SYNTHESIS OF (E)-4-ETHOXYPHENYLIMINOMETHYLARYLS
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1
In the H NMR spectra of the Schiff bases IIIa–
IIIv, IVa–IVj, VIIa–VIId there are the proton signals
of the p-phenetidine fragment (δ, ppm): 1.2–1.7 t (Me),
3.8–4.3 q (CH2), 6.7–7.4 m (С6Н4), 8.4–8.7 s (HC=N),
which indicates their E-configuration [4]. The MeO
proton signals are singlets in the range of 3.8–4.0 ppm
(IIIc, IIIe–IIIv, IVb, VIIb). The EtO proton signals in
IVa–IVj, VIIc are observed in the range of 1.2–1.7
(t, Me) and 3.8–4.3 (q, CH2). In the 1H NMR spectra of
the hydrochlorides Va–Vv, VIa–VIj the singlet signals
in the ranges of 10.0–10.2 and 10.1–11.2 ppm belong
to the HC=N+ and HN+Cl– groups.
methanol, and dried in air for 6–8 h.
Bisazomethines (VIIa–VIId). A solution of 10 mmol
of p-phenetidine I and 5 mmol of the appropriate
dibasic aromatic aldehyde II in 50 ml of anhydrous
methanol was refluxed for 45 min. The target products
were isolated as described above.
4-Ethoxyphenyliminomethylaryles hydrochlorides
(Va–Vv, VIa–VIj). Dry hydrogen chloride [5] was
bubbled through a cooled (0–5°C) solution of 1 mmol
of azomethine IIIa–IIIv or IVa–IVj in 30–50 ml of
anhydrous ether for 10–15 min. The formed precipitate
was filtered off, washed with cold ether, and dried in
air for 3–4 h.
1
The IR and H NMR spectra of compounds IIIa–
IIIv, IVa–IVj, Va–Vv, VIa–VIj, VIIa–VIId contain
the absorption band and the proton signals confirming
the presence of all the corresponding structural
fragments of the ester groups.
REFERENCES
1. Mashkovskii, M.D., Lekarstvennye preparaty (Drugs),
Moscow: Novaya Volna, 2001, vols. 1, 2.
2. Stahl, P.H. and Wermuth, C.G., Handbook of
Pharmaceutical Salts. Properties, Selection, and Use,
Weinhem: Wiley-VCH Verlag GmbH & Co. KgaA,
2002.
3. Dikusar, E.A., Kozlov, N.G., Potkin, V.I., Tlegenov, R.T.,
and Uteniyazov, K.U., Aminovye soli organicheskikh
kislot: sintez, svoistva, biologicheskaya aktivnost’ i
primenenie (Amine Salts of Organic Acids: Synthesis,
Properties, Biological Activity, and Application),
Nukus: Karakalpakstan, 2009.
4. Dyer, J.R., Prolozheniyz absorbtsionnoi spectroskopii
organicheskikh soedinenii (Applications of Absorption
Spectroscopy of Organic Compounds), Moscow:
Khimiya, 1970.
5. Karyakin, Yu.V. and Angelov, I.I., Chistye khimicheskie
veshchestva (Pure Chemicals), Moscow: Khimiya,
1974.
EXPERIMENTAL
The IR spectra were recorded on a spectro-
photometer Protege-460 Nicolet FTIR (thin layer,
KBr). The H NMR spectra were registered on a
spectrometer Tesla BS-587A (100 MHz) relative to
internal TMS using deuterochloroform or DMSO-d6 as
the solvents. The molecular weights of the
azomethines obtained were determined by the cryo-
scopy in benzene.
1
(E)-4-Ethoxyphenyliminomethylaryles (IIIa–IIIv,
IVa–IVj). A solution of 5 mmol of p-phenetidine I
and 5 mmol of the appropriate aromatic aldehyde II in
40 ml of anhydrous methanol was refluxed for 30–
45 min. The solution was cooled to 0–5°C. The
azomethines were filtered off, washed with cold
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 82 No. 11 2012
Dikusar
