A concise synthetic method for 1,3,5-Triazinane-2,4-dithiones

Article abstract of DOI:10.1590/S0103-50532011001000015

1,3,5-Triazinane-2,4-dithiones were efficiently synthesized via condensation of 2 equiv. of 1-arylthioureas with 1 equiv. of aliphatic carboxylic acids using ferric chloride hexahydrate as a catalyst. This protocol has the advantages of high yield, mild c

Full text of DOI:10.1590/S0103-50532011001000015

J. Braz. Chem. Soc., Vol. 22, No. 10, 1939-1943, 2011.
Printed in Brazil - ©2011 Sociedade Brasileira de Química
0103 - 5053 $6.00+0.00
Article
A
A Concise Synthetic Method for 1,3,5-Triazinane-2,4-Dithiones
Zheng Li,* Hongfang Cai, Jingya Yang, Pengxian Niu and Chenhui Liu
College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou, Gansu,
730070, P. R. China
1,3,5-Triazinane-2,4-ditionas foram sintetizadas eficientemente via condensação de 2 equiv. de
1-aril-tiouréa com 1 equiv. de ácidos carboxílicos alifáticos usando cloreto férrico hexahidratado
como catalisador. Este protocolo tem as vantagens de alto rendimento, condições brandas e
procedimento simples.
1,3,5-Triazinane-2,4-dithiones were efficiently synthesized via condensation of 2 equiv. of
1-arylthioureas with 1 equiv. of aliphatic carboxylic acids using ferric chloride hexahydrate as
a catalyst. This protocol has the advantages of high yield, mild condition and simple procedure.
Keywords: 1,3,5-triazinane-2,4-dithione, 1,3,5-triazinane, thiourea, carboxylic acid, synthesis
Introduction
multi-component reactions of phosphonates, nitriles,
aldehydes and isocyanates,20 the condensation of
trifluoromethanesulfonamide with formaldehyde,21 and
the reactions of thiosemicarbazones with potassium
thiocyanate and benzoyl chloride.22 However, some
methods use expensive reagents, toxic organic solvents,
rigorous conditions, tedious workup procedure and
long reaction time. Therefore, it is necessary to develop
simple and efficient synthetic methods to 1,3,5-triazinane
derivatives.
Heterocyclic compounds have long been known
to exhibit remarkable biological and pharmacological
properties.1 Among the heterocycles, triazine derivatives
have attracted much attention because they can connect
with other molecules by hydrogen or coordination bond to
form network supramolecular materials,2 and they can serve
as luminescent or n-type electron-carrying materials after
connected with some substituents like diphenylacetylene,
naphthalene and anthracene.3 Triazine derivatives constitute
well-known compounds that have been used as fungicidal,4
antiplasmodial,5 anti-HIV 6 and herbicidal agents,7 and
chiral discriminators,8 hydrogen sulfide scavengers9 and
low-toxicity drug deliverers.10 They were also applied
in organic synthesis,11 enantiodifferentiating coupling
reagents,12 catalysis,13 molecular tectonics,14 and polymeric
materials.15 Meanwhile, heterocycles containing a thiourea
structural unit have a special place among pharmaceutically
important natural and synthetic materials, showing
powerful antiproliferative action,16 antibacterial properties17
and anticancer activity.18 For these reasons, 1,3,5-triazinane
derivatives incorporating thiourea unit may be important
in many fields.
In this article, we report the synthesis of 1,3,5-triazinane-
2,4-dithiones by reactions of 2 equiv. of 1-arylthioureas
with 1 equiv. of aliphatic carboxylic acids using ferric
chloride hexahydrate as a catalyst.
Results and Discussion
Initially, the synthesis of 1,3,5-triazinane-2,4-dithione
was attempted by reaction of 1-phenylthiourea with acetic
acid at room temperature under catalyst-free condition,
however, no product was observed. Subsequently,
the mixture of 1-phenylthiourea and acetic acid was
o
heated at 80 C for several hours, a new compound was
isolated in low yield, which was identified to be a novel
heterocyclic compound, 6-hydroxy-6-methyl-1,5-diphenyl-
1,3,5-triazinane-2,4-dithione. In our further research, it was
found that some Brønsted acids, such as p-toluenesulfonic
acid (PTSA) and trichloroacetic acid (TCA), and Lewis
The general synthetic methods for 1,3,5-triazinane
derivatives involve the reactions of N,N’-bis(aryl-
methylidene)arylmethane diimines with thioureas,19 the
•
acids, such as AlCl3, CuCl2, NiCl2, FeCl3 and FeCl3 6H2O,
*e-mail: lizheng@nwnu.edu.cn

1940
A Concise Synthetic Method for 1,3,5-Triazinane-2,4-Dithiones
J. Braz. Chem. Soc.
could efficiently catalyze the reaction (Table 1). Among
lower yield under similar conditions (Table 1, entry 19).
Aliphatic carboxylic acids from C2-C7 were examined for the
reactions, and afforded the corresponding products in high
yield. In addition, aromatic carboxylic acids, such as various
(un)substituted benzoic acids, were also attempted for the
similar reactions, but no desired products were observed.
The resulting compounds 6-hydroxy-6-alkyl-1,5-diaryl-
1,3,5-triazinane-2,4-dithiones are highly soluble in polar
organic solvents including CHC13, CH2C12, DMSO,
DMF and EtOH, but insoluble in toluene, benzene, ether
and n-hexane. The structures of all compounds were
•
them, FeCl3 6H2O could give the best yield if the reaction
was carried out at 80 oC using 10 mol% amount of catalyst
(Table 1, entry 8). In addition, in this reaction, acetic acid
was acted as a reactant and solvent.
To explore the generality and scope of the synthetic
reactions, and synthesis of a series of 6-hydroxy-6-alkyl-
1,5-diaryl-1,3,5-triazinane-2,4-dithiones (Scheme 1),
different 1-arylthioureas and aliphatic carboxylic acids
as substrates were examined under optimal conditions
(Table 2). It was found that various 1-arylthioureas could
efficiently react with aliphatic carboxylic acids at 80 °C
1
13
identified by infrared (IR), H and C nuclear magnetic
resonance (NMR) spectroscopies and elemental analysis.
•
in the presence of FeCl3 6H2O to give the corresponding
1
products in high yield. In comparison with 1-phenylthiourea,
it was found that 1-arylthioureas including electron-donating
groups, such as methyl and methoxyl, on the aromatic rings
gave the corresponding products in higher yield and in
faster rate (Table 2, entries 7-18). 1-Arylthioureas bearing
electron-withdrawing substituents, such as chloro, on
aromatic rings gave the corresponding product in slightly
The H NMR spectra of 6-hydroxy-6-alkyl-1,5-diaryl-
1,3,5-triazinane-2,4-dithiones show the singlets of
hydroxyls at 5.89-6.12 ppm and the multiplets of
aromatic rings at 6.84-8.12 ppm. The IR spectra show the
characteristic adsorption of hydroxyls at 3359-3450 cm-1.
A possible mechanism for the synthesis of
1,3,5-triazinane-2,4-dithione is shown in Scheme 2.
Table 1. Synthesis of 6-hydroxy-6-methyl-1,5-diphenyl-1,3,5-triazinane-2,4-dithione under different conditionsa
HH
SS
NN
SS
HH
CCaattaallyysstt
33 hh
NN NNHH22
++
22
CCHH33CCOOOOHH
NN
NN
PPhh
PPhh
SS
PPhh
OOHH
HH33CC
entry
1
Catalyst
−
Amount of catalyst / (mol%)
Temperature / oC
Yield / %b
10
0
80
80
80
80
80
80
80
80
20
40
60
100
80
80
2
PTSA
TCA
AlCl3
CuCl2
NiCl2
FeCl3
10
10
10
10
10
10
10
10
10
10
10
5
48
3
56
4
51
5
60
6
70
7
74
8
FeCl3·6H2O
FeCl3·6H2O
FeCl3·6H2O
FeCl3·6H2O
FeCl3·6H2O
FeCl3·6H2O
FeCl3·6H2O
88
9
20
10
11
12
13
14
46
70
60
85
15
86
aReaction conditions: 1-phenylthiourea (2 mmol), acetic acid (3 mmol) under different conditions; bisolated yields.
H
S
N
S
H
FeCl3 6H2O
80 °C
R2-COOH
R2=alkyl
N
NH2
2
+
N
N
R1
R1
R1
S
R2
OH
R1=aryl
Scheme 1. Synthesis of 6-hydroxy-6-alkyl-1,5-diaryl-1,3,5-triazinane-2,4-dithiones.

Vol. 22, No. 10, 2011
Li et al.
1941
Table 2 Synthesis of 6-hydroxy-6-alkyl-1,5-diaryl-1,3,5-triazinane-2,4-dithionesa
H
N
S
S
H
FeCl3 6H2O
80 °C
R2-COOH
N NH2
2
+
N
N
R1
R1
R1
S
R2
OH
entry
1
R1
R2
time / h
mp / oC
254-256
197-198
133-135
155-157
124-126
105-106
239-241
160-162
154-155
123-124
119-121
127-129
126-127
111-113
103-104
218-219
243-245
219-221
208-210
Yield / %b
87
C6H5
C6H5
C6H5
C6H5
C6H5
C6H5
CH3
3
3
3
4
4
4
3
3
3
4
2
2
2
3
3
3
4
4
4
2
C2H5
85
3
n-C3H7
n-C4H9
n-C5H11
n-C6H13
CH3
84
4
80
5
80
6
79
7
2-CH3C6H4
2-CH3C6H4
2-CH3C6H4
2-CH3C6H4
4-CH3C6H4
4-CH3C6H4
4-CH3C6H4
4-CH3C6H4
4-CH3C6H4
4-CH3OC6H4
4-CH3OC6H4
4-CH3OC6H4
4-ClC6H4
82
8
C2H5
88
9
n-C3H7
n-C4H9
C2H5
83
10
11
12
13
14
15
16
17
18
19
85
88
n-C3H7
n-C4H9
n-C5H11
n-C6H13
CH3
90
86
80
81
80
C2H5
84
n-C3H7
CH3
78
66
aReaction conditions: 1-arylthiourea (2 mmol), aliphatic carboxylic acid (3 mmol) and ferric chloride hexahydrate (0.2 mmol) at 80 oC; bisolated yields.
S
S
S
S
NH
NH3
H
H
R1
R
N
NH
NH2
N
R1
R
2
2
R1
N
N
N
R
N
N
N
H
H
H
H
H
H
S
S
A
A
1
1
FeCl
FeCl3
FeCl
FeCl3
O
O
O
O
R2
OH
OH
R2
OH
OH
R
R
B
B
2
2
H O
H2O
H
H
H
S
S
H
S
S
N
N
S
S
S
S
N
N
NH
N
N
NH
N
N
N
N
R1
R1
R
R2
R1
R1
R
R
R
R
R2
OH
OH
R
FeCl
FeCl3
O
O
FeCl
FeCl3
C
C
Scheme 2. The possible mechanism for the synthesis of 1,3,5-triazinane-2,4-dithiones.
Presumably, condensation of 2 equiv. of 1-arylthiourea 1
releasing a mole of ammonia first generates an intermediate
A. One of amino groups of A subsequent reacts with
a mole of complex B, which is formed from aliphatic
carboxylic acid 2 and ferric chloride in the solution, to give
intermediate C by loss of water. Subsequently the carbonyl

1942
A Concise Synthetic Method for 1,3,5-Triazinane-2,4-Dithiones
J. Braz. Chem. Soc.
group of C undergoes the nuleophilic addition of its amino
group by releasing ferric chloride to form a six-membered
heterocyclic compound, 1,3,5-triazinane-2,4-dithione 3.
References
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Conclusion
An efficient and concise method has been developed
for the synthesis of 1,3,5-triazinane-2,4-dithiones via
condensation of 2 equiv. of 1-arylthioureas with 1 equiv. of
aliphatic carboxylic acids using ferric chloride hexahydrate
as a catalyst. This protocol has the advantages of high yield,
mild condition and simple procedure.
2. Cai,Y. Q.; Wu, W.; Wang, H.; Miyake, J.; Qian, D. J.; Surf. Sci.
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1
Centauri FTIR spectrophotometer and H and 13C NMR
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or DMSO-d6 as solvents and Me4Si as internal standard.
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melting point apparatus. Flash column chromatography
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pressure. Aromatic thioureas were synthesized according
to the literature methods.23
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General procedure for the preparation of 6-hydroxy-
6-alkyl-1,5-diaryl-1,3,5-triazinane-2,4-dithiones
The mixture of 1-arylthioureas (2 mmol), aliphatic
carboxylic acids (3 mmol) and ferric chloride hexahydrate
o
(0.2 mmol) was heated at 80 C for appropriate time
according to Table 2. The progress of the reactions was
monitored by TLC (thin layer chromatography). After the
completion of the reactions, the systems were cooled to
room temperature, and the mixture was subjected to silica
gel flash column chromatography (ethyl acetate, petroleum
ether, 1:6) to obtain pure products.
12. Kaminski, Z. J.; Kolesinska, B.; Kaminska, J. E.; Gora, J.;
J. Org. Chem. 2001, 66, 6276.
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Supplementary Information
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Full set of characterization data (IR, 1H and 13C NMR
spectra) are available free of charge at http://jbcs.sbq.org.br
as PDF file.
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Silva, C. C.; Sacoman, J. L.; Kohn, L. K.; Sarragiotto, M. H.;
J. Braz. Chem. Soc. 2006, 17, 954.
Acknowledgements
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825.
The authors thank the National Natural Science
Foundation of China (20772096) and Key Laboratory of
Polymer Materials of Gansu Province for the financial
support of this work.
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2010, 46, 7691.
19. Kaboudin, B.; Ghasemi, T.; Yokomatsu, T.; Synthesis 2009,
3089.

Vol. 22, No. 10, 2011
Li et al.
1943
20. Groenendaal, B.; Vugts, D. J.; Schmitz, R. F.; Kanter, F. J. J.;
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Submitted: May 13, 2011
Published online: August 11, 2011

J. Braz. Chem. Soc., Vol. 22, No. 10, S1-S32, 2011.
Printed in Brazil - ©2011 Sociedade Brasileira de Química
0103 - 5053 $6.00+0.00
Supplementary Information
SI
A Concise Synthetic Method for 1,3,5-Triazinane-2,4-Dithiones
Zheng Li,* Hongfang Cai, Jingya Yang, Pengxian Niu and Chenhui Liu
College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou, Gansu,
730070, P. R. China
General procedure for the preparation of 6-hydroxy-
6-alkyl-1,5-diaryl-1,3,5-triazinane-2,4-dithiones
6-Hydroxy-6-propyl-1,5-diphenyl-1,3,5-triazinane-
2,4-dithione (3)
White solid, mp 133-135 °C; IR (KBr) νmax/cm-1 3410,
3054, 2960, 2927, 2862, 1601, 1586, 1543, 1475, 1442,
1377, 1349, 1282, 1231, 1210, 1157, 751, 690; 1H NMR
(CDC13, 400 MHz) d 7.05-7.71 (m, 10H, Ph-H), 6.11 (s,
1H, OH), 2.47 (t, 2H, J 7.4 Hz, CH2), 1.60-1.68 (m, 2H,
CH2), 0.90 (t, 3H, J 7.4 Hz, CH3); 13C NMR (CDCl3, 100
MHz) d 185.9, 177.2, 145.7, 137.7, 133.8, 130.7 (3C),
129.1 (2C), 128.1 (2C), 123.7, 118.8 (2C), 41.0, 18.8, 13.9;
Anal. calcd. for C18H19N3OS2: C, 60.47; H, 5.36; N, 11.75;
Found C, 60.50; H, 5.35; N, 11.74.
The mixture of 1-arylthioureas (2 mmol), aliphatic
carboxylic acids (3 mmol) and ferric chloride hexahydrate
o
(0.2 mmol) was heated at 80 C for appropriate time
according to Table 2. The progress of the reactions was
monitored by TLC (thin layer chromatography). After the
completion of the reactions, the systems were cooled to
room temperature, and the mixture was subjected to silica
gel flash column chromatography (ethyl acetate, petroleum
ether, 1:6) to obtain pure products. The spectral data and
scanned spectra for products are given below.
6-Hydroxy-6-butyl-1,5-diphenyl-1,3,5-triazinane-
2,4-dithione (4)
6-Hydroxy-6-methyl-1,5-diphenyl-1,3,5-triazinane-
2,4-dithione (1)
White solid, mp 155-157 °C; IR (KBr) νmax/cm-1 3418,
3059, 2949, 2864, 1617, 1602, 1585, 1541, 1477, 1443,
1349, 1290, 1204, 752, 694; 1H NMR (CDCl3, 400 MHz)
d 7.05-7.71 (m, 10H, Ph-H), 6.11 (s, 1H, OH), 2.49 (t, 2H,
J 7.4 Hz, CH2), 1.57-1.64 (m, 2H, CH2), 1.26-1.33 (m, 2H,
CH2), 0.87 (t, 3H, J 7.4 Hz, CH3); 13C NMR (CDCl3, 100
MHz) d 186.1, 177.2, 145.7, 137.7, 133.8, 130.7 (3C),
129.1 (2C), 128.1 (2C), 123.7, 118.8 (2C), 38.8, 27.5, 22.4,
13.9; Anal. calcd. for C19H21N3OS2: C, 61.42; H, 5.70; N,
11.31; Found C, 61.54; H, 5.71; N, 11.29.
White solid, mp 254-256 °C; IR (KBr) νmax/cm-1 3409,
2925, 2861, 1614, 1582, 1533, 1473, 1442, 1301, 1251,
1157, 759, 697; 1H NMR (CDC13, 400 MHz) d 7.06-7.71
(m, 10H, Ph-H), 6.10 (s, 1H, OH), 2.24 (s, 3H, CH3);
13C NMR (DMSO-d6, 100 MHz) d 181.6, 177.4, 147.8,
139.3, 134.2, 130.0, 129.9 (2C), 128.7 (2C), 128.4 (2C),
122.7, 120.0 (2C), 25.9; Anal. calcd. for C16H15N3OS2: C,
58.33; H, 4.59; N, 12.76; Found: C, 58.22; H, 4.57; N, 12.73.
6-Hydroxy-6-ethyl-1,5-diphenyl-1,3,5-triazinane-
2,4-dithione (2)
6-Hydroxy-6-pentyl-1,5-diphenyl-1,3,5-triazinane-
2,4-dithione (5)
White solid, mp 197-198 °C; IR (KBr) νmax/cm-1 3359,
3064,2986,2915,1616,1579,1539,1483,1443,1350,1216,
1060, 750, 690;1HNMR(CDC13, 400MHz)d7.05-7.71(m,
10H, Ph-H), 6.11 (s, 1H, OH), 2.51 (q, 2H, J 7.6 Hz, CH2),
1.13 (t, 3H, J 7.6 Hz, CH3); 13C NMR (CDCl3, 100 MHz)
d 186.7, 177.3, 145.7, 137.8, 133.8, 130.8 (3C), 129.2 (2C),
128.2 (2C), 123.7, 118.8 (2C), 32.30, 9.50; Anal. calcd.
for C17H17N3OS2: C, 59.45; H, 4.99; N, 12.23; Found: C,
59.54; H, 4.98; N, 12.19.
White solid, mp 124-126 °C; IR (KBr) νmax/cm-1 3448,
2955, 2927, 2864, 1616, 1578, 1539, 1513, 1480, 1441,
1350, 1245, 1201, 752, 692; 1H NMR (CDCl3, 400 MHz)
d 7.05-7.70 (m, 10H, Ph-H), 6.12 (s, 1H, OH), 2.48 (t, 2H,
J 7.4 Hz, CH2), 1.60-1.64 (m, 2H, CH2), 1.26-1.27 (m, 4H,
CH2), 0.85 (t, 3H, J 7.4 Hz, CH3); 13C NMR (CDCl3, 100
MHz) d 186.1, 177.2, 145.7, 137.7, 133.8, 130.7 (3C),
129.1 (2C), 128.1 (2C), 123.7, 118.8 (2C), 39.0, 31.5, 25.0,
22.4, 13.9;Anal. calcd. for C20H23N3OS2: C, 62.30; H, 6.01;
N, 10.90; Found C, 62.22; H, 5.99; N, 10.88.
*e-mail: lizheng@nwnu.edu.cn

S2
A Concise Synthetic Method for 1,3,5-Triazinane-2,4-Dithiones
J. Braz. Chem. Soc.
6-Hydroxy-6-hexyl-1,5-diphenyl-1,3,5-triazinane-
2,4-dithione (6)
6-Hydroxy-6-butyl-1, 5-di(2-methylphenyl)-
1,3,5-triazinane-2,4-dithione (10)
White solid, mp 105-106 °C; IR (KBr) νmax/cm-1: 3450,
2945, 2921, 2850, 1614, 1577, 1539, 1481, 1439, 1348,
1299, 1240, 1199, 752, 692; 1H NMR (CDCl3, 400 MHz)
d 7.05-7.71 (m, 10H, Ph-H), 6.11 (s, 1H, OH), 2.48 (t, 2H,
J 7.4 Hz, CH2), 1.58-1.63 (m, 2H, CH2), 1.22-1.31 (m,
6H, CH2), 0.85 (t, 3H, J 7.4 Hz, CH3); 13C NMR (CDCl3,
100 MHz) d 186.1, 177.2, 145.7, 137.7, 133.8, 130.7 (2C),
129.1 (2C), 128.5 (2C), 128.1, 123.7, 118.8 (2C), 39.1, 31.6,
29.0, 25.3, 22.5, 14.0; Anal. calcd. for C21H25N3OS2: C,
63.12; H, 6.31; N,10.52; Found C, 63.01; H, 6.30; N, 10.47.
White solid, mp 123-124 °C; IR (KBr) νmax/cm-1 3383,
2961, 2924, 2857, 1600, 1535, 1512, 1471, 1408, 1341,
1240, 1201, 1070, 804; 1H NMR (CDC13, 400 MHz) d 8.09
(d, 1H, J 8.0 Hz, Ph-H), 6.99-7.56 (m, 7H, Ph-H), 5.90 (s,
1H, OH), 2.49 (t, 2H, J 7.6 Hz, CH2), 2.20 (s, 3H, CH3),
1.88 (s, 3H, CH3), 1.57-1.65 (m, 2H, CH2), 1.26-1.33 (m,
2H, CH2), 0.87 (t, 3H, J 7.2 Hz, CH3); 13C NMR (CDCl3,
100 MHz) 186.1, 176.5, 145.8, 137.0, 135.9, 132.6, 132.3,
131.2, 130.4, 128.2, 128.0, 127.1, 126.7, 124.1, 119.9, 38.8,
27.5, 22.4, 17.4, 16.9, 13.8; Anal. calcd. for C21H25N3OS2:
C, 63.12; H, 6.31; N, 10.52; Found C, 63.05; H, 6.30; N,
10.49.
6-Hydroxy-6-methyl-1,5-di(2-methylphenyl)-
1,3,5-triazinane-2,4-dithione (7)
White solid, mp 239-241 °C; IR (KBr) νmax/cm-1 3415,
2961, 2925, 2856, 1617, 1587, 1544, 1484, 1455, 1363, 1300,
1256,752;1HNMR(CDC13,400MHz)d8.11(d,1H,J8.4Hz,
Ph-H), 7.00-7.59 (m, 7H, Ph-H), 5.89 (s, 1H, OH), 2.24 (s,
3H, CH3), 2.20 (s, 3H, CH3), 1.88 (s, 3H, CH3); 13C NMR
(CDCl3, 100 MHz) d 183.3, 176.9, 145.8, 136.9, 135.9,
132.7, 132.4, 131.3, 130.5, 128.3, 128.1, 127.2, 126.7, 124.1,
119.9, 26.1, 17.5, 16.9; Anal. calcd. for C18H19N3OS2: C,
60.47; H, 5.36; N, 11.75; Found C, 60.53; H, 5.35; N, 11.71.
6-Hydroxy-6-ethyl-1, 5-di(4-methylphenyl)-
1,3,5-triazinane-2,4-dithione (11)
White solid, mp 119-121 °C; IR (KBr) νmax/cm-1 3396,
3264,3041,2962,2925,2857,1600,1583,1534,1513,1472,
1454, 1370, 1223, 1062, 810; 1H NMR (CDCl3, 400 MHz) d
7.44 (d, 2H, J 8.0 Hz, Ph-H), 7.26-7.33 (m, 4H, Ph-H), 7.10
(d, 2H, J 8.0 Hz, Ph-H), 6.07 (s, 1H, OH), 2.51 (s, 3H, CH3),
2.51 (q, 2H, J 7.4 Hz, CH2), 2.29 (s, 3H, CH3), 1.12 (t, 3H,
J 7.4 Hz, CH3); 13C NMR (CDCl3, 100 MHz) d 186.5, 177.5,
146.2, 141.0, 135.2, 133.3, 131.3 (2C), 131.0, 129.6 (2C),
127.8 (2C), 119.1 (2C), 32.3, 21.4, 20.7, 9.5; Anal. calcd.
for C19H21N3OS2: C, 61.42; H, 5.70; N, 11.31; Found C,
61.38; H, 5.70; N, 11.29.
6-Hydroxy-6-ethyl-1, 5-di(2-methylphenyl)-
1,3,5-triazinane-2,4-dithione (8)
White solid, mp 160-162 °C; IR (KBr) νmax/cm-1 3413,
3061, 2972, 2925, 2860, 1618, 1587, 1549, 1489, 1456, 1371,
1226,748;1HNMR(CDC13,400MHz)d8.10(d,1H,J8.0Hz,
Ph-H),6.97-7.58(m,7H,Ph-H),5.90(s,1H,OH),2.53(q,2H,
J 7.4 Hz, CH2), 2.17 (s, 3H, CH3), 1.88 (s, 3H, CH3), 1.13 (t,
3H, J 7.4 Hz, CH3); 13C NMR (CDCl3, 100 MHz) d 186.7,
176.6, 145.8, 137.0, 135.9, 132.7, 132.3, 131.2, 130.5, 128.2,
128.1, 127.2, 126.7, 124.1, 119.9, 32.3, 17.5, 16.9, 9.5;Anal.
calcd. for C19H21N3OS2: C, 61.42; H, 5.70; N, 11.31; Found
C, 61.47; H, 5.69; N, 11.28.
6-Hydroxy-6-propyl-1,5-di(4-methylphenyl)-
1,3,5-triazinane-2,4-dithione (12)
White solid, mp 127-129 °C; IR (KBr) νmax/cm-1 3412,
3321, 3035, 2961, 2925, 2870, 1604, 1539, 1512, 1459,
1409, 1377, 1279, 1208, 1067, 813; 1H NMR (CDCl3, 400
MHz) d 7.44 (d, 2H, J 8.0 Hz, Ph-H), 7.26-7.33 (m, 4H,
Ph-H), 7.10 (d, 2H, J 8.0 Hz, Ph-H), 6.09 (s, 1H, OH),
2.49 (s, 3H, CH3), 2.46 (t, 2H, J 7.4 Hz, CH2), 2.29 (s, 3H,
CH3), 1.61-1.67 (m, 2H, CH2), 0.89 (t, 3H, J 7.4 Hz, CH3);
13C NMR (CDCl3, 100 MHz) d 185.7, 177.4, 146.2, 141.0,
135.2, 133.3, 131.3 (2C), 131.0, 129.5 (2C), 127.7 (2C),
119.1 (2C), 41.0, 21.4, 20.7, 18.8, 13.8; Anal. calcd. for
C20H23N3OS2: C, 62.30; H, 6.01; N, 10.90; Found C, 62.37;
H, 6.00; N, 10.87.
6-Hydroxy-6-propyl-1,5-di(2-methylphenyl)-
1,3,5-triazinane-2,4-dithione (9)
White solid, mp 154-155 °C; IR (KBr) νmax/cm-1 3409,
3009, 2963, 2928, 2841, 1609, 1547, 1511, 1468, 1366, 1300,
1254,668;1HNMR(CDC13,400MHz)d8.10(d,1H,J8.4Hz,
Ph-H),7.00-7.56(m,7H,Ph-H),5.89(s,1H,OH),2.47(t, 2H,
J 7.6 Hz, CH2), 2.20 (s, 3H, CH3), 1.88 (s, 3H, CH3), 1.62-
1.68 (m, 2H, CH2), 0.90 (t, 3H, J 7.2 Hz, CH3); 13C NMR
(CDCl3, 100 MHz) d 186.0, 176.6, 145.8, 137.0, 135.9,
132.7, 132.3, 131.2, 130.5, 128.2, 128.1, 127.2, 126.7,
124.1, 119.9, 41.0, 18.9, 17.5, 16.9, 13.8; Anal. calcd. for
C20H23N3OS2: C, 62.30; H, 6.01; N, 10.90; Found C, 62.15;
H, 5.99; N, 10.87.
6-Hydroxy-6-butyl-1, 5-di(4-methylphenyl)-
1,3,5-triazinane-2,4-dithione (13)
White solid, mp 126-127 °C; IR (KBr) νmax/cm-1 3425,
3032, 2958, 2924, 2857, 1599, 1581, 1533, 1508, 1458,
1350, 1282, 1244, 1209, 810; 1H NMR (CDCl3, 400 MHz)
d 7.43 (d, 2H, J 8.0 Hz, Ph-H), 7.25-7.33 (m, 4H, Ph-H),
7.09 (d, 2H, J 8.0 Hz, Ph-H), 6.08 (s, 1H, OH), 2.48 (t,

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Li et al.
S3
2H, J 7.6 Hz, CH2), 2.48 (s, 3H, CH3), 2.29 (s, 3H, CH3),
1.56-1.64 (m, 2H, CH2), 1.25-1.32 (m, 2H, CH2), 0.86 (t,
3H, J 7.4 Hz, CH3); 13C NMR (CDCl3, 100 MHz) d 185.9,
177.4, 146.2, 141.0, 135.2, 133.3, 131.3 (2C), 131.0, 129.5
(2C), 127.7 (2C), 119.1 (2C), 38.8, 27.4, 22.4, 21.4, 20.8,
13.8; Anal. calcd. for C21H25N3OS2: C, 63.12; H, 6.31; N,
10.52; Found C, 63.18; H, 6.29; N, 10.48.
OCH3), 2.22 (s, 3H, CH3); 13C NMR (CDCl3, 100 MHz) d
183.1, 178.0, 161.0, 156.2, 147.0, 130.8, 129.3 (2C), 126.0,
121.4 (2C) (2C), 116.0 (2C), 114.3 (2C), 55.6, 55.5, 26.1;
Anal. calcd. for C18H19N3O3S2: C, 55.51; H, 4.92; N, 10.79;
Found C, 55.60; H, 4.90; N, 10.74.
6-Hydroxy-6-ethyl-1,5-di(4-methoxyphenyl)-
1,3,5-triazinane-2,4-dithione (17)
6-Hydroxy-6-pentyl-1,5-di(4-methylphenyl)-
1,3,5-triazinane-2,4-dithione (14)
White solid, mp 243-245 °C; IR (KBr) νmax/cm-1 3410,
3007, 2963, 2932, 2837, 1606, 1548, 1511, 1469, 1366,
1301, 1252, 824; 1H NMR (CDCl3, 400 MHz) d 7.33-7.36
(m, 4H, Ph-H), 7.13 (d, 2H, J 8.8 Hz, Ph-H), 6.85 (d, 2H,
J 8.8 Hz, Ph-H), 5.98 (s, 1H, OH), 3.92 (s, 3H, OCH3), 3.78
(s, 3H, OCH3), 2.51 (q, 2H, J 7.4 Hz, CH2), 1.13 (t, 3H, J
7.4 Hz, CH3); 13C NMR (CDCl3, 100 MHz) d 186.6, 177.8,
160.9, 156.2, 147.0, 130.8, 129.3 (2C), 126.0, 121.4 (2C),
115.9 (2C), 114.3 (2C), 55.6, 55.5, 32.3, 9.5; Anal. calcd.
for C19H21N3O3S2: C, 56.55; H, 5.25; N, 10.41; Found C,
56.46; H, 5.26; N, 10.37.
Yellowish solid, mp 111-113 °C; IR (KBr) νmax/cm-1
3407, 2953, 2929, 2862, 1622, 1588, 1543, 1486, 1456,
1381, 1348, 1287, 1258, 1198, 753; 1H NMR (CDC13, 400
MHz) d 7.45 (d, 2H, J 8.4 Hz, Ph-H), 7.26-7.33 (m, 4H,
Ph-H), 7.10 (d, 2H, J 8.4 Hz, Ph-H), 6.07 (s, 1H, OH), 2.50
(s, 3H, CH3), 2.48 (t, 2H, J 7.6 Hz, CH2), 2.30 (s, 3H, CH3),
1.52-1.63 (m, 2H, CH2), 1.25-1.31 (m, 4H, CH2), 0.85 (t,
3H, J 7.0 Hz, CH3); 13C NMR (CDCl3, 100 MHz) d 186.0,
177.4, 146.2, 141.0, 135.2, 133.3, 131.3 (2C), 131.1, 129.6
(2C), 127.8 (2C), 119.1 (2C), 39.0, 31.5, 25.1, 22.4, 21.4,
20.7, 13.9;Anal. calcd. for C22H27N3OS2: C, 63.89; H, 6.58;
N, 10.16; Found C, 63.97; H, 6.59; N, 10.12.
6-Hydroxy-6-propyl-1,5-di(4-methoxyphenyl)-
1,3,5-triazinane-2,4-dithione (18)
White solid, mp 219-221 °C; IR (KBr) νmax/cm-1 3369,
3008, 2961, 2835, 1599, 1543, 1510, 1471, 1379, 1246, 1170,
820; 1H NMR (CDCl3, 400 MHz) d 7.32-7.36 (m, 4H, Ph-H),
7.13(d,2H,J8.8Hz,Ph-H),6.85(d,2H,J8.8Hz,Ph-H),6.01
(s, 1H, OH), 3.91 (s, 3H, OCH3), 3.78 (s, 3H, OCH3), 2.46
(t, 2H, J 7.2 Hz, CH2), 1.62-1.67 (m, 2H, CH2), 0.89 (t, 3H,
J 7.4 Hz, CH3); 13C NMR (CDCl3, 100 MHz) d 185.8, 177.7,
160.9, 156.2, 147.0, 130.8, 129.3 (2C), 126.0, 121.4 (2C),
115.8 (2C), 114.3 (2C), 55.6, 55.5, 41.0, 18.8, 13.8; Anal.
calcd. for C20H23N3O3S2: C, 57.53; H, 5.55; N, 10.06; Found
C, 57.58; H, 5.57; N, 10.01.
6-Hydroxy-6-hexyl-1, 5-di(4-methylphenyl)-
1,3,5-triazinane-2,4-dithione (15)
White solid, mp 103-104 °C; IR (KBr) νmax/cm-1 3387,
3063, 2929, 2862, 1600, 1539, 1513, 1476, 1382, 1348,
1298, 1241, 1199, 815; 1H NMR (CDCl3, 400 MHz) d 7.43
(d, 2H, J 8.4 Hz, Ph-H), 7.26-7.33 (m, 4H, Ph-H), 7.10 (d,
2H, J 8.4 Hz, Ph-H), 6.07 (s, 1H, OH), 2.49 (s, 3H, CH3),
2.47 (t, 2H, J 7.6 Hz, CH2), 2.29 (s, 3H, CH3), 1.59-1.63 (m,
2H, CH2), 1.21-1.28 (m, 6H, CH2), 0.85 (t, 3H, J 7.4 Hz,
CH3); 13C NMR (CDCl3, 100 MHz) d 186.0, 177.4, 146.2,
141.0, 135.2, 133.3, 131.3 (2C), 131.0, 129.6 (2C), 127.8
(2C), 119.1 (2C), 39.1, 31.6, 29.0, 25.3, 22.5, 21.4, 20.7,
14.1; Anal. calcd. for C23H29N3OS2: C, 64.60; H, 6.84; N,
9.83; Found C, 64.43; H, 6.83; N, 9.79.
6-Hydroxy-6-methyl-1,5-di(4-chlorophenyl)-
1,3,5-triazinane-2,4-dithione (19)
White solid, mp 208-210 °C; IR (KBr) νmax/cm-1 3449,
3286, 2960, 2925, 2856, 1605, 1539, 1491, 1450, 1373,
1300, 1250, 1090, 825; 1H NMR (CDC13, 400 MHz) d 7.66
(d, 2H, J 8.4 Hz, Ph-H), 7.39-7.45 (m, 4H, Ph-H), 7.27 (d,
2H, J 8.4 Hz, Ph-H), 6.09 (s, 1H, OH), 2.23 (s, 3H, CH3);
13C NMR (CDCl3, 100 MHz) d 183.3, 177.3, 145.1, 137.2,
136.2, 131.9, 131.2 (2C), 129.6 (2C), 129.2 (2C), 128.8,
120.1 (2C), 26.1;Anal. calcd. for C16H13Cl2N3OS2: C, 48.24;
H, 3.29; N, 10.55; Found C, 48.10; H, 3.30; N, 10.58.
6-Hydroxy-6-methyl-1,5-di(4-methoxyphenyl)-
1,3,5-triazinane-2,4-dithione (16)
White solid, mp 218-219 °C; IR (KBr) νmax/cm-1 3414,
2959, 2930, 2863, 1619, 1588, 1531, 1456, 1251, 1193,
1
754; H NMR (CDCl3, 400 MHz) d 7.33-7.38 (m, 4H,
Ph-H), 7.13 (d, 2H, J 8.8 Hz, Ph-H), 6.85 (d, 2H, J 8.8 Hz,
Ph-H), 6.01 (s, 1H, OH), 3.91 (s, 3H, OCH3), 3.78 (s, 3H,

S4
A Concise Synthetic Method for 1,3,5-Triazinane-2,4-Dithiones
J. Braz. Chem. Soc.
Figure S1. IR (KBr) spectrum of 6-hydroxy-6-methyl-1,5-diphenyl-1,3,5-triazinane-2,4-dithione (1).
Figure S2. 1H NMR (CDCl3) spectrum of 6-hydroxy-6-methyl-1,5-diphenyl-1,3,5-triazinane-2,4-dithione (1).

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Figure S3. 13C NMR (DMSO-d6) spectrum of 6-hydroxy-6-methyl-1,5-diphenyl-1,3,5-triazinane-2,4-dithione (1).
Figure S4. IR (KBr) spectrum of 6-hydroxy-6-ethyl-1,5-diphenyl-1,3,5-triazinane-2,4-dithione (2).

S6
A Concise Synthetic Method for 1,3,5-Triazinane-2,4-Dithiones
J. Braz. Chem. Soc.
Figure S5. 1H NMR (CDCl3) spectrum of 6-hydroxy-6-ethyl-1,5-diphenyl-1,3,5-triazinane-2,4-dithione (2).
Figure S6. 13C NMR (CDCl3) spectrum of 6-hydroxy-6-ethyl-1,5-diphenyl-1,3,5-triazinane-2,4-dithione (2).

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S7
Figure S7. IR (KBr) spectrum of 6-hydroxy-6-propyl-1,5-diphenyl-1,3,5-triazinane-2,4-dithione (3).
Figure S8. 1H NMR (CDCl3) spectrum of 6-hydroxy-6-propyl-1,5-diphenyl-1,3,5-triazinane-2,4-dithione (3).

S8
A Concise Synthetic Method for 1,3,5-Triazinane-2,4-Dithiones
J. Braz. Chem. Soc.
Figure S9. 13C NMR (CDCl3) spectrum of 6-hydroxy-6-propyl-1,5-diphenyl-1,3,5-triazinane-2,4-dithione (3).
Figure S10. IR (KBr) spectrum of 6-hydroxy-6-butyl-1,5-diphenyl-1,3,5-triazinane-2,4-dithione (4).

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Figure S11. 1H NMR (CDCl3) spectrum of 6-hydroxy-6-butyl-1,5-diphenyl-1,3,5-triazinane-2,4-dithione (4).
Figure S12. 13C NMR (CDCl3) spectrum of 6-hydroxy-6-butyl-1,5-diphenyl-1,3,5-triazinane-2,4-dithione (4).

S10
A Concise Synthetic Method for 1,3,5-Triazinane-2,4-Dithiones
J. Braz. Chem. Soc.
Figure S13. IR (KBr) spectrum of 6-hydroxy-6-pentyl-1,5-diphenyl-1,3,5-triazinane-2,4-dithione (5).
Figure S14. 1H NMR (CDCl3) spectrum of 6-hydroxy-6-pentyl-1,5-diphenyl-1,3,5-triazinane-2,4-dithione (5).

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Figure S15. 13C NMR (CDCl3) spectrum of 6-hydroxy-6-pentyl-1,5-diphenyl-1,3,5-triazinane-2,4-dithione (5).
Figure S16. IR (KBr) spectrum of 6-hydroxy-6-hexyl-1,5-diphenyl-1,3,5-triazinane-2,4-dithione (6).

S12
A Concise Synthetic Method for 1,3,5-Triazinane-2,4-Dithiones
J. Braz. Chem. Soc.
Figure S17. 1H NMR (CDCl3) spectrum of 6-hydroxy-6-hexyl-1,5-diphenyl-1,3,5-triazinane-2,4-dithione (6).
Figure S18. 13C NMR (CDCl3) spectrum of 6-hydroxy-6-hexyl-1,5-diphenyl-1,3,5-triazinane-2,4-dithione (6).

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Figure S19. IR (KBr) spectrum of 6-hydroxy-6-methyl-1,5-di(2-methylphenyl)-1,3,5-triazinane-2,4-dithione (7).
Figure S20. 1H NMR (CDCl3) spectrum of 6-hydroxy-6-methyl-1,5-di(2-methylphenyl)-1,3,5-triazinane-2,4-dithione (7).

S14
A Concise Synthetic Method for 1,3,5-Triazinane-2,4-Dithiones
J. Braz. Chem. Soc.
Figure S21. 13C NMR (CDCl3) spectrum of 6-hydroxy-6-methyl-1,5-di(2-methylphenyl)-1,3,5-triazinane-2,4-dithione (7).
Figure S22. IR (KBr) spectrum of 6-hydroxy-6-ethyl-1,5-di(2-methylphenyl)-1,3,5-triazinane-2,4-dithione (8).

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Figure S23. 1H NMR (CDCl3) spectrum of 6-hydroxy-6-ethyl-1,5-di(2-methylphenyl)-1,3,5-triazinane-2,4-dithione (8).
Figure S24. 13C NMR (CDCl3) spectrum of 6-hydroxy-6-ethyl-1,5-di(2-methylphenyl)-1,3,5-triazinane-2,4-dithione (8).

S16
A Concise Synthetic Method for 1,3,5-Triazinane-2,4-Dithiones
J. Braz. Chem. Soc.
Figure S25. IR (KBr) spectrum of 6-hydroxy-6-propyl-1,5-di(2-methylphenyl)-1,3,5-triazinane-2,4-dithione (9).
Figure S26. 1H NMR (CDCl3) spectrum of 6-hydroxy-6-propyl-1,5-di(2-methylphenyl)-1,3,5-triazinane-2,4-dithione (9).

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S17
Figure S27. 13C NMR (CDCl3) spectrum of 6-hydroxy-6-propyl-1,5-di(2-methylphenyl)-1,3,5-triazinane-2,4-dithione (9).
Figure S28. IR (KBr) spectrum of 6-hydroxy-6-butyl-1,5-di(2-methylphenyl)-1,3,5-triazinane-2,4-dithione (10).

S18
A Concise Synthetic Method for 1,3,5-Triazinane-2,4-Dithiones
J. Braz. Chem. Soc.
Figure S29. 1H NMR (CDCl3) spectrum of 6-hydroxy-6-butyl-1,5-di(2-methylphenyl)-1,3,5-triazinane-2,4-dithione (10).
Figure S30. 13C NMR (CDCl3) spectrum of 6-hydroxy-6-butyl-1,5-di(2-methylphenyl)-1,3,5-triazinane-2,4-dithione (10).

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Figure S31. IR (KBr) spectrum of 6-hydroxy-6-ethyl-1,5-di(4-methylphenyl)-1,3,5-triazinane-2,4-dithione (11).
Figure S32. 1H NMR (CDCl3) spectrum of 6-hydroxy-6-ethyl-1,5-di(4-methylphenyl)-1,3,5-triazinane-2,4-dithione (11).

S20
A Concise Synthetic Method for 1,3,5-Triazinane-2,4-Dithiones
J. Braz. Chem. Soc.
Figure S33. 13C NMR (CDCl3) spectrum of 6-hydroxy-6-ethyl-1,5-di(4-methylphenyl)-1,3,5-triazinane-2,4-dithione (11).
Figure S34. IR (KBr) spectrum of 6-hydroxy-6-propyl-1,5-di(4-methylphenyl)-1,3,5-triazinane-2,4-dithione (12).

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Figure S35. 1H NMR (CDCl3) spectrum of 6-hydroxy-6-propyl-1,5-di(4-methylphenyl)-1,3,5-triazinane-2,4-dithione (12).
Figure S36. 13C NMR (CDCl3) spectrum of 6-hydroxy-6-propyl-1,5-di(4-methylphenyl)-1,3,5-triazinane-2,4-dithione (12).

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Figure S37. IR (KBr) spectrum of 6-hydroxy-6-butyl-1,5-di(4-methylphenyl)-1,3,5-triazinane-2,4-dithione (13).
Figure S38. 1H NMR (CDCl3) spectrum of 6- ydroxyl-6-butyl-1,5-di(4-methylphenyl)-1,3,5-triazinane-2,4-dithione (13).

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Figure S39. 13C NMR (CDCl3) spectrum of 6-hydroxy-6-butyl-1,5-di(4-methylphenyl)-1,3,5-triazinane-2,4-dithione (13).
Figure S40. IR (KBr) spectrum of 6-hydroxy-6-pentyl-1,5-di(4-methylphenyl)-1,3,5-triazinane-2,4-dithione (14).

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A Concise Synthetic Method for 1,3,5-Triazinane-2,4-Dithiones
J. Braz. Chem. Soc.
Figure S41. 1H NMR (CDCl3) spectrum of 6-hydroxy-6-pentyl-1,5-di(4-methylphenyl)-1,3,5-triazinane-2,4-dithione (14).
Figure S42. 13C NMR (CDCl3) spectrum of 6-hydroxy-6-pentyl-1,5-di(4-methylphenyl)-1,3,5-triazinane-2,4-dithione (14).

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Figure S43. IR (KBr) spectrum of 6-hydroxy-6-hexyl-1,5-di(4-methylphenyl)-1,3,5-triazinane-2,4-dithione (15).
Figure S44. 1H NMR (CDCl3) spectrum of 6-hydroxy-6-hexyl-1,5-di(4-methylphenyl)-1,3,5-triazinane-2,4-dithione (15).