Condensation–cyclization reaction for one-pot synthesis of 1,3-thiazolidin-4-one derivatives by poly(p-phenylenediamine) grafted on LDHs as a catalyst with green tool

Article abstract of DOI:10.1080/17415993.2020.1812611

The three-component reaction between amine, carbonyl compound and thioglycolic acid is now considered as a major strategy for synthesis of 1,3-thiazolidin-4-ones, which consists of the following steps: (i) condensation of aldehyde and amine which results

Full text of DOI:10.1080/17415993.2020.1812611

Journal of Sulfur Chemistry
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Condensation–cyclization reaction for one-pot
synthesis of 1,3-thiazolidin-4-one derivatives by
poly(p-phenylenediamine) grafted on LDHs as a
catalyst with green tool
Maryam Mirzaei-Mosbat & Ramin Ghorbani-Vaghei
To cite this article: Maryam Mirzaei-Mosbat & Ramin Ghorbani-Vaghei (2020):
Condensation–cyclization reaction for one-pot synthesis of 1,3-thiazolidin-4-one derivatives
by poly(p-phenylenediamine) grafted on LDHs as a catalyst with green tool, Journal of Sulfur
Chemistry, DOI: 10.1080/17415993.2020.1812611
To link to this article: https://doi.org/10.1080/17415993.2020.1812611
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JOURNAL OF SULFUR CHEMISTRY
https://doi.org/10.1080/17415993.2020.1812611
Condensation–cyclization reaction for one-pot synthesis of
1,3-thiazolidin-4-one derivatives by
poly(p-phenylenediamine) grafted on LDHs as a catalyst with
green tool
Maryam Mirzaei-Mosbat and Ramin Ghorbani-Vaghei
Department of Organic Chemistry, Faculty of Chemistry, Bu-Ali Sina University, Hamedan, Iran
ABSTRACT
ARTICLE HISTORY
Received 25 March 2020
Accepted 14 August 2020
The three-component reaction between amine, carbonyl compound
and thioglycolic acid is now considered as a major strategy for syn-
thesis of 1,3-thiazolidin-4-ones, which consists of the following steps:
(i) condensation of aldehyde and amine which results the formation
of an imine; (ii) the reaction between thioglycolic acid and the imine
which is followed by an intramolecular cyclization reaction, which
leads to the formation of the final product. In this way, if no suit-
able catalyst is employed, the completion of the reaction will not be
achieved. Hence, it is of great importance to select an appropriate
catalyst so that these compounds can be successfully synthesized.
Herein, we employed LDHs@PpPDA as a versatile catalyst for the
fabrication of novel derivatives of 1,3-thiazolidin-4-one.
KEYWORDS
Synthesize; condensation;
intramolecular cyclization;
thioglycolic acid;
1,3-thiazolidin-4-ones
1. Introduction
In heterocyclic compounds, which are regarded as a main category in the field of organic
chemistry and take a significant part in both pure and applied chemistry, some or all
the atoms present in their molecules are joined together in rings which not only con-
tain carbon atoms but also consist of at least one atom of other elements. They are
CONTACT Ramin Ghorbani-Vaghei
rgvaghei@yahoo.com
Department of Organic Chemistry, Faculty of
Chemistry, Bu-Ali Sina University, Hamedan 6517838683, Iran
Supplemental data for this article can be accessed here. https://doi.org/10.1080/17415993.2020.1812611
© 2020 Informa UK Limited, trading as Taylor & Francis Group

2
M. MIRZAEI-MOSBAT AND R. GHORBANI-VAGHEI
considered as one of the largest groups of organic chemistry materials which are widely
employed in numerous applications, e.g. the fabrication of pharmaceutical compounds [1]
along with intermediates for preparation of the drugs which present antivirals, antibiotics,
anti-tumors, antimicrobials, anti-inflammatories, antifungals, and antidiabetics activities
[2].
Multi-component reactions (MCRs) are very appropriate for construction of the hetero-
cyclic cores [3,4]. MCRs include reactions in which three or more starting materials react
in a one-pot process to form a new product. The advantages of MCRs extend from high
atom economy, the ability to build complex molecules, avoiding the necessity of isolation
and purifications of the intermediates, consistency with the principles of green chemistry,
operational simplicity, and minimizing waste, labor, and cost [5–9].
Thiazolidine-4-one is a five-membered heterocyclic ring with N and S heteroatoms and
one carbonyl group, utilized in many strategies for fabrication of the pharmaceuticals, and
therefore, it is present in the structure of the fabricated medicines [10–13]. Nowadays,
innumerable studies have been carried out around the world to investigate the biologi-
cal activity of thiazolidine-4-one, whose extensive applications have been demonstrated
in a variety of domains, e.g. anti-HIV [14–18], antimicrobials [19,20], antihistamines
[21,22], anti-YFV (Yellow fever virus) [23], anti-cancers [24], anti-inflammatories [25],
and antioxidants [26]. It is noticeable that the fabrication of assorted derivatives with var-
ious biological properties can be carried out by modification of the substitutions which
exist in the structure of the compounds. For example, Rawal et al. could introduce a type
of derivatives named 2,3-diaryl-1,3-thiazolidin-4-one, which is a vital drug for the ther-
apy of the HIV virus [16]. Regarding the above-mentioned importance and applications
of thiazolidinones in pharmaceutical industry and commercial markets, finding the supe-
rior synthesis approaches is very important. So far, innumerable approaches have been
proposed by researchers for the fabrication of thiazolidinediones, among which there is
a commonly employed strategy which consists of one-pot three-component condensa-
tion of amine, the carbonyl compound and thioglycolic acid. According to the literatures,
various conditions and catalysts have been investigated in this reaction. For instance, in
2002, Srivastava et al. [27] synthesized 4-thiazolidinones by using DCC catalyst and THF
solvent in room temperature. In another study which was reported in 2013, Foroughifar
et al. could synthesize 1,3-thiazolidin-4-ones at 70°C in solvent-free conditions by using
Bi(SCH2COOH)3 as a catalyst [28]. In another work reported in 2016, Safaei-Ghomi et al.
fabricated novel derivatives of these compounds by using nano-sized CdZr4(PO4)6 cata-
lyst under ultrasonic irradiation [29]. Herein, we decide to fabricate innovative derivatives
of 1,3-thiazolidin-4-one in agreement with green chemistry. The schematic illustration of
Scheme 1. Synthesis of 1,3-thiazolidin-4-ones catalyzed by LDHs@PpPDA.

JOURNAL OF SULFUR CHEMISTRY
3
Figure 1. The structure of LDHs@PpPDA.
the synthesis route is exhibited in Scheme 1. As presented in Figure 1, LDHs@PpPDA [30]
was utilized as a catalyst for this reaction and the advantages of this is its facile synthetic
steps, available raw materials, recyclability and cost-efficiency.
2. Results and discussion
Organic chemists have made numerous efforts to find out the reactions which follow the
principles of green chemistry. Therefore, this is very important to consider all the param-
eters which effect on the expansion of such reactions. Herein, we describe the synthesis of
1,3-thiazolidin-4-ones through the condensation reaction of substituted aldehydes, amine
and thioglycolic acid in the presence of LDHs@PpPDA.
In this work, the reaction among 2-pyridinecarbaldehyde, 4-methyl aniline and thio-
glycolic acid has been selected as a model reaction, and the effects of various parameters
including temperature, solvent, and catalyst have been investigated. At the First, the effect
of a variety of catalysts was investigated for the synthesis of 1,3-thiazolidin-4-ones, as
depicted in Table 1, based on which, the LDHs@PpPDA catalyst was the foremost efficient
catalyst in this synthesis approach.
Numerous effective basic sites were provided in the catalyst by –NH2 and –NH groups,
which lead to the superior catalytic activity of LDHs@PpPDA. The reaction conditions,
including solvent, temperature and catalyst content, were optimized and listed in Table 2,
based on which it was demonstrated that no reaction observed in the absence of the catalyst
Table 1. Comparison of various catalysts for the synthesis of 1,3-thiazolidin-4-one derivatives.
Entry
Catalyst
Solvent
Temp. (°C)
Time (min)
Yield (%)
Ref.
1
2
3
4
5
6
MNPs@SiO2-IL
Bi(SCH2COOH)3
DDC
Nano-CdZr4(PO4)6
Fe3O4/SiO2/Salen/Mn/IL
LDHs@PpPDA
–
–
70
70
r.t.
60
120
50
25
50
94
75
91
88
94
95
[31]
[28]
[27]
[29]
[32]
THF
PhMe
–
Ultrasonic irradiation
r.t.
70
EtOH
90
This work

4
M. MIRZAEI-MOSBAT AND R. GHORBANI-VAGHEI
Table 2. Optimization of the reaction conditions for the synthesis of 1,3-
thiazolidin-4-one derivatives using the LDHs@PpPDA catalyst.
Entry
Catalyst
Solvent
Temp. (°C)
Time (min)
Yield (%)
1
2
3
4
5
6
7
8
0.05
0.05
0.05
0.05
0.05
0.05
0.05
0.02
0.04
0.08
0.05
–
H2O
EtOH
CH2Cl2
PhMe
Solvent-free
DMF
EtOAc
EtOH
EtOH
Reflux
70
25
70
70
70
70
70
70
240
90
42
95
38
20
53
68
87
68
85
95
90
N.R.
240
240
240
240
240
90
90
90
90
90
9
10
11
12
EtOH
EtOH
EtOH
70
60
70
and the presence of 0.05 g of the catalyst was a suitable amount for accomplishment of the
reaction. Furthermore, the more decrement of amount of the catalyst, decreased the effi-
ciency of reaction. Also, as expected, no considerable effects was observed on the progress
of yield in the reaction by enhancing the catalyst amount (Table 2, entries 8–10). Subse-
quently, the effect of temperatures was investigated in the model reaction, in which the
highest yield of the product could be provided at the temperature of 70°C (Table 2, entries
11). Additionally, the effect of the solvents on the reaction was investigated (Table 2, entries
1–7), among which EtOH proved that could be selected as a most appropriate solvent for
this reaction. Therefore, the best desired conditions for the synthesis of 1,3-thiazolidin-
4-one derivatives can be obtained by using 0.05 g of the catalyst, EtOH solvent and a
temperature of 70°C.
After the optimization of the conditions, the reaction of aromatic aldehyde (1.0 mmol),
aryl amine (1.0 mmol), and thioglycolic acid (1.0 mmol), in the presence of 0.05 g of
the catalyst, solvent (EtOH), and temperature of 70°C was studied. In this way, different
aldehydes and amines with different electron-withdrawing and electron-donating groups
were used, as exhibited in Table 3. In this work, it was demonstrated that the reaction
could more proceed when an aldehyde with electron-withdrawing group and an amine
with electron-donating group were employed. For investigation of the retrievability and
reusability characteristic of catalyst, the model reaction was investigated in the presence
of EtOH (5 mL) and 0.05 g of the catalyst at the temperature of 70°C. After completion of
the reaction, the separated catalyst was washed several times with water and hot ethanol,
followed by being placed in an oven to dry out. The catalyst recyclability is exhibited in
Figure 2.
Since green chemistry aims to design products and processes of more environmentally
friendliness along with less chemicals hazards, applying EtOH as a green solvent and uti-
lization of a catalyst with well recyclability properties throughout the reactions are in line
with the purpose of this work to comply with these rules.

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5
Table 3. Synthesis of 1,3-thiazolidin-4-one derivatives using the LDHs@PpPDA catalyst.
The characterization of the catalyst was carried out by using different techniques includ-
ing FT-IR spectroscopy, scanning electron microscopy (SEM), thermogravimetric analysis
(TGA), X-ray diffraction (XRD), and EELS maps [30]. In addition, the structure of the
recovered catalyst was investigated prior and after the accomplishment of the reaction.
LDHs@PpPDA was collected after the reaction and various analyses were conducted on
them.
The FT-IR spectra of the catalyst before and after reaction are shown in Figure 3. As can
be seen, the analogous characteristic bands of LDHs@PpPDA demonstrate the stability of
the catalyst throughout the recycling process.

6
M. MIRZAEI-MOSBAT AND R. GHORBANI-VAGHEI
Figure 2. Recyclability of the LDHs@PpPDA.
Figure 3. FT-IR spectra of LDHs@PpPDA before (a) and after (b) the reaction.
The EDX spectra of the catalyst before and after the reaction were almost identical,
which indicated that there was no obvious changes for the catalyst composition after the
reaction (Figure 4). In both spectra, the clear presence of N and C signals illustrate that the
layered double hydroxides have been successfully coated with PpPDA.
SEM images of the catalyst before and after the reaction are exhibited in Figure 5. As
shown, no significant alteration in the morphology of the catalyst was observed after the
reaction, which definitely affirms the LDHs@PpPDA recyclability and stability under the
reaction condition.
Figure 6 illustrates the X-ray diffraction patterns of the catalyst before and after the
reaction. The positions and relative intensities of all characteristic diffractions at 2θ values
of 10°, 30° and 40° indicated that the original structure and crystallinity of LDHs@PpPDA
was successfully protected after the organic reaction.
Figure 7 shows FT-IR spectra for LDHs, PpPDA and LDHs@PpPDA. As shown, the
characteristic peaks of LDHs and PpDA in 500–2000 cm−1 and 2500–4000 cm−1 were

JOURNAL OF SULFUR CHEMISTRY
7
Figure 4. EDX spectra of LDHs@PpPDA before (a) and after (b) the reaction.
Figure 5. SEM images of LDHs@PpPDA before (a) and after (b) the reaction.
changed when LDHs coated with the polymer. These results confirm that PpPDA is coated
on the surface of the LDHs.
A schematic illustration of a feasible mechanism for the synthesis of 1,3-thiazolidin-4-
one derivatives by using LDHs@PpPDA catalyst, carried out through a three-component

8
M. MIRZAEI-MOSBAT AND R. GHORBANI-VAGHEI
Figure 6. XRD pattern of LDHs@PpPDA before (a) and after (b) the reaction.
Figure 7. FT-IR spectra of LDH, PpPDA and LDHs@PpPDA.
reaction, is presented in Scheme 2. At the first step, in order to synthesize the intermediate
(I), the condensation reaction between aldehyde and aryl amine is carried out by using
LDHs@PpPDA, as the catalyst. In the next step, sulfur atom attacks as an electron-rich
source to the imine bond and forms the intermediate (II). At the final step, intermediate
(II) is activated by the catalyst and the product is produced by intramolecular cyclization.
3. Conclusion
A novel approach for the synthesis of 1,3-thiazolidin-4-one derivatives, as a high-
importance class of heterocyclic compounds, has been reported in this research study.
For this purpose, LDHs@PpPDA was employed as an outstanding and recyclable catalyst
which can provide a significant catalytic activity in the preparation of 1,3-thiazolidin-4-one
derivatives under various reaction conditions to follow the principles of green chemistry.
By employing this process, numerous advantages including facile reaction work-up, superb

JOURNAL OF SULFUR CHEMISTRY
9
Scheme 2. Suggested reaction mechanism for the synthesis of 1,3-thiazolidin-4-one derivatives.
recyclability and reusability of the catalyst, short reaction time, considerable yield, and
green mild reaction conditions could be obtained. The characterization of the newly pre-
pared derivatives was carried out by using conventional spectroscopy techniques, and their
structures were corroborated.
4. Experimental section
4.1. Chemicals and instruments
All commercial materials were supplied by Merck and Fluka Companies .1H NMR and
13C NMR spectra were analyzed by a spectrometer at 400 and 100 MHz, respectively, in
DMSO-d6. Fourier transform infrared (FT-IR) spectra were also analyzed by a Shimadzu
435-U-04 FT spectrophotometer from KBr pellets. A BUCHI 510 apparatus was utilized
to measure melting points, carried out in open capillary tubes. Mass spectra were also
analyzed by a Shimadzu QP 1100 BX mass spectrometer.
4.2. General procedure for preparation of LDHs@PpPDA catalyst
There are totally two major steps for the synthesis procedure of LDHs@PpPDA. First,
layered double hydroxides (LDHs) were prepared through co-precipitation of solutions

10
M. MIRZAEI-MOSBAT AND R. GHORBANI-VAGHEI
containing Zn2+ and Cr3+ metal salts [33]. Then, the LDHs reacted with poly (p-
phenylenediamine) to yield LDHs@PpPDA [30].
4.3. General procedure for synthesis of 1,3-thiazolidin-4-ones
In a 10-mL Round-bottom flask, a solution of an aromatic aldehyde (1.0 mmol), an aryl
amine (1.0 mmol) and LDHs@PpPDA (0.05 g) in EtOH (5 mL) was stirred at 70°C for
about 30 min. Afterward, thioglycolic acid (1.0 mmol) was added, and the mixture was
stirred for appropriate times. TLC was employed to investigate the completion of the reac-
tion. After that, when the reaction was accomplished, the reaction mixture was poured
into a centrifuge tube in order to separate the catalyst by using centrifugation. The result-
ing solution was poured into a petri dish and the resulting precipitates were collected and
washed with cold diethyl ether so that a highly pure product could be obtained. Physical
and spectroscopic data (FT-IR, NMR, MS, and CHN) were employed to characterize pure
crystals of 1,3-thiazolidin-4-ones.
4.4. Analytical data of products
2,3-diphenylthiazolidin-4-one (4b)
White powder. M.p. 129–130°C. Yield: 0.25 g (87%). 1H NMR (400 MHz, DMSO-d6, δ,
ppm): 6.6–7.63 (m, 11H), 3.31–3.61 (m, 2H). 13C NMR (100 MHz, DMSO-d6, δ, ppm):
25.59, 63.22, 124.6, 129.59, 134.66, 153.31, 156.8, 191.33.
3-phenyl-2-(thiophen-2-yl)thiazolidin-4-one (4c)
Cream powder. M.p. 148–149°C. Yield: 0.25 g (85%). 1H NMR (400 MHz, DMSO-d6, δ,
ppm): 6.56–7.97 (m, 8H), 5.67 (s, 1H), 3.37–3.68 (m, 2H). 13C NMR (100 MHz, DMSO-d6,
δ, ppm): 17.88, 54, 09.51, 122.65, 125.83, 127.26, 129.04, 143.97, 146.79, 169.19.
2-(pyridin-2-yl)-3-(p-tolyl)thiazolidin-4-one (4e)
Cream powder. M.p. 158–162°C. Yield: 0.28 g (95%). FT-IR (KBr, ν, cm−1): 2921, 1713,
1598, 1518, 1378, 1289, 790. 1H NMR (400 MHz, DMSO-d6, δ, ppm): 8.5(s, 1H), 7.74 (s,
1H), 7.15-7.48 (m, 7H), 6.48 (s, 1H), 3.78 (m, 2H), 3.35 (s, 3H). 13C NMR (100 MHz,
DMSO-d6, δ, ppm): 21.29, 32.12, 64.2, 120.64, 123.28, 124.52, 126.02, 128.69, 138.05,
149.25, 159.7, 170.87. Mass (m/z): 270. Anal. Calcd. For C15H14N2OS: C, 66.64; H, 5.22;
N, 10.36. Found: C, 66.6; H, 5.24; N, 10.29.
2-(1H-indol-3-yl)-3-phenylthiazolidin-4-one (4g)
Red powder.. M.p. 168–169°C. Yield: 0.3 g (92%). FT-IR (KBr, ν, cm−1): 3303, 2969,
1709, 1591, 1497, 1235, 743. 1H NMR (400 MHz, DMSO-d6, δ, ppm): 13C NMR (100 MHz,
DMSO-d6, δ, ppm): 15.46, 65.29, 112.06, 118.17, 121.61, 128.78, 135.95, 139.7, 175.53. Mass
(m/z): 294. Anal. Calcd. For C17H14N2OS: C, 69.36; H, 4.79; N, 9.53. Found: C, 69.31; H,
4.82; N, 9.48.
2-(1H-indol-3-yl)-3-(p-tolyl)thiazolidin-4-one (4h)
Red powder. M.p. 171–174°C. Yield: 0.32 g (94%). FT-IR (KBr, ν, cm−1): 3184, 1709,
1657, 1590, 1503, 1351, 1223, 745. 1H NMR (400 MHz, DMSO-d6, δ, ppm): 11.15(s, 1H),
7.99–8.81 (m, 2H), 6.49–7.7 (m, 7H), 5.63 (s, 1H), 3.27 (m, 2H), 2.5 (s, 3H). 13C NMR
(100 MHz, DMSO-d6, δ, ppm): 19.91, 33.87, 45.83, 110.68, 113.07, 119.21, 120.92, 129.46,
133.55, 137.3, 154.7, 170.75. Mass (m/z): 308. Anal. Calcd. For C18H16N2OS: C, 70.1; H,
5.23; N, 9.08. Found: C, 70.02; H, 5.28; N, 9.15.

JOURNAL OF SULFUR CHEMISTRY
11
2-(4-chloro-3-nitrophenyl)-3-(p-tolyl)thiazolidin-4-one (4i)
Yellow powder. M.p. 146–148°C. Yield: 0.32 g (85%). FT-IR (KBr, ν, cm−1): 2922, 1714,
1605, 1518, 1350, 1134, 807. 1H NMR (400 MHz, DMSO-d6, δ, ppm): 7-8.77 (m, 7H), 6.78
(s, 1H), 3.41 (m, 2H), 2.5 (s, 3H). 13C NMR (100 MHz, DMSO-d6, δ, ppm): 20.23, 31.83,
68.7, 120.59, 129.82, 134.22, 139.34, 141.74, 150.59, 179.28. Mass (m/z): 348. Anal. Calcd.
For C16H13ClN2O3S: C, 55.1; H, 3.76; N, 8.03. Found: C, 55.04; H, 3.85; N, 7.98.
2-(4-chloro-3-nitrophenyl)-3-phenylthiazolidin-4-one (4j)
Yellow powder. M.p. 153–155°C. Yield: 0.29 g (80%). FT-IR (KBr, ν, cm−1): 2923, 1714,
1607, 1534, 1344, 1138, 735. 1H NMR (400 MHz, DMSO-d6, δ, ppm): 6.87-8.35 (m, 8H),
6.61 (s, 1H), 3.49 (m, 2H). 13C NMR (100 MHz, DMSO-d6, δ, ppm): 30.13, 60.17, 123.99,
129.8, 133.55, 136.61, 139.01, 142.41, 147.24, 172.46. Mass (m/z): 334. Anal. Calcd. For
C15H11ClN2O3S: C, 53.82; H, 3.31; N, 8.37. Found: C, 53.75; H, 3.37; N, 8.31.
2-(furan-2-yl)-3-phenylthiazolidin-4-one (4k)
Yellow powder. M.p. 138–140°C. Yield: 0.24 g (88%). 1H NMR (400 MHz, DMSO-d6, δ,
ppm): 6.26–7.79 (m, 8H), 5.79 (s, 1H), 3.29–379 (m, 2H). 13C NMR (100 MHz, DMSO-d6,
δ, ppm): 30.62, 48.88, 112.92, 115.65, 117.59, 124.96, 127.66, 130.79, 143.98, 145.52, 188.62.
2-(4-methoxyphenyl)-3-(p-tolyl)thiazolidin-4-one (4l)
Yellow powder. M.p. 130–132°C. Yield: 0.29 g (89%). FT-IR (KBr, ν, cm−1): 2960, 1672,
1591, 1496, 1438, 1393, 746. 1H NMR (400 MHz, DMSO-d6, δ, ppm): 6.77-7.36 (m, 8H),
5.3 (s, 1H), 3.84 (m, 2H), 3.41 (s, 3H), 2.57 (s, 3H). 13C NMR (100 MHz, DMSO-d6, δ,
ppm): 20.57, 31.15, 60.51, 71.77, 117.5, 125, 127.41, 130.13, 135.26, 138.32, 161.88, 172.47.
Mass (m/z): 299. Anal. Calcd. For C17H17NO2S: C, 68.2; H, 5.72; N, 4.68. Found: C, 68.11;
H, 5.79; N, 4.59.
2-(2-chlorophenyl)-3-(p-tolyl)thiazolidin-4-one (4m)
White powder. M.p. 128–131°C. Yield: 0.31 g (93%). FT-IR (KBr, ν, cm−1): 2919, 1691,
1609, 1518, 1439, 807. 1H NMR (400 MHz, DMSO-d6, δ, ppm): 8.87 (s, 1H), 6.73-7.48 (m,
7H), 6.5 (s, 1H), 3.32 (m, 2H), 2.5 (s, 3H). 13C NMR (100 MHz, DMSO-d6, δ, ppm): 19.79,
31.36, 69.41, 103.76, 114.74, 119.02, 120.14, 124.27, 129.47, 130.59, 135.43, 139.54, 178.71.
Mass (m/z): 303. Anal. Calcd. For C16H14ClNOS: C, 63.26; H, 4.65; N, 4.61. Found: C,
63.18 H, 4.72; N, 4.54.
2-(2-bromophenyl)-3-(p-tolyl)thiazolidin-4-one (4n)
Cream powder. M.p. 136–138°C. Yield: 0.34 g (90%). FT-IR (KBr, ν, cm−1): 2906,
1715, 1609, 1518, 1439, 807. 1H NMR (400 MHz, DMSO-d6, δ, ppm): 7.47–7.59 (m, 2H),
6.31–7.04 (m, 6H), 5.76 (s, 1H), 3.25 (m, 2H), 2.51 (s, 3H). 13C NMR (100 MHz, DMSO-d6,
δ, ppm): 19.9, 30.82, 67.34, 113.41, 117.52, 129.11, 132.86, 135.58, 139.02, 145.84, 148.24,
151.31, 178.95. Mass (m/z): 347. Anal. Calcd. For C16H14BrNOS: C, 55.18; H, 4.05; N,
4.02. Found: C, 55.09; H, 4.14; N, 3.98.
Acknowledgements
We would like to thank Bu-Ali Sina University, Center of Excellence in Development of Envi-
ronmentally Friendly Methods for Chemical Synthesis (CEDEFMCS) for financial support of this
study.
Disclosure statement
No potential conflict of interest was reported by the author(s).

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M. MIRZAEI-MOSBAT AND R. GHORBANI-VAGHEI
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