum of biological activity, from herbicides
 to antitumor agents ; also, these compounds are
used as complexones for noble metals. The main syn-
thetic route to these compounds involves nucleophilic
substitution in polar solvents in the presence of bases.
In the process, the main reaction of electrophile ad-
dition to the sulfur or nitrogen atom of the heterocycle
is accompanied by base hydrolysis of the initial and
final products with ring cleavage. This side reaction
significantly decreases the yield of the target products
and complicates their purification. It is known  that
the nucleophilic substitution is preceded by the forma-
tion of salts of the substrate with a base, and in some
cases, these intermediate salts are isolated to prevent
hydrolysis. However, synthesis of these salts is also
labor-consuming and requires proper choice of sol-
vents for neutralization and crystallization.
To eliminate these drawbacks, we attempted to pre-
pare alkylammonium salt of 4-oxothiazolidine-2-thi-
one by solid-phase synthesis. Crystalline 4-oxothiazo-
lidine-2-thione I was treated with triethylamine vapor
at 503120oC in a tubular reactor with false bottom.
The reaction gives no by-products, and the desired
4-oxothiazolidine-2-thione triethylammonium salt II
is formed in 98% yield.
776 I +[(C
The resulting product contains no impurities and
does not require additional purification. Its composi-
tion was confirmed by elemental analysis, and the
structure, by a mixing test with an authentic sample.
Found, (%): N 11.8, S 27.3.
Calculated (%): N 12.0, S 27.4.
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