ISSN 1070-3632, Russian Journal of General Chemistry, 2013, Vol. 83, No. 1, pp. 146–147. © Pleiades Publishing, Ltd., 2013.
Original Russian Text © Yu.V. Popov, T.K. Korchagina, E.A. Karataeva, 2013, published in Zhurnal Obshchei Khimii, 2013, Vol. 83, No. 1, pp. 154–155.
LETTERS
TO THE EDITOR
Synthesis of N-Methyl-N-phenyl-3-phenoxyphenylamidine
Yu. V. Popov, T. K. Korchagina, and E. A. Karataeva
Volgograd State Technical University, ul. Lenina 28, Volgograd, 400005 Russia
e-mail: korolevavstu@yandex.ru
Received March 23, 2012
DOI: 10.1134/S1070363213010301
The N-substituted amidines containing diphenyl-
oxide fragment are of great practical interest, since they
exhibit various biological activities. In particular, N-methyl-
N-phenyl-3-phenoxyphenylamidine may find application
in pharmacology owing to the predicted high biological
activities such as anti-tumor, anti-cancer and anti-thrombosis
with virtually absent toxic and carcinogenic effects. The
amidine can also serve as a starting reagent for the
synthesis of some pharmacologically active derivatives.
The reaction proceeds at room temperature in
anhydrous dioxane for 2 h at a molar ratio amidine
hydrochloride –triethylamine of 1:1.
The structure of the synthesized amidine was
confirmed by the IR and 1H NMR spectroscopy.
N-Methyl-N-phenyl-3-phenoxyphenylamidine (V).
To a solution of 1 g (0.0035 mol) of phenoxybenzoic
acid 3-ethylimidate hydrochloride in 15 ml of an-
hydrous dioxane was slowly added 0.43 ml (0.0042 mol)
of N-methylaniline in 5 ml of anhydrous dioxane. The
reaction mixture was refluxed under stirring for 4 h.
After cooling to room temperature, to the reaction
mixture was slowly added with the stirring 0.49 ml
(0.0035 mol) of triethylamine in 5 ml of anhydrous
dioxane. After 2 h the reaction mixture was cooled,
and the precipitated triethylamine hydrochloride was
filtered off. The solvent was removed in a vacuum
(2.4 mm Hg). The amidine was recrystallized from
anhydrous CCl4. Yield 0.64 g (0.0021 mol, 60%),
white crystals, mp 124°C. IR spectrum, ν, cm–1: 1290
3-Phenoxybenzyl acid ethylimidate hydrochloride I
derived from 3-phenoxybenzonitrile via the Pinner
reaction [1] was used as a precursor for the synthesis
of N-methyl-N-phenyl-3-phenoxyphenylamidine.
The synthesis was performed via the intermediate
formation of hydrochloride III in the reaction of
ethylimidate I with N-methylaniline II.
The reaction takes place at 101°C in anhydrous
dioxane for 4 h at a molar ratio I:II = 1:1.2.
Free N-methyl-N-phenyl-3-phenoxyphenylamidine
V was obtained by reacting hydrochloride III with
triethylamine IV as a strong base.
1
(С–О–С), 1650 (С=N), 1200 (C–N), 1700 (N–H). Н
NMR spectrum, δ, ppm: 4.1 s (1H, NH), 6.9–7.22 m
NH2Cl
NH2Cl
O
O
C
C
CH3
HN
N
OC2H5
+
_C2H5OH
H3C
II
III
I
NH2Cl
N CH3
NH
O
O
C
C
N CH3
+ N(C2H5)3
_N(C2H5)3 HCl
IV
V
III
146
Popov, Yu. V.
