Efficient synthesis of 6-hydroxy-6-aryloxymethyl-1,5-diaryl-1,3,5- triazinane-2,4-dithiones

Article abstract of DOI:10.3184/174751912X13333538103037

An efficient and convenient method for the synthesis of 6-hydroxy-6-aryloxymethyl-1,5-diaryl-1,3,5-triazinane-2,4-dithiones via condensation of 2 equiv. of 1-arylthioureas with aryloxyacetic acids using ferric chloride hexahydrate as catalyst is described

Full text of DOI:10.3184/174751912X13333538103037

290 RESEARCH PAPER
MAY, 290–292
JOURNAL OF CHEMICAL RESEARCH 2012
Efficient synthesis of 6-hydroxy-6-aryloxymethyl-1,5-diaryl-
1,3,5-triazinane-2,4-dithiones
Zheng Li* and Hongfang Cai
College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou, Gansu, 730070, P. R. China
An efficient and convenient method for the synthesis of 6-hydroxy-6-aryloxymethyl-1,5-diaryl-1,3,5-triazinane-2,4-
dithiones via condensation of 2 equiv. of 1-arylthioureas with aryloxyacetic acids using ferric chloride hexahydrate
as catalyst is described. Triazine derivatives have important medicinal properties, are widely used in the textile, plas-
tic and rubber industries, and have applications as pesticides, dyestuffs, optical bleaches, explosives and surface
active agents.
Keywords: 1,3,5-triazinane-2,4-dithione, thiourea, aryloxyacetic acid, synthesis
Triazine derivatives have attracted much attention due to their
antimalarial,1 antiplasmodial,2 antimicrobial,3 anti-angiogene-
sis4 and antitumour5 activities. They also have widespread
applications in the textile, plastic and rubber industries, and
are used as pesticides, dyestuffs, optical bleaches, explosives
and surface active agents.6 Meanwhile, heterocycles contain-
ing a thiourea structural unit show powerful antiproliferative,7
antibacterial8 and anticancer activities.9 Hence, triazinane
derivatives incorporating a thiourea unit may be important in
many fields.
The general synthetic methods for 1,3,5-triazinane deriva-
tives involve the reactions of N,N′-bis(arylmethylidene)aryl-
methane diimines with thioureas,10 the multi-component reactions
of phosphonates, nitriles, aldehydes and isocyanates,11 the
condensation of trifluoromethanesulfonamide with formalde-
hyde,12 or the reactions of thiosemicarbazones with potassium
thiocyanate and benzoyl chloride.13 However, some methods
use expensive reagents, toxic organic solvents, rigorous con-
ditions, tedious workup procedure and long reaction time.
Therefore, it is necessary to develop simple and efficient
synthetic methods to 1,3,5-triazinane derivatives.
Table 1 The effect of catalysts on the yield of 6-hydroxy-6-
phenoxymethyl-1,5-diphenyl-1,3,5-triazinane-2,4-dithionea
Entry
Catalyst
Amount of catalyst/mol% Yield/%b
1
2
3
4
5
6
7
8
9
–
–
38
60
56
55
70
74
78
88
80
PTSA
10
10
10
10
10
5
TCA
AlCl3
NiCl2
FeCl3
FeCl3·6H2O
FeCl3·6H2O
FeCl3·6H2O
10
15
a Reaction conditions: 1-phenylthiourea (2 mmol), phenoxyacetic
acid (1.5 mmol) in EtOAc (5 mL) at 80 °C using different cata-
lysts.
b Isolated yields.
in EtOH, MeCN, THF, C2H4Cl2 and EtOAc could give the
corresponding products. Among them, the reaction in EtOAc
gave the product in highest yield.
To explore the generality and scope of the synthetic reac-
tions and synthesis of a series of novel 6-hydroxyl-6-aryloxy-
1,5-diaryl-1,3,5-triazinane-2,4-dithiones (Scheme 1), various
1-arylthioureas and different aryloxyacetic acids as substrates
were examined under optimal conditions (Table 3). It was
found that various 1-arylthioureas could efficiently react
with aryloxyacetic acids at 80 °C to give the corresponding
In continuation of an ongoing programme to synthesise
biologically active compounds and develop synthetic strategy
for important heterocyclic compounds,14–18 we now report the
simple and efficient synthesis of novel heterocyclic compounds
including 1,3,5-triazinane-2,4-dithiones by reactions of 1-aryl-
thioureas with aryloxyacetic acids in ethyl acetate using ferric
chloride hexahydrate as a catalyst.
Results and discussion
Table 2 The effect of solvents on the yield of 6-hydroxy-6-
phenoxymethyl-1,5-diphenyl-1,3,5-triazinane-2,4-dithionea
Initially, the synthesis of 6-hydroxy-6-aryloxymethyl-1,5-diaryl-
1,3,5-triazinane-2,4-dithiones was attempted by reaction of
1-phenylthiourea and phenoxyacetic acid at room temperature
under catalyst-free condition. However, none of the desired
product was detected. Subsequently, when a mixture of 1-
phenylthiourea and phenoxyacetic acid was heated at 80 °C
for several hours, a new compound was isolated in low yield,
which was identified as a novel heterocyclic compound,
6-hydroxy-6-phenoxymethyl-1,5-diphenyl-1,3,5-triazinane-
2,4-dithione. In the latter research, it was found that some
Bronsted acids such as p-toluenesulfonic acid (PTSA) and
trichloroacetic acid (TCA), and Lewis acids, such as AlCl3,
NiCl2, FeCl3 and FeCl3 ·6H2O, could catalyse the reaction.
Among them, FeCl3 ·6H2O could efficiently give product in
highest yield (Table 1, entry 8).
Entry
Solvent
Time/h
Yield/%b
1
2
3
4
5
6
7
CH2Cl2
MeOH
EtOH
MeCN
THF
CH2ClCH2Cl
EtOAc
20
20
10
10
10
10
10
0
0
46
50
40
62
88
a Reaction conditions: 1-phenylthiourea (2 mmol), phenox-
yacetic acid (1.5 mmol) and FeCl3·6H2O (0.2 mmol) in 5 mL of
solvents.
b Isolated yields.
Solvents also played a crucial role in the synthesis of
6-hydroxy-6-phenoxymethyl-1,5-diphenyl-1,3,5-triazinane-
2,4-dithione (Table 2). The reactions in CH2Cl2 and MeOH
could not give the desired products. However, the reactions
Scheme 1 Synthesis of 6-hydroxyl-6-aryloxy-1,5-diaryl-1,3,5-
* Correspondent. E-mail: lizheng@nwnu.edu.cn
triazinane-2,4-dithiones

JOURNAL OF CHEMICAL RESEARCH 2012 291
Conclusion
An efficient and concise method for the synthesis of 6-hydroxy-
6-aryloxymethyl-1,5-diaryl-1,3,5-triazinane-2,4-dithiones via
reactions of 2 equiv. of 1-arylthioureas with aryloxyacetic
acids in EtOAc using ferric chloride hexahydrate as a catalyst
has been developed. This protocol has the advantages of using
easily obtainable materials, simple work-up procedure, mild
condition and high yield.
Table 3 Synthesis of 6-hydroxy-6-aryloxymethyl-1,5-diaryl-
1,3,5-triazinane-2,4-dithionesa
Compd.
R1
R2
Time/h M.p./°C Yield /%b
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
C6H5
C6H5
C6H5
C6H5
4-CH3C6H4
2-ClC6H4
4-ClC6H4
C6H5
7
8
9
6
7
10
8
9
9
8
7
9
8
9
165–166
188–190
154–156
249–251
131–133
176–178
231–233
82–84
195–196
157–159
150–152
181–182
246–248
210–211
223–224
88
72
76
80
81
78
80
73
81
84
76
78
80
72
75
C6H5
4-CH3C6H4
4-CH3C6H4 3-CH3C6H4
4-CH3C6H4 4-CH3C6H4
4-CH3C6H4 2-ClC6H4
4-CH3C6H4 3-ClC6H4
4-CH3C6H4 4-ClC6H4
4-ClC6H4
4-ClC6H4 3-CH3C6H4
4-ClC6H4 4-CH3C6H4
Experimental
IR spectra were recorded using KBr pellets on an Alpha Centauri
1
FTIR spectrophotometer and H NMR and 13C NMR spectra on a
Mercury-400BB instrument using CDCl3 or DMSO-d6 as solvents and
Me4Si as internal standard. Elemental analyses were performed on a
Vario El ElementalAnalysis instrument. Melting points were observed
in an electrothermal melting point apparatus. All reactions were mon-
itored by TLC. Flash column chromatography was carried out using
200–300 mesh silica gel at increased pressure. 1-Arylthioureas19–20
and aryloxyacetic acids21 were synthesised according to the literature
methods.
C6H5
4-ClC6H4
4-ClC6H4
2-ClC6H4
4-ClC6H4
7
a Reaction conditions: 1-arylthiourea (2 mmol), aryloxyacetic
acid (1.5 mmol), and ferric chloride hexahydrate (0.2 mmol) in
EtOAc (5 mL) at 80 °C.
b Isolated yields.
Synthesis of 6-hydroxy-6-aryloxymethyl-1,5-diaryl-1,3,5-triazinane-
2,4-dithiones; general procedure
A mixture of 1-arylthiourea (2 mmol), aryloxyacetic acid (1.5 mmol)
and ferric chloride hexahydrate (0.2 mmol) in EtOAc (5 mL) was
stirred at 80 °C for the time indicated in Table 3. The progress of the
reaction was monitored by TLC. After the completion of the reaction,
the mixture was cooled to room temperature, washed with 15% of
sodium carbonate solution. Then the organic layer was concentrated,
and the residue was subjected to silica gel flash column chromato-
graphy (ethyl acetate-petroleum ether, 1:8) to obtain the pure product.
The analytical and spectral data of the products are given below.
6-Hydroxy-6-phenoxymethyl-1,5-diphenyl-1,3,5-triazinane-2,4-
dithione (1): White solid, m.p. 165–166 °C; IR (KBr, ν, cm–1): 3419
(OH), 3257 (NH), 1238 (C=S). 1H NMR (CDC13, 400 MHz): δ 7.67–
6.85 (m, 15H, Ph-H), 6.16 (s, 1H, OH), 4.78 (s, 2H, OCH2). 13C NMR
(CDCl3, 100 MHz): δ 180.3, 178.2, 158.3, 146.0, 137.5, 133.4, 130.9,
130.8, 129.3, 129.2, 128.1, 123.9, 121.0, 118.9, 114.7, 69.1. Anal.
Calcd for C22H19N3O2S2: C, 62.68; H, 4.54; N, 9.97. Found: C, 62.56;
H, 4.55; N, 9.94%.
6-Hydroxy-1,5-diphenyl-6-(4-tolyloxymethyl)-1,3,5-triazinane-2,4-
dithione (2): White solid, m.p. 188–190 °C; IR (KBr, ν, cm–1): 3422
(OH), 3257 (NH), 1238 (C=S). 1H NMR (CDCl3, 400 MHz): δ 7.63–
6.68 (m, 14H, Ph-H), 6.08 (s, 1H, OH), 4.67 (s, 2H, OCH2), 2.19 (s,
3H, CH3). 13C NMR (CDCl3, 100 MHz): δ 180.4, 178.1, 156.2, 145.9,
137.5, 133.4, 130.9, 130.8, 130.2 129.8, 129.2, 128.1, 123.9, 118.9,
114.5, 69.3, 20.5. Anal. Calcd for C23H21N3O2S2: C, 63.42; H, 4.86; N,
9.65. Found: C, 63.49; H, 4.85; N, 9.63%.
products in good to high yields. 1-Arylthioureas and aryloxy-
acetic acids bearing either electron-donating or electron-with-
drawing groups have no obvious influence on the efficiency of
the reactions. However, it was found that, for ortho-substituted
aryloxyacetic acids, the corresponding products were obtained
in slightly lower yield than para-substituted ones (Table 3,
entries 3, 8 and 14), presumably due to the steric effect. In
addition, the similar reactions of 1-arylthioureas with aromatic
carboxylic acids, such as (un)substituted benzoic acids, were
also attempted for the reactions, but no desired products were
observed.
A possible mechanism for the synthesis of 6-hydroxy-6-
aryloxymethyl-1,5-diaryl-1,3,5-triazinane-2,4-dithiones is shown
in Scheme 2. Presumably, condensation of 2 equiv. of 1-
arylthioureas releasing ammonia generates intermediates A,
One of amino groups of A subsequent reacts with a mole of
complexes B, which are formed from aryloxyacetic acid
and ferric chloride in the solution, to give intermediates C by
loss of water. Subsequently the carbonyl group of C undergoes
the nuleophilic addition of another amino group to form a
six-membered heterocyclic compounds, 6-hydroxy-6-aryloxy-
methyl-1,5-diaryl-1,3,5-triazinane-2,4-dithiones.
6-(2-Chlorophenoxymethyl)-6-hydroxy-1,5-diphenyl-1,3,5-triazinane-
2,4-dithione (3): White solid, m.p. 154–156 °C; IR (KBr, ν, cm–1): 3414
Scheme 2 The possible mechanism for the synthesis of 6-hydroxy-6-aryloxymethyl-1,5-diaryl-1,3,5-triazinane-2,4-dithiones.

292 JOURNAL OF CHEMICAL RESEARCH 2012
(OH), 3058 (NH), 1255 (C=S). 1H NMR (CDCl3, 400 MHz): δ 7.60–6.66
(m, 14H, Ph-H), 6.07 (s, 1H, OH), 4.68 (s, 2H, OCH2).13C NMR
(CDCl3, 100 MHz): δ 181.2, 177.9, 156.9, 146.6, 141.3, 134.9, 133.7,
131.4, 131.1, 130.6, 130.3, 129.7, 129.3, 127.7, 125.8, 119.2, 116.0,
69.2. Anal. Calcd for C22H18ClN3O2S2: C, 57.95; H, 3.98; N, 9.22.
Found: C, 57.88; H, 3.97; N, 9.25%.
6-(4-Chlorophenoxymethyl)-6-hydroxy-1,5-diphenyl-1,3,5-triazinane-
2,4-dithione (4): White solid, m.p. 249–251 °C; IR (KBr, ν, cm–1):
3396 (OH), 3320 (NH), 1238 (C=S). 1H NMR (CDCl3, 400 MHz): δ
7.67–6.75 (m, 14H, Ph-H), 6.15 (s, 1H, OH), 4.74 (s, 2H, OCH2).13C
NMR (CDCl3, 100 MHz): δ 179.8, 178.3, 156.9, 146.1, 137.5, 133.3,
130.9, 130.8, 129.2, 129.1, 128.0, 125.8, 124.0, 118.9, 116.0, 69.2.
Anal. Calcd for C22H18ClN3O2S2: C, 57.95; H, 3.98; N, 9.22. Found: C,
58.03; H, 3.99; N, 9.20%.
6-Hydroxy-6-phenoxymethyl-1,5-di(4-tolyl)-1,3,5-triazinane-2,4-
dithione (5): White solid, m.p. 131–133 °C; IR (KBr, ν, cm–1): 3422
(OH), 3313 (NH), 1225 (C=S). 1H NMR (CDC13, 400 MHz): δ 7.44–
6.85 (m, 13H, Ph-H), 6.12 (s, 1H, OH), 4.76 (s, 2H, OCH2), 2.50 (s,
3H, CH3), 2.30 (s, 3H, CH3). 13C NMR (DMSO-d6, 100 MHz): δ
180.1, 178.3, 158.2, 146.5, 141.2, 134.9, 133.6, 131.4, 130.6, 129.6,
129.3, 127.7, 120.9, 119.2, 114.6, 69.1, 21.4, 20.8. Anal. Calcd for
C24H23N3O2S2: C, 64.12; H, 5.16; N, 9.35. Found: C, 64.20; H, 5.17;
N, 9.32%.
6-Hydroxy-1,5-di(4-tolyl)-6-(3-tolyloxymethyl)-1,3,5-triazinane-
2,4-dithione (6): White solid, m.p. 176–178 °C; IR (KBr, ν, cm–1):
3414 (OH), 3059 (NH), 1256 (C=S). 1H NMR (CDC13, 400 MHz): δ
7.45–6.65 (m, 12H, Ph-H), 6.11 (s, 1H, OH), 4.75 (s, 2H, OCH2), 2.51
(s, 3H, CH3), 2.30 (s, 3H, CH3), 2.29 (s, 3H, CH3). 13C NMR (CDCl3,
100 MHz): δ 180.1, 178.3, 158.2, 146.5, 141.2, 139.3, 135.0, 133.6,
131.4, 130.7, 129.6, 129.0, 127.7, 121.8, 119.2, 115.5, 111.4, 69.0,
21.5, 21.4, 20.8. Anal. Calcd for C25H25N3O2S2: C, 64.77; H, 5.44; N,
9.06. Found: C, 64.80; H, 5.43; N, 9.08%.
3414 (OH), 3061 (NH), 1256 (C=S). 1H NMR (CDCl3, 400 MHz): δ
7.45-6.65 (m, 12H, Ph-H), 6.11 (s, 1H, OH), 4.75 (s, 2H, OCH2), 2.29
(s, 3H, CH3). 13C NMR (CDCl3, 100 MHz): δ 180.1, 178.3, 158.2,
146.5, 141.2, 139.3, 135.0, 133.6, 131.4, 130.7, 129.6, 129.0, 127.7,
121.8,119.2,115.5,111.4,69.0,21.4.Anal.CalcdforC23H19Cl2N3O2S2:
C, 54.76; H, 3.80; N, 8.33. Found: C, 54.68; H, 3.81; N, 8.31%.
6-Hydroxy-6-(4-tolyloxymethyl)-1,5-di(4-chlorophenyl)-1,3,5-triazinane-
2,4-dithione (13): White solid, m.p. 256–258 °C; IR (KBr, ν, cm–1):
1
3415 (OH), 3060 (NH), 1238 (C=S). H NMR (CDCl3-DMSO-d6,
400 MHz): δ 8.67 (s, 1H, OH), 7.65–6.69 (m, 12H, Ph-H), 4.70 (s, 2H,
OCH2), 2.23 (s, 3H, CH3). 13C NMR (CDCl3-DMSO-d6, 100 MHz):
δ 177.6, 175.9, 154.1, 145.6, 136.2, 133.2, 130.7, 128.7, 128.1, 127.7,
127.5, 126.4, 124.9, 119.6, 112.4, 66.9, 18.3. Anal. Calcd for
C23H19Cl2N3O2S2: C, 54.76; H, 3.80; N, 8.33. Found: C, 54.82; H,
3.79; N, 8.35%.
6-(2-Chlorophenoxymethyl)-6-hydroxy-1,5-di(4-chlorophenyl)-
1,3,5-triazinane-2,4-dithione (14): White solid, m.p. 210–211 °C; IR
(KBr, ν, cm–1): 3414 (OH), 3060 (NH), 1256 (C=S). 1H NMR (CDCl3,
400 MHz): δ 7.45–6.73 (m, 12H, Ph-H), 6.10 (s, 1H, OH), 4.75 (s, 2H,
OCH2).13C NMR (CDCl3, 100 MHz): δ 179.7, 178.5, 156.9, 146.6,
141.4, 134.9, 133.7, 130.6, 129.7, 129.7, 129.3, 129.1, 127.7, 125.8,
119.2, 115.9, 114.6, 69.2. Anal. Calcd for C22H16Cl3N3O2S2: C, 50.34;
H, 3.07; N, 8.01. Found: C, 50.27; H, 3.08; N, 8.04%.
6-(4-Chlorophenoxymethyl)-6-hydroxy-1,5-di(4-chlorophenyl)-
1,3,5-triazinane-2,4-dithione (15): White solid, m.p. 223–224 °C; IR
(KBr, ν, cm–1): 3435 (OH), 1234 (C=S). 1H NMR (CDCl3, 400 MHz):
δ 7.63–6.75 (m, 12H, Ph-H), 6.09 (s, 1H, OH), 4.75 (s, 2H, OCH2).
13C NMR (CDCl3-DMSO-d6, 100 MHz): δ 177.1, 175.9, 155.0, 145.7,
136.2, 133.2, 130.7, 128.7, 128.1, 127.1, 126.3, 124.9, 122.8, 119.6,
114.3, 67.0. Anal. Calcd for C22H16Cl3N3O2S2: C, 50.34; H, 3.07; N,
8.01. Found: C, 50.40; H, 3.06; N, 7.99%.
6-Hydroxy-1,5-di(4-tolyl)-6-(4-tolyloxymethyl)-1,3,5-triazinane-
2,4-dithione (7): White solid, m.p. 231–233 °C; IR (KBr, ν, cm–1):
3442 (OH), 3035 (NH), 1234 (C=S). 1H NMR (CDC13, 400 MHz): δ
7.45–6.75 (m, 12H, Ph-H), 6.10 (s, 1H, OH), 4.74 (s, 2H, OCH2), 2.51
(s, 3H, CH3), 2.30 (s, 3H, CH3), 2.27 (s, 3H, CH3). 13C NMR (CDCl3,
100 MHz): δ 180.3, 178.3, 156.2, 146.5, 141.3, 135.0, 133.6, 131.4,
130.7, 130.1, 129.7, 129.6, 127.7, 119.2, 114.5, 69.3, 21.4, 20.8, 20.5.
Anal. Calcd for C25H25N3O2S2: C, 64.77; H, 5.44; N, 9.06. Found: C,
64.88; H, 5.45; N, 9.05%.
The authors thank the National Natural Science Foundation of
China (21162024) for the financial support of this work.
Received 9 February 2012; accepted 24 February 2012
Paper 1201156 doi: 10.3184/174751912X13333538103037
Published online: 10 May 2012
6-(2-Chlorophenoxymethyl)-6-hydroxy-1,5-di(4-tolyl)-1,3,5-triazinane-
2,4-dithione (8): White solid, m.p. 82–84 °C; IR (KBr, ν, cm–1): 3414
(OH), 3059 (NH), 1238 (C=S). 1H NMR (CDC13, 400 MHz): δ 7.44–
6.76 (m, 12H, Ph-H), 6.09 (s, 1H, OH), 4.74 (s, 2H, OCH2), 2.51 (s,
3H, CH3), 2.30 (s, 3H, CH3). 13C NMR (CDCl3, 100 MHz): δ 183.7,
181.2, 156.9, 146.6, 141.3, 135.0, 133.6, 131.4, 131.1, 130.6, 130.3,
129.7, 129.3, 129.1, 127.7, 119.2, 116.0, 69.2, 21.5, 20.8. Anal. Calcd
for C24H22ClN3O2S2: C, 59.55; H, 4.58; N, 8.68. Found: C, 59.63; H,
4.59; N, 8.65%.
6-(3-Chlorophenoxymethyl)-6-hydroxy-1,5-di(4-tolyl)-1,3,5-triazinane-
2,4-dithione (9): White solid, m.p. 195–196 °C; IR (KBr, ν, cm–1):
3414 (OH), 3059 (NH), 1256 (C=S). 1H NMR (CDCl3, 400 MHz): δ
7.45–6.65 (m, 12H, Ph-H), 6.11 (s, 1H, OH), 4.75 (s, 2H, OCH2), 2.30
(s, 3H, CH3), 2.29 (s, 3H, CH3). 13C NMR (CDCl3, 100 MHz): δ 180.1,
178.3, 158.2, 146.5, 141.2, 139.3, 135.0, 133.6, 131.4, 130.7, 129.6,
129.0, 127.7, 121.8, 119.2, 115.5, 111.4, 69.0, 21.5, 21.4. Anal. Calcd
for C24H22ClN3O2S2: C, 59.55; H, 4.58; N, 8.68. Found: C, 59.50; H,
4.58; N, 8.70%.
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6-(4-Chlorophenoxymethyl)-6-hydroxy-1,5-di(4-tolyl)-1,3,5-triazinane-
2,4-dithione (10): White solid, m.p. 157–159 °C; IR (KBr, ν, cm–1):
1
3444 (OH), 1236 (C=S). H NMR (CDC13, 400 MHz): δ 7.44–6.78
(m, 12H, Ph-H), 6.10 (s, 1H, OH), 4.76 (s, 2H, OCH2), 2.51 (s, 3H,
CH3), 2.30 (s, 3H, CH3). 13C NMR (CDCl3, 100 MHz): δ 179.7, 178.5,
157.0, 146.6, 141.3, 135.0, 133.7, 131.4, 130.6, 129.7, 129.1, 127.7,
125.8, 119.2, 116.0, 69.3, 21.4, 20.8. Anal. Calcd for C24H22ClN3O2S2:
C, 59.55; H, 4.58; N, 8.68. Found: C, 59.48; H, 4.57; N, 8.71%.
6-Hydroxyl-6-phenoxymethyl-1,5-di(4-chlorophenyl)-1,3,5-triazinane-
2,4-dithione (11): White solid, m.p. 150–152 °C; IR (KBr, ν, cm–1):
3427 (OH), 3063 (NH), 1238 (C=S). 1H NMR (DMSO-d6, 400 MHz):
δ 8.59 (s, 1H, OH), 7.61–6.80 (m, 13H, Ph-H), 4.74 (s, 2H, OCH2).13C
NMR (CDCl3-DMSO-d6, 100 MHz): δ 178.3, 176.8, 156.8, 146.2,
136.5, 134.4, 131.1, 128.9, 128.1, 127.0, 126.3, 120.3, 119.6, 113.1,
67.5. Anal. Calcd for C22H17Cl2N3O2S2: C, 53.88; H, 3.49; N, 8.57.
Found: C, 53.78; H, 3.48; N, 8.55%.
13 T.E.S. Ali and W.R. Abdel-Monem, Phosphorus, Sulfur, Silicon Relat.
Elem., 2008, 183, 2161.
14 Z. Li and X.R. Mao, Heterocycl. Commun., 2011, 17, 219.
15 Z. Li and Y.B. Li, J. Chem. Res., 2011, 35, 689.
16 Z. Li, H.F. Cai, J.Y. Yang, P.X. Niu and C.H. Liu, J. Braz. Chem. Soc.,
2011, 22, 1939.
17 Z. Li, Y.B. Li, H.F. Cai, J. Xu and J.H. Shi, Lett. Org. Chem., 2010, 7,
467.
18 Z. Li and Y.L. Zhao, Synth. Commun., 2009, 39, 3816.
19 P. Thanigaimalai, T.A.L. Hoang, K.C. Lee, S.C. Bang, V.K. Sharma,
C.Y. Yun, E. Roh, B.Y. Hwang, Y. Kim and S.H. Jung, Bioorg. Med. Chem.
Lett., 2010, 20, 2991.
20 S.S. Ubarhande, V.G. Thakare and B.N. Berad, J. Indian Chem. Soc., 2010,
87, 1137.
6-Hydroxy-6-(3-tolyloxymethyl)-1,5-di(4-chlorophenyl)-1,3,5-triazinane-
21 Y.J. Li, Y.J. Dai and J.C. Chen, Chem. J. Chin. Univ., 1988, 9, 584; Chem.
Abstr., 1989, 110, 74986h.
2,4-dithione (12): White solid, m.p. 181–182 °C; IR (KBr, ν, cm–1):

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