REACTION OF 1-AMINO-3-PROPOXY-2-PROPANOL WITH ALDEHYDES
1657
The structures of VI VIII were confirmed by
NMR and IR spectroscopy.
0.5 g of ZnCl2. The mixture was heated at 60 70 C
for 4 h and then cooled to 20 C in a vacuum. Com-
pound I was isolated by distillation; yield 25.6 g
(90%), bp 93 94 C (20 mm Hg), n2D0 = 1.4398. Pub-
1
In the H NMR spectrum of oxazlidine VI, the
lished data [11]: bp 97 98 C (20 mm Hg), nD20
=
methyl group gives a triplet at 0.85 ppm. The meth-
ine proton bonded to the CH3 group gives a multiplet
at 4.2 ppm. The two CH2N protons give a doublet
at 2.9 ppm. The methine group in the CH2CHCH2
fragment appears as a quintet at 4.1 4.4 ppm. The
1H NMR spectra of VII and VIII are similar to that
of VI and differ only in the signals of R.
1.4378.
3-Propoxy-1,2-epoxypropane III. A three-necked
flask was charged with 15.3 g of I and 50 ml of dry
diethyl ether, after which 11.2 g of finely divided
KOH was added in portions, and the mixture was
heated on a water bath at 50 C for 1 h. After cooling,
the precipitate was separated and washed with three
portions of diethyl ether. The solvent was removed,
and the product was distilled. Yield 7 g (60%), bp
147 148 C, n2D0 = 1.4716. Published data [12]: bp
63 C (11 mm Hg), n2D0 = 1.4691.
The IR spectra of 1,3-oxazolidines VI VIII contain
an absorption band of the five-membered ring at 1381,
1
1355, and 1240 cm , respectively. The N H stretch-
1
ing vibrations are manifested at about 3150 cm .
Compounds VI XI were tested as antimicrobial
additives to DS-11 oil [GOST (State Standard) 9.052
75]. The antimicrobial activity of these compounds
was assessed by the zone diffusion method using
microorganisms (GOST 9.052 75). The procedure is
described below.
N-(3-Propoxy-2-hydroxypropyl)urea IV. Com-
pound III (23.2 g) was added dropwise to 12 g of
molten (135 140 C) urea, and the mixture was heated
at 135 140 C for 3 h, after which it was cooled and
extracted with hot chloroform. The white crystalline
substance that precipitated from chloroform was fil-
tered off. Yield 5 g (14%), mp 121 122 C.
A culture medium (20 25 ml) was placed in
a Petri dish, cooled, and seeded with microorgan-
isms. Then four holes (10 mm in diameter, 4 5 mm
deep) were made with sterile tools on the surface of
the culture medium, and 0.3 0.4 ml of a 5% solution
of a test compound in T-46 oil was introduced into
these holes. The Petri dishes with bacteria were kept
in a thermostat for 2 days at 28 30 C, and those
with fungi, at the required humidity for 4 days.
Found, %: C 47.53, H 9.29, N 15.71.
C7H16N2O3.
Calculated, %: C 47.71, H 9.15, N 15.90.
1-Amino-3-propoxy-2-propanol V. A flask equip-
ped with a thermometer and a reflux condenser was
charged with 8.8 g of IV and 2 g of 20% NaOH.
The mixture was refluxed for 15 h, cooled, dried over
KOH, and distilled in a vacuum. Yield 4 g (60%), bp
85 86 C (1 mm Hg), n2D0 = 1.4520.
We found that the compounds synthesized are
readily soluble in oil, exhibit pronounced antimicrobi-
al effect at low concentrations (0.5 1.0 mol %), and
do not stimulate corrosion. With 0.5 1.0 mol % of V,
the width of the suppression zone is 0.9 1.6 cm for
bacteria and 1.1 1.3 cm for fungi. As a reference we
chose the widely used sodium pentachlorophenolate;
at its concentration of 0.5 1.0 mol %, the width of
the suppression zone is 0.7 1.3 cm for bacteria and
0.7 1.4 cm for fungi.
2-Methyl-5-propoxymethyl-1,3-oxazolidine VI and
1-methylimino-3-propoxy-2-propanol IX. A three-
necked flask equipped with a thermometer and a drop-
ping funnel was charged with 13.3 g of V and 50 ml
of benzene. Then 3.4 g of acetaldehyde was added
with vigorous stirring from the dropping funnel.
The stirring was continued for 1 h at room tem-
perature and then for 2 h at 65 70 C. The solvent
was distilled off on a water bath, and the residue
was distilled in a vacuum. Two fractions were iso-
lated: (i) 5.9 g (37%) of VI and (ii) 7.5 g (47%)
of IX.
The antimicrobial activities of oxazolidines VI
VIII and azomethines IX XI are lower than that of
amino alcohol V.
EXPERIMENTAL
1-Chloro-3-propoxy-2-propanol I. A three-necked
flask equipped with a thermometer was charged with
10 g of 1-propanol, 18.5 g of epichlorohydrin II, and
Compounds VII, VIII, X, and XI were obtained
similarly. The physicochemical constants of VI XI
are listed in the table.
RUSSIAN JOURNAL OF APPLIED CHEMISTRY Vol. 78 No. 10 2005