Med Chem Res (2012) 21:1199–1206
1205
2-(2-Chloro-5-nitrophenyl)-3-{4-[(2-phenyl-4-
quinazolinyl)amino]benzoyl}-1,3,4-thiadiazolium-5-
thiolate 12(c)
obtained was filtered off and recrystallized from ethanol.
m.p. 252–254°C.
Potassium salt of 2-({4-[(2-phenylquinazoline-4-yl)amino]
phenyl} carbonyl) hydrazine carbodithioic acid (11)
Yield: 87%. m.p. 228–231°C. IR (KBr): 3255, 1700, 1617,
1567, 1375, 1306, 1056 cm-1 1H NMR (400 MHz,
;
DMSO-d6): d 7.52–8.96 (m, 16H, Ar–H), 10.62 (s, 1H,
NH); 13C NMR (40 MHz, DMSO-d6): d 108.57, 110.78,
122.75, 126.75, 127.58, 128.73, 128.86, 129.56, 129.72,
130.38, 131.00, 132.42, 133.43, 134.21, 135.73, 135.95,
136.84, 139.84, 143.10, 148.68, 152.84, 156.57, 162.95,
164.85, 174.75; MS: m/z 599 (M? ? 2). Anal (%) for
C29H17N6O3S2Cl. Calcd. C, 58.34; H, 2.87; N, 14.08.
Found: C, 58.41; H, 2.94; N, 14.17.
To a stirred solution of 4-[(2-phenylquinazoline-4yl)amino]
benzohydrazine (0.005 mol) and potassium hydroxide
(0.005 mol) in absolute alcohol (25 ml), carbon disulfide
(0.01 mol) was added and the mixture was stirred for about
1 h at room temperature. The dark yellow colored precipi-
tate was treated with ether (50 ml). The solid which sepa-
rated was filtered, washed with ether, and dried.
2-Substituted-3-{4-[(2-phenyl-4-quinazolinyl)
amino]benzoyl}-1,3,4-thiadiazolium-5-thiolate 12(a–h)
2-(4-Chloro-3-nitrophenyl)-3-{4-[(2-phenyl-4-
quinazolinyl)amino]benzoyl}-1,3,4-thiadiazolium-5-
thiolate 12(d)
To a stirred solution of potassium salt of 2-({4-[(2-phe-
nylquinazoline-4yl)amino]phenyl}carbonyl)hydrazine car-
bodithioic acid (0.005 mol) in water was added acetyl
chloride (0.005 mol). The reaction mixture was stirred for
2 h at room temperature. The yellowish solid which sep-
arated was filtered, washed repeatedly with water, and re-
crystallized from ethanol.
Yield: 89%. m.p. 268–272°C. IR (KBr): 3258, 1689, 1620,
1554, 1348, 1317, 1047 cm-1
;
1H NMR (400 MHz,
DMSO-d6): d 7.46–8.84 (m, 16H, Ar–H), 10.60 (s, 1H,
NH); 13C NMR (40 MHz, DMSO-d6): d 109.78, 110.53,
122.65, 122.75, 126.32, 127.05, 128.67, 129.46, 130.60,
131.66, 131.80, 132.74, 134.16, 134.52, 135.63, 135.75,
135.90, 138.55, 143.06, 150.37, 152.10, 157.25, 162.98,
164.89, 174.33; MS: m/z 599 (M? ? 2). Anal (%) for
C29H17N6O3S2Cl. Calcd. C, 58.34; H, 2.87; N, 14.08.
Found: C, 58.41; H, 2.82; N, 14.15.
Similarly other compounds were synthesized by using
various aromatic and aliphatic acid chlorides.
2-Methyl-3-{4-[(2-phenyl-4-quinazolinyl)amino]benzoyl}-
1,3,4-thiadiazolium-5-thiolate 12(a)
2-(4-Methoxy-3-nitrophenyl)-3-{4-[(2-phenyl-4-
quinazolinyl)amino]benzoyl}-1,3,4-thiadiazolium-5-
thiolate 12(e)
Yield: 87%. m.p. 231–234°C. IR (KBr): 3240, 2957, 2864,
1
1718, 1603, 1297 cm-1; H NMR (400 MHz, DMSO-d6):
d 2.38 (s, 3H, CH3), 7.19–8.90 (m, 13H, Ar–H), 10.40 (s,
1H, NH); 13C NMR (40 MHz, DMSO-d6): d 17.93, 108.62,
110.07, 123.78, 126.28, 129.04, 129.25, 130.75, 130.84,
131.07, 133.93, 134.00, 135.06, 139.52, 142.46, 152.07,
158.78, 162.86, 164.75, 175.58; MS: m/z 456 (M?). Anal
(%) for C24H17N5OS2. Calcd. C, 63.28; H, 3.76; N, 15.37.
Found: C, 63.33; H, 3.84; N, 15.24.
Yield: 90%. m.p. 211–215°C. IR (KBr): 3250, 2965, 2843,
1685, 1607, 1536, 1340, 1293, 1257 cm-1 1H NMR
;
(400 MHz, DMSO-d6): d 4.00 (s, 3H, CH3), 7.55–8.79 (m,
16H, Ar–H), 10.53 (s, 1H, NH); 13C NMR (40 MHz, DMSO-
d6): d 58.84, 108.20, 110.73, 113.74, 120.70, 122.57, 123.69,
126.40, 129.36, 129.76, 130.63, 131.06, 131.63, 131.84,
133.97, 134.18, 135.85, 139.67, 142.75, 143.64, 152.83,
155.37, 157.28, 162.77, 164.32, 175.24; MS: m/z 593 (M?).
Anal (%) for C30H20N6O4S2. Calcd. C, 60.80; H, 3.40; N,
14.18. Found: C, 60.87; H, 3.34; N, 14.27.
2-Phenyl-3-{4-[(2-phenyl-4-quinazolinyl)amino]benzoyl}-
1,3,4-thiadiazolium-5-thiolate 12(b)
Yield: 85%. m.p. 243–247°C. IR (KBr): 3245, 1715, 1635,
1
1288 cm-1; H NMR (400 MHz, DMSO-d6): d 7.34–8.94
2-(4-Chlorophenyl)-3-{4-[(2-phenyl-4-quinazolinyl)
amino]benzoyl}-1,3,4-thiadiazolium-5-thiolate 12(f)
(m, 18H, Ar–H), 10.57 (s, 1H, NH); 13C NMR (40 MHz,
DMSO-d6): d 108.42, 110.64, 122.87, 126.56, 128.73,
129.20, 129.74, 130.29, 130.65, 131.03, 131.21, 131.58,
132.36, 133.68, 134.07, 137.13, 138.75, 142.87, 152.31,
156.38, 162.87, 164.85, 174.58; MS: m/z 518 (M?). Anal
(%) for C29H19N5OS2. Calcd. C, 67.29; H, 3.70; N, 13.53.
Found: C, 67.33; H, 3.65; N, 13.61.
Yield: 83%. m.p. 238–242°C. IR (KBr): 3242, 1697, 1618,
1290, 1030 cm-1 1H NMR (400 MHz, DMSO-d6): d
;
7.67–8.83 (m, 17H, Ar–H), 10.64 (s, 1H, NH); 13C NMR
(40 MHz, DMSO-d6): d 108.74, 110.68, 123.57, 123.80,
126.58, 128.69, 130.57, 130.70, 130.78, 131.05, 131.74,
123