Magnetic phosphonium ionic liquid: Application as a novel dual role acidic catalyst for synthesis of 2′-aminobenzothiazolomethylnaphthols and amidoalkyl naphthols

Article abstract of DOI:10.1007/s11164-019-03996-w

Abstract: In this investigation, a novel magnetic phosphonium ionic liquid (MPIL) was designed and synthesized through a two-step process. The resulting magnetic ionic liquid was fully characterized using different techniques including Fourier-transform i

Full text of DOI:10.1007/s11164-019-03996-w

Research on Chemical Intermediates
https://doi.org/10.1007/s11164-019-03996-w
Magnetic phosphonium ionic liquid: Application
as a novel dual role acidic catalyst for synthesis
of 2′‑aminobenzothiazolomethylnaphthols and amidoalkyl
naphthols
1
1
1
2
Morteza Torabi · Meysam Yarie · Mohammad Ali Zolfgol · Saeid Azizian
Received: 26 August 2019 / Accepted: 25 September 2019
©
Springer Nature B.V. 2019
Abstract
In this investigation, a novel magnetic phosphonium ionic liquid (MPIL) was
designed and synthesized through a two-step process. The resulting magnetic ionic
liquid was fully characterized using diꢀerent techniques including Fourier-transform
infrared spectroscopy (FT-IR), thermogravimetric analysis (TGA), derivative ther-
mogravimetric analysis (DTG), energy-dispersive X-ray spectroscopy (EDX) and
vibrating sample magnetometer (VSM). The prepared dual acidic MPIL represents
brilliant catalytic performance towards the synthesis of 2′-aminobenzothiazolometh-
ylnaphthol and amidoalkyl naphthol derivatives. Combination of magnetic, Bronsted
and Lewis acid ability within a single compound is the major advantage of prepared
MPIL. The present work can open up a new and promising insight in the course of
rational design, synthesis and applications of task-speciꢁc multi-rule magnetic ionic
liquids for various purposes.
Graphic abstract
A novel magnetic phosphonium ionic liquid promoted the synthesis of 2′-aminoben-
zothiazolomethylnaphthols and amidoalkyl naphthol derivatives.
Electronic supplementary material The online version of this article (https://doi.org/10.1007/s1116
4
-019-03996-w) contains supplementary material, which is available to authorized users.
Extended author information available on the last page of the article
Vol.:(012
1
3456789)
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M. Torabi et al.
Keywords Ionic liquids · Magnetic ionic liquids · Phosphonium ionic liquid ·
2
′-aminobenzothiazolomethylnaphthols · Amidoalkyl naphthols · Multicomponent
reactions
Introduction
Since the discovery of magnetic ionic liquids by Hayashi and Hamaguchi, these
compounds triggered a cascade of innovation in numerous areas of chemistry [1,
2
]. As a subclass of functional ionic liquids, magnetic ionic liquids have magnetic
components in their cationic or anionic parts. Due to the incorporation of paramag-
netic centre within the structure of magnetic ionic liquids, these structures have a
strong macroscopic response to external magnetic ꢁelds. Therefore, knowledge-
based design of magnetic ionic liquids as versatile structures leads to preparation of
magnetoactive compounds which inherit unique features of ionic liquids including
excellent thermal and chemical stability, high electrochemical properties, good solu-
bility and excellent potent of recyclability. Also, paramagnetic features and struc-
tural adjustability have enabled these scaꢀolds to represent wide applicability per-
spectives in interdisciplinary ꢁelds such as process and product engineering [3–15].
On the other hand, comparing with conventional multistep preparation processes,
multicomponent reactions represent elegant advantages such as convergence nature,
facile automation, simplicity of operational protocols, reduce the number of workup
steps, minimizing waste productions and rendering the transformations based on
green chemistry metrics. Therefore, combination of the above-mentioned excellent
features of magnetic ionic liquids and multicomponent reaction processes yields to
an eꢂcient protocol for the preparation of complex molecules through an “ideal syn-
thetic” manner [16–22].
As substituted Betti’s base derivatives, 2′-aminobenzothiazolomethylnaphthol
and amidoalkyl naphthol derivatives are two inꢃuential cores which show an intrigu-
ing role in both synthetic and medicinal processes. Molecules featuring 2-amin-
obenzothiazole like 2′-aminobenzothiazolomethylnaphthols are ubiquitous in varied
pharmaceutical active molecules, and they could be applied as anti-inꢃammatory,
anti-epileptic, antimicrobial, antitumor, antidiabetic and anticonvulsant agents [23,
2
4]. Also, amidoalkyl naphthols are widely used in pharmacological active mole-
cules. These versatile structures can be easily converted to 1,3-oxazine derivatives
which present a broad scope of pharmaceutical applications such as antibiotic, anti-
tumor, analgesic, antianginal, antipsychotic, antimalarial, antirheumatic and antihy-
pertensive features [25–30].
Although several catalytic protocols with a lot of potential improvements have
been reported towards the preparation of 2′-aminobenzothiazolomethylnaph-
thol [31–40] and amidoalkyl naphthol derivatives [41–58], most of them encoun-
tered some defects in synthetic chemistry, like harsh reaction conditions, elevated
operational reaction temperatures and prolonged reaction times with low yields.
1
3

Magnetic phosphonium ionic liquid: Application as a novel…
Scheme 1 General route for the synthesis of a novel acidic of MPIL B
Scheme 2 Preparation of 2′-aminobenzothiazolomethylnaphthols in the presence of MPIL B
Scheme 3 Preparation of amidoalkyl naphthol in the presence of MPIL B
Therefore, introducing a new time-saving protocol with mild and green reaction
conditions for their preparation is a great demand.
In order to follow up our research goals towards the knowledge-based design,
synthesis and application of task-speciꢁc catalysts [59–65] and preparation of phos-
phonium-based ionic liquids for diꢀerent goals [66–69], herein we wish to combine
magnetic, Bronsted and Lewis acid ability within a single compound. With this aim,
a novel MPIL with both protic and Lewis acid ability was synthesized and used as
an excellent catalyst for the facile preparation of 2′-aminobenzothiazolomethylnaph-
thol and amidoalkyl naphthol derivatives as portrayed in Schemes 1, 2 and 3.
1
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M. Torabi et al.
Result and discussion
Nowadays, catalysis science and technology play major role in the pollution pre-
vention in our environment. To the best of our knowledge, multi-rule catalysts
have a great demand for both fundamental and applied researches. In continuation
of our previously reported imidazolium-based magnetic ionic liquid [70], herein
we describe synthesis, characterization and application of a novel MPIL with both
protic and Lewis acid ability. The structure of ionic liquid A and MPIL B was con-
ꢁ
rmed using diꢀerent techniques.
1
13
The H NMR and C NMR spectra of ionic liquid A are depicted Figs. 1–2. The
acidic proton related to –SO H functional group appears at 8.66 ppm. The three
3
terminal methyl groups can be easily distinguished by a triplet signal at 0.90 ppm.
All remained –CH protons resonate as multiplet in the aliphatic region (Fig. 1). In
2
1
3
C NMR, terminal methyl groups resonate as a separate singlet at 13.9 ppm. Also,
1
3
as indicated in the expanded C NMR spectrum, other –CH carbon atoms within
2
the structure of ionic liquid A coupled with phosphorus atom and resonated in their
related aliphatic region (Fig. 2). Also, the structure of ionic liquid A was veriꢁed by
3
1
P NMR with an observation of a singlet peak at 70.9 ppm (Fig. 2).
Resulting data from FT-IR spectrum of the prepared novel MPIL B are
depicted in Fig. 3. All anticipated functional groups appear in their related
domain. Acidic group within the structure of MPIL B appears as a broadband at
−
1
3
346 cm . The corresponding stretching mods of aliphatic hydrogens related to
Fig. 1 1H NMR spectrum of ionic liquid A
1
3

Magnetic phosphonium ionic liquid: Application as a novel…
Fig. 2 13C NMR and 31P NMR spectra of ionic liquid A
Fig. 3 FT-IR spectrum of MPIL (B)
1
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M. Torabi et al.
Fig. 4 EDX analysis of novel MPIL B
(
a)
(b)
Fig. 5 (a) TG and DTG analysis of novel MPIL B and (b) TG analysis of ionic liquid A
−
1
butyl chains are distinguishable in 2962 cm . Also, stretching mode of –S=O
−
1
groups is conꢁrmed by observation of a peak at 1229 cm .
In order to explore the elemental composition of MPIL, energy-dispersive
X-ray spectroscopy (EDX) was conducted. The obtained data conꢁrmed the exist-
ence all anticipated elements including carbon, phosphorus, sulphur, oxygen, iron
and chlorine atoms (Fig. 4). The obtained data verify the successful formation of
desired MPIL B.
The experimental analysis for the thermal behaviour and stability of the MPIL
B is depicted in Fig. 5. The thermal gravimetry (TG) and diꢀerential thermal
gravimetric (DTG) analysis anticipated a high operational thermal stability at
high temperatures for the prepared MPIL B. Also, the thermal behaviour of MPIL
1
3

Magnetic phosphonium ionic liquid: Application as a novel…
Fig. 6 Magnetization curve of MPIL B
Scheme 4 Screening the optimal reaction parameters for compound 1a as a model structure
B and ionic liquid A was compared by using TG analysis which represents high
thermal stability for the prepared MPIL B (Fig. 5).
Also, using VSM analysis, the magnetic behaviour of the prepared MPIL B
was investigated.
The magnetization curve which appraises the values of magnetic moment of
MPIL B is depicted in Fig. 6.
Due to the existence of both Bronsted acid and Lewis acidic sites within the
structure of the novel MPIL B, it is predicted that it can be a powerful catalyst
for multicomponent reactions. Therefore, the catalytic performance of MPIL B
towards the synthesis of diꢀerent substituted Betti’s bases including 2′-aminoben-
zothiazolomethylnaphthol and amidoalkylnaphthol derivatives was studied in the
present work.
The ꢁrst investigated reaction is the multicomponent synthesis of 2′-aminoben-
zothiazolomethylnaphthols. For this goal, initially we tried to screen the eꢀective
reaction parameters such as amount of catalyst, operational reaction temperature and
solvent, upon the reaction of benzaldehyde, 2-naphthol and 2-aminobenzothiazole
for achieving the optimal reaction conditions (Scheme 4). The acquired experimen-
tal data are listed in Table 1. Obtained data show that 1 mol% of MPIL B catalyst is
adequate for promoting the reaction towards the desired molecule 1a at 45 °C under
solvent-free conditions in short reaction time with excellent yield (Table 1, Entry 3).
1
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M. Torabi et al.
Table 1 Optimizing of the eꢀective reaction parameters for the synthesis of target molecule 1aa
Entry
Solvent
Temperature (°C)
Load of catalyst Time (min)
mol%)
Yield (%)b
(
1
2
3
4
5
6
7
–
–
–
–
–
–
–
–
–
–
70
60
45
45
45
45
45
45
1
1
1
2
0.5
–
–
1
1
1
Immed.
Immed.
Immed.
Immed.
30
360
5
5
5
25
60
60
60
60
60
96
96
95
95
81
51
Trace
78
34
74
93
Trace
84
85
c
8
9
d
45
r.t.
1
1
1
1
1
1
0
1
2
3
4
5
H O
C H OH
EtOA
CH2Cl2
Reꢃux
Reꢃux
Reꢃux
Reꢃux
Reꢃux
1
1
1
1
2
2
5
c
n-Hexane
1
79
a
Reaction conditions: benzaldehyde (1 mmol, 0.106 g), 2-naphthol (1 mmol, 0.144 g) and 2-aminobenzo-
thiazole (1 mmol, 0.150 g)
Isolated yields
The reaction tested in the presence of ionic liquid A
The reaction tested in the presence of FeCl3
b
c
d
It is worthy to mention that the indispensability of the catalyst for the reaction was
investigated by performing the model reaction under an un-catalyzed process which
resulted in unsatisfactory amount of desired product 1a (Table 1, Entry 6). Increas-
ing the amount of catalyst and operational reaction temperature shows insigniꢁcant
improvement in the results.
In continue, for investigation the scope, limitation and eꢂciency of the presented
MPIL B catalyst, at the above-mentioned optimized reaction conditions, a variety of
aromatic aldehydes (possessing electron-releasing substituents, electron-withdraw-
ing substituents and halogens) were reacted with 2-naphthol and 2-aminobenzothia-
zole. The related data of synthesized molecular library are presented in Scheme 1.
All the reactions furnished the related molecules in high to excellent yields in short
reaction times (Scheme 5).
In another study, we compared our obtained data with those other reported sys-
tems towards the 2′-aminobenzothiazolomethylnaphthols. As shown in Table 2, our
reported system using MPIL as catalyst presents remarkable progress for the syn-
thesis of target structures from diꢀerent aspects including the reaction conditions,
obtained operational yields and reaction.
The second multicomponent reaction is the synthesis of amidoalkyl naphthol
derivatives through the reaction of diꢀerent arylaldehydes, 2-naphthol and aceta-
mide or benzamide as starting materials. In this regard, benzaldehyde, 2-naphthol
1
3

Magnetic phosphonium ionic liquid: Application as a novel…
Scheme 5 Synthesized molecular library of 2′-aminobenzothiazolomethylnaphthols
Table 2 Comparison of novel MPIL catalyst with those other reported systems for synthesis of 2′-amin-
obenzothiazolomethylnaphthols
Entry Reaction conditions
Time
Yield (%) References
1
2
3
4
5
6
Hydrotalcite, 70 °C
Maltose (20 mol%), Solvent free, 80 °C
2.4–3 h
5–15 min
3–5 min
4–30 min
4–10 min
10–35 min
78–92
45–95
87–94
52–95
88–95
88–95
[31]
[32]
[33]
[34]
[35]
[36]
RHA-[pmim]HSO (12 mol%), Solvent free, 100 °C
4
NaHSO ·H O (10 mol%), Solvent free, 100 °C
4
2
[PVP-SO H]HSO (50 mg), Solvent free, 100 °C
3
4
[H -DABCO][HSO ] (0.097 mmol), Solvent free,
2
4 2
1
20 °C
7
8
9
1
1
SLS/cetrimide/Triton X-100 (10 mol%), Water, r.t.
Triton X-100, Water, 60 °C
100–120 °C
Acidic ionic liquid, Solvent free, 80 or 100 °C
MPIL (1 mol%), Solvent free, 45 °C
100–140 min 75–96
[37]
[38]
[39]
[40]
1–1.8 h
75–95
86–95
54–93
87–96
40–55 min
50–30 min
3–10 min
0
1
This work
1
3

M. Torabi et al.
Scheme 6 Screening the optimal reaction parameters for compound 2a as a model molecule
Table 3 Optimizing of the eꢀective reaction parameters for the synthesis of target molecule 2aa
Entry
Solvent
Temperature (°C)
Load of catalyst Time (min)
mol%)
Yield (%)b
(
1
2
3
4
5
6
7
8
9
–
–
–
–
–
–
–
–
–
–
–
–
90
80
70
60
45
45
45
45
45
45
45
r.t.
Reꢃux
Reꢃux
Reꢃux
Reꢃux
Reꢃux
Reꢃux
1
1
1
1
1
2
0.5
–
–
1
1
1
1
1
1
1
1
1
8
8
95
94
94
93
93
93
91
35
Trace
80
45
83
Trace
56
92
91
95
10
10
10
10
50
600
10
10
10
120
360
60
60
60
60
60
1
1
1
1
1
1
1
1
1
0c
d
1
2
3
4
5
6
7
8
H O
C H OH
CH CN
EtOAc
CH2Cl2
n-Hexane
2
2
5
3
94
a
Reaction conditions: benzaldehyde (1 mmol, 0.106 g), 2-naphthol (1 mmol, 0.144 g) and acetamide
1 mmol, 0.06 g)
Isolated yields
The reaction tested in the presence of ionic liquid A
The reaction tested in the presence of FeCl3
(
b
c
d
1
3

Magnetic phosphonium ionic liquid: Application as a novel…
Scheme 7 Prepared molecular library of amidoalkyl naphthols
Table 4 Comparison of novel MPIL catalyst and other systems for synthesis of 2′-aminobenzothiazolo-
methylnaphthols
Entry Reaction condition
Time
Yield (%) References
1
2
3
4
H N+SO -,)))), 28–30 °C, Neat or DCE
10–120 min 55–94
2–6 min 82–95
15–30 min 84–93
[41]
[42]
[48]
[49]
3
3
[Msim]FeCl (5 mol%), Solvent free, 110 °C
4
Graphene oxide (35 wt%), Solvent free, 120 °C
{[1,4-DHPyrazine][C(NO ) ] } (1 mol%), Solvent free,
5–25 min
92–98
2
3 2
r.t.
5
6
7
8
9
1
1
Acidic ionic liquid (80 mg), Solvent free, 85 °C
Silica chloride (0.1 g),)))), 28–30 °C,
Ce(SO ) (1 eq), CH CN, 85 °C,
5–15 min
9–36 min
16–48 h
0.75–4 h
10–110 min 80–94
3–18 min
5–30 min
80–94
90–98
40–72
83–94
[51]
[52]
[53]
[55]
[57]
[58]
This work
4
2
3
TrCl (10 mol%), CH CN, r.t.
3
[C OHmim]FeCl Br (5 mol%), Neat, 85 °C
2
3
0
1
SCSC, Neat, 125 °C
MPIL (1 mol%), Solvent free, 45 °C
88–98
75–94
1
3

M. Torabi et al.
Scheme 8 A typical plausible catalytic reaction mechanism for the preparation of target molecule 1a
and acetamide were selected as model substrates (Scheme 6). The corresponding
data related to the scrutinizing of the eꢀective reaction parameters including the
amount of catalyst, reaction temperature and diꢀerent solvents are classiꢁed in
Table 3. As it can be seen from the experimental data, the best results were obtained
under solvent-free condition at 45 °C using 1 mol% of MPIL B catalyst (Table 3,
entry 5). Also, increasing the reaction temperature and the load of catalyst shows no
improvement on the time and yield of reaction.
In order to verify the eꢀectiveness and productivity of the presented method for
the preparation of amidoalkyl naphthols, a good range of aromatic aldehydes (bear-
ing electron-releasing substituents, electron-withdrawing substituents and halogens)
was treated with 2-naphthol and acetamide or benzamide. Under the optimal reac-
tion conditions and using the new practical method, all reactions proceeded satis-
factorily towards the relevant molecules 2a–d. The prepared molecular library is
depicted in Scheme 7.
As in the case of 2′-aminobenzothiazolomethylnaphthols, we compared our
obtained data with some previously reported protocols for the synthesis of ami-
doalkyl naphthols (Table 4). The collected data revealed that the presented proce-
dure shows excellent improvement in results for the preparation of target amidoalkyl
naphthol derivatives.
In a typical catalytic reaction mechanism (Scheme 8), it is suggested that the
intermediate b is generated through a catalytic dehydration process of the pro-
duced intermediate a from the reaction between an activated benzaldehyde as
electrophile and 2-naphthol as nucleophile. Thus, the intermediate b acts as a
Michael acceptor and undergoes a nucleophilic attack by 2-aminobenzimidazole
to furnish the desired molecule 1a.
1
3

Magnetic phosphonium ionic liquid: Application as a novel…
Conclusion
In this study, design, synthesis and characterization of a novel m MPIL B are
reported. The synthesized MPIL B was successfully applied as an eꢂcient cata-
lyst for the convenient preparation of diꢀerent substituted Betti’s bases under
mild and green reaction conditions. The promising features of the presented
methods are benign nature of the protocols, ease of reaction procedures, robust
catalytic activity and time saving with excellent yields of target molecules. The
prepared MPIL B has both protic and Lewis acidic abilities. The obtained results
from this research will support the idea of rational design, synthesis and appli-
cations of tasked-speciꢁc catalysts and catalytic systems for various purposes.
Experimental
General procedure for preparation of MPIL B
MPIL B was prepared via a two-step process as depicted in Scheme 1. Initially,
5
mmol (0.58 g) of ClSO H was dropwise added to the 5 mmol (1.01 g) of
3
2
tributylphosphine under N atmosphere at 0–5 °C and the reaction was contin-
ued for 3 h to furnish the desired ionic liquid A as a viscose oil. Afterwards,
the obtained ionic liquid A (5 mmol, 1.59 g) was treated with FeCl (5 mmol,
3
0
.81 g) at ambient temperature for 6 h to yield the MPIL B.
General procedure for the catalytic synthesis of diꢀerent substituted Betti’s bases
in the presence of MPIL B
To a well-ground mixture of aromatic aldehyde (1 mmol), 2-naphthol (0.144 g,
1
mmol) and 2-aminobenzothiazole, acetamide or benzamide (1 mmol) in a round-
bottomed ꢃask, 1 mol% of MPIL B was added as the catalyst. The resulting mixture
was stirred in an oil bath at 45 °C for appropriate times as reported in Schemes 5
and 7. After completion of the reaction, as checked out by TLC, the reaction mixture
was cooled to room temperature. The crude products were puriꢁed by recrystalliza-
tion from ethanol to obtain the desired products.
Selected spectral data of the prepared structures
1
‑((Benzo[d]thiazol‑2‑ylamino)(4‑chloro‑3‑nitrophenyl)methyl)naphtha‑
len‑2‑ol (1g) Melting point=233–235 °C.
−1
FT-IR (KBr): υ (cm )=3387, 3068, 1627, 1538, 1328, 1271, 1050, 756
δ H (300 MHz, DMSO) 10.33 (s, 1H), 8.96 (d, 1H, J=6 Hz) 7.94–7.85 (m, 4H),
.71 (t, 2H, J=9 Hz), 7.55–7.43 (m, 3H), 7.38–7.22 (m, 4H), 7.07 (t, 1H, J=9 Hz).
7
1
3

M. Torabi et al.
δ C (75 MHz, DMSO) 166.5, 153.9, 152.4, 147.7, 144.9, 132.5, 132.1, 131.9,
1
5
31.4, 130.8, 129.2, 129.0, 127.4, 126.00, 123.5, 123.2, 121.8, 121.5, 118.9, 117.8,
2.9.
1
‑((Benzo[d]thiazol‑2‑ylamino)(4‑isopropylphenyl)methyl)naphthalen‑2‑ol
(
1i) Melting point=204–206 °C.
−1
FT-IR (KBr): υ (cm )=3313, 2959, 1626, 1538, 1312, 1272, 1088, 778
δ H (300 MHz, DMSO) 10.19 (s, 1H), 8.83 (d, 1H, J=6 Hz), 7.97 (brs, 1H), 7.82
t, 2H, J=9 Hz), 7.69 (d, 1H, J=6 Hz), 7.41–7.14 (m, 10 H), 7.03 (t, 1H, J=9 Hz),
(
2
.83 (s, 1H, J=6 Hz) 1.16 (d, 6H, J=6 Hz).
δ C (75 MHz, DMSO) 166.8, 153.6, 152.6, 146.7, 140.2, 132.7, 131.2, 129.9,
29.0, 126.7, 126.6, 126.5, 125.9, 122.9, 121.4, 121.4, 119.2, 118.9, 118.6, 53.6,
3.5, 24.4, 24.3.
1
3
N‑((2‑Hydroxynaphthalen‑1‑yl)(4‑isopropylphenyl)methyl)acetamide
(
2e) Melting point=214–216 °C.
−1
FT-IR (KBr): υ (cm )=3404, 2957, 1526, 1516, 1279, 1061, 818
δ H (300 MHz, DMSO) 10.01 (s, 1H), 8.47 (d, 1H, J=9 Hz), 7.93 (d, 1H,
J=6 Hz), 7.84–7.77 (m, 2H), 7.40 (t, 1H, J=9 Hz), 7.31–7.23 (m, 2H), 7.13–7.11
(
m, 5H), 2.89–2.76 (s, 1H, J=9 Hz), 2.00 (s, 3H), 1.16 (d, 6 H, J=9 Hz).
δ C (75 MHz, DMSO) 169.5, 153.6, 146.7, 140.4, 132.8, 129.6, 129.0, 128.9,
1
26.8, 126.7, 126.4, 123.7, 122.9, 119.4, 119.0, 48.3, 33.5, 24.4, 24.4, 23.2.
N‑((3,4‑Difluorophenyl)(2‑hydroxynaphthalen‑1‑yl)methyl)acetamide
(
2h) Melting point=216-218 °C.
−1
FT-IR (KBr): υ (cm )=3398, 2972, 1624, 1519, 1278, 1063, 825.
δ H (300 MHz, DMSO) 10.12 (s, 1H), 8.53 (bs, 1H), 7.81 (bs, 3H), 7.40-7.11 (m,
H), 6.93 (bs, 3H), 2.00 (s, 3H).
6
δ C (75 MHz, DMSO) 167.0, 153.7, 151.3, 151.2, 150.0, 149.8, 148.1, 147.9,
46.8, 146.6, 141.2, 132.6, 130.1, 129.1, 128.9, 127.1, 123.4, 123.1, 123.0, 118.9,
18.5, 117.6, 117.4, 115.5, 115.3, 47.7, 23.1.
1
1
N‑((3,5‑Difluorophenyl)(2‑hydroxynaphthalen‑1‑yl)methyl)acetamide
(
2i) Melting point=244–246 °C.
−1
FT-IR (KBr): υ (cm )=3418, 3090, 1657, 1514, 1335, 1114, 817.
δ H (300 MHz, DMSO) 10.16 (s, 1H), 8.56 (d, 1H, J=9 Hz), 7.89–7.81 (m,
H), 7.44 (t, 1H, J=6 Hz), 7.33–7.24 (m, 2H), 7.15 (d, 1H, J=6 Hz), 7.05 (tt, 1 H,
3
J=9 Hz and 3 Hz), 6.84 (d, 1H, J=6 Hz), 2.04 (s, 3H).
δ C (75 MHz, DMSO) 170.1, 164.5, 164.3, 161.2, 161.1, 153.8, 148.7, 148.6,
1
1
48.47, 132.6, 130.3, 129.1, 128.9, 127.2, 123.4, 123.1, 118.9, 118.3, 109.7, 109.6,
09.5, 109.4, 102.4, 102.1, 101.7, 48.0, 23.0.
N‑((2,6‑Difluorophenyl)(2‑hydroxynaphthalen‑1‑yl)methyl)acetamide
(
2j) Melting point=237–239 °C.
−1
FT-IR (KBr): υ (cm )=3447, 3056, 1644, 1516, 1271, 1012, 793.
1
3

Magnetic phosphonium ionic liquid: Application as a novel…
δ H (300 MHz, DMSO) 9.98 (s, 1H), 8.50 (d, 1H, J=6 Hz), 8.07 (d, 1H,
J=9 Hz), 7.84–7.76 (m, 2H), 7.50 (t, 1H, J=9 Hz), 7.34–7.14 (m,4H), 6.95 (t, 2H,
J=9 Hz), 1.93 (s, 3H).
δ C (75 MHz, DMSO) 169.4, 163.0, 162.9, 159.8, 159.7, 154.1, 132.8, 130.1,
1
1
29.1, 128.8, 128.6, 128.5, 127.1, 122.9, 122.6, 119.3, 119.1, 119.0, 118.9, 117.2,
12.1, 112.0, 111.9, 111.8, 42.7, 22.8.
N‑((3,5‑Bis(trifluoromethyl)phenyl)(2‑hydroxynaphthalen‑1‑yl)methyl)
acetamide (2k) Melting point=227–229 °C.
−1
FT-IR (KBr): υ (cm )=3411, 3069, 1643, 1517, 1376, 1285, 1162, 812.
δ H (300 MHz, DMSO) 10.17 (s, 1H), 8.73 (d, 1H, J=9 Hz), 8.02–7.96 (m, 2H),
.88–7.80 (m, 4H), 7.49 (t, 1H, J=9 Hz), 7.34 (t, 1H, J=9 Hz), 7.24–7.20 (m, 2H),
.03 (s, 3H).
7
2
δ C (75 MHz, DMSO) 170.3, 153.9, 147.1, 132.7, 131.0, 130.6, 130.6, 130.1,
29.7, 129.2, 128.7, 127.5, 127.1, 125.7, 123.2, 122.9, 122.1, 120.6, 118.9, 117.9,
8.3, 23.0.
1
4
Acknowledgements We thank Bu-Ali Sina University and Iran National Science Foundation (INSF)
Grant Number: 98001912), for ꢁnancial support.
(
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Aꢀliations
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Morteza Torabi · Meysam Yarie · Mohammad Ali Zolfgol · Saeid Azizian
*
Meysam Yarie
myari.5266@gmail.com
*
Mohammad Ali Zolꢁgol
mzolꢁgol@yahoo.com; zolꢁ@basu.ac.ir
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2
Department of Organic Chemistry, Faculty of Chemistry, Bu-Ali Sina University,
Hamedan 6517838683, Iran
Department of Physical Chemistry, Faculty of Chemistry, Bu-Ali Sina University,
Hamedan 6517838683, Iran
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