1990
MIRZOEVA et al.
Compounds III–VII were synthesized and purified
similarly in 62–66% yield (Table 1).
1-Heptylthio-2-(N,N-diethylaminomethoxy)-3-(2'-
chlorophenoxy)propane (XIV). To a mixture of 6.34 g of
compound I, 0.6 g of paraform, and 30 ml of anhydrous
benzene was added dropwise, at room temperature
under agitation for 0.5 h, 1.46 g of diethylamine. The
agitation was continued for additional 1 h at the same
temperature and for 2 h at 40–50°C. After benzene was
evaporated, 1-heptylthio-2-(N,N-diethylaminomethoxy)-
3-(2'-chlorophenoxy)propane (XIV) was isolated from
the remaining mass by vacuum distillation.
1-Heptylthio-2-phenylthiocarbamato-3-(2'-
chloro-phenoxy)propane (VII). To a mixture of 5.64 g
(0.02 mol) of compound I, 25 ml of anhydrous benzene,
and 2.02 g (0.02 mol) of freshly distilled triethylamine
was added dropwise, at 80–85°C, 2.70 g (0.02 mol)
of phenylisocyanate dissolved in 25 ml of anhydrous
benzene. Then, the mixture was agitated for additional
10–12 h and cooled, 2/3 of benzene was evaporated,
25 ml of anhydrous hexane was added, and the mixture
was kept for 20–24 h. The precipitated crystals of VIII
were separated, many times decanted with benzene, and
recrystallized from hexane.
Compounds XV–XVI were synthesized similarly in
65–70% yield (Table 2).
CONCLUSIONS
Compound IX was synthesized and purified similarly
in 60% yield (Table 1).
(1) The reaction of 1-heptylthio-3-chloro-2-propanol
with o-chlorophenol in the presence of an alkali was used
to obtain 1-heptylthio-3-(2'-chlorophenoxy)-2-propanol,
which is a key compound for synthesis of carbamates,
thiocarbamates, and alkoxymethyl and aminomethyl
derivatives.
1-Heptylthio-3-(2'-chlorophenoxy)-2-methoxy-
methyleneoxypropane (X). To a mixture of 6.34 g of
compound I, 25 ml of anhydrous benzene, and 3.63 g
of freshly distilled dimethylaniline was added, at
a temperature of 15–20°C in the course of 1 h, 2.41 g
of a freshly distilled α-chloromethyl ether. After the
whole amount of α-chloromethyl ether was added. The
mixture was agitated for 1 h at the same temperature and
then for 4–5 h at 40–50°C. The mixture was cooled and
washed with a 5% aqueous solution of hydrochloric acid
and then with water to a neutral reaction. Then it was
dried with anhydrous sodium sulfide. After the solvent
was evaporated, the remaining mass was subjected to
a vacuum distillation.
(2) Owing to their anticorrosion properties, some of
the arylcarbamates and arylthiocarbamates synthesized
improve the M-11 lubricating oil and surpass the industrial
additive IKhP-21 in efficiency.
REFERENCES
1. Kuliev, A.M., Khimiya i tekhnologiya prisadok k maslam i
toplivam (Chemistry and Technology of Additives to Oils
and Fuels), Leningrad: Khimiya, 1985.
Compounds XI–XII were synthesized similarly in
60–65% yield (Table 2).
2. Allakhverdiev, M.A., Babai, R.M., Farzaliev, V.M., et al.,
1-Heptylthio-2-acetoxy-3-(2'-chlorophenoxy)-
propane (XIII). To a mixture of 6.34 g of compound
I, 25 ml of anhydrous benzene, and 3.63 g of freshly
prepared dimethylaniline was added, at a temperature of
15–20°C in the course of 1 h, 2.25 g of acetyl chloride.
After the whole amount of acetyl chloride was added, the
mixture was agitated for 1 h at the same temperature and
then for 4–5 h at 40–50°C. The mixture was cooled and
washed first with a 5% aqueous solution of hydrochloric
acid and then with water to a neutral reaction. Then it was
dried with anhydrous sodium sulfide. After the solvent
was evaporated, the remaining mass was subjected to
a vacuum distillation. 1-Heptylthio-2-acetoxy-3-(2'-
chlorophenoxy)propane (XIII) was obtained in 66%
yield (Table 2).
Neftekhimiya, 2001, vol. 41, no. 2, pp. 153–157.
3. Farzaliev, V.M., Allakhverdiev, M.A., Shamkhalova, S.A.,
and Rzaeva, I.A., Zh. Prikl. Khim., 2004, vol. 77, no. 5,
pp. 787–790.
4. Sadygova, S.E., Magerramov, M.A., and Allakhverdiev,
M.A., Zh. Obshch. Khim., 2003, vol. 73, no. 12, pp. 2043–
2046.
5. Rzaeva, I.A., Sadygova, S.E., Vekilova, T.M., et al.,
Neftekhimiya, 2005, vol. 45, no. 6, pp. 470–475.
6. Silverstein, R.M., Bassler, G.C., and Morrill, T.C.,
Spectrometric Identification of Organic Compounds, New
York: Wiley, 1974.
7. Mathias,A., Anal. Chim. Acta, 1964, vol. 31, no. 6, pp. 598–
601.
RUSSIAN JOURNAL OF APPLIED CHEMISTRY Vol. 82 No. 11 2009