Synthesis and antimicrobial activity of some 1-arylideneamino-4-(4-chlorobenzylidene)-2-methyl-1H-imidazolin-5(4H)-one compounds

Article abstract of DOI:10.13005/ojc/350245

4-Chlorobenzylidene-2-methyl-(4H)-oxazol-5-one, which were prepared from 4-chlorobenzaldehyde and acetylglycine in reaction with hydrazine hydrate in ethanol gave 1-amino-4-(4-chlorobenzylidene)-2-methyl-1H-imidazolin-5(4H)-one. However, treatment of 4-ch

Full text of DOI:10.13005/ojc/350245

ISSN: 0970-020 X
CODEN: OJCHEG
2019, Vol. 35, No.(2):
Pg. 822-828
ORIENTAL JOURNAL OF CHEMISTRY
An International Open Access, Peer Reviewed Research Journal
www.orientjchem.org
Synthesis and Antimicrobial Activity of Some
1-arylideneamino-4-(4-chlorobenzylidene)-2-methyl-
1H-imidazolin-5(4H)-one Compounds
CONG TIEN NGUYEN1*, DAO THI HONG DINH1,THIN VAN NGUYEN2,
GIANG DUC LE2 and HIEN CAO NGUYEN3
1Faculty of Chemistry, Ho Chi Minh City University of Education, 280 An Duong Vuong St.,
District 5, 700000, Ho Chi Minh City, Vietnam.
2School of Natural Sciences Education, Vinh University, 182 Le Duan St., 460000, Vinh City, Vietnam.
3Department of Chemical Technology, Ho Chi Minh City University of Food Industry, 140 Le Trong Tan St.,
Tan Phu District, 700000, Ho Chi Minh City, Vietnam.
*Corresponding author E-mail: congnt@hcmue.edu.vn
http://dx.doi.org/10.13005/ojc/350245
(Received: August 09, 2018; Accepted: March 17, 2019)
AbSTRACT
4-Chlorobenzylidene-2-methyl-(4H)-oxazol-5-one, which were prepared from
4-chlorobenzaldehyde and acetylglycine in reaction with hydrazine hydrate in ethanol gave
1-amino-4-(4-chlorobenzylidene)-2-methyl-1H-imidazolin-5(4H)-one. However, treatment of
4-chlorobenzylidene-2-methyl-(4H)-oxazol-5-one with hydrazine hydrate in pyridine yielded
3-(4-chlorophenyl)propanohydrazide. Reaction of 1-amino-4-(4-chlorobenzylidene)-2-methyl-1H-
imidazolin-5(4H)-one with aromatic aldehydes gave eight corresponding Schiff’s bases namely
1-arylideneamino-4-(4-chlorobenzylidene)-2-methyl-1H-imidazolin-5(4H)-ones.The structure of the
3-(4-chlorophenyl)propanohydrazide and the imidazoline-5-one compounds was confirmed by IR,
1H-NMR, 13C-NMR and MS spectral data. The Schiff’s bases were tested for antimicrobial activities
against several strains of Gram-positive, Gram-negative bacteria, molds and yeasts.
Keywords: 1-amino-4-(4-chlorobenzylidene)-2-methyl-1H-imidazolin-5(4H)-one, Antimicrobial
activities, 4-chlorobenzylidene-2-methyl-(4H)-oxazol-5-one, Schiff bases, Spectral data.
INTRODUCTION
Schiff’s bases have been shown as
biologically versatile compounds having anti-
inflammatory, anticonvulsant, antimalarial, antiviral,
antifungal and antibacterial4,5. Recently, some
Schiff’s bases containing imidazole nucleus have
been reported to possess various biological
The imidazole nucleus has proven to be
unusually fertile source of medicinal agents such
as anticancer agents, antioxidant agents, antifungal
agents and antimicrobial agents1,2,3
.
This is an
Open Access article licensed under a Creative Commons license: Attribution 4.0 International (CC- BY).
Published by Oriental Scientific Publishing Company © 2018

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NGUYEN et al., Orient. J. Chem., Vol. 35(2), 822-828 (2019)
properties like antioxidant and antimicrobial activity
6,7. To contribute to the study of the synthesis and
properties of the Schiff’s bases, we report here the
preparation of Schiff’s bases containing imidazolin-
5-one moiety starting from 4-chlorobenzaldehyde
and N-acetylglycine via 4-chlorobenzylidene-2-
methyl-(4H)-oxazol-5-one first and then 1-amino-
4-(4-chlorobenzylidene)-2-methyl-1H-imidazolin-
5(4H)-one. Next, the antimicrobial activities of
the synthesized Schiff’s bases were investigated.
Besides that, in the present work, the transformations
of the oxazole compound in solvents such as ethanol
and pyridine were also mentioned.
Melting points were measured in open
capillary tubes on a Gallenkamp melting point
apparatus and are uncorrected. The IR spectra
of synthesized compounds were recorded on
FTIR–8400S–SHIMADZU spectrometer using KBr
1
pellets. H-NMR was recorded on Bruker Avance
spectrometer at 500 MHz using a DMSO-d6 as a
solvent and tetramethylsilane (TMS) as an internal
standard, as well as the 13C-NMR, HSQC, HMBC
spectra were recorded at 125 MHz.The MS spectra
were recorded on a Bruker micrOTOF–Q 10187
spectrometer.
MATERIALS AND METHODS
ThesynthesisoftheSchiff'sbasescontaining
2-methylimidazolin-5-one heterocycles were performed
following the steps shown in Scheme 1.
All reagents are of commercial quality and used
without any further purification
CH3CONHCH2COOH
NH2NH2
O
Cl
O
Cl
Cl
CHO
CH3COONa
(CH3CO)2O,
reflux, 6 h
ethanol, reflux, 4 h
(1)
(3)
O
N
NH2
N
N
(2)
(56%)
(60%)
CH3
CHO
CH3
X
NH2NH2
pyridine, reflux,
6 h
ethanol, reflux,
6 h
H
Cl
O
Cl
N
NH2
H
5
( )
4a-f
)
(
X
N
O
N
N
(68%)
CH3
4a
X = 4-CH3O ( , 80%); X = 4-CH3
4b
(
, 66%)
4c
4d
X = 2-F ( , 78%); X = 4-F ( , 74%)
4e 4f
X = H ( , 68%); X = 2-NO2
4g 4h
, 81%); X = 4-NO2 (
(
, 77%)
X = 3-NO2
(
, 84%)
Scheme 1. Pathway for synthesis of 1-arylideneamino-4-arylidene-2-methyl-1H-imidazolin-5(4H)-one compounds
Synthesisof4-(4-chlorobenzylidene)-2-methyloxazol-
5(4H)-one (2)
Synthesis of 1-amino-4-(4-chlorobenzylidene)-2-
methyl-1H-imidazolin-5-one (3)
Oxazole (2) was synthesized according to
To a solution of compound (2) (2.22 g, 0.0l
the procedure reported previously8,9: An equimolar
mixture of 4-chlorobenzaldehyde (7.03 g, 0.05
mol) and acetylglycine (5.85 g, 0.05 mol) in freshly
distilled acetic anhydride (25 mL) containing fused
anhydrous sodium acetate (4.1 g) was refluxed for 3
h and then cooled.The solid was triturated with cold
saturated solution of sodium carbonate and filtered,
washed with water, air dried and recrystallized from
ethanol. Yield 60%, mp. 158-160°C; IR (ν, cm-1):
mole) in 50 ml of absolute ethanol, hydrazine hydrate
50% (7.5 mL, 0.03 mole) was added and the reaction
mixture was refluxed for 4.0 hours. On cooling, the
formed precipitate was filtered off and crystallized
from ethanol. Yield 56 %, mp. 192-193°C; IR
(ν, cm-1):3318, 3209 (N-H), 1705, 1643 (C=O, C=N,
C=C); 1H-NMR (δ, ppm and J, Hz): 8.22 (2H, d, 3J
= 8.5, Ar-H), 7.50 (2H, d, 3J = 8.5, Ar-H), 6.98 (1H,
s, ClC6H4CH=), 5.11 (2H, s, NH2) and 2.31 (3H, s,
CH3); 13C-NMR: 168.8, 166.0 (C=O, C=N), 137.8,
134.4, 133.4, 133.0, 128.7, 123.2 (C aromatic and
C olefilic) and 14.5 (CH3).
1
1800, 1772, 1661, 1605; H-NMR (δ, ppm and J,
Hz): 8.19 (2H, d, 3J = 8.0, ArH), 7.57 (2H, d, 3J =
8.0, ArH), 7.52 (2H, d, 3J = 8.5, ArH), 7.23 (1H, s,
ClC6H4CH=) and 2.39 (3H, s, CH3).

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NGUYEN et al., Orient. J. Chem., Vol. 35(2), 822-828 (2019)
Generalprocedureforsynthesisof1-arylideneamino-
4-(chlorobenzylidene)-2-methyl-1H-imidazolin-
5(4H)-one compounds (4a-h)
of test microorganisms was regarded as MIC.Proper
controls were kept for each experiment.
An equimolar quantity of imidazolin-5-one
RESULTS AND DISCUSSION
(3) and a definite aldehyde was refluxed in ethanol for
6.0 hours.The reaction mixture was cooled down to
room temperature and the precipitate obtained was
filtered off and crystallized from dioxane to give the
corresponding products.As the result, yellow crystals
are obtained for all cases.Yields, physical properties
and IR spectral data of these Schiff's bases were
shown in Table 1. 1H-NMR and 13C-NMR data of the
synthesized Schiff's bases were summarized inTable
2 and 3, respectively.
The most important method for the
synthesis of 1-aminoimidazolin-5-one compounds
may be treatment of oxazolones with hydrazine.
Therefore, as shown in Scheme 1, to obtain 1-amino-
4-(4-chlorobenzylidene)-2-methyl-1H-imidazolin-
5(4H)-one, hydrazine hydrate was treated with 4-(4-
chlorobenzylidene)-2-methyloxazol-5(4H)-one (2),
which was prepared by Erlenmeyer condensation
of acetyl glycine with 4-chlorobenzaldehyde in
presence of sodium acetate and acetic anhydride.
Synthesis of 3-(4-chlorophenyl)propanohydrazide (5)
To a solution of compound (2) (2.22 g, 0.0l
The synthesis of 4-(4-chlorobenzylidene)-2-
methyloxazol-5(4H)-one(2)from4-chlorobenzaldehyde
and acetyl glycine was carried out according to the
method described in our earlier work8,9.The structure
of the synthesized compound was conformable
to its spectral data. According to the literatures,
aminoimidazolin-5-one may be afforded by refluxing
mole) in 30 ml of pyridine, hydrazine hydrate 50%
(7.5 mL, 0.03 mole) was added and the reaction
mixture was refluxed for 6.0 hours. On cooling, the
formed precipitate was filtered off and crystallized
from ethanol. Yield 68%, mp. 161-162°C; IR (ν,
cm-1): 3379, 3302 and 3179 (N–H), 2924, 2855
1
(C–Haliphatic), ~1700 (C=O); H-NMR: 8.94
mixture of oxazolone and hydrazine in pyridine10,11
.
(1H, s, N-H), 7.31 (2H, d, 3J = 8.5, Ar-H), 7.21 (2H,
d, 3J = 8.5, Ar-H), 4.15 (2H, br, NH2), 2.80 (2H, t,
3J = 7.5, CH2CO), and 2.31 (2H, t, 3J = 7.5, ArCH2);
13C-NMR: 170.5 (C=O), 140.2, 130.5, 130.1, 128.2
(C aromatic) and 34.8, 30.2 (C aliphatic).
However, the product yielded in the reaction of
4-(4-chlorobenzylidene)-2-methyloxazol-5(4H)-
one (2) with hydrazine in pyridine was not desired
1-amino-4-(4-chlorobenzylidene)-2-methyl-1H-
imidazolin-5(4H)-one compound. Mass spectrum of
the product showed [M+H]+ ion peak at m/z 199.0684
which is not agreement with the molecular formula
of the C11H10ClN3O (M = 235.0512) of 1-amino-4-(4-
chlorobenzylidene)-2-methyl-1H-imidazolin-5(4H)-
one.The 1H-NMR spectrum show the appearance of
two adjacent methylene groups as two triplet signals
at 2.79 and 2.31 ppm with intensity of 2H for each
signals. The aromatic area appeared two doublet
signals, both with intensity of 2H. Besides that,
there are two broad signals, one at 8.94 ppm with
intensity of 1H and one at 4.15 ppm with intensity
of 2H corresponding with protons of the hydrazine
group (-NHNH2). The 13C-NMR spectrum show the
appearance of a signal of carbonyl carbon at 170.5
ppm, four signals of aromatic carbons at 128.2-
140.2 ppm and two signals of aliphatic carbons at
30.2-34.8 ppm. All data showed that the product is
3-(4-chlorophenyl)propanohydrazide (C9H11ClN2O,
M = 198.0560).
Antimicrobial Activity Assay
Antimicrobial activity of test samples
was assayed using microbroth dilution methods of
McKane, L., and Kandel12. This means, the serial
dilution technique was performed using 96-well
microplates to determine the minimum inhibitory
concentration (MIC) of the samples against test
microorganisms, including Escherichia coli (ATCC
25922), Pseudomonas aeruginosa (ATCC 25923),
Bacillus subtilis (ATCC 11774), Staphylococcus
aureus subsp. (ATCC 11632), Aspergillus niger
(439), Fusarium oxysporum (M 42), Saccharomyces
cerevisiae (SH 20) and Candida albicans (ATCC
7754). Briefly, the activated microorganisms were
diluted with the growth medium broth (Eugon Broth
(Difco, USA) for bacteria, Mycophil (Difco, USA) for
fungi) to give a turbidity equivalent to the McFarland
0.5 standard and used for susceptibility testing.The
plates were covered and incubated overnight at
37oC for bacteria and at 30oC for 48 h for fungi.The
lowest concentration which inhibited visible growth
In the our previous work8,9, the reaction of
oxazole (2) with hydrazine hydrate occurs at room

825
NGUYEN et al., Orient. J. Chem., Vol. 35(2), 822-828 (2019)
temperature to give 2-(acetamido)-3-(4-chlorophenyl)
acrylohydrazide easily8,9.Thus, we assume that after
the formation of the hydrazide, this compound was
transformed into N-(3-(4-chlorophenyl)-1-hydrazinyl-
1-oxopropan-2-ylidene)acetamide, which was
reduced by hydrazine to form 3-(4-chlorophenyl)
propanohydrazide as description in the Figure 1.
2-methyl-1H-imidazolin-5(4H)-one. The HR-MS
of this product showed the molecular ion peak
[M+ H]+ = 236.0637, which was agreement with mass
calculated for C11H10ClN3O with 235.0512.
1-Amino-4-(4-chlorobenzylidene)-2-methyl-
1H-imidazolin-5(4H)-one compound (3) reacted
with aromatic aldehydes in absolute ethanol to form
azomethine derivatives (4a-h), respectively. Yields,
physical properties and IR spectral data of these
azomethines were shown inTable 1.The IR spectra of
Schiff's bases (4a-h) obtained from amine (3) showed
not only a lack of stretching band at 3227-3424 cm-1
(νNH2) but also an appearance of the absorption
band of imine group (C=N) around 1645-1666 cm-1.
1H-NMR spectra of (4a-h) compounds show a new
signal observed at 9.44-10.07 ppm integrating for the
proton of the azomethine group (CH=N) (seeTable 2).
In the HMBC spectra (see the example of the HMBC
correlations of(4g) compoundshownin theFig.2), the
singlet around 9.44-10.07 ppm in the 1H-NMR spectra
made cross peak with signals of carbon atoms in the
benzene ring of benzylidene moiety bonded to nitrogen.
The values of chemical shift of the azomethine protons
were also similar to values of chemical shift of these
protonsinthe1H-NMRof1-arylideneamino-4-arylidene-
2-phenyl-1H-imidazolin-5(4H)-one compounds10.
Using the HSQC and HMBC spectra, the other
13C signals of the Schiff's bases were assigned and
summarized in Table 3.
H
H
Cl
NHNH2
O
Cl
NHNH2
O
Cl
NHNH2
O
N
H
N
H
N
C
O
O
O
H3C
H3C
H3
- N2
NH2NH2
Cl
NHNH2
+
H2N
H3C
O
O
Fig. 1. Proposed mechanism for formation of
3-(4-chlorophenyl)propanohydrazide from 2-(acetamido)
-3-(4-chlorophenyl)acrylohydrazide
Changing the condition of reaction, we
found out that 1-amino-4-(4-chlorobenzylidene)-2-
methyl-1H-imidazolin-5(4H)-one compound (3) may
be formed by refluxing 4-(4-chlorobenzylidene)-
2-methyloxazol-5(4H)-one with hydrazine hydrate
in ethanol. The structure of the product was first
confirmed via its IR spectral data in which the
presence of a characteristic absorption band around
3201-3456 cm-1 and a medium one around 1622-
1647 cm-1 was in turn represented for N-H bonds
and C=O group. Beside signal of the amino group
at δ 5.11 ppm (2H, singlet), signals of benzene ring
(two doublet with J = 8.5 Hz at δ 8.22 ppm and δ
7.50 ppm), signal of olefinic proton (1H, singlet)
at δ 6.98 ppm and signal of the methyl group
(3H, singlet) at and δ 2.31 ppm were also easily
detected. Nine signals in the 13C-NMR spectrum of
(3) were considered to be accordant with expected
structure of the 1-amino-4-(4-chlorobenzylidene)-
H
O
Cl
H
NO2
N
N
N
4g
(
)
CH3
Fig. 2. The HMbC correlations of the (4g) compound
Table 1: Physical and IR spectral data of the Schiff's bases (4a-h)
(Comp.)/X
M.p. (oC)
Yield(%)
IR (ν, cm-1)
[M+ H]+ [Calc.]
C-H
C=O
C=C, C=N
(4a)/4-CH3O
(4b)/4-CH3
(4c)/2-F
(4d)/4-F
(4e)/H
(4f)/ 2-NO2
(4g)/3-NO2
(4h)/4-NO2
176-178
182-184
196-197
184-185
173-174
175-177
181-182
213-214
80
66
78
74
68
77
81
84
3060 2930
2924 2855
1717 1678 1605 1561
354.1051 [354.1009]
360.0867 * [360.0880]
342.0824 [342.0809]
342.0818 [342.0809]
324.0928 [324.0904]
369.0751 [369.0754]
369.0746 [369.0754]
369.0783 [369.0754]
1705 1651
1717 1651
1713 1651
1713 1651
1705 1643
1713
1589
1591
1589
1589
1582
1589
1582
-
-
2960
2847
3079
2924
1705 1643
*(4b): [M+ Na]+.

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NGUYEN et al., Orient. J. Chem., Vol. 35(2), 822-828 (2019)
Additionally, structure of the Schiff's bases
was further confirmed by HR-MS data. Molecular
ion peaks in the mass spectra of the products were
conformity with molecular formulas of the desired
1-arylideneamino-4-(4-chlorobenzylidene)-2-methyl-
1H-imidazolin-5(4H)-one compounds (see Table 1).
Table 2: Signals in the 1H-NMR spectra (δ, ppm and J, Hz) of the Schiff's bases (4a-h)
8
9
H
6
7
10
O
Cl
H
4 5
17
16X
15
11
12
13
N1
3 N
N
2
2a
14
CH3
X
(4a)
(4b)
(4c)
2-F
(4d)
4-F
(4e)
H
(4f)
(4g)
(4h)
Number
4-CH3O
4-CH3
2-NO2
3-NO2
4-NO2
2a
6
2.47, s
7.08, s
8.24, d
J=8.5
2.48, s
7.10, s
8.28, d
J=8.5
2.49, s
7.06, s
2.48, s
7.10, s
8.29, d
J=8.5
2.49, s
7.12, s
8.28, d
J=8.5
2.50, s
7.12, s
8.27, d
J=8.5
7.54, d
J=8.5
10.07, s
-
2.50, s
7.06, s
8.20, d
J=8.5
2.52, s
7.12, s
8.26, d
8
8.22, d
J=8.5
7.50, d
J=8.5
9.79, s
-
J=8.5
9
7.52, d
J=8.5
7.55, d
J=8.5
7.54, d
J=8.5
7.55, d
J=8.5
7.47, d
J=8.5
7.53, d
J=8.5
11
13
9.44, s
9.52, s
9.59, s
7.95, dd
9.58, s
9.70, s
8.57, s
9.75, s
7.79, d J=8.0 7.75, d J=8.0
7.87, dd
8.11, d J=8.5
J=8.0,J=6.0
7.37, dd
J=8.0,J=8.0
-
J=8.0,J=2.0
7.55, m
14
15
16
7.05, d
J=8.0
-
7.32, d
J=8.0
-
7.33, m
7.58, m
7.33, m
8.12, m
-
8.31, d
J=8.5
-
7.55, m
7.55, m
7.76, dd
J1=J2=8.0
7.86, dd
8.23, d J=8.0
7.05, d
J=8.0
7.32, d
J=8.0
7.37, dd
J=8.0,J=8.0
7.95, dd
J=8.0,J=6.0
-
7.77, dd
J1=J2=8.0
8.29, d
J=8.0
8.31, d
J=8.5
8.11, d
J=8.5
-
J1=J2=8.0
8.12, m
17
7.79, d J=8.0 7.75, d J=8.0
7.99, dd
J1=J2=7.5
-
7.87, dd
J=8.0,J=2.0
-
others
3.84, s
2.37, s
-
-
(CH3OAr)
(CH3Ar)
Table 3: Signals in the 13C-NMR spectra (δ, ppm) of the Schiff's bases (4a-h)
X
(4a)
(4b)
(4c)
2-F
(4d)
4-F
(4e)
H
(4f)
(4g)
(4h)
Number
4-CH3O
4-CH3
2-NO2
3-NO2
4-NO2
2
2a
4
163.3
14.8
163.6
15.2
162.8
14.5
165.3
15.2
163.6
15.2
163.3
15.1
162.6
14.5
162.9
14.7
137.2
165.6
125.8
132.4
133.3
128.5
134.7
154.7
124.5
129.2
114.3
161.8
114.3
129.2
55.2
137.3
165.9
124.9
132.7
133.7
128.9
135
136.8
165.6
124.9
132.2
133.3
128.4
134.8
146.6
126.3
160.1
115.3
120.9
124.6
133
137.2
165.9
125
137.2
165.9
125
136.9
166
136.6
165.4
125
136.7
165.5
125.2
132.3
133.5
128.4
135
5
6
125.5
132.5
133.8
128.9
135.2
148.8
131.9
148.5
124.7
128.6
133.8
128
7
132.6
133.7
128.9
135
132.6
133.7
128.9
135.1
154.3
133.6
129
132.1
133.3
128.3
134.8
151.1
135.2
121.3
148.1
133.2
130.1
124.9
-
8
9
10
11
12
13
14
15
16
17
others
154.6
130.9
127.7
129.6
141.6
129.6
127.7
21.1
153.1
130.3
130.1
116.1
163
151
139.5
128.5
123.7
148.7
123.7
128.5
-
127.7
131.5
127.7
129
116.1
130.1
-
-
-
-
(CH3OAr) (CH3Ar)

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NGUYEN et al., Orient. J. Chem., Vol. 35(2), 822-828 (2019)
Schiff's bases (4a-f) were examined for
antimicrobial activity against Escherichia coli,
Pseudomonas aeruginosa (Gram-negative bacteria);
Bacillus subtilis, Staphylococcus aureus (Gram-
positive bacteria); Aspergillus niger, Fusarium
oxysporum (mold) and Saccharomyces cerevisiae,
Candida albicans (yeast). These compounds were
subjected to examination of their MIC values
according to the reported method12 and the data are
shown in Table 4. The two-fold microdilution broth
method was used and all of the tested samples
demonstrated inhibitory effects in a concentration-
dependent manner. However, the results showed
that only 4a, 4b and 4 h exhibited any significant
inhibition against Staphylococcus aureus with MIC
values of 100 μg/mL.
Table 4:The minimum inhibitory concentrations (MIC) of the Schiff's bases against bacteria and fungi
Sample
MICa (mg/mL)
Bacteria Gr (+)
Bacteria Gr (-)
E.C
Mold
Yeast
P. A
B.S
S.A
A.N
F.O
S.C
C.A
4a
4b
4c
4d
4e
4f
(-)b
(-)
(-)
(-)
(-)
(-)
(-)
(-)
(-)
(-)
(-)
(-)
(-)
(-)
(-)
(-)
(-)
(-)
(-)
(-)
(-)
(-)
(-)
(-)
100
100
(-)
(-)
(-)
(-)
(-)
(-)
(-)
(-)
(-)
(-)
(-)
(-)
(-)
(-)
(-)
(-)
(-)
(-)
(-)
(-)
(-)
(-)
(-)
(-)
(-)
(-)
(-)
(-)
(-)
(-)
(-)
(-)
(-)
(-)
(-)
(-)
4g
4h
(-)
100
aE.C - Escherichia coli, P.A - Pseudomonas aeruginosa, B.S - Bacillus subtilis, S.A - Staphylococcus aureus, A.N -
Aspergillus niger, F.O - Fusarium oxysporum, S.C - Saccharomyces cerevisiae and C.A - Candida albicans.
bMIC > 100 μg/mL and not determined
CONCLUSION
against tested microorganisms including Escherichia
coli, Pseudomonas aeruginosa (Gram-negative
bacteria); Bacillus subtilis, Staphylococcus aureus
(Gram-positive bacteria); Aspergillus niger, Fusarium
oxysporum (mold) and Saccharomyces cerevisiae,
Candida albicans (yeast).
Refluxingmixtureof4-(4-chlorobenzylidene)
-2-methyloxazol-5(4H)-one and hydrazine hydrate in
different solvents forms different products.In ethanol,
the product is 1-amino-4-(4-chlorobenzylidene)-
2-methyl-1H-imidazolin-5-one but in pyridine, the
product is 3-(4-chlorophenyl)propanohydrazide.
ACKNOwLEDGEMENT
Thereactionof1-amino-4-(4-chlorobenzylidene)
-2-methyl-1H-imidazolin-5-one with aromatic
aldehydes yielded eight Schiff's bases, respectively.
The structure of the Schiff's bases was determined
This research was not supported by any
organizations.
Conflict of Interests
The authors declare that there is no conflict
of interests regarding the publication of this paper.
1
by IR, H-NMR, 13C-NMR and MS spectral data.
Most of the Schiff’s bases exhibited low activity
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