Russian Journal of Applied Chemistry, Vol. 77, No. 12, 2004, pp. 2034 2035. Translated from Zhurnal Prikladnoi Khimii, Vol. 77, No. 12, 2004,
pp. 2059 2060.
Original Russian Text Copyright
2004 by Gasanov, Allakhverdiev.
BRIEF
COMMUNICATIONS
A Procedure for Preparing N-Hydroxyethyl-Substituted
Succinimide and Phthalimide
R. A. Gasanov and M. A. Allakhverdiev
Institute of Chemistry of Additives, National Academy of Sciences of Azerbaijan, Baku, Azerbaijan
Received May 13, 2004
Abstract Conditions of synthesis of N-hydroxyethyl-substituted succinimide and phthalimide by reactions
of dicarboxylic acid imides with aminoethanol were optimized.
Synthesis of N-hydroxyethyl-substituted succin-
imide and phthalimide has been the subject of numer-
ous papers [1, 2]. N-(Alkoxyethyl)succinimides are
and phthalimide IV by the reaction of aminoethanol
with succinimide and phthalimide.
Freshly distilled aminoethanol (31 g) was added
dropwise to an equimolar amount of phthalimide
used as SO absorbents [3], and N-(2-hydroxyethyl)-
2
phthalimide, as a synthetic precursor of N-vinylphthal-
imide, a monomer for preparing polymers with a high
softening point (200 C) [4].
(73 g) or succinimide (49 g). The mixture warmed
up and foamed owing to evolution of ammonia. Then
the mixture was heated on a bath with Wood’s alloy
to 200 250 C. After the gas evolution ceased, the
heating was stopped. In the case of IV, the mixture
was poured into cold water. The crystalline precipitate
was filtered off, dried, and twice recrystallized from
benzene. Colorless crystals of IV were obtained in
Condensation of 2-(diethylamino)ethanol with suc-
cinimide and phthalimide at 360 C yielded N-[2-(di-
ethylamino)ethyl]succinimide I and N-[2-(diethylami-
no)ethyl]phthalimide II [1, 2]. The subsequent reac-
tions of I and II with aminoethanol yielded N-hydrox-
yethyl-substituted succinimide III and phthalimide IV:
87% yield (83 g); mp 127 128 C. In the case of III,
the reaction mixture was cooled and vacuum-distilled;
the fraction boiling at 178 (5 mm Hg) or 215 C
OC
(
C H ) NCH CH OH + HN
R
R
2
5 2
2
2
(
6 mm Hg) was crystallzed from hot benzene. The
OC
OC
crystals of III were filtered off and dried; yield of
colorless crystals of III 82% (58 g), mp 58 C:
(
C H ) NCH CH N
2
5 2
2
2
CO
H O
2
OC
NH + H NCH CH OH
I, II
R
2
2
2
CO
R
I, II + H NCH CH OH
2
2
2
CONH2
CONHCH CH OH
(
C H ) NCH CH NH
2
5 2
2
2
2
H O
2
2
2
OC
CO
+
HOCH CH N
R
2
2
OC
R
NCH CH OH
2 2
III, IV
NH3
CO
III, IV
where R = (CH ) (I, III), o-C H (II, IV).
2
2
6
4
The structures of III and IV were confirmed by IR
and H and C NMR spectroscopy.
EXPERIMENTAL
1
13
We have developed a single-step procedure for
preparing N-hydroxyethyl-substituted succinimide III
The IR spectra were recorded on a Specord M 80-
IR spectrometer (liquid films and mulls in mineral
1
070-4272/04/7712-2034 2004 MAIK Nauka/Interperiodica