The reaction of thioacids with α-haloketones in water: An environmentally green synthesis of thioester derivatives

Article abstract of DOI:10.1080/10426507.2012.740704

The reaction between a thioacid and an α-haloketone in water affords thioester derivatives in high yields. The reaction proceeded smoothly and cleanly under mild conditions and no side reactions were observed.

Full text of DOI:10.1080/10426507.2012.740704

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The Reaction of Thioacids with
α-Haloketones in Water: an
Environmentally Green Synthesis of
Thioester Derivatives
Ali Ramazani a & Fatemeh Zeinali Nasrabadi b
a Department of Chemistry, Zanjan Branch , Islamic Azad University ,
Zanjan , Iran
b Department of Chemistry , University of Zanjan , Zanjan , Iran
Accepted author version posted online: 01 Nov 2012.Published
online: 16 Aug 2013.
To cite this article: Ali Ramazani & Fatemeh Zeinali Nasrabadi (2013) The Reaction of Thioacids with
α-Haloketones in Water: an Environmentally Green Synthesis of Thioester Derivatives, Phosphorus,
Sulfur, and Silicon and the Related Elements, 188:9, 1214-1219, DOI: 10.1080/10426507.2012.740704
To link to this article: http://dx.doi.org/10.1080/10426507.2012.740704
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Phosphorus, Sulfur, and Silicon, 188:1214–1219, 2013
Copyright ꢀC Taylor & Francis Group, LLC
ISSN: 1042-6507 print / 1563-5325 online
DOI: 10.1080/10426507.2012.740704
THE REACTION OF THIOACIDS WITH α-HALOKETONES
IN WATER: AN ENVIRONMENTALLY GREEN SYNTHESIS
OF THIOESTER DERIVATIVES
Ali Ramazani1 and Fatemeh Zeinali Nasrabadi2
1Department of Chemistry, Zanjan Branch, Islamic Azad University, Zanjan, Iran
2Department of Chemistry, University of Zanjan, Zanjan, Iran
GRAPHICAL ABSTRACT
Abstract The reaction between a thioacid and an α-haloketone in water affords thioester
derivatives in high yields. The reaction proceeded smoothly and cleanly under mild conditions
and no side reactions were observed.
[Supplementary materials are available for this article. Go to the publisher’s online edition of
Phosphorus, Sulfer, and Silicon and the Related Elements for the following free supplemental
files: Additional figures.]
Keywords Thioacid; α-haloketone; thioester; water; green chemistry
INTRODUCTION
α-haloketones are significant organic reagents, which have been used in the synthesis
of an enormous number of both aliphatic and heterocyclic compounds. α-haloketones
were obtained and described at the end of the eighteenth century.1 They have increasingly
attracted attention as a building block for the preparation of compounds of various classes
because of their high reactivity and selective transformations with different reagents. The
reactivity of α-haloketones toward nucleophiles was described by Tchoubar in 1955.2
During the past few decades, a great deal of effort has been made to develop method-
ologies that form carbon−sulfur bonds in the synthesis of molecules with various biological
applications. Thioacids have little reactivity because of their low nucleophilic characteris-
tic. However, the thioesters obtained from thioacids as nucleophiles are synthetically much
valuable due to their widespread application in pharmaceutical chemistry and also they
serve as key intermediates in the synthesis of various bioactive molecules. Meanwhile,
thioesters are used as coupling partners in organometallic reactions, building blocks for the
synthesis of heterocyclic compounds, and acyl transfer reactions.3–15 Also, thioesters are
Received 24 June 2012; accepted 14 October 2012.
Address correspondence to Ali Ramazani, Department of Chemistry, Zanjan Branch, Islamic Azad
University, Zanjan 49195-467, Iran. E-mail: aliramazani@gmail.com
1214

REACTION OF THIOACIDS WITH α-HALOKETONES IN WATER
Table 1 Synthesis of thioester derivatives 3 in H2O (see Scheme 1)
1215
Entry
3
R
Rꢁ
X
Yield (%)a
1
2
3
4
5
6
7
8
3a
3b
3c
3d
3d
3e
3e
3f
4-Methoxyphenyl
Methyl
Chloromethyl
Phenyl
Phenyl
Phenyl
Ph
Ph
Ph
Ph
Ph
CH3
CH3
CH3
Br
Cl
Cl
Cl
Br
Br
Cl
Br
94
92
87
87
90
90
88
91
Phenyl
4-Methoxyphenyl
aYield of isolated 3.
multipurpose intermediates in natural products synthesis, which have multifarious appli-
cations in synthetic chemistry as precursors to aldehydes, ketones, acids, esters, lactones,
amides, lactams, and heterocycles.16,17
Recently, we have established a one-pot method for the preparation of organic com-
pounds including heterocyclic and nonheterocyclic compounds.18–24 As part of our ongoing
program to develop efficient and robust methods for the synthesis of heteroatom-containing
compounds,25–32 we wish to report the preparation of a new class of thioester derivatives
3a–f by condensation reaction of thioacid 2 and α-haloketone 1 in water with excellent
yields (Scheme 1).
Scheme 1 Synthesis of thioester derivatives 3 (See Experimental and Table 1).
RESULTS AND DISCUSSION
We examined the reaction of thioacid with α-haloketone in water at r.t. (25◦C) and
we obtained the corresponding thioester derivatives 3 (Scheme 1 and Table 1).
We also used methanol, dichloromethane, and acetonitrile as solvent instead of water
in this reaction; however, an increase of reaction times and a decrease of yields of 3 were
observed. Also, this reaction has been performed in solvent-free conditions, the first time in
the solid phase (silica gel powder) and the second time as neat conditions. Under both the
conditions, an increase in reaction times and a decrease in yields of 3 was seen (Table 2).
Also, 2-chloro-2-phenylacetophenone, 2-bromo-4ꢁ-phenylacetophenone, 2-chloro-
3ꢁ,4ꢁ-dihydroxyacetophenone, 3-chloro-2-butanone, and 1,4-dibromo-2,3-butanedione
were used in the reaction; however, no corresponding products 3 were observed, and they
were recovered without any reaction at the end of the reaction. So, these α-haloketones
are not suitable as starting materials in this reaction. However, the reactions proceeded
efficiently with α-haloketones, shown in Table 1.
Among the compounds we reported, compounds 3d and 3e are available commer-
cially. Also, we compared spectral data of compound 3d with the compound reported in

1216
A. RAMAZANI AND F. Z. NASRABADI
Table 2 Synthesis of thioester 3b under various conditions
Entry
Solvent
Temp.
Time (h)
Yield (%)a
1
2
3
4
5
6
H2O
r.t.
r.t.
r.t.
r.t.
r.t.
r.t.
12
24
24
24
24
24
92
50
50
50
30
30
CH3CN
CH3OH
CH2Cl2
Silica gel powder (0.1 g)
Neat
aYield of isolated 3.
previous literatures.33 In comparison with other reported methods in previous literatures,
the important advantage of the reported method in this paper is the use of water as it is eas-
ily available, cheap, nontoxic, and environmentally green solvent at ambient temperature,
without using any kind of reagent.
In summary, the reported method offers a mild, simple, and efficient route for the
preparation of thioester derivatives 3. 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.
EXPERIMENTAL
General
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 TLC and NMR, which indicated that there is no side product. Melting points
were measured on an Electrothermal 9100 apparatus and were uncorrected. IR spectra were
1
measured on a Jasco 6300 FTIR spectrometer. H and 13C NMR spectra were measured
(CDCl3) with a BRUKER DRX-250 AVANCE spectrometer at 250.0 MHz 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 layer chromatography (PLC) plates were prepared
from Merck silica gel (F254) powder.
General Procedure for the Preparation of 3a–f
A mixture of α-haloketone (1.0 mmol; 0.23 g [R = 4-methoxyphenyl, X = Br],
0.08 mL [R = CH3, X = Cl], 0.12 g [R = Chloromethyl, X = Cl], 0.15 g [R = phenyl,
X = Cl], and 0.2 g [R = phenyl, X = Br]), and thioacid (1.0 mmol; 0.12 mL [Rꢁ = Ph]),
0.07 mL [Rꢁ = CH3]) in H2O (5 mL) was stirred at r.t. (25 ◦C) for 12 h. The solvent was
removed under reduced pressure, and the viscous residue was purified by preparative layer
chromatography (PLC) (silica gel [F254] powder; petroleum ether–ethyl acetate [3:1]). The
characterization data of the compounds are given as follows.
2-(4-Methoxyphenyl)-2-oxoethyl 1-benzenecarbothioate (3a). White pow-
◦
1
der, mp 72–74 C, H NMR (CDCl3, 250 MHz): δH (ppm) 3.86 (s, 3H, OCH3), 4.54 (s,
2H, CH2), 6.95 (d, 2H, 3JHH = 8.7 Hz, CH arom), 7.42–8.05 (m, 7H, CH arom). 13C NMR
(CDCl3, 62.5 MHz): δC (ppm) 36.3 (CH2), 55.6 (OCH3), 114.0, 127.4, 128.7, 132.0, 133.7

REACTION OF THIOACIDS WITH α-HALOKETONES IN WATER
1217
(9CH), 136.0, 136.3, 164.0 (3C), 190.6 (S–C = O), 191.92 (C O). IR (KBr) (υmax, cm−1):
3001, 2921, 1700, 1659, 1599, 1447, 1262, 1205, 1169, 916, 822, 775, 688. Ms m/z (%)
286 (16), 167 (40), 149 (56), 135 (100), 105 (96), 77 (94), 69 (64), 57 (44). Anal. calcd.
for C16H14O3S (286): C, 67.11; H, 4.93. Found: C, 67.18; H, 4.86.
2-Oxopropyl 1-benzenecarbothioate (3b). Yellow oil, 1H NMR (CDCl3,
250 MHz): δH (ppm) 2.34 (s, 3H, CH3), 3.93 (s, 2H, CH2), 7.43–7.99 (m, 5H, CH arom).
13C NMR (CDCl3, 62.5 MHz): δC (ppm) 28.9 (CH3), 39.5 (CH2), 127.4, 128.8, 133.9
(5CH), 136.1 (C), 190.4 (S–C O), 202.04 (C O). IR (KBr) (υmax, cm−1): 3061, 2926,
1720, 1680, 1581, 1448, 1208, 1161, 913, 773, 688. Anal. calcd. for C10H10O2S (194): C,
61.83; H, 5.19; Found: C, 61.89; H, 5.13.
3-Chloro-2-oxopropyl 1-benzenecarbothioate (3c). White powder, mp
58–60 ◦C, 1H NMR (CDCl3, 250 MHz): δH (ppm) 4.05 (s, 2H, CH2), 4.36 (s, 2H, CH2),
7.47–8.09 (m, 5H, CH arom). 13C NMR (CDCl3, 62.5 MHz): δC (ppm) 36.3, 47.8 (2CH2),
127.5, 128.8, 134.2 (5CH), 135.7 (C), 190.4 (S–C O), 196.67 (C O). IR (KBr) (υmax
,
cm−1): 3075, 2962, 1735, 1681, 1649, 1447, 1204, 1042, 910, 774, 690. Anal. calcd. for
C10H9ClO2S (228): C, 52.52; H, 3.97. Found: C, 52.46; H, 3.91.
2-Ooxo-2-phenylethyl 1-benzenecarbothioate (3d). White powder, mp
59–61 ◦C, 1H NMR (CDCl3, 250 MHz): δH (ppm) 4.59 (s, 2H, CH2), 7.43–8.07 (m, 10H,
CH arom). 13C NMR (CDCl3, 62.5 MHz): δC (ppm) 36.6 (CH2), 127.5, 128.6, 128.72,
128.8, 133.8, 133.9 (10CH), 135.6, 136.3 (2C), 190.4 (S–C O), 193.40 (C O). IR (KBr)
(υmax, cm−1): 3050, 2918, 1700, 1656, 1577, 1445, 1285, 1207, 1195, 917, 775, 689. Anal.
calcd. for C15H12O2S (256): C, 70.29; H, 4.72. Found: C, 70.22; H, 4.65.
2-Ooxo-2-phenylethyl Ethanethioate (3e). Yellow oil, 1H NMR (CDCl3,
250 MHz): δH (ppm) 2.41 (s, 3H, CH3), 4.41 (s, 2H, CH2), 7.46–8.01 (m, 5H, CH arom). 13
C
NMR (CDCl3, 62.5 MHz): δC (ppm) 30.3 (CH3), 36.7 (CH2), 128.5, 128.8, 133.7 (5CH),
135.5 (C), 193.2 (S–C O), 194.2 (C O). IR (KBr) (υmax, cm−1): 2920, 2851, 1685, 1596,
1448, 1201, 1131, 990, 747, 688. Anal. calcd. for C10H10O2S (194): C, 61.83; H, 5.19.
Found: C, 61.89; H, 5.25.
1
2-(4-Methoxyphenyl)-2-oxoethyl Ethanethioate (3f). Yellow oil, H NMR
(CDCl3, 250 MHz): δH (ppm) 2.39 (s, 3H, CH3), 3.87 (s, 3H, OCH3), 4.35 (s, 2H, CH2),
6.94 (d, 2H, 3JHH = 8.7 Hz, CH arom), 7.97 (d, 2H, 3JHH = 8.7 Hz, CH arom). 13C NMR
(CDCl3, 62.5 MHz): δC (ppm) 30.3 (CH3), 36.3 (CH2), 55.5 (OCH3), 113.9, 130.9 (4CH),
128.5, 164.0 (2C), 191.8 (S–C O), 194.4 (C O). IR (KBr) (υmax, cm−1): 2919, 2849,
1682, 1599, 1500, 1420, 1206, 1170, 989, 827. Anal. Calcd. for C11H12O3S (224): C,
58.91; H, 5.39. Found: C, 58.84; H, 5.46.
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