Reaction of 2-thiazolidinethione with halohydrocarbon: Synthesis of novel N-alkylated 2-thiazolidinethione and S-alkylated thiazoline derivatives

Article abstract of DOI:10.1515/HC.2010.015

Reaction of 2-thiazolidinethione with halohydrocarbon in ethanol gave a series of N-alkylated 2-thiazolidinethione and S-alkylated thiazoline derivatives in excellent yields. The reaction was carried out under mild conditions using NaOH as a base and it did not require protection from air.

Full text of DOI:10.1515/HC.2010.015

Heterocycl. Commun., Vol. 16(4-6), pp. 275–278, 2010 • Copyright © by Walter de Gruyter • Berlin • New York. DOI 10.1515/HC.2010.015
Reaction of 2-thiazolidinethione with halohydrocarbon:
synthesis of novel N-alkylated 2-thiazolidinethione and
S-alkylated thiazoline derivatives
to afford the desired N- and S-alkylated products in yields
that were good to excellent. The results are summarized in
Table 1.
Yufa Liu*, Junwei Liu and Xiuming Liu
College of Chemistry, Chemical Engineering and
Materials Science, Engineering Research Center of
Pesticide and Medicine Intermediate Clean Production,
Ministry of Education, Shandong Normal University,
Jinan 250014, China
The reaction of 2-thiazolidinethione with low-molec-
ular-weight halohydrocarbons (1–9) in refluxing ethanol
gave the corresponding N-alkylated 2-thiazolidinethione
derivatives I1a-I9a in high yields of 64–75%. The alternative
S-alkylated isomers of I1b-I9b were not isolated. The reac-
tion of 2-thiazolidinethione was extended to include alky-
lation with higher-molecular-weight halohydrocarbon, such
as bromododecane (10), bromohexadecane (11) and aryl
halides (12–14). For these reactions, as depicted in Table 1,
both the N- and S-alkylated derivatives I10a–14a and I10b–14b
were isolated. The structures of the products were confirmed
by hydrogen nuclear magnetic resonance (1H NMR), carbon
magnetic resonance (13C NMR), infrared spectrometry (IR),
and mass spectrometry (MS).
*Corresponding author
e-mail: yufaliu@yahoo.cn
Abstract
Reaction of 2-thiazolidinethione with halohydrocarbon in
ethanol gave a series of N-alkylated 2-thiazolidinethione and
S-alkylated thiazoline derivatives in excellent yields. The
reaction was carried out under mild conditions using NaOH
as a base and it did not require protection from air.
Keywords: halohydrocarbon; isomers; 2-thiazolidinethione;
thiazole derivatives.
Conclusion
A method for efficient synthesis of a novel thiazole system
by reaction of 2-thiazolidinethione with various halohydro-
carbons at appropriate temperature is reported. The reaction
could be carried out in ethanol or in other alcohols, without
the need for protection from air. Ethanol proved to be a good
solvent in the reactions, and it was convenient for product
isolation.
The reaction of 2-thiazolidinethione with low-molecular-
weight halohydrocarbon (chain hydrocarbon, C≤10, 1–9)
afforded N-alkylated 2-thiazolidinethione derivatives (I1a–9a).
The yields dropped from 75 to 64% with increasing molec-
ular weight of the halohydrocarbon. On the other hand,
the reaction of 2-thiazolidinethione with bromododecane
(10), bromohexadecane (11) or other aryl halides (12–14)
gave isomeric mixtures of N-alkylated 2-thiazolidinethione
(I10a–14a) and S-alkylated thiazoline (I10b–14b). In each case, the
N-alkylated 2-thiazolidinethione derivatives were obtained as
the main products, and the yields ranged from 48 to 64%.
The isolated yields for the S-alkylated isomers ranged from
9 to 26%.
Introduction
2-Thiazolidinethione (Rachinskii et al., 1958) is the deriva-
tive of thiazole (Ingo et al., 2001) that belongs to an impor-
tant group of heterocyclic compounds, many of which are
widely used in medicinal and pesticidal fields (Kazuo et al.,
1999). Some derivatives of thiazolidine have diverse biologi-
cal activities, such as bactericidal, pesticidal, antiphlogistic,
anticonvulsant, tuberculostatic, anti-inflammatory, anal-
gesic, antiparasitic, and herbicidal agents (Tsymbal et al.,
1968; Jean et al., 1990; Moulard et al., 1993; Masae et al.,
2003; Tenorio et al., 2005; Kucukguzel et al., 2006; Li et al.,
2006). Also, some thiazole derivatives are potent anti-HIV
(Jan et al., 2002) and anticancer (Chandrappa et al., 2008)
agents. Therefore, the synthesis and biological activity of
thiazole derivatives have received much attention recently.
Accordingly, we report here results from the reaction of
2-thiazolidinethione with 14 halohydrocarbon reagents using
conventional heating.
Experimental
Results and discussion
Melting points were determined in soft-glass capillaries on the
Electrothermal Melting Point apparatus and were uncorrected.
Qualitative and quantitative thin-layer chromatography (TLC) was
conducted on TLC silica gel sheets. 1H NMR and 13C NMR spectra
The strategy for the synthesis of 2-thiazolidinethione and
its derivatives is outlined in Scheme 1. The halohydrocar-
bons (1–14) reacted efficiently with 2-thiazolidinethione
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276 Y. Liu et al.
H NCH CH OH
+
H2SO4
H O
2
H NCH CH OSO H
2
2
2
+
2
2
2
3
S
H O
KHSO
S
NH
+
+
+
H2NCH2CH2OSO3H CS2 KOH
+
2
4
S
S
S
NaOH
S
+
S
NH
+
RBr
S
N
R
CH3CH2OH
N
R
Ia
Ib
Scheme 1 Synthesis of 2-thiazolidinethione and its derivatives.
were recorded at 300 MHz and 75 MHz, respectively, on a Bruker
DRX 300 instrument using CDCl3 as solvent. The chemical shifts
are reported in ppm. IR spectra were recorded on the Bruker Tensor
27 FTIR spectrometer with KBr pellet. Mass spectra were obtained
on an AGILENT 5973N MSD mass spectrometer with EI. All com-
pounds were homogeneous on TLC plates in various solvent sys-
tems, such as petroleum ether-acetic ether (20:1-10:3) and normal
hexane-dichloromethane (20:1-5:1). 2-Aminoethylsulfuric acid and
2-thiazolidinethione were synthesized using published procedures
(Owen, 1967; Taguchi et al., 1969; Kazuo et al., 1983; Kenso and
Miyuki, 1984; Sugita, 1984).
Characterization of products
2-Thiazolidinethione: White solid; 5.67 g (68%); mp 105–106°C.
1H NMR: δ 3.56 (t, 2H, J=8.8 Hz, -S-CH2), 3.99 (t, 2H, J=8.8 Hz,
-S-CH2-CH2), 8.14 (s, 1H, NH); 13C δ NMR: 35.12, 58.95,
201.63.
I1a:Yellow oil; 0.28 g (75%); 1H NMR: δ 1.29 (t, 3H, J=6.7 Hz, CH3),
3.02 (t, 2H, J=7.4 Hz, -S-CH2), 3.32 (m, 2H, -CH2CH3), 4.15 (t, 2H,
J=7.4 Hz, -S-CH2-CH2); 13C NMR: δ 23.2, 34.9, 38.1, 64.4, 165.1;
IR: 2929, 2850, 1715, 1571, 1448, 1372, 1305, 1266, 1218, 1058,
1017, 994, 964, 921, 756, 639 cm-1; EI-MS: m/z 148.26 (M++1).
General procedure for the preparation of the
derivatives of 2-thiazolidinethione (I1–14b
)
I2a:Yellow oil; 0.30 g (74%); 1H NMR: δ 0.98 (t, 3H, J=7.3 Hz, CH3),
1.64–1.77 (m, 2H, -CH2CH3), 3.06 (t, 2H, J=7.9 Hz, -SCH2), 3.36 (t,
A mixture of 2-thiazolidinethione (0.30 g, 2.50 mmol), NaOH
(0.10 g, 2.50 mmol) and the appropriate halohydrocarbon (Table
1) in ethanol (10 ml) was stirred at refluxing temperature and the
time indicated in Table 1. The progress of the reaction was moni-
tored by TLC. The by-product NaX was removed by filtration and
the residue was washed with ethanol (3×10 ml). The filtrate was
washed with hydrochloric acid (1%, 3×10 ml) and dried with an-
hydrous MgSO4. Derivatives I1a–9a were purified with the silica gel
column chromatography. Derivatives I10a–14a and I10b–14ab were
purified with the silica gel column chromatography. The products
were obtained in good purity indicated by 1H NMR, 13C NMR, IR
and MS.
3H, J=7.3 Hz, -N-CH2CH2CH3), 4.19 (t, 2H, J=7.9 Hz, -NCH2); 13
C
NMR: δ 13.5, 22.7, 34.7, 35.3, 64.2, 165.9; IR: 3445, 2963, 2931,
2360, 1570, 1456, 1303, 1017, 994, 921, 783, 732, 639, 530 cm-1;
EI-MS: m/z 162.29 (M++1).
1
I3a: Yellow oil; 0.27 g (66%); H NMR: δ 1.34 [d, 6H, J=6.8 Hz,
-CH(CH3)2], 3.32 (t, 2H, J=8.0 Hz, -S-CH2), 3.74–3.83 (m, 1H,
-N-CH), 4.19 (t, 2H, J=8.0 Hz, -S-CH2-CH2); 13C NMR: δ 14.5, 30.8,
30.8, 35.1, 64.1, 206.6; IR: 2962, 2927, 2864, 1567, 1448, 1383,
1365, 1304, 1240, 1191, 1157, 1057, 1013, 994, 963, 920, 882, 703,
650 cm-1; EI-MS: m/z 162.30 (M++1).
Table 1 Reaction of 2-thiazolidinethione with halohydrocarbons in the presence of NaOH in ethanol under reflux conditions (see Experimental
for additional details).
Starting material
mmol
Product
Time (h)
Yield (%)
CH3CH2Br (1)
CH3CH2CH2Br (2)
(CH3)2CHBr (3)
3.00
3.00
3.50
3.00
3.50
3.50
3.50
3.50
4.00
4.00
4.00
3.00
3.00
3.00
I1a
I2a
I3a
I4a
I5a
I6a
I7a
I8a
I9a
2.5
2.5
3.0
3.0
3.0
3.5
4.0
4.0
4.5
5.0
5.0
1.5
2.0
2.5
75
74
66
70
68
66
65
65
64
56+11
48+9
64+26
61+22
57+18
CH3CH2CH2CH2Br (4)
(CH3)2CHCH2Br (5)
CH3CH2CH(CH3)Br (6)
CH3(CH2CH2)2Br (7)
CH3(CH2CH2)3CH2Br (8)
CH3(CH2CH2)4CH2Br (9)
CH3(CH2CH2)5CH2Br (10)
CH3(CH2CH2)7CH2Br (11)
PhCH2Cl (12)
I10a+I 10b
I11a+I 11b
I12a+I 12b
I13a+I 13b
I14a +I 14b
p-NO2PhCH2Cl (13)
PhCH2CH2Cl (14)
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Reaction of 2-thiazolidinethione with halocarbon 277
1
I4a: Yellow oil; 0.31 g (70%); H NMR: δ 0.90 (t, 3H, J=7.8 Hz,
3443, 2919, 2848, 1637, 1572, 1469, 1302, 996, 914, 719, 645, 582,
-CH3), 1.34–1.46 (m, 2H, -CH2CH3), 1.60–1.69 (m, 2H, -CH2-
CH2CH3), 3.10 (t, 2H, J=7.9 Hz, -SCH2), 3.37 (t, 2H, J=7.3 Hz,
-N-CH2CH2CH2CH3), 4.18 (t, 2H, J=7.9 Hz, -NCH2); 13C NMR:
δ 13.5, 22.1, 29.3, 31.3, 35.3, 64.3, 165.7; IR: 2957, 2930, 2854,
1571, 1463, 1378, 1303, 1273, 1228, 1191, 1017, 995, 964, 921, 745,
639 cm-1; EI-MS: m/z 176.31 (M++1).
526 cm-1; EI-MS: m/z 344.63 (M++1).
1
I11b: White solid; Mp 61–63°C; 0.08 g (9%); H NMR: δ 0.86 (t,
3H, J=3.3 Hz, -CH3), 1.25 [m, 26H, -(CH2)13CH3], 1.66 [m, 2H,
-CH2(CH2)13CH3], 3.27 [t, 2H, J=7.8 Hz, -CH2(CH2)14CH3], 3.75 (t,
2H, J=7.6 Hz, -SCH2), 4.07 (t, 2H, J=7.9 Hz, -NCH2); 13C NMR: δ
14.1, 22.7, 26.8, 27.2, 29.3 (two signals), 29.5, 29.5, 29.6, 29.7, 31.9,
49.3, 56.6, 196.1; EI-MS: m/z 344.63 (M++1).
1
I5a: Yellow oil; 0.29 g (68%); H NMR: δ 0.84 (d, 3H, J=3.7 Hz,
-CH3), 1.00 (d, 3H, J=3.7 Hz, CH3), 1.34 (m, 1H, -CH), 3.09 (m,
2H, -CH2CH), 3.66 (t, 2H, J=7.8 Hz, -SCH2), 4.20 (t, 2H, J=7.8 Hz,
-NCH2); 13C NMR: δ 14.3, 20.0, 27.0, 35.1, 44.5, 64.2, 165.8; IR:
2964, 2930, 2852, 1567, 1455, 1379, 1303, 1225, 1190, 1150, 1060,
994, 963, 920, 646 cm-1; EI-MS: m/z 176.32 (M++1).
I12a: White solid; Mp 72–74°C; 0.34 g (64%); 1H NMR: δ 3.40 (t, 2H,
J=8.0 Hz, -SCH2), 4.24 (t, 2H, J=8.0 Hz, -NCH2), 4.38 (s, 2H, CH2-
Ar), 7.26–7.38 (m, 5H, -Ar); 13C NMR: δ 25.5, 48.0, 52.0, 126.1,
127.2, 128.1, 128.2, 128.4, 130.2, 172.1; IR: 3452, 3023, 2944, 1660,
1489, 1448, 1410, 1363, 1315, 1243, 1178, 1075, 1043, 982, 918,
730, 692, 587 cm-1; EI-MS: m/z 210.33 (M++1).
1
I6a: Yellow oil; 0.30 g (66%); H NMR: δ 0.99 (t, 3H, J=7.3 Hz,
-CH2CH3), 1.36 (m, 3H, -CHCH3), 1.60 (m, 2H, -CH2CH3), 3.32
(t, 2H, J=7.9 Hz, -SCH2), 3.66 (m, 1H, J=7.0 Hz, -CHCH3), 4.20 (t,
2H, J=7.9 Hz, -NCH2); 13C NMR: δ 8.2, 21.1, 29.6, 34.9, 44.7, 64.3,
165.83; IR: 2964, 2930, 2852, 1567, 1455, 1379, 1303, 1225, 1190,
1150, 1060, 994, 963, 920, 646 cm-1; EI-MS: m/z 176.31 (M++1).
1
I12b: White solid; Mp 94–96°C; 0.14 g (26%); H NMR: δ 3.23 (t,
2H, J=7.9 Hz), 3.94 (t, 2H, J=7.9 Hz), 4.99 (s, 2H), 7.26–7.34 (m,
5H); 13C NMR: δ 32.1, 38.1, 127.2, 127.9, 128.9, 139.6, 162.6;
EI-MS: m/z 210.33 (M++1).
1
I7a: Yellow oil; 0.31 g (65%); H NMR: δ 0.87 (t, 3H, J=6.9 Hz,
1
I
13a: White solid; Mp 79–81°C; 0.39 g (61%); H NMR: δ 3.43 (t,
-CH3), 1.34–1.69 [m, 6H, -(CH2)3CH3], 3.08 [t, 2H, J=7.3 Hz,
-CH2(CH2)3CH3], 3.35 (t, 2H, J=7.9 Hz, -SCH2), 4.18 (t, 2H, J=7.9 Hz,
-NCH2); 13C NMR: δ 13.9, 28.9, 31.8, 32.7, 35.3, 38.9, 64.3, 165.7;
IR: 2956, 2929, 2854, 1571, 1464, 1378, 1303, 1260, 1190, 1061,
1017, 996, 965, 920, 730, 639 cm-1; EI-MS: m/z 190.34 (M++1).
2H, J=7.9 Hz), 4.22 (t, 2H, J=7.9 Hz), 4.42 (s, 2H), 7.53 (d, 2H, J=8.5
Hz), 8.15 (d, 2H, J=8.5 Hz); 13C NMR: δ 35.8, 36.0, 63.6, 123.7,
129.9, 144.7, 147.2, 165.5; EI-MS: m/z 255.33 (M++1).
I13b: White solid; Mp 114–116°C; 0.14 g (22%); 1H NMR: δ 3.46 (t,
2H, J=7.9 Hz), 4.31 (t, 2H, J=7.9 Hz), 4.57 (s, 2H), 7.55 (d, 2H, J=8.6
Hz), 8.19 (d, 2H, J=8.6 Hz); 13C NMR: δ 35.9, 36.1, 64.3, 125.4,
130.7, 146.8, 149.0, 166.5; EI-MS: m/z 255.33 (M++1).
1
I8a: Yellow oil; 0.31 g (65%); H NMR: δ 0.85 (t, 3H, J=6.9 Hz,
-CH3), 1.26–1.39 [m, 10H, -(CH2)5CH3], 1.68 [t, 2H, J=7.3 Hz,
-CH2(CH2)5CH3], 3.09 [t, 2H, J=5.4 Hz, -CH2(CH2)6CH3], 3.37 (t,
2H, J=7.9 Hz, -SCH2), 4.21 (t, 2H, J=7.9 Hz, -NCH2); 13C NMR: δ
14.0, 22.6, 28.7, 29.1, 29.2, 29.7, 31.8, 34.1, 38.9, 64.3, 165.7; IR:
2925, 2853, 2361, 1649, 1570, 1460, 1302, 1190, 1017, 994, 965,
919, 722 cm-1; EI-MS: m/z 232.42 (M++1).
1
I14a: White solid; Mp 84–86°C; 0.32 g (57%); H NMR: δ 3.02 (t,
2H, J=7.6 Hz), 3.34–3.42 (m, 4H), 4.23 (t, 2H, J=7.9 Hz), 7.23–7.39
(m, 5H); 13C NMR: δ 35.2, 35.4, 35.7, 64.2, 126.6, 128.5, 128.6,
139.8, 165.7; EI-MS: m/z 224.35 (M++1).
I9a:Yellow oil; 0.39 g (64%); 1H NMR: δ 0.83 (t, 3H, J=3.4 Hz, -CH3),
1.23–1.37 [m, 14H, -(CH2)7CH3], 1.64 [m, 2H, -CH2(CH2)7CH3],
3.07 [t, 2H, J=7.3 Hz, -CH2(CH2)8CH3], 3.35 (t, 2H, J=7.9 Hz,
-SCH2), 4.19 (t, 2H, J=7.9 Hz, -NCH2); 13C NMR: δ 14.0, 22.6, 28.7,
29.1, 29.2, 29.4, 29.5, 31.8, 32.6, 35.0, 64.0, 166.1; IR: 2925, 2853,
2361, 1649, 1570, 1460, 1302, 1190, 1017, 994, 965, 919, 722 cm-1;
EI-MS: m/z 260.47 (M++1).
I14b: White solid; Mp 107–109°C; 0.10 g (18%); 1H NMR: δ 3.08 (t,
2H, J=7.7 Hz), 3.39–3.58 (m, 4H), 4.41 (t, 2H, J=7.9 Hz), 7.26–7.41
(m, 5H); 13C NMR: δ 35.5, 35.6, 35.7, 64.8, 127.1, 129.0, 129.3,
139.9, 167.6; EI-MS: m/z 224.36 (M++1).
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1
I10a: White solid; Mp 44–46°C; 0.40 g (56%); H NMR: δ 0.87
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1
I
10b: White solid; Mp 65–67°C; 0.08 g (11%); H NMR: δ 0.87
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33.9, 35.2, 64.2, 166.3; EI-MS: m/z 288.53 (M++1).
1
I11a: White solid; Mp 40–41°C; 0.42 g (48%); H NMR: δ 0.89 (t,
3H, J=6.0 Hz, -CH3), 1.25 [m, 26H, -(CH2)13CH3], 1.68 [m, 2H,
-CH2(CH2)13CH3], 3.09 [t, 2H, J=7.3 Hz, -CH2(CH2)14CH3], 3.37 (t,
2H, J=7.9 Hz, -SCH2), 4.20 (t, 2H, J=7.9 Hz, -NCH2); 13C NMR: δ
14.1, 22.7, 26.8, 24.2, 29.1 (two signals), 29.2 (three signals), 29.3
(two signals), 29.4, 29.5, 29.6, 31.8, 31.9, 49.3, 59.6, 196.1; IR:
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