The reaction of carbon disulfide with bromoacetophenone in the presence of primary amines: Synthesis of 3-alkyl-4-phenyl-1,3-thiazole-2(3 H)-thione derivatives

Article abstract of DOI:10.1080/17415993.2011.635794

A three-component reaction between a primary amine, carbon disulfide, and bromoacetophenone that affords novel 3-alkyl-4-phenyl-1,3-thiazole-2(3H)-thione derivatives is reported. The reaction sequence consists of an initial nucleophilic addition of primary amines to carbon disulfide, followed by the nucleophilic attack of carbamodithioic acid so obtained to the bromoacetophenone, and then ring closure by intramolecular attack of nitrogen to the carbonyl carbon to afford the products. This cascade reaction sequence represents a rapid and unprecedented route to the described molecules that have biological specifications.

Full text of DOI:10.1080/17415993.2011.635794

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The reaction of carbon disulfide with
bromoacetophenone in the presence
of primary amines: synthesis of 3-
alkyl-4-phenyl-1,3-thiazole-2(3H)-
thione derivatives
Javad Safaei-Ghomi a , Fariba Salimi a , Ali Ramazani b , Fatemeh
Zeinali Nasrabadi b & Yavar Ahmadi c
a Department of Organic Chemistry, Faculty of Chemistry,
University of Kashan, 51167, Kashan, Iran
b Chemistry Department, Zanjan University, PO Box 45195-313,
Zanjan, Iran
c Young Researchers Club, Zanjan Branch, Islamic Azad University,
Zanjan, Iran
Published online: 28 Nov 2011.
To cite this article: Javad Safaei-Ghomi , Fariba Salimi , Ali Ramazani , Fatemeh Zeinali Nasrabadi
& Yavar Ahmadi (2012) The reaction of carbon disulfide with bromoacetophenone in the presence
of primary amines: synthesis of 3-alkyl-4-phenyl-1,3-thiazole-2(3H)-thione derivatives, Journal of
Sulfur Chemistry, 33:1, 87-92, DOI: 10.1080/17415993.2011.635794
To link to this article: http://dx.doi.org/10.1080/17415993.2011.635794
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Journal of Sulfur Chemistry
Vol. 33, No. 1, February 2012, 87–92
The reaction of carbon disulfide with bromoacetophenone in the
presence of primary amines: synthesis of
3-alkyl-4-phenyl-1,3-thiazole-2(3H)-thione derivatives
Javad Safaei-Ghomia, Fariba Salimia, Ali Ramazanib*, Fatemeh Zeinali Nasrabadib and
Yavar Ahmadic
aDepartment of Organic Chemistry, Faculty of Chemistry, University of Kashan, 51167 Kashan, Iran;
c
bChemistry Department, Zanjan University, PO Box 45195-313, Zanjan, Iran; Young Researchers Club,
Zanjan Branch, Islamic Azad University, Zanjan, Iran
(Received 10 October 2011; final version received 24 October 2011)
A three-component reaction between a primary amine, carbon disulfide, and bromoacetophenone that
affords novel 3-alkyl-4-phenyl-1,3-thiazole-2(3H)-thione derivatives is reported. The reaction sequence
consists of an initial nucleophilic addition of primary amines to carbon disulfide, followed by the nucle-
ophilic attack of carbamodithioic acid so obtained to the bromoacetophenone, and then ring closure by
intramolecular attack of nitrogen to the carbonyl carbon to afford the products. This cascade reaction
sequence represents a rapid and unprecedented route to the described molecules that have biological
specifications.
S
O
S
CH3OH
Br
CS2
R
RNH2
N
+
+
r.t.,24h
Ph
Ph
Keywords: carbon disulfide; bromoacetophenone; primary amines; thiazole; nucleophilic addition
1. Introduction
In recent years, multicomponent reactions (MCRs) have become important tools in modern pri-
mary synthetic chemistry because these reactions increase the efficiency by combining several
operational steps without any isolation of intermediates or changes of the conditions (1–10). So,
this principle is very efficient in terms of time as well as resources (11). Among the known MCRs,
the most valuable reactions are those based on isocyanides. Isocyanide-based MCRs (abbreviated
to IMCRs by Ugi and Dömling) (11–14) due to their synthetic potential, their inherent atom effi-
ciency, convergent nature, ease of implementation, and molecular diversity have attracted much
*Corresponding author. Email: aliramazani@gmail.com
ISSN 1741-5993 print/ISSN 1741-6000 online
© 2012 Taylor & Francis
http://dx.doi.org/10.1080/17415993.2011.635794
http://www.tandfonline.com

88 J. Safaei-Ghomi et al.
attention. Therefore, because of these advantages they offer, they are a valuable tool in the field
of combinatorial chemistry (12–14).
Organiccompoundscontainingfive-memberedaromaticheterocyclicringsformawiderangeof
compounds in the nature and often play an important role in diverse biochemical processes. Conse-
quently, aromatic heterocycles such as thiophenes, benzothiophene derivatives, and their reduced
forms are important structural fragments in many pharmaceutical and chemical compounds.
Thiophenes and thiazole compounds have been found to indicate nematocidal, insecticidal,
antibacterial, antifungal, antiviral, and antioxidant activity (15–17). Tetrahydrothiophene is an
important building block of a large quantity of compounds that are very interesting from the point
of view of biological activity. Its derivatives have exhibited antisecretory and antiulcer activities
(18). In particular, it is found in structures of nucleoside analogs and certain compounds where
the sulfur atom is in the ring, such as sulfimides, salicinol, and kotalanol, which are excellent
glycosidase inhibitors (19–21).
As part of our ongoing program to develop efficient and robust methods for the preparation of
heterocyclic compounds (22–31), we sought to develop a easy preparation of 3-alkyl-4-phenyl-
1,3-thiazole-2(3H)-thione derivatives 4a–i. Herein, we express a new one-pot three-component
reaction, which starting from readily available carbon disulfide, bromoacetophenone 3, and
primary amine, affords 4a–i (Scheme 1).
S
O
S
CH3OH
Br
CS2
R
RNH2
N
+
+
r.t., 24h
Ph
3
1
2
Ph
4
4a: R = 4-methylbenzyl, 4b: R = benzyl, 4c: R = 4-fluorobenzyl, 4d: R = 4-methoxybenzyl, 4e:
R = 2-methoxybenzyl, 4f: R = Furan-2-ylmethyl, 4g: R = naphthyl, 4h: R = 3, 4-dichlorobenzyl,
4i: R = 2-methoxy ethyl
Scheme 1. Three-component synthesis of 3-alkyl-4-phenyl-1,3-thiazole-2(3H)-thione deriva-
tives 4 (see Section 4).
2. Results and discussion
We examined the reaction of primary amines with carbon disulfide in the presence of bro-
moacetophenone in dry CH3OH at room temperature (25◦C) and we obtained the corresponding
3-alkyl-4-phenyl-1,3-thiazole-2(3H)-thione derivatives 4 in excellent yields. The reaction pro-
ceedssmoothlyandcleanlyundermildandneutralconditions, andnosideproductswereobserved.
The compounds 4 were stable when stored at room temperature for several months. We have also
used chloroacetophenone instead of bromoacetophenone 1 in this reaction, but no corresponding
products 4 were observed and unreacted chloroacetophenone was recovered.
1
The structures of the products were deduced from their H NMR, 13C NMR, IR, and mass
spectra. The mass spectra of these compounds displayed molecular ion peaks at the appropriate
m/z values. The 1H NMR spectrum of 4a consisted of a singlet for CH3 at δ 2.28, a singlet for CH2
at δ 4.48, a singlet for CH at δ 6.00, two doublets for four aromatic protons at δ 6.83 and 7.01,
and a multiplet at δ 7.16–7.41 for five aromatic protons. The 1H decoupled 13C NMR spectrum
of 4a showed 12 distinct resonances, partial assignment of these resonances is given in Section
4. The 1H and 13C NMR spectra of compounds 4b–i were similar to those of 4a, except for the
aromatic moiety, which exhibited characteristic signals with appropriate chemical shifts.
A possible mechanism for the present reaction is shown in Scheme 2, which envisages a tandem
sequence. On the basis of established chemistry of trivalent nitrogen nucleophiles, the successful

Journal of Sulfur Chemistry 89
nucleophilic attack by amines on a carbon atom is facilitated when the latter is conjugated with
a carbonyl group, or when it is a part of an otherwise activated unsaturated bond. First, the
nucleophilic addition of the primary amine 3 to carbon disulfide 2 generates the nucleophilic
carbamodithioic acid 5 (32). The next step involves nucleophilic attack of carbamodithioic acid 5
at the methylene carbon of bromoacetophenone 1, leading to intermediate 6, and then ring closure
by intramolecular attack of nitrogen at the carbonyl carbon to afford the 3-alkyl-4-phenyl-1,3-
thiazole-2(3H)-thione derivatives 4.
S
S
R
RNH2
+
N
SH
C
H
5
3
S
2
S
R
S
Ph
S
Br
+
R
NH
Br
O
Ph
OH
N
SH
H
1
6
S
S
- H2O
-HBr
N
R
Ph
4
Scheme 2. Proposed mechanism for the formation of 3-alkyl-4-phenyl-1,3-thiazole-
2(3H)-thione derivatives 4a–i.
3. Conclusions
The reported method offers a mild, simple, and efficient route for the preparation of 3-alkyl-4-
phenyl-1,3-thiazole-2(3H)-thione derivatives 4. Its ease of work-up, high yields, and fairly mild
reaction conditions make it a useful addition to modern synthetic methodologies. Other aspects
of this process are under investigation.
4. Experimental
Starting materials and solvents were obtained from Merck (Germany) and Fluka (Switzerland)
and were used without further purification. The methods used to follow the reactions are thin-layer

90 J. Safaei-Ghomi et al.
chromatography (TLC) and NMR, which indicated that there is no side product. Melting points
were measured on an Electrothermal 9100 apparatus and are uncorrected. IR spectra were mea-
sured on a Jasco 6300 FTIR spectrometer. 1H and 13C NMR spectra were measured (CDCl3) with
a BRUKER DRX-250 AVANCE spectrometer at 250.0 and 62.5 MHz, respectively. Elemental
analyses were performed using a Heraeus CHN-O-Rapid analyzer. Mass spectra were recorded
on a FINNIGAN-MAT 8430 mass spectrometer operating at an ionization potential of 70 eV.
Preparative TLC was prepared from Merck silica gel (F254) powder.
4.1. General procedure for the preparation of 4a–i
The solution of primary amine (1.0 mmol) and carbon disulfide (1.0 mmol) in CH3OH (7 ml) was
stirred for 1 h and then bromoacetophenone 3 (1.0 mmol) was added, and the mixture was stirred
for 24 h. The solvent was removed under reduced pressure and the viscous residue was purified by
preparative TLC (silica gel; petroleum ether–ethyl acetate (10:2)). The solvent was removed under
reduced pressure and the products were obtained. The characterization data of the compounds are
given below.
4.1.1. 3-(4-Methylbenzyl)-4-phenyl-1,3-thiazole-2(3H)-thione (4a)
Colorless viscous oil; yield 90%; IR (KBr) (υmax, cm−1): 3100, 3000, 1650, 1600, 1475, 1200.
1H NMR (250 MHz, CDCl3): δ 2.28 (s, 3H, CH3), 4.84 (s, 2H, CH2), 6.00 (s, 1H, CH of alkene),
6.83 (d, 2H, J = 7.5 Hz, CH arom), 7.01 (d, 2H, J = 7.5 Hz, CH arom), 7.16–7.41 (m, 5H, CH
arom). 13C NMR (62.5 MHz, CDCl3): δ 21.06 (CH3), 47.00 (CH2), 98.81 (CH of alkene), 127.12,
128.57, 129.15, 129.27 (9CH), 131.52, 133.47, 136.85 (3C), 152.39 (C of alkene), 194.17 (C9S).
MS (EI, 70 eV): m/z(%) = 297 (2), 281 (60), 149 (10), 105 (100), 77 (24). Anal. Calcd. for
C17H15NS2 (297): C, 68.65; H, 5.08; N, 4.71. Found: C, 68.60; H, 5.13; N, 4.76 %.
4.1.2. 3-Benzyl-4-phenyl-1,3-thiazole-2(3H)-thione (4b)
Colorless viscous oil; yield 89%; IR (KBr) (υmax, cm−1): 3100, 3000, 1600, 1475, 1200. 1H NMR
(250 MHz, CDCl3): δ 4.87 (s, 2H, CH2), 6.02 (s, 1H, CH of alkene), 6.94–7.34 (m,10H, CH arom).
13C NMR (62.5 MHz, CDCl3): δ 47.22 (CH2), 98.88 (CH of alkene), 127.09, 127.45, 128.50,
128.58, 129.09, 129.31(10CH), 131.44, 136.47, 137.80 (3C), 153.39 (C of alkene), 179.17 (C9S).
MS (EI, 70 eV): m/z(%) = 283 (4), 267(70), 181(7), 91 (100), 77 (4), 65 (10), 45 (4). Anal. Calcd.
for C16H13NS2 (283): C, 67.81; H, 4.62; N, 4.94. Found: C, 67.87; H, 4.67; N, 4.88 %.
4.1.3. 3-(4-Fluorobenzyl)-4-phenyl-1,3-thiazole-2(3H)-thione (4c)
Colorless viscous oil; yield 86%; IR (KBr) (υmax, cm−1): 3150, 3000, 1625, 1600, 1475, 1300,
1
1100. H NMR (250 MHz, CDCl3): δ 4.84 (s, 2H, CH2), 6.00 (s, 1H, CH of alkene), 6.88 (d,
2H, J = 6.8 Hz, CH arom), 7.01–7.57 (m, 5H, CH arom), 7.96 (d, 2H, J = 7.5 Hz, CH arom).13C
2
NMR (62.5 MHz, CDCl3): δ 46.48 (CH2), 99.05 (CH of alkene), 115.56 (d, 2CH, J = 22.0,
CH arom), 128.62, 128.72, 133.54 (5CH), 129.04 (d, 2CH, 3J = 6.3, CH arom), 135.40, 137.52
(2C), 153.25 (C of alkene), 159.5 (d, C, 1J = 440.3, CH arom), 194.17 (C=S). Anal. Calcd. for
C16H12FNS2 (301): C, 63.76; H, 4.01; N, 4.54. Found: C, 63.81; H, 4.06; N, 4.59 %.

Journal of Sulfur Chemistry 91
4.1.4. 3-(4-Methoxybenzyl)-4-phenyl-1,3-thiazole-2(3H)-thione (4d)
Colorless viscous oil; yield 80%; IR (KBr) (υmax, cm−1): 3150, 3000, 1650, 1600, 1470, 1200,
1100. 1H NMR (250 MHz, CDCl3): δ 3.75 (s, 3H, OCH3), 4.82 (s, 2H, CH2), 5.99 (s, 1H, CH of
alkene), 6.72 (d, 2H, J = 7.8 Hz, CH arom), 6.84–7.61 (m, 5H, CH arom), 7.97 (d, 2H, J = 6.8 Hz,
CH arom). 13C NMR (62.5 MHz, CDCl3): δ 46.67 (CH2), 55.20 (OCH3), 98.50 (CH of alkene),
113.83, 128.62, 128.72, 129.16, 133.54 (9CH), 133.54, 135.40 (2C), 153.15 (C of alkene), 159.32
(C), 194.17 (C9S). Anal. Calcd. for C17H15NOS2 (313): C, 65.14; H, 4.82; N, 4.47. Found: C,
65.09; H, 4.87; N, 4.52 %.
4.1.5. 3-(2-Methoxybenzyl)-4-phenyl-1,3-thiazole-2(3H)-thione (4e)
Colorless viscous oil; yield 80%; IR (KBr) (υmax, cm−1): 3150, 3000, 1650, 1600, 1470, 1200,
1100. 1H NMR (250 MHz, CDCl3): δ 3.62 (s, 3H, OCH3), 4.90 (s, 2H, CH2), 6.03 (s, 1H, CH
of alkene), 6.71–7.98 (m, 9H, CH arom).13C NMR (62.5 MHz, CDCl3): δ 42.73 (CH2), 55.09
(OCH3), 98.67 (CH of alkene), 110.00, 120.52, 128.36, 128.44, 128.63, 128.73, 129.01, 133.55
(9CH), 127.13, 135.40 (2C), 156.39 (C of alkene and C arom), 194.17 (C9S). Anal. Calcd. for
C17H15NOS2 (313): C, 65.14; H, 4.82; N, 4.47. Found: C, 65.09; H, 4.87; N, 4.52 %.
4.1.6. 3-(2-Furyl methyl)-4-phenyl-1,3-thiazole-2(3H)-thione (4f)
Colorless viscous oil; yield 86%; IR (KBr) (υmax, cm−1): 3100, 3000, 1650, 1600, 1475, 1200. 1H
NMR (250 MHz, CDCl3): δ 4.82 (s, 2H, CH2), 6.11(s, 1H, CH of furan), 6.23 (s, CH of furan),
6.45 (s, CH of alkene), 7.26–8.08 (m, 6H, CH arom and CH of furan). 13C NMR (62.5 MHz,
CDCl3): δC 44.22 (CH2), 108.67 (CH of alkene), 109.64, 110.45, 126.20, 128.78, 129.61, 142.10
(8CH), 144.53, 147.90 (2C); 155.53 (C of alkene), 192.17 (C9S). Anal. Calcd. for C14H11NOS2
(273): C, 61.51; H, 4.06; N, 5.12. Found: C, 61.57; H, 4.12; N, 5.18 %.
4.1.7. 3-(2-Naphthyl methyl)-4-phenyl-1,3-thiazole-2(3H)-thione (4g)
Colorless viscous oil; yield 86%; IR (KBr) (υmax, cm−1): 3100, 3000, 1650, 1600, 1475, 1200.
1H NMR (250 MHz, CDCl3): δ 3.98 (s, 2H, CH2), 6.10 (s, 1H, CH of alkene), 6.94–7.98 (m,
12H, CH arom). 13C NMR (62.5 MHz, CDCl3): δ 45.39 (CH2), 99.09 (CH of alkene), 123.73,
125.31, 125.80, 126.31, 128.01, 128.63, 128.73, 133.56 (12CH), 122.51, 129.27, 131.53, 135.04
(4C), 172.49 (C of alkene), 194.17 (C9S). Anal. Calcd. for C20H15NS2 (333): C, 72.03; H, 4.53;
N, 4.20. Found: C, 72.08; H, 4.48; N, 4.25 %.
4.1.8. 3-(3,4-Dichlorobenzyl)-4-phenyl-1,3-thiazole-2(3H)-thione (4h)
Colorless viscous oil; yield 86%; IR (KBr) (υmax, cm−1): 3150, 3000, 1625, 1600, 1475, 1300,
1100. 1H NMR (250 MHz, CDCl3): δ 4.81 (s, 2H, CH2), 6.04 (CH of alkene), 6.78–7.98 (m, 8H,
CH arom). 13C NMR (62.5 MHz, CDCl3): δ 46.08 (CH2), 99.28 (CH of alkene), 126.71, 128.63,
128.73, 129.39, 129.64, 133.56 (8CH), 130.52, 135.39, 136.63, 137.23 (4C), 172.72 (C of alkene),
194.17 (C9S). Anal. Calcd. for C16H11Cl2NS2 (350): C, 54.55; H, 3.15; N, 3.98. Found: C, 54.49;
H, 3.10; N, 3.93 %.

92 J. Safaei-Ghomi et al.
4.1.9. 3-(2-Methoxyethyl)-4-phenyl-1,3-thiazole-2(3H)-thione (4i)
Colorless viscous oil; yield 86%; IR (KBr) (υmax, cm−1): 3100, 3000, 1650, 1600, 1475, 1200,
1100. 1H NMR (250 MHz, CDCl3): δ 3.16 (t, 2H, NCH2), 3.35 (s, 3H, OCH3), 3.63 (t, 2H, OCH2),
6.07 (s, 1H, CH of alkene), 7.41–7.98 (m, 5H, CH arom).13C NMR (62.5 MHz, CDCl3): δ 46.40
(NCH2), 58.88 (OCH3), 68.79 (OCH2), 105.68 (CH of alkene), 126.12, 128.73, 128.94 (5CH),
133.56 (C), 163.72 (C of alkene), 194.17 (C9S). Anal. Calcd. for C12H13NOS2 (251): C, 57.34;
H, 5.21; N, 5.57. Found: C, 57.29; H, 5.26; N, 5.62 %.
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