KCC-1 aminopropyl-functionalized supported on iron oxide magnetic nanoparticles as a novel magnetic nanocatalyst for the green and efficient synthesis of sulfonamide derivatives

Article abstract of DOI:10.1002/aoc.5321

A new magnetic nanocatalyst (Fe₃O₄@KCC-1-npr-NH₂) was synthesized directly through the reaction of Fe₃O₄@KCC-1 with (3-aminopropyl) triethoxysilane (APTES) using a hydrothermal protocol. Prepared nanocomposite was used as a magnetically reusable nanocatalyst for an efficient synthesis of a broad range of sulfonamide derivatives in water as a green solvent at room temperature and the products are collected by filtration with excellent yields (85–97%). The nanocatalyst could be remarkably recovered and reused after ten times without any significant decrease in activity. This mild and simple synthesis method offers some advantages including short reaction time, high yield and simple work-up procedure.

Full text of DOI:10.1002/aoc.5321

Received: 16 August 2019
DOI: 10.1002/aoc.5321
Revised: 5 October 2019
Accepted: 5 October 2019
F U L L P A P E R
KCC‐1 aminopropyl‐functionalized supported on iron oxide
magnetic nanoparticles as a novel magnetic nanocatalyst
for the green and efficient synthesis of sulfonamide
derivatives
1
2
1
Sajjad Azizi | Nasrin Shadjou | Mohammad Hasanzadeh
1
Pharmaceutical Analysis Research
A new magnetic nanocatalyst (Fe O @KCC‐1‐npr‐NH ) was synthesized
Center, Tabriz University of Medical
Sciences, Tabriz, Iran
3
4
2
directly through the reaction of Fe O @KCC‐1 with (3‐aminopropyl)
3
4
2
Department of Nanochemistry,
triethoxysilane (APTES) using a hydrothermal protocol. Prepared nanocom-
posite was used as a magnetically reusable nanocatalyst for an efficient synthe-
sis of a broad range of sulfonamide derivatives in water as a green solvent at
room temperature and the products are collected by filtration with excellent
yields (85–97%). The nanocatalyst could be remarkably recovered and reused
after ten times without any significant decrease in activity. This mild and sim-
ple synthesis method offers some advantages including short reaction time,
high yield and simple work‐up procedure.
Nanotechnology Research Center, Urmia
University, Urmia, Iran
Correspondence
Mohammad Hasanzadeh, Pharmaceutical
Analysis Research Center, Tabriz
University of Medical Sciences, Tabriz,
Iran.
Email: mhmmd_hasanzadeh@yahoo.com;
hasanzadehm@tbzmed.ac.ir
KEYWORDS
fibrous nano‐silica, green synthesis, magnetic nano‐catalyst, sulfonamides
[
14,15]
1
| INTRODUCTION
un‐substituted sulfonamides using metal‐catalyzed,
oxidation of sulfinimides or sulfonamides,
[
16,17]
oxidative
Sulfonamides are well‐known class of organic com-
pounds found in numerous natural products, materials
and pharmaceutical compounds which commonly
employed as chemotherapeutic and preventive agents
coupling reactions between an amine and a sulfonate
[
18]
salts have been developed.
These methods have some
disadvantages including, non‐environmentally friendly
reagents, harsh conditions and limitation in scope.
[1–3]
[19]
[20]
against several diseases (Figure 1).
Pharmaceutical
Recently, metal oxides such as nano ZnO,
CuO
[
21]
and biological importance of sulfonamides are in the
fields of the antibacterial, antifungal, antiinflammatory
and anticonvulsant activities, as well as several enzymes
inhibition including glycogen phosphorylase, carbonic
anhydrase, serine protease, cholesterol acyltransferase,
and CdO
have been used as effective heterogeneous
catalysts in various sulfonylation reactions from amines.
Despite the effective progress, there remains need to
development of metal catalysts for the synthesis of sulfon-
amide compounds particularly using highly efficient het-
erogeneous catalysts. Although metal oxide catalysts
display as both Lewis acid and base, surface area of metal
oxide materials and nature of metal cation have widely
[
4–9]
cyclooxygenase and matrix metalloproteinase.
In
addition, it has been reported that sulfonamide deriva-
[10,11]
[12]
tives act as a herbicide, dye
and plaguicides.
[
22,23]
The conventional method and practical way for the syn-
thesis of sulfonamide derivatives involves the reaction
between sulfonyl chlorides and amine nucleophiles, using
employed to their catalytic properties.
Ferric oxide
catalysts are cheap metal oxide which has been used as
a common catalyst in numerous organic transforma-
[13]
[14]
a base.
Also, one‐pot reactions of monosubstituted or
tions.
Moreover, surface functionalized mesoporous
Appl Organometal Chem. 2019;e5321.
wileyonlinelibrary.com/journal/aoc
© 2019 John Wiley & Sons, Ltd.
1 of 8
https://doi.org/10.1002/aoc.5321

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AZIZI ET AL.
FIGURE 1 Structure of important
sulfonamide‐based drugs
materials have appeared as one of the most significant
research areas in the concerning of advanced functional
materials. Particularly, Polshettiwar et al., reported
Micromeritics NOVA 2000 (Florida, USA) apparatus at
77 K using nitrogen as the adsorption gas. The particle
size distribution and zeta potential values were deter-
mined using Malvern particle size analyzer (Malvern,
UK). The purity determination of the products and reac-
tion monitoring were accomplished by TLC on silica gel
poly gram SILG/UV 254 plates.
fibrous nano‐silica (KCC‐1), with the high surface area
2
(
typically >700 m /g), broad pore size distribution, large
[24,25]
pore sizes,
ease of surface modification, low density,
stability and low toxicity with good biocompatibility.
This Dendritic fibrous nanosilica showed special activ-
ities as heterogeneous catalysis.
[
26–
2
8]
[29]
2
.2 | General procedure for the synthesis
of Fe O magnetic nanoparticles
Herein, we report a simple and facile method for the
synthesis of sulfonamides using Fe O @KCC‐1‐npr‐NH
3 4
3
4
2
as a reusable and efficient nanocatalyst in water as a
green solvent at room temperature in excellent yields.
This approach involves various amines as nitrogen donor
and paratoluenesulfonylchloride as the sulfur source for
the preparation of sulfonamides.
The synthesis procedure of hydrophilic nanoparticles
Fe O is explained as follows:
3
4
Briefly, FeCl .6H O (3.25 g) was dispersed along with
3
2
sodium acetate (NaAc, 6.0 g) and trisodium citrate
1.3 g) in the ethylene glycol (100 ml) with stirring. The
(
collected yellow solution was transferred in a Teflon‐
lined stainless‐steel autoclave with 200 ml capacity and
the heating process of autoclave was continued about
2
2
| EXPERIMENTAL
10 hr at 200 °C. After cooling at room temperature the
.1 | Materials and methods
black product was rinsed several times with water and
[
30]
ethanol.
All of materials and solvents were purchased from Merck,
Sigma Aldrich and Fluka in high purity and used without
further purification. Melting points were measured in
open capillariesusing an Electrothermal MEL‐TEMP
apparatus (model 9200). X‐ray diffraction (XRD) patterns
of KCC‐1 based materials were recorded by Siemens D
2.3 | General procedure for the synthesis
of Fe O @KCC‐1 magnetic nanoparticles
3
4
At first stage the mixture of 0.1 g of the Fe O NPs and
3
4
5
000 X‐Ray diffractometer (Texas, USA) with a Cu Kα
1.8 g of urea in 15 ml of water were sonicated about
30 mins. Then, 1.0 g of cetyl trimethyl ammonium bro-
mide (CTAB), 1.0 g of n‐butyl alcohol 1.0 g and 20 g of
cyclohexane were added respectively and stirred for
30 mins. At this stage tetraethyl orthosilicate (TEOS)
(1.00 g) was added drop wise and stirred with mechanical
stirrer for 24 hr at 70 °C. Then, the product was washed
with ethanol and water a few times for further process
and dried in vacuum at 80 °C for 12 hr. Finally, the
anode (λ = 1.54 A°) operating at 40 kV and 100 mA.
The Scanning Electron Microscopy (SEM) images and
Energy Dispersive X‐Ray (EDX) were recorded with
FEG‐SEM MIRA3 TESCAN, Czech Republic) at
1
000 kV. Transmission Electron Microscopy (TEM) anal-
ysis was conducted on a Carl Zeiss LEO 906 electron
microscope operated at 100 kV (Oberkochen, Germany).
Brunauer–Emmett–Teller (BET) was recorded by

AZIZI ET AL.
3 of 8
synthesized material was calcined at 550 °C for 5 hr in air
to remove CTAB as template.
3 | RESULTS AND DISCUSSION
The synthesis of Fe O @ KCC‐1‐npr‐NH magnetic
3
4
2
nanocatalyst involved several steps (Scheme 1). To inves-
2
.4 | General procedure for the synthesis
tigation of the morphology of Fe @KCC‐1‐npr‐NH
MNPs, the FESEM images were recorded (Figure 2a).
3
O
4
2
of nanocatalyst (Fe O @ KCC‐1‐npr‐NH )
3
4
2
Moreover, the structure and size of the Fe O @ KCC‐1‐
3
4
For this purpose, Fe O @KCC‐1 (0.2 g) was added in tol-
npr‐NH2 MNPs were evaluated utilizing transmission
electron microscopy (TEM). As shown in Figure 2b, the
uniform fibers of the magnetic KCC‐1 with high surface
area have several Si‐OH groups that could grow from
the center to outside. TEM images revealed the porous,
fibrous and dendritic structure of those magnetic
nanomaterials which the fibrous system is as a result of
using the CTAB for the MNPs design while the fibrous‐
3
4
uene (100 ml) and sonicated for 30 min. Then, (3‐
aminopropyl) triethoxysilane (APTES) (500 μL) were
added in the mixture and the solution was refluxed for
2
4 hr under N . After that, the product was centrifuged,
2
and was further purified by washing with ethanol and tol-
uene several times and dried at 80 °C. Scheme 1 shows
synthesized procedure of Fe O @ KCC‐1‐npr‐NH as an
3
4
2
advanced nanocatalyst.
sphere reveals the formation of Fe
O @KCC‐1. The size
3 4
of the Fe O MNPs is about 15 nm as can be seen in
3
4
Figure 2 (a and b). Also, Fe O @KCC‐1‐npr‐NH MNPs
3
4
2
2
.5 | General procedures for the
have a particle size range of 20 nm (Figure S1 (see
supporting information)). In addition, EDX results indi-
cate the atomic structure of the produced compound that
the KCC‐1 is composed only with Si and O. Moreover,
functionalization of KCC‐1 with APTES, the weight per-
cent of N, O and C are increased which confirmed suc-
synthesize of sulfonamides (3a‐o)
A mixture of paratoluenesulfonylchloride (1 mmol) (1)
and various amines (1 mmol) (2a‐m) and Fe O @KCC‐
3
4
1‐npr‐NH (0.1 mg) in water (3 ml) was magnetically
2
stirred for 30–60 min at ambient temperature. Then, the
purely mixture monitored by TLC and after completion
of the reaction, the catalyst Fe O @ KCC‐1‐npr‐NH
cessful functionalization of KCC‐1 by npr‐NH (Figure
2
S2 (see supporting information)). Though, the carbon is
arising from the SEM grid and CTAB as a pattern agent
3
4
2
MNPs were separated by strong external magnet. The
obtained precipitate was filtered and washed with cool
EtOH to afford the pure product and then dried well
under vacuum pump.
NH (Figure S3 (see supporting information)).
2
The powder X‐ray diffraction patterns of Fe O @KCC‐
3 4
1‐npr‐NH are shown in Figure 3. The XRD pattern of
2
Fe O @KCC‐1‐npr‐NH NPs was performed from 5.0°
3
4
2
SCHEME 1 Schematic for the synthesis
of Fe O @KCC‐1‐npr‐NH
3 4 2
3 4 2
FIGURE 2 SEM (a) and TEM (b) images of Fe O @KCC‐1‐npr‐NH

4
of 8
AZIZI ET AL.
The N adsorption–desorption isotherms of Fe O @
2
3 4
KCC‐1‐npr‐NH2 are shown in (Figure S4 (c) (see
supporting information)). The BET and BJH analyses of
the Fe O @ KCC‐1‐NH MNPs were used to determine
3
4
2
the porous essence of the synthesized nanocatalyst
Figure S2. (c) (see supporting information). The specific
surface area and porosity of the nanomaterials were
determined using the adsorption isotherm and calcu-
lated by BET. Also, BJH technique was used to evaluate
the pore volume of the KCC‐1, KCC‐1‐npr‐NH2 and
Fe O4
@
KCC‐1‐npr‐NH2 (Figure S2 (a‐c) (see
3
supporting information)). The surface area of KCC‐1,
KCC‐1‐npr‐NH2 and Fe O @ KCC‐1‐npr‐NH was
3
4
2
3 4 2
FIGURE 3 XRD analysis of Fe O @KCC‐1‐NH
2
−1
observed about 617, 367 and 87 m g , and also the
average pore size is 5.8 nm. The pore volumes, pore size,
and surface area of KCC‐1, KCC‐1‐npr‐NH and Fe O
(2θ) to 100.0° (2θ) to investigate the crystallinity of the
2
3 4
synthesized nanomaterial in order to obtain additional
information about their molecule structures. As can be
observed in Figure 3, sample possess the diffraction peaks
at (220), (311), (400), (422), (511) and (440), which are in
similarity with the data for a standard Fe O sample, as
@ KCC‐1‐npr‐NH are clearly proved by the reported
results.
2
[
32,33]
Zeta potentials of Fe O @KCC‐1‐npr‐NH was checked
3
4
2
at pH 7.5 to control the surface charge to determine the
possible surface modification. The zeta potential of the
Fe O @KCC‐1‐npr‐NH shows positive charges which
3
4
°
reported in this work. The wide peak between 20 and
3
4
2
°
3
0 is related to the amorphous silica and proved the
verify the anchoring amine and Fe O groups on the sur-
3 4
[
32]
effective coating of the silica on Fe O core. It is impor-
face of the fibrous system, respectively. Also, DLS result
3
4
tant to point out that the XRD templates of the
of the Fe O @KCC‐1‐npr‐NH approves again the success-
3
4
2
Fe O @KCC‐1‐npr‐NH NPs are similar to the fibrous
ful functionalization of KCC‐1 with npr‐NH and Fe O
3
4
2
2
3 4
[31]
mesoporous nanosilica with Fe O core.
which the first peak related to Fe O and the second peak
3 4
3
4
TABLE 1 The effect of solvent and temperature for the synthesis of sulfonamides
Entry
Solvent
Temp. (°C)
Yield (%)
1
2
3
4
5
6
7
8
9
EtOH
r.t.
r.t.
60
75
97
97
97
23
29
38
44
39
47
30
66
59
H
2
H
2
H
2
O
O
O
reflux
r.t.
r.t.
r.t.
r.t.
r.t.
r.t.
r.t.
r.t.
r.t.
n‐Hexane
CCl
THF
4
CH
3
2
CN
Cl
CH
2
1
1
1
1
0
1
2
3
CHCl
3
DMF
Methanol
i‐PrOH
3 4 2
Reaction conditions: 4‐toluenesulfonyl chloride (1 mmol), 4‐methoxy aniline (1 mmol), Fe O @ KCC‐1‐npr‐NH (0.1 mg), water (4 ml), r.t. for 30 min. Isolated
yield (%).

AZIZI ET AL.
5 of 8
related to KCC‐NH2 (Figure S5 (see supporting
information)).
After characterization of Fe O @ KCC‐1‐npr‐NH the
3
4
2
catalytical performance of this nanomatrial was tested
for the synthesis of various sulfonamides. In order to opti-
mize the sulfonation reaction conditions and to obtain
good catalytic activity, the synthesis of sulfonamides
obtained from 4‐toluenesulfonyl chloride (1) and 4‐
methoxy aniline (2a) was used as a model reaction and
investigated under different reaction parameters includ-
ing amount of the catalyst, time, temperature, and solvent
type. Initially, the effect of most commonly used organic
solvents and water on the synthesis of sulfonamide com-
FIGURE 4 Optimization of the conditions for synthesis of
sulfonamides: 4‐toluenesulfonyl chloride (1 mmol), 4‐methoxy
aniline (1 mmol), Fe O @ KCC‐1‐npr‐NH (0.1 gm), water (4 ml), r.
3 4 2
pounds using the Fe O @KCC‐1‐npr‐NH
as
a
3
4
2
nanocatalyst was investigated. It is obtained that, the sol-
vent type has a significant effect the performance of the
t. for 1 hr
nanocatalyst. For example, n‐Hexane and CCl which
4
are non‐polar solvents, gave sulfonamides in a lower yield
than other solvents (Table 1, entry 5 and 6). Also, some
aprotic solvents including THF, CH CN, CH Cl , CHCl
3
3
2
2
and DMF lead to low efficiency (Table 1, entry 7–11).
But, the protic solvents improved reaction performance.
Methanol and iPrOH gave sulfonamides in average yields
(
Table 1, entries 12 and 13). In contrast, the use of Etha-
nol gave a better yield, while the yield was considerably
increased up to 97% when water was used as a green sol-
vent in the presence of Fe O @KCC‐1‐npr‐NH MNPs.
3
4
2
Also, the temperature showed no impact in the synthesis
of sulfonamides in the presence of Fe O @KCC‐1‐npr‐
3
4
NH2 MNPs. In this regard, the sulfonamides were
obtained with excellent isolated yield at room tempera-
ture and results clearly indicated that reaction completion
isn't related to reaction temperature and even conven-
tional heating under reflux conditions in ethanol and
water (Table 1) have no important effect on the yield of
desired compounds. On the other hand, high tempera-
FIGURE
toluenesulfonyl chloride (1 mmol), 4‐methoxy aniline (1 mmol),
Fe @ KCC‐1‐npr‐NH (0.1 gm), water (4 ml), r.t. for 1 hr
5
Effect of time on yield of sulfonamides: 4‐
3
O
4
2
TABLE 2 Influence of different nanocatalysts for the synthesis of sulfonamides
Entry
Catalyst
Yield (%)
1
2
3
4
5
KCC‐1
‐
KCC‐1‐npr‐NH
2
‐
Fe
Fe
Fe
3
3
3
O
4
O
4
O
4
10
20
97
@KCC‐1
@KCC‐1‐npr‐NH
2
Reaction conditions: 4‐toluenesulfonyl chloride (1 mmol), 4‐methoxy aniline (1 mmol), Fe3O4@ KCC‐1‐npr‐NH
2
(0.1 mg), water (4 ml), r.t. for 30 min. Isolated
yield (%).

6
of 8
AZIZI ET AL.
(Table 1, entry 2–4). However, the reaction at 30–60 min
in the presence 0.0001 g of Fe O @KCC‐1‐npr‐NH is
3
4
2
optimum condition for the synthesis of sulfonamides.
Finally, the amount of nanocatalyst on the reaction
efficiently was evaluated. According to obtained results,
the variation in the Fe O @KCC‐1‐npr‐NH MNPs
3
4
2
amount had a key role on the reaction efficiency. The
optimum amount of Fe O @KCC‐1‐NH MNP was
3
4
2
0
.1 mg, which obtained the desired product in 97% yields
(Figure 4). It is important to point out that, we could
achieve to excellent yields of sulfonamides synthesize
using this nanocatalyst in 60 min (Figure 5).
To further investigate the efficiency of the
nanocatalyst, we compared the catalytic performance of
the newly nanocatalyst with different control experi-
ments and the results are shown in Table 2. Originally,
a standard reaction was accomplished using KCC‐1,
KCC‐1‐npr‐NH , Fe O and KCC‐1‐Fe O ; and the results
2
3
4
3 4
confirmed that the desired product was poorly formed
SCHEME
3
Possible mechanism for the synthesis of
(Table 2, entries 3 and 4) after 1 hr of reaction time in
3 4 2
sulfonamides using Fe O @KCC‐1‐npr‐NH
SCHEME 2 Synthesis of sulfonamides
3a‐l) in the presence of KCC‐1‐NH
Fe @KCC‐1‐npr‐NH NPs.
(
2
‐
3
O
4
2
TABLE 3 Fe
3
O
4
2
@KCC‐1‐npr‐NH catalyzed synthesis of sulfonamides
a
Entry
R
R'
Product. No.
Time (min)
Yield (%) [Ref.]
[
[
[
[
[
[
[
[
[
[
[
[
[
20]
20]
20]
20]
20]
20]
20]
20]
20]
20]
20]
20]
34]
1
2
3
4
5
6
7
8
9
p‐OMePh
Morpholine
Ph
H
H
H
H
H
H
H
H
H
H
H
H
Et
3a
3b
30
30
30
60
35
40
50
60
55
50
60
40
30
97
96
97
85
90
93
88
87
90
94
86
92
90
3c
p‐NO
2
Ph
3d
P‐MePh
p‐BrPh
o‐MePh
3e
3f
3 g
3 h
3i
3
p‐CF Ph
Cyclohexane
1
1
1
1
0
1
2
3
N,N‐diMethylPh
3j
p‐CNPh
Bu
3 k
3 l
3 m
Et
3 4 2
Reaction conditions: 4‐toluenesulfonyl chloride (1 mmol), various amines (1 mmol), Fe O @ KCC‐1‐npr‐NH (0.1 mg), water (4 ml), r.t. for 30–60 min.
aIsolated yield (%).

AZIZI ET AL.
7 of 8
3 4 2
FIGURE 6 (a) Reusability of Fe O @ KCC‐1‐npr‐NH MNPCs and (b) separation of the nanocatalyst by external magnet
TABLE 4 Comparison of different catalysts for synthesis of N‐(phenyl)‐p‐toluenesulfonamide (3c)
Entry
Catalyst
Conditions
Time (min)
Yield (%)
Ref.
[
[
[
[
[
19]
20]
21]
35]
36]
1
2
3
4
5
6
Nano ZnO
50 °C
60
120
10
94
88
95
95
95
97
CuO
r.t.
CdO nanopowder
Zn‐Al hydrotalcite
Natrolite zeolite
Reflux
Ultrasound
Ultrasound
r.t
10
15
Fe
3
O
4
@KCC‐1‐npr‐NH
2
30
This work
any amount. When, Fe O @KCC‐1‐NH was used as the
nanocatalyst, a reaction was performed and completed
the reaction mixture was washed with chloroform and
dried at room temperature and reused for subsequent
reactions. It is obvious that the heterogeneous and mag-
netic property of the Fe O @KCC‐1‐NH MNP facilitates
3
4
2
(Table 2, entry 5).
Ultimately, the reaction conditions were optimized. To
3
4
2
carry out this approach, we specially evaluated this meth-
odology utilizing 4‐toluenesulfonyl chloride (1) and a vari-
ety of different amines (2a‐m) in the presence of
Fe O @KCC‐1‐NH MNP in water under optimized reac-
the effective recovery of the nanocatalyst from the reac-
tion mixture by external magnet during the work‐up pro-
cedure so that the catalyst could be recycled and reused
up to ten consecutive trials without remarkable loss of
its catalytic activity (Figure 6 (a and b)) These results
indicated that the proposed nanocatalyst was stable and
could tolerate the sulfonation reaction conditions.
3
4
2
tion conditions (Scheme 2). As can be seen in Table 3, the
type of substituents on the aromatic ring and electronic
effects did not show extremely evident effects in terms of
yields under the reaction conditions. As can be seen in
Table 2, it is clear that the aromatic amines containing
electron‐donating groups and electron‐withdrawing which
were used in this research, were reacted well to afford the
desired sulfonamides in excellent yields with high purity.
In addition, secondary amine such as diethylamine also
react effectively to prepare the desired product in excellent
yield (Table 3, entire 13). Also, the proposed mechanism
for the synthesis of sulfonamides using Fe O @KCC‐1‐
In order to show the special efficiency of the
Fe O @KCC‐1‐npr‐NH MNP in comparison with
3
4
2
different catalysts which used for similar reactions, we
summarize numerous results for the synthesis of
N‐(phenyl)‐p‐toluenesulfonamide (3c) in Table 4. Our
study has some advantages in compare with other mention
studies including high yield of synthetic compound, rea-
sonable time reaction and easy catalyst recovery. In this
regard, some of other reported have shorter reaction time.
3
4
npr‐NH MNP is presented in Scheme 3.
2
The recovery and reuse of catalyst materials are highly
preferable. In this regard, the recyclability of the
Fe O @KCC‐1‐npr‐NH MNP was investigated using
4
| CONCLUSIONS
3
4
2
In summary, a novel magnetic nanocatalyst (Fe O @KCC‐
3 4
the model reaction 4‐toluenesulfonyl chloride and vari-
ous amines under identical reaction conditions. After
the completion of reaction, the recovered catalyst from
1‐npr‐NH ) was prospered and used for the synthesis of
sulfonamide derivatives in water as a green solvent in
excellent yield. This nanocatalyst could be recovered and
2

8
of 8
AZIZI ET AL.
reused at least ten times with no considerable decrease in
its activity and selectivity. Proposed method, has some
advantages, containing short reaction times, mild reaction
conditions, reusability of the solid catalyst, high yields and
convenient workup process. In addition, the desired sul-
fonamides were collected by filtration without utilizing
any chromatographic separation or organic solvent for
extraction confirming a high mass efficiency.
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[
[
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[
[
[
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ACKNOWLEDGEMENT
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