Synthetic and spectroscopic studies of some new 2-[1-aryl-4{4- methoxyphenyl}-6-thioxo-1,6-dihydro-1,3,5-triazinyl]amino/hydrazonothiazolidin- 4-ones

Article abstract of DOI:10.1002/jhet.5570450317

(Chemical Equation Presented) A series of 4-thiazolidinones having triazinethione moieties have been synthesized by the systematic chemical modification of S-benzylmercapto-1-aryl-4-(4-methoxyphenyl)-1,6-dihydro-1,3,5- triazine-6-thione.

Full text of DOI:10.1002/jhet.5570450317

May-Jun 2008
741
Synthetic and Spectroscopic Studies of Some New 2 - [1-Aryl -4
{4-methoxyphenyl}-6-thioxo-1,6-dihydro-1,3,5-triazinyl]amino/
hydrazonothiazolidin-4-ones
P. K. Roychowdhuary,*1 K. K. Upadhay,2 Rakesh K. Mishra,2 Ajit Kumar,2
Sangeeta Mehrotra,1 Sugandh Srivastava1 & Shalini Upadhyay2
1Analytical Division, Chembiotek Research International, Kolkata- 700091, India
2Department of Chemistry, Faculty of Science, Banaras Hindu University, Varanasi-221005, India
purnendu@chembiotek.com
Received May 22, 2007
S
Ar
N
N
C6H4-4CH3
O
N
NH2
CH2 Ph
N
NH
4-OCH3C6H4
NCS
N
C
S
S
+
Ar
N
N
C6H5
S
OCH3
N
NH
N
4-OCH3C6H4
O
A series of 4-thiazolidinones having triazinethione moieties have been synthesized by the systematic
chemical modification of S-benzylmercapto-1-aryl-4-(4-methoxyphenyl)-1,6-dihydro-1,3,5-triazine-6-
thione.
J. Heterocyclic Chem., 45, 741 (2008).
-OCH3 and -CH3 exhibited the ν>C=N and ν>C=S at compara-
tively lower wave numbers than the triazinethione with
electron withdrawing substituents. The NMR spectra of
triazinethiones showed signals in the ranges 3.8-2.6 δ
ppm (s, 3H, –OCH3) and 4.9-3.6 δ ppm (s, 2H, –CH2) in
addition to the aromatic protons. The electron releasing/
electron withdrawing effects of substituents were
observed in NMR spectral pattern on the similar line of IR
spectral pattern. Reaction of 2-mercaptobenzyl triazinethi-
ones 1a-d with hydrazine hydrates lead to the formation
of hydrazinothiazine 2a-d. This conversion is clearly
reflected in the IR and NMR spectral pattern. IR spectra
of compounds 2a-d showed bands in the region 3390-
3330 cm-1 and 3280-3270 cm-1 for νN-H which were absent
INTRODUCTION
4-Thiazolidinone derivatives have been known for their
antibacterial [1-5], antifungal [6-8], anti HIV [9],
antituberculosis [10,11], anti-inflammatory [12,13], anti
cancer [14,15], antioxidant [16] properties and as follicle
stimulating hormone (FSH) agonists [17]. The 1,3,5-
triazine cores posses an important position in the field of
drug research due to the presence of three symmetrically
positioned N-atoms, which may be substituted by
different medicinally relevant substituents [18].
Furthermore, triazine-5-ones have been synthesized by
several workers for their screening as anti cancer and anti
HIV agents [19-21].
1
Hence, it was thought worthwhile to couple thiazol-
idinone as well as triazinethione in order to synthesize
some new potential candidates from the view point of
pharmaceutics. The overall synthesis can be summarized
through Scheme 1.
in IR spectra of triazinethiones. The H NMR spectra
showed peaks in δ ppm range of 4.8-4.5 (b, 2H, -NHNH2)
and 5.2-5.0 (b, 1H, –NHNH2) which disappeared on
exchange with deuterium oxide. Hydrazinothiazins 2a-d
on treatment with 2-tolyl isothiocynates and benzaldehyde
afforded corresponding triazinyl thiosemicarbazides 3a-d
and Schiff base 4a-d respectively.
RESULTS AND DISCUSSION
The interaction of 4-methoxybenzoylisothiocynate and
S-benzyl-N-aryl isothiourea afforded the 2-benzylmer-
capto-1-aryl-4-(methoxyphenyl)-1,6-dihydro-1,3,5-triazine-
The formation of the semicarbazides 3a-b was
supported by the enhancement of the integration of
aromatic protons as well as appearance of new signal in
the range of 2.1-2.4 δ ppm for the –CH3 group. On the
other hand formation of Schiff base 4a-d was confirmed
by the appearance of a signal in the range of 7.9-7.6 δ
ppm and disappearance of a signal in the range of 4.8-4.5
δ ppm. At the same time a broad peak in the range of 4.4-
4.0 δ ppm was assigned to –NH–. The aromatic protons
1
6-thione 1a-d. The IR and H NMR spectral studies were
used for establishing their structures. The IR spectral band
in the region 1645-1540 cm-1 and 1200-1165 cm-1 were
assigned as ν>C=N and ν>C=S respectively in accordance
with literature reports [22]. It is worth mentioning that
triazinethiones with electron releasing substituents like

742
P. K. Roychowdhuary, K. K. Upadhay, R. K. Mishra, A. Kumar,
S. Mehrotra, S. Srivastava and S. Upadhyay
Vol 45
Scheme 1
NH2
+
4-OCH3C6H4NCS
Benzene
Ar-N=C-SCH2Ph
Stirring
15 min.
S
Ar
N
N
N
1
SCH2Ph
4-OCH3C6H4
NH2NH2.H2O
Benzene
Stirring for 10 hrs 40-50°C
S
Ar
N
N
4-OCH3C6H4
N
NHNH2
2
Benzaldehyde
Reflux in Ethanol, 8 hrs
Glacial acetic acid 2-3 drops
2-Methylphenylisothiocyanate
Heating, 45 min.
S
S
Ar
Ar
N
N
N
N
N
3
4-OCH3C6H4
NHNHCSNHC6H4-4-CH3
4-OCH3C6H4
N
4
NHN=CHC6H5
ClCH2COOH/CH3COONa
Reflux in Ethanol, 3 hrs
Mercaptoaceticacid/ Sodium sulphate
Reflux in Benzene, 8 hrs
S
S
Ar
Ar
C6H4-4CH3
O
N
N
N
N
C6H5
S
4-OCH3C6H4
N
NH
N
4-OCH3C6H4
N
NH
N
S
5
6
O
Excess of solvent was removed on flash evaporator and residue
thus obtained was neutralized with cold, dilute sodium
bicarbonate solution. The free base was extracted with ether and
evaporation of ether afforded the desired free base. The other
S-benzyl-N-aryl isothioureas were prepared by similar procedure.
General method of preparation of 2-Benzylmercapto-1-(4-
chloropheny1)-4-(4-methoxypheny1)-1,6-dihydro-1,3-5-tria-
zine-6-thione (la). A solution of 4-methoxybenzoyl isothio-
cyanate in benzene (9.6. g, 0.05 mole) was gradually added with
vigorous stirring to S-benzy1-4-(4-chloropheny1) isothiourea
(13.8 g, 0.05 mole) in benzene over a period of 15 min. An
exothermic reaction took place and a golden yellow solid
separated after 20-30 min. It was recrystallized from ethanol–
DMF (4:1) mixture.
were observed slightly downfield after the Schiff base
formation. Formation of thiazolidinones 5a-d, 6a-d from
corresponding thiosemicarbazides 3a-d and Schiff bases
4a-d respectively were confirmed by their corresponding
IR and NMR spectral patterns.
CONCLUSION
The present communication reports new protocol for
the synthesis of a series of new thiozolidinones with
triazine thione moieties. The compounds reported under
present studies may be potential candidates form the view
point of pharmacy.
General method of preparation of 1-(4-chlorophenyl)-2-
hydrazino-4-(4-methoxyphenyl)-1,6-dihydro-1,3,5-triazine-6-
thione (2a). 1a (9.0 g, 0.02 mole) was dissolved in excess of
benzene (200 mL) hydrazine hydrate (1.0 g, 0.02 mole) was
added and the reaction mixture was stirred at 40-50 °C for 10 h.
A greenish yellow precipitate thus formed was filtered and
washed with excess of petroleum ether and benzene. The
resulting hydrazino compound was recrystallized from ethanol–
DMF mixture.
EXPERIMENTAL
Melting Points were determined through open capillary
method and are uncorrected. IR spectra were recorded on
1
JASCO/FTIR-5300 spectrophotometer as KBr pellets. H NMR
spectra were recorded on JEOL FX 90Q Fourier transform
spectrometer using tetramethylsilane (TMS) as an internal
standard.
S-Benzy1-N-(4-chloropheny1)isothiourea. A mixture of (4-
chloropheny1)-2-thiourea (18.6 g, 0.1 mole) and benzyl chloride
(12.7 g, 0.1 mole) in 150 mL ethanol was refluxed for 2.5 hrs.
1-(4-Chlorophenyl)-2-hydrazino-4-(4-methoxyphenyl)-1,6-
dihydro-1,3,5-triazin-6-thione (2a). Yield (56%). m.p 218 °C.
IR (KBr): 3290, 1645, 1165 cm-1. 1H NMR (DMSO-d6): δ 3.8 (s,

May-Jun 2008
Some New 2-[1-Ary-4{4-methoxypheny}-6-thioxo-1,6-dihydro-
1,3,5-triazinyl]amino/hydrazonothiazolidin-4-ones
743
3H, –OCH3), 4.8 (br, 2H, –NHNH2), 5.1 (br, 1H, –NHNH2), 6.9-
7.6 (m, 8H, ArH). Anal. Calcd. for (C16H14N5OSCl): C, 53.41;
H, 3.92; N, 19.46, S, 8.91; Cl, 9.85. Found: C, 53.62; H, 3.73; N,
19.81; S, 9.64; Cl, 9.48.
1-(4-Methylphenyl)-2-hydrazino-4-(4-methoxyphenyl)-1,6-
dihydro-1,3,5-triazin-6-thione (2b). Yield (47%). m.p 188 °C.
IR (KBr): 3290, 1645, 1165 cm-1. 1H NMR (DMSO-d6): δ 2.1 (s,
3H, –CH3), 3.8 (s, 3H, –OCH3), 4.8 (br, 3H, –NHNH2), 5.1 (br,
1H, –NHNH2), 6.9-7.6 (m, 8H, ArH). Anal. Calcd. for
(C17H17N5OS): C, 60.16; H, 5.05; N, 20.63; S, 9.45. Found: C,
60.52; H, 4.95; N, 20.89; S, 10.35.
1-(4-Nitrophenyl)-2-hydrazino-4-(4-methoxyphenyl)-1,6-
dihydro-1,3,5-triazin-6-thione (2c). Yield (52%). m.p 182 °C;
IR (KBr): 3290, 1645, 1360, 1320, 1165 cm-1. 1H NMR (DMSO-
d6): δ 3.8 (s, 3H, –OCH3), 4.8 (br, 2H, –NHNH2), 5.1 (br, 1H,
-NHNH2), 6.9-7.6 (m, 8H, ArH). Anal. Calcd. for
(C16H14N6O3S): C, 51.88; H, 3.81; N, 22.69; S, 8.66. Found: C,
52.07; H, 3.92; N, 22.51; S, 10.38.
1-(2-Methoxy-5-chlorophenyl)-2-hydrazino-4-(4-methoxy-
phenyl)-1,6-dihydro-1,3,5-triazin-6-thione (2d). Yield (46%).
m.p 188 °C. IR (KBr): 3290, 1645, 1165 cm-1. 1H NMR
(DMSO-d6): δ 3.8 (s, 6H, –OCH3), 4.8 (br, 2H, –NHNH2), 5.1
(br, 1H, –NHNH2), 6.9-7.6 (m, 7H, ArH). Anal. Calcd. for
(C17H16N5O2SCl): C, 52.37; H, 4.14; N, 17.96; S, 8.22; Cl, 9.09.
Found: C, 52.59; H, 4.36; N, 18.38; S, 8.98; Cl, 8.72.
(C25H23N6O2S2Cl): C, 55.70; H, 4.30; N, 15.59; S, 11.90; Cl,
6.58. Found: C, 55.94; H, 4.62; N, 16.00; S, 12.22; Cl, 6.82.
General method of preparation N-[1-4-chloropheny)-4-(4-
methoxyphenyl)-6-thioxo-1,6-dihydro-1,3,5-traiazin-2-yl]-N-
benzylidine hydrazine (4a). A mixture of (2a) (7.0 g, 0.02
mole), benzaldehyde (0.2 g, 0.02 mole) and 2-3 drops of glacial
acetic acid were taken in ethanol. The reaction mixture was
refluxed for about 8 hours. It was then filtered and the filtrate
was allowed to cool overnight. The title compound was
separated out as fine yellow needles.
N-[1-(4-chlorophenyl)]-4-[(4-methoxyphenyl)-6-thioxo-1,6-
dihydro1,3,5triazin-2-yl]-N'benzylidene hydrazine (4a).
1
Yield (69%). m.p 212 °C. IR (KBr): 3340, 1630, 1090 cm-1. H
NMR (DMSO-d6): δ 3.8 (3H, s, –OCH3), 4.4 (br, 1H, –NH–),
6.9-7.7 (m, 13H, ArH), 7.9 (s, 1H, –N=CH–). Anal. Calcd. for
(C23H18N5OSCl): C, 61.67; H, 4.05; N, 15.63; S, 7.16; Cl, 7.91.
Found: C, 61.94; H, 4.41; N, 15.95; S, 7.38; Cl, 7.48.
N-[1-(4-Methylphenyl)]-4-[(4-methoxyphenyl)-6-thioxo-1,6-
dihydro-1,3,5-triazin-2-yl]-N'-benzylidene hydrazine (4b).
1
Yield (51%). m.p 260 °C. IR (KBr): 3340, 1630, 1090 cm-1. H
NMR (DMSO-d6): δ 2.1 (s, 3H, –CH3), 3.8 (s, 3H, -OCH3), 4.4
(br, 1H, –NH–), 6.9-7.7 (m, 13H, ArH), 7.9 (s, 1H, –N=CH–).
Anal. Calcd. for (C24H21N5OS): C, 67.43; H, 4.95; N, 16.38. S,
7.50. Found: C, 67.76; H, 5.22; N, 16.64; S, 7.96.
N-[1-(4-Nitrophenyl)]-4-[(4-methoxyphenyl)-6-thioxo-1,6-
dihydro-1,3,5-triazin-2-yl]-N'-benzylidene hydrazine (4c).
Yield (56%). mp 230 °C. IR (KBr): 3340, 1630, 1360, 1320,
General method of preparation of N-[2-methylphenyl]-N-
1(4-chlorophbenyl)-4-(4-mehthoxyphenyl)-6-thioxo-1,6-
1
1090 cm-1. H NMR (DMSO-d6): δ 3.8 (s, 3H, –OCH3), 4.4 (br,
dihydro-1,3,5-triazinylthiosemicarbazide
(3a). 4-Methyl
phenylisothiocyanate (10.0 g, 0.02 mole) was mixed with (2a)
(17.0 g, 0.02 mole) and a paste thus formed was heated on a
water bath for a period of 45 min. It was then washed with
petroleum ether to remove excess of isothiocyanate and
recrystallized from benzene.
1H, –NH–), 6.9-7.7 (m, 13H, ArH), 7.9 (s, 1H, –N=CH–). Anal.
Calcd. for (C23H18N6O3S): C, 60.25; H, 3.96; N, 18.33; S, 6.99.
Found: C, 60.55; H, 4.16; N, 18.67; S, 7.52.
N-[1-(2-Methoxy-5chlorophenyl)]-4-[(4-methoxy phenyl)-
6-thioxo-1,6-dihydro-1,3,5-triazin-2-yl]-N'-benzylidene
hydrazine (4d). Yield (52%). m.p 214 °C. IR (KBr): 3340,
N-[2-Methylphenyl]-N"-1-[(4-chlorophenyl)-4-(4-methoxy-
phenyl)]-6-thioxo-1,6-dihydro-1,3,5-triazinylthiosemicarba-
zide (3a). Yield (39%). m.p 186 °C. IR (KBr): 3290, 3100,
1
1630, 1090 cm-1. H NMR (DMSO-d6): δ 3.8 (s, 6H, –OCH3),
4.4 (br, 1H, –NH–), 6.9-7.7 (m, 12H, ArH), 7.9 (s, 1H,
-N=CH-). Anal. Calcd. for (C24H20N5O2SCl): C, 60.31; H, 4.22;
N, 14.65; S, 6.71; Cl, 7.42. Found: C, 60.62; H, 3.98; N, 14.84;
S, 7.11; Cl, 7.95.
General method of preparation of 2-[1-(4-chlorophenyl)-4-
(4-methoxyphenyl)-6-thioxo-1,6-dihydro-1,3,5-triazin-2-yl]-
hydrazino-3-(2-methlphenyl)thiazolidione (5a). A mixture of
(3a) (10.0 g, 0.02 mole), chloroacetic acid (1.0 g, 0.02 mole) and
sodium acetate (3.0 g) were taken in ethanol and refluxed for 3
h. It was then poured into crushed ice, filtered and the product
was recrystallized from ethanol.
2-[1-(4-Chlorophenyl)]-4-[(4-methoxyphenyl)-6-thioxo-1,6-
dihydro-1,3,5-triazin2yl]hydrazono-3-(2-methylphenyl)thia-
zolidinone (5a). Yield (69%). m.p 212 °C. IR (KBr): 3340,
2900, 1630, 1690, 1090 cm-1. 1H NMR (DMSO-d6): δ 4.2 (s, 2H,
–CH2), 3.8 (s, 3H, –OCH3), 4.4 (br, 1H, –NH–), 6.9-7.7 (m,
13H, ArH). Anal. Calcd. for (C25H21N6O2S2Cl): C, 55.91; H,
3.94; N, 15.65; S, 11.94; Cl, 6.60. Found: C, 56.23; H, 4.11; N,
15.94; S, 12.36; Cl, 7.12.
2-[1-(4-Methylphenyl)]-4-[(4-methoxyphenyl)-6-thioxo-1,6-
dihydro-1,3,5-triazin-2-yl]hydraozono-3-(2-methyl phenyl)-
thiazolidinone (5b). Yield (51%). mp 260 °C. IR (KBr): 3340,
2900, 1690, 1630, 1090 cm-1. 1H NMR (DMSO-d6): δ 2.1 (s, 3H,
–CH3), 4.2 (s, 2H, –CH2–), 3.8 (s, 3H, –OCH3), 4.4 (br, 1H,
-NH–), 6.9-7.7 (m, 13H, ArH). Anal. Calcd. for (C26H24N6O2S2):
C, 60.44; H, 4.68; N, 16.27; S, 12.41. Found: C, 60.78; H, 5.01;
N, 16.07; S, 12.78.
1
1540, 1105 cm-1. H NMR (DMSO-d6): δ 2.1 (s, 3H, -CH3), 3.8
(s, 3H,–OCH3), 4.6 (br, 1H, –NHNH–), 5.1 (br, 1H, -NHNH–),
6.9-7.2 (m, 12H, ArH). Anal. Calcd. for (C24H21N6OS2Cl): C,
56.63; H, 4.16; N, 16.51; S, 12.60; Cl, 6.96. Found: C, 56.79; H,
4.01; N, 16.88; S, 13.29; Cl, 7.39.
N-[2-Methylphenyl]-N"-1-[(4-mehylphenyl)-4-(4-methoxy-
phenyl)]-6-thioxo-1,6-dihydro-1,3,5-triazinylthiosemicarba-
zide (3b). Yield (55%). m.p 196 °C. IR (KBr): 3290, 3100, 1540,
1
1105 cm-1. H NMR (DMSO-d6): δ 2.1 (s, 6H, –CH3), 3.8 (s, 3H,
-OCH3), 4.6 (br, 1H, –NHNH–), 5.1 (br, 1H, –NHNH–), 6.9-7.2
(m, 12H, ArH). Anal. Calcd. for (C25H24N6OS2): C, 61.45; H, 4.95;
N, 17.20, S, 13.12. Found: C, 61.69; H, 5.14; N, 16.92; S, 12.56.
N-[2-Methylphenyl]-N"-1-[(4-nitrophenyl)-4-(4-methoxy
phenyl)]-6-thioxo1,6-dihydro-1,3,5-triazinylthiosemicarbazide
(3c). Yield (55%). m.p 196 °C. IR (KBr): 3290, 3100, 1540,
1360, 1320, 1105 cm-1. 1H NMR (DMSO-d6): δ 2.1 (s, 3H,
-CH3), 3.8 (s, 3H, –OCH3), 4.6 (br, 1H, –NHNH–), 5.1 (br, 1H,
–NHNH–), 6.9-8.2 (m, 12H, ArH). Anal. Calcd. for
(C24H21N7O3S2): C, 55.48; H, 4.07; N, 18.87; S, 12.34. Found: C,
55.89; H, 4.41; N, 18.98; S, 11.82.
N-[2-Methylphenyl]-N"-1-[(2-methoxy-5-chlorophenyl)-4-
(4-methoxyphenyl)]-6-thioxo-1,6-dihydro-1,3,5-triazinylthio-
semicarbazide (3d). Yield (55%). m.p 196 °C. IR (KBr): 3290,
3100, 1540, 1105 cm-1. 1H NMR (DMSO-d6): δ 2.1 (s, 3H,
-CH3), 3.8 (s, 6H, –OCH3), 4.6 (br, 1H, –NHNH–), 5.1 (br, 1H,
–NHNH–), 6.9-7.2 (m, 11H, ArH). Anal. Calcd. for

744
P. K. Roychowdhuary, K. K. Upadhay, R. K. Mishra, A. Kumar,
S. Mehrotra, S. Srivastava and S. Upadhyay
Vol 45
2-[1-(4-Nitrophenyl)]-4-[(4-methoxyphenyl)-6-thioxo-1,6-
6H, –OCH3), 4.2 (s, 2H, –CH2–), 5.6 (br, 1H, –NH–), 6.9-7.7
(m, 12H, ArH). Anal. Calcd. for (C26H22N5O3S2Cl): C, 56.57; H,
4.02; N, 12.69; S, 11.62; Cl, 6.42. Found: C, 56.75; H, 4.37; N,
12.88; S, 11.98; Cl, 6.75.
dihydro-1,3,5-triazin-2-yl]hydrazono-3-(2-methyl phenyl)-
thiazolidinone (5c). Yield (56%). mp 230 °C. IR (KBr): 3340,
2910, 1690, 1630, 1360, 1320, 1090 cm-1. 1H NMR (DMSO-d6):
δ 3.8 (s, 3H, –OCH3), 4.2 (s, 2H, –CH2–), 4.4 (br, 1H, –NH–),
6.9-7.7 (m, 13H, ArH). Anal. Calcd. for (C25H21N7O4S2): C,
54.83; H, 3.87; N, 17.90; S, 11.71. Found: C, 55.15; H, 4.17; N,
18.27; S, 12.19.
REFERENCES
[1] Ali, S; Alam, M. Arch. Pharmacol. Res. 1994, 17, 131.
[2] Ates, O.; Kocabalkanlı, A.; Sanıs-Otuk, G.; Ekinci, A.C.;
Vidin, A. Arzneim .Forsch/ Drug, Res. 1997, 47, 1134.
[3] Ates, O.; Altıntas, H.; Otuk, G. Arzneim.-Forsch/Drug, Res.
2000, 50, 569.
2-[1-(2-Methoxy-5-chlorophenyl)]-4-[(4-methoxyphenyl)-6-
thioxo-1,6-dihydro-1,3,5-triazin-2-yl]hydrazono-3-(2-methyl-
phenyl)methylphenyl)thiazolidinone (5d). Yield (52%). m.p
1
214 °C. IR (KBr): 3340, 2910, 1690, 1630, 1090 cm-1. H NMR
(DMSO-d6): δ 3.8 (s, 6H, –OCH3), 4.2 (s, 2H, –CH2–), 4.4 (br,
1H, –NH–), 6.9-7.7 (m, 12H, ArH). Anal. Calcd. for
(C26H23N6O3S2Cl): C, 55.07; H, 4.09; N, 14.82; S, 11.31; Cl,
6.25. Found: C, 55.46; H, 4.29; N, 14.78; S, 11.65; Cl, 6.62.
General method of preparation of 2-Phenyl-3-[1-(4-
chlorophenyl)-4-(methoxyphenyl)-6-thioxo-1,6-dihydro-1,3,5-
triazine-2-yl]amino-thiazolidione (6a). A mixture of (4a) (9.0
g, 0.02 mole), mercaptoacetic acid (0.80 g, 0.02 mole) and
sodium sulphate (5.0 g) were taken in 100 mL of benzene and
refluxed for 8 h. It was filtered and the solvent was evaporated
in vacuum. The product was then washed with sodium
bicarbonate solution to remove unreacted acid and finally
recrystallized from ethanol.
2-Phenyl-3-[1-(4-chlorophenyl)]-4-[(4-methoxyphenyl)-6-
thioxo-1,6-thioxo-1,6-dihydro-1,3,5-triazin-2-yl]aminothia-
zolidin-4-one (6a). Yield (39%). m.p 262 °C. IR (KBr): 2900,
2140, 1695 cm-1. 1H NMR (DMSO-d6) δ 3.8 (s, 3H, –OCH3), 4.2
(s, 2H, –CH2–), 5.6 (br, 1H, –NH–), 6.9-7.7 (m, 13H, ArH).
Anal. Calcd. for (C25H20N5O2S2Cl): C, 57.52; H, 3.86; N, 13.42;
S,12.28, Cl, 6.79. Found: C, 57.86; H, 4.08; N, 13.66; S, 12.61;
Cl, 7.15.
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2-Phenyl-3-[1-(4-methylphenyl)]-4-[(4-methoxyphenyl)-6-
thioxo-1,6-thioxo-1,6-dihydro-1,3,5-triazin-2-yl]aminothia-
zolidin-4-one (6b). Yield (39%). m.p 262 °C. IR (KBr): 2900,
2140, 1695 cm-1. 1H NMR (DMSO-d6): δ 2.1 (s, 3H, -CH3), 3.8 (s,
3H, –OCH3), 4.2 (s, 2H, –CH2–), 5.6 (br, 1H, -NH–), 6.9-7.7 (m,
13H, ArH). Anal. Calcd. for (C26H23N5O2S2): C, 62.25; H, 4.62; N,
13.96; S, 12.78. Found: C, 62.56; H, 4.85; N, 14.22; S, 13.14.
2-Phenyl-3-[1-(4-nitrophenyl)]-4-[(4-methoxyphenyl)-6-
thioxo-1,6-thioxo-1,6-dihydro-1,3,5-triazin-2-yl]aminothia-
zolidin-4-one (6c). Yield (46%). m.p 251 °C. IR (KBr): 2900,
2140, 1710, 1360, 1320 cm-1. 1H NMR (DMSO-d6): δ 3.8 (s, 3H,
–OCH3), 4.2 (s, 2H, –CH2–), 5.6 (br, 1H, –NH–), 6.9-7.7 (m,
13H, ArH). Anal. Calcd. for (C25H20N6O4S2): C, 56.38; H, 3.79;
N, 15.78; S, 12.04. Found: C, 56.66; H, 3.96; N, 16.14; S, 12.42.
2-Phenyl-3-[1-(2methoxy-5-chlorophenyl)]-4-[(4-ethoxy
phenyl)-6-thioxo-1,6-thioxo-1,6-dihydro-1,3,5-triazin-2-yl]
amino-thiazolidin-4-one (6d). Yield (48%). m.p 212 °C. IR
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1
(KBr): 2900, 2140, 1705 cm-1. H NMR (DMSO-d6): δ 3.8 (s,