A novel and green method for N-acylation of amines and sulfonamides under ultrasound irradiation

Article abstract of DOI:10.13005/ojc/330348

A facile and versatile method for acylation of structurally diverse amines and sulfonamides under focused ultrasonic irradiation in catalyst-free and solvent-free conditions is reported. There are several advantages to this approach such as simple and eas

Full text of DOI:10.13005/ojc/330348

ISSN: 0970-020 X
CODEN: OJCHEG
017, Vol. 33, No. (3):
Pg. 1454-1460
ORIENTAL JOURNAL OF CHEMISTRY
An International Open Free Access, Peer Reviewed Research Journal
2
www.orientjchem.org
A Novel and Green Method for N-acylation of Amines and
Sulfonamides under Ultrasound Irradiation
1
,2
1
1
RADIA BOUASLA , KHAOULA BECHLEM , BILLEL BELHANI ,
1
1
1
ISMAHENE GRIB , NOUR-EDDINE AOUF and MALIKA BERREDJEM *
1
Department of chemistry, Badji-Mokhtar - Annaba University, Box 12, 23000 Annaba, Algeria.
2
Higher School of Industrial Technologies-Annaba, Box 218, 23000 Annaba, Algeria.
*
Corresponding author E-mail: malika.berredjem@univ-annaba.org.
http://dx.doi.org/10.13005/ojc/330348
(Received: Otober 13, 2016; Accepted: March 02, 2017)
ABSTRACT
A facile and versatile method for acylation of structurally diverse amines and sulfonamides
under focused ultrasonic irradiation in catalyst-free and solvent-free conditions is reported.There are
several advantages to this approach such as simple and easier workup conditions, small amount of
time and high yielding. The acylation reaction was carried out with acetic anhydride. All structures
of synthesized products have been identified by NMR and mass spectroscopy.
Keywords: N-acylation, sulfonamide, ultrasonic irradiation, green chemistry.
INTRODUCTION
by the condensation of the various sulfonamides
with acyl chloride or anhydride under basic
conditions . Acylation of sulfonamides can also be
7
The N-acylsulfonamidemoietyisacommon
feature in several important bio molecules and has
emerged as an important class drug synthesis
8
9
achieved with concentrated H SO , Lewis acids
2 4
1
-3
10
.
or heterogeneous solid acid in acetonitrile under
acidic conditions. Another attractive method based
on using of palladium-catalyzed acylation of aryl with
A large number of novel N-acylated-sulfonamides-
sulfonamides molecules have been investigated
4
11
for antibacterial activity . They are also known as
sulfonamides under microwave irradiation .
5
therapeutic agents for Alzheimer’s disease and anti-
6
proliferative agents .
Recently, an efficient method for acylation
of sulfonamides in acetonitrile with H P W O as
6
2
18 62
In the literature, several reaction pathways
for the preparation of N-acyl sulfonamides have
been developed, most of them were carried out
acidic solid catalyst is described by Bougheloum
et al . Synthetic methods should be developed, to
produce molecules that are no toxic to human health
12

1455
BOUASLA et al., Orient. J. Chem., Vol. 33(3), 1454-1460 (2017)
and the environment, because we are all inhabitants using (CDCl ) as solvent and (TMS) as an internal
3
on Earth, everyone is a stakeholder, and every standard. IR spectra were recorded on a Perkin-
person aims contributing to environmental protection Elmer FT-600 spectrophotometer.Mass spectra were
locally, nationwide and worldwide.
performed on a Shimadzu QP operating at an IP of
0 or 70 eV.
3
Chemists have focused on maximizing
yield, reducing energy and minimizing the number of
Typical experimental procedure for
steps by application of the green chemistry principle N-acylation of amines and sulfonamides
of atom economy to chemical reactions.
In a glass tube was placed a mixture of
Chemical synthesis usually requires an amine or sulfonamide derivatives (1 equiv) and acetic
energy source; there are several types of traditional anhydride (1equiv) at room temperature.The mixture
energy such as: light, heat and ionizing radiation. was immersed in the water of the sonicator bath for
Sonication chemistry can be replaced the traditional appropriate time at room temperature.Reaction was
energy used for the chemical reaction by irradiation monitored by TLC.
ultrasonic.
After completion of the reaction, the reaction
In this protocol, ultrasound provides strange mixture was diluted with the water, and extracted
mechanism for supplying high energy chemistry, with ethyl acetate, the organic layer was dried over
1
3-16
based on acoustic cavitation .It was suggested anhydrous sodium sulfate and the resulting residue
that sonication also assists in the breakdown of was purified by silica gel chromatography using
intermediates and desorption of the products from dichloromethane-petroleum ether (9:1), to give
the surface, The use of ultrasound in chemical the N-acylamines or N-acylsulfonamides in good
reactions provides specific activation based on a yieds.
physical-chemical phenomena which are currently
17-18
a matter of advanced research . In recent years, N-Phenylacetamide
ultrasound irradiation has been considered as a Oil;88 % yield; H NMR (CDCl ):7.2-7.5 (m,
successful method in organic synthesis, because 5H, Ar), 2.2 (s, 3H, CH ); C NMR (CDCl ): 168.9,
1
3
13
3
3
it has several advantages such as; shorter reaction 138.5, 128.9, 128.0, 121.6, 24.0; LCMS (+) m/z,
19-22
+
time, higher yield and milder conditions
.
136.07 [M+H] , C H NO.
8 9
Herein, we describe a practical procedure N-(4-Methoxyphenyl)acetamide
1
for the acylation of various amines and sulfonamides
Oil;89 % yield; H NMR (CDCl ):6.9-7.4 (m,
3
13
with acetic anhydride at room temperature and 4H, Ar), 2.2 (s, 3H, CH ), 3.6 (s, 3H, CH ); C NMR
3
3
without a solvent using ultrasonic irradiation.
(CDCl ):168.9, 158.9, 130.8, 122.6, 114.5, 55.8, 24.2;
3
+
LCMS (+) m/z, 166 [M+H] , C H NO .
9
11
2
EXPERIMENTAL
General
N-(3,4-Dihydroisoquinolin-2(1H)-yl)acetamide
The sulfonamide derivatives were prepared
according to the literature . All reactions were (KBr): 1660 (CO); H NMR (CDCl ):7.2–7.0 (m, 4H,
Powder; 70 % yield; mp 110-111 °C; IR
2
3
1
3
monitored by thin layer chromatography using Merck Ar), 4.4 (s, 2H, CH ), 3.4 (t, 2H, J5.5 Hz, CH ), 2.6
2
2
1
3
TLC Silicagel 60 F254, using the solvents indicated. (t, 2H, J5.8 Hz, CH ), 2.1 (s, 3H, CH ); C NMR
2
3
Silica gel column chromatography was performed (CDCl ):169.2, 134.1, 127.7, 127.5, 126.9, 126.3,
3
+
over. Sonication was performed in a FUNGILAB 49, 47, 28.6, 21.1;LCMS (+) m/z, 176.10 [M+H] ,
ultrasonic bath at a frequency of 40 kHz and nominal C H NO.
11
13
power 260 W.Melting points were measured in open
capillary tubes on an electro thermal-apparatus.
N-(4-Phenylpiperazin-1-yl)acetamide
Powder; 74 % yield; mp 113-114 °C;
1
13
1
H-NMR and C-NMR spectra were IR (KBr): 1752 (CO); H NMR (CDCl ):7.45-6.95
3
recorded on Bruker spectrometer (400 and 100MHz) (m, 5H, Ar), 3.62 (t, 4H, J5.2, 4.8 Hz, CH ), 3.25
2

BOUASLA et al., Orient. J. Chem., Vol. 33(3), 1454-1460 (2017)
1456
1
3
(
t, 4H, J5.2, 4.8 Hz, CH ), 2.1 (s, 3H, CH );
C
(DMSO-d ):22.9, 44.2, 125.8, 126.2, 126.7, 127.9,
2
3
6
+
NMR (CDCl ):168.9, 149.6, 129.6, 121.9, 114.3,
3.3, 46.2, 21.1;LCMS (+) m/z, 205.13 [M+H] ,
128.6, 142.3; MS (+) m/z, 246.06 [M+NH ] ,
3
4
+
5
C H N O S.
9
12
2
3
C H N O.
1
2
16
2
N-(N-(3-Fluorophenyl)sulfamoyl) acetamide
Powder; 93 % yield; mp 147-148 °C; IR
N-(N-Cyclohexylsulfonyl) acetamide
Powder; 94 % yield; mp 198-199 °C; IR
(KBr): 3260 and3068 (NH), 1694 (CO), 1368 and
1
(
1
5
(
(
KBr): 3372 and 3265 (NH), 1730(CO), 1360 and
1162 (SO ); H NMR (CDCl ):1.95 (s, 3 H, CH ), 6.9
2
3
3
1
13
153 (SO ); H NMR (CDCl ):1.6-2.1 (m, 10H, CH ),
(m, 1H, Ar), 7.06 (m, 2H, Ar), 7.3 (m, 1H, Ar); C
2
3
2
13
.2 (d, 1H, J7.35 Hz, CH), 2.0 (s, 3H, CH ); C NMR
NMR (DMSO-d ):22.9, 105.6, 110.1, 114.6, 130.7,
3
6
+
CDCl ):171.0, 43.9, 32.6, 25.7, 24.8, 21.6; LCMS
139.5, 163.9, 168.6; MS (+) m/z, 250.04 [M+NH ] ,
3
4
+
+) m/z, 222.09 [M+H] , C H N O .
C H N O SF.
8
16
2
3
8
9
2
3
N-(N-Propylsulfonyl) acetamide
N-(3,4-Dihydroisoquinolin-2(1H)-yl-sulfonyl)
acetamide
Powder; 90 % yield; mp 168-169 °C;
IR (KBr): 3370 and 3263(NH), 1721(CO), 1380,
Cristal;90% yield;mp 173-174 °C;IR (KBr):
1
1
1
154(SO ); H NMR (CDCl ):3.2 (m, 2H, CH ), 2.1
3261 (NH), 1695 (CO), 1361 and 1155 (SO ); H
2
3
2
2
(
s, 3H, CH ), 1.65 (m, 2H,CH ), 1.01 (t, 3H, J 5.02
NMR (CDCl ):8.1 (s, 1H, NH), 7.2-7.0 (m, 4H, Ar), 4.5
3
3
2
3
1
Hz, CH ); C NMR (CDCl ):172.1, 42.5, 21.9, 21.6,
1
(s, 2H, CH ), 3.7 (t, 2H, J 5.7 Hz, CH ), 2.9 (t, 2H, J5.8
3
3
2
2
+
13
1.2; LCMS (+) m/z, 181.06 [M+H] ,C H N O S.
Hz, CH ), 2.1 (s, 3H, CH ); C NMR (CDCl ):173,
5
12
2
3
2
3
3
1
34.1, 127.5, 126.9, 126.3, 125.7, 48.1, 47.2, 25.3,
+
N-(N-(Tert-butyl)sulfamoyl) acetamide
21.6; MS (+) m/z, 255.07 [M+NH ] , C H N O S.
4
11 14
2
3
Powder; 95 % yield; mp 136-137 °C; IR
(
KBr): 3374 and 3267 (NH), 1735 (CO), 1362 and
N-((4-Phenylpiperazin-1-yl)sulfonyl) acetamide
1
1
2
3
154 (SO ); H NMR (CDCl ):1.15 (s, 9H, 3CH ),
Cristal;94 % yield;mp 176-177 °C;IR (KBr):
2
3
3
13
1
.01 (s, 3H, CH ); C NMR (DMSO-d ):19.1, 30.6,
0.6, 30.6, 38.7; MS (+) m/z, 212.07 [M+NH ] ,
3260 (NH), 1697(CO), 1361 and 1155 (SO ); H NMR
3
6
2
+
(CDCl ):7.7-6.9 (m, 5H, Ar), 3.1 (t, 4H, J5.4 Hz, CH ),
4
3
2
13
C H N O S.
2.5 (t, 4H, J5.2 Hz, CH ), 2.3 (s, 3H, CH ); C NMR
6
14
2
3
2
3
(
CDCl ):173, 149.6, 129.6, 121.9, 114.3, 50.3, 43.4,
3
+
N-(N-Benzylsulfamoyl) acetamide
Powder; 96% yield; mp 121-122 °C; IR
KBr): 3371 and 3268 (NH), 1738 (CO), 1363
21.5; LCMS (+) m/z, 284.10 [M+H] , C H N O S.
12
17
3
3
(
N-(N-(4-Methoxyphenyl)sulfamoyl) acetamide
Powder; 80% yield; mp 151-152 °C; IR
(KBr): 3260 and 3251 (NH), 1690 (CO), 1365 and
1
and 1156 (SO ); H NMR (CDCl ):1.90 (s, 3H,
2
3
13
CH ), 4.06 (s, 2 H, CH ), 7.2 (m, 1H, Ar); C NMR
3
2
Table 1: Synthesis of N-acylamines
Substrate Product
Entry
Time (min)
Yield (%)
NH2
O
1
15
88
N
H
CH3
O
MeO
MeO
NH2
N
CH
3
2
3
4
15
30
30
89
70
74
H
O
NH
N
N
CH3
O
N
NH
N
CH3

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BOUASLA et al., Orient. J. Chem., Vol. 33(3), 1454-1460 (2017)
1
1
(
158 (SO ); H NMR (CDCl ):7.1-7.5 (m, 4H, Ar), 3.8 (R)-N-(N-(1-Phenylethyl)sulfamoyl) acetamide
2
3
13
s, 3H, CH ) 2.3 (s, 3H, CH ); C NMR (CDCl ):171,
Powder; 85 % yield; mp 171-172 °C; IR
3
3
3
1
2
53.3, 130, 124.5, 115.1, 55.8, 21.6; LCMS (+) m/z, (KBr): 3370 and 3265 (NH), 1698 (CO), 1361and
+
1
45.05 [M+H] , C H N O .
1152 (SO ); H NMR (CDCl ):8.1 (s, 1H, NH), 7.5-
2 3
9
12
2
4
7.2 (m, 5H, Ar), 5.9 (s, 1H, NH), 5.15 (m, 1H, *CH),
Table 2: Synthesis of N-acyl sulfonamides
Product Time (min)
Entry
Substrate
Yield (%)
O O
S
O O
S
O
5
NH
NH2
NH
N
CH3
30
15
15
30
30
94
H
O
O
O
O
O
O
6
7
8
9
90
95
96
93
S
S
N
H
N
CH
3
NH
NH2
H
O
O O
S
NH S O
NH2
N
H
N
CH3
H
O
O
O O
O
S
S
N
H
N
CH
3
NH
H
NH
2
F
F
O
O
O
O
O
S
S
N
H
N
CH3
NH
H
NH
2
O O
O
O
O
S
S
1
1
0
1
N
N
CH
3
40
60
90
60
N
NH2
H
O
O
O
O
S
O
S
N
N
N
N
N
CH
3
NH2
H
MeO
MeO
O
O
O
O
O
1
1
1
2
3
4
35
20
30
80
85
83
S
S
N
N
H
N
CH3
NH2
H
H
O O
S
O
O O
S
N
N
CH3
N
NH2
H
H
H
O
O
OEt
O
OEt
O O O
S
N S O
NH2
N
N
CH3
H

BOUASLA et al., Orient. J. Chem., Vol. 33(3), 1454-1460 (2017)
1458
1
3
2
.00 (s, 3H, CH ), 1.50 (d, 3H, J 6.9 Hz, CH ); C
The N-acylation of amines was successfully
achieved using acetic anhydride under ultrasound
irradiation. The reactions proceed smoothly in high
yields (70-89 %) and in short reaction time (table 1).
Thestructuresofallcompoundswereunambiguously
confirmed by spectroscopic methods.Proton nuclear
magnetic resonance spectra showed singlets at
2.20-2.25 ppm corresponding to the proton of CH3
acetyl.Infrared spectra showed bands at 1650-1700
3
3
NMR (CDCl ): 171.3; 145.1; 128.2; 126.8; 126.4;
7.2;21.0;20.6 ppm;LCMS (+) m/z, 243.07 [M+H] ,
3
+
4
C H N O S.
1
0
14
2
3
Ethyl-1-(N-acetylsulfamoyl)pyrrolidine-2-
carboxylate
Powder; 83 % yield; mp 199-200°C; IR
KBr): 3254 (NH), 1733 (CO), 1692 (CO), 1369 and
(
1
1
-1
166 (SO ); H NMR (CDCl ):8.7 (s, 1H, NH), 4.7
cm of functional group C=O.
2
3
(
m, 1H, *CH), 4.3 (q, 2 H, J 2.4 Hz, CH ), 3.4-3.7
2
(
3
5
m, 6H, CH ), 2.1 (s, 3H, CH ), 1.3 (t, 3H, J 2.4 Hz,
Encouraged by this result, we extended the
reaction to sulfonamides derivatives using ultrasonic
irradiation (Scheme 2). The results are reported in
(Table 2, entry 5-14). In all cases, we obtained the
corresponding products N-acyl sulfonamides in good
to excellent yields.
2
3
13
H, CH ); C NMR (CDCl ):171.1, 171.0, 61.3, 60.6,
3
3
5.2, 27.7, 21.4, 21.6, 14.1; LCMS (+) m/z, 265.08
+
[M+H] , C H N O S.
9
16
2
5
RESULTS AND DISCUSSION
Following our efforts to develop novel
O
O
O
O
)))) 40 kHz
O
S
O
O
24-27, 12
methods for acylation
and in continuation of our
S
R
+
R
N
H
NH
2
H C
O
CH
3
Solvent-free
15-60 min
rt
N
N
CH3
investigation on the use of ultrasound irradiation to
3
H
H
28-30
accelerate reactions , we describe a novel method
for acylation the different amines and sulfonamides
with acetic anhydride under ultrasonic irradiation, in
absence of solvent and catalyst.
R = aryl and alkyl
(5-14)
Scheme 2: Catalyst-free synthesis of
N-acylsulfonamides under ultrasonic
irradiation
The main mechanism of sonochemical was
For the resulting products, Infrared spectra
showed band at 1650-1700 cm of functional
31
the formation of cavitation bubbles , under certain
conditions, some bubbles implode, generating very
high temperatures and pressures, these transient,
localized hot spots drive high-energy chemical
-1
group (C=O) of acetyl moiety and band at 1170-
-1
1
395 cm of sulfonyl group. In Proton nuclear
magnetic resonance spectra, the structure of N-acyl
sulfonamides was confirmed by a singlet at 2.27 ppm
3
2-34
reactions
.
corresponding to CH group.
3
In order to carry out the acylation of the
amine function under ultrasonic irradiation, the
amine was chosen as a model substrate, the reaction
of amine with acetic anhydride using ultrasonic
irradiation as shown in scheme 1, the reaction was
completed at 15-30 min, the acylated products were
isolated in good yields (Scheme 1).
The structures of all molecules synthesized
were confirmed by usual spectroscopic methods, IR,
1
13
H NMR, C NMR and mass spectrometry.
CONCLUSION
In summary, the acylation of amines or
sulfonamides was successfully achieved using
acetic anhydride under ultrasound irradiation.
This methodology provides a green and much
improved approach over the classic methods.
Ultrasound can be an effective technology for
process intensification in with cavitational collapse
can affect chemical transformations. The use of
R2
NH
R1
O
O
O
R2
)
))) 40 kHz
+
N
H C
O
CH
3
3
Solvent-free
1
H C
R
1
3
5-30min
(
1 - 4)
R , R = H, aryl and alkyl
1
2
Scheme 1: Catalyst-free synthesis of
N-acylamines under ultrasonic irradiation

1459
BOUASLA et al., Orient. J. Chem., Vol. 33(3), 1454-1460 (2017)
ultrasound is expected to enhance the rate of
reaction by various mechanisms.
ACKNOꢀLEDGEMENTS
We gratefully acknowledge the support
The non-conventional method offer of this work by DG-RSDT and Algerian Ministry of
advantages over conventional process, short time Scientific Research.
span to complete reaction, easy work procedure and
excellent yields.
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