P. Valentina et al.
3-[2-(20,60-Dichloro phenyl) amino phenyl acetoxy
methyl]-6-[2-(3-hydroxy benzene sulphonic acid)]-1,2,4
triazolo-[3,4-b]-1,3,4-thiadiazole (6d)
(C-19), 172.0 (C-20), 174.1 (C-21), 35.7 (C-22), 175.2 (C-
23), 51.8 (C-24); m/z: 527 (M?2, 49 %); Anal. Calcd. for
C24H17Cl2N5O3S (525) C, 54.42; H, 3.23; N, 14.95 Found:
C, 54.39; H, 3.29; N, 14.90.
Orange solid; yield: 69 %; m.p:115–116 °C; Rf: 0.63; FT-
IR (KBr) mmax: 3545, 3215, 2980, 1751, 1533, 1351, 1301,
1239, 1170, 1091, 1018, 782, 748, 670 cm-1; 1H NMR
(CDCl3, 300 MHz): d = 6.3–7.9 (m, 10H, aromatic), 6.3
(s, 1H, –OH), 5.2 (s, 2H, –COOCH2–), 4.45 (s, 1H, NH),
3.7 (s, 2H, –CH2COO–), 2.1 (s, 1H, -SO3H);13CNMR d
(CDCl3, ppm):148.3 (C-1), 124.9 (C-2), 130.5 (C-3), 124.0
(C-4), 130.7 (C-5), 123.0 (C-6), 153.2 (C-7), 119.1 (C-8),
127.8 (C-9), 140.0 (C-10), 129.8 (C-11), 120.0 (C-12),
115.8 (C-13),1534.2 (C-14), 130.9 (C-15), 135.9 (C-16),
138.0 (C-17), 132.8 (C-18), 161.5 (C-19), 170.3 (C-20),
172.8 (C-21), 35.3 (C-22), 174.4 (C-23), 52.1 (C-24); m/z:
607 (M?2,75 %); Anal. Calcd. for C24H17Cl2N5O6S2
(605):C, 48.18; H, 2.76; N, 12.77. Found: C, 48.23; H,
2.82; N, 12.80.
3-[2-(20,60-Dichloro phenyl)amino phenyl acetoxy methyl]-
6-(2,4-dichloro phenyl)-1,2,4 triazolo-[3,4-b]-1,3,4-
thiadiazole (6g)
Pale yellow crystals; yield: 60 %; m.p: 206–207 °C; Rf:
0.51; FT-IR (KBr) mmax: 3411, 3084, 2861, 1732, 1240,
1543, 1361, 1343, 1173, 791, 748, 671 cm-1; 1H NMR
(CDCl3, 300 MHz): d = 6.4–8.5 (m, 10H,ArH), 5.5 (s, 2H,
–COOCH2–), 4.55 (s, 1H, NH), 3.65 (s, 2H, –CH2COO–);
13CNMR d (CDCl3, ppm):148.3 (C-1), 124.9 (C-2), 130.5
(C-3), 124.0 (C-4), 130.7 (C-5), 123.0 (C-6), 153.2 (C-7),
119.1 (C-8), 127.8 (C-9), 140.0 (C-10), 129.8 (C-11), 120.0
(C-12), 128.9 (C-13), 134.8 (C-14), 130.9 (C-15), 135.9
(C-16), 120.1 (C-17), 132.8 (C-18), 162.8 (C-19), 171.0
(C-20), 173.2 (C-21), 36.7 (C-22), 175.8 (C-23), 51.0 (C-
24); m/z: 580 (M?1, 45 %); Anal. Calcd. for C24H15Cl4-
N5O2S (579): C, 50.69; H, 2.51; N, 13.44.Found: C, 50.74;
H, 2.59; N, 13.40.
3-[2-(20,60-Dichloro phenyl)amino phenyl acetoxy methyl]-
6-(3-bromo phenyl)-1,2,4 triazolo-[3,4-b]-1,3,4-thiadiazole
(6e)
3-[2-(20, 60-Dichloro phenyl) amino phenyl acetoxy
methyl]-6-(2, 4-dihydroxy phenyl)-1, 2, 4 - triazolo-[3,4-
b]-1,3,4-thiadiazole (6h)
Pale yellow powder; yield: 61 %; m.p:169–170 °C; Rf:
0.80; FT-IR (KBr) mmax: 3435, 3232, 2916, 1732, 1511,
1360, 1237, 1032, 782, 744, 670, 540 cm-1; 1H NMR
(CDCl3, 300 MHz): d = 6.5–8.0 (m, 11H, ArH), 5.5 (s,
2H, –COOCH2–), 4.3 (s, 1H, NH), 3.45 (s, 2H, –CH2COO–
); 13C-NMR d (CDCl3, ppm):147.5 (C-1), 123.9 (C-2),
131.2 (C-3), 124.2 (C-4), 131.6 (C-5), 123.5 (C-6), 153.4
(C-7), 119.8 (C-8), 126.7 (C-9), 140.6 (C-10), 130.2 (C-
11), 121.0 (C-12), 129.2 (C-13), 132.2 (C-14), 122.9 (C-
15), 125.9 (C-16), 130.2 (C-17), 127.2 (C-18), 161.6 (C-
19), 171.5 (C-20), 172.2 (C-21), 36.2 (C-22), 175.2 (C-23),
52.3 (C-24); m/z: 605(M?2,67 %); Anal. Calcd. for C24-
H16BrCl2N5O2S (603): C, 49.74; H, 2.66; N, 13.18. Found:
C, 49.80; H, 2.71; N, 13.15.
Pale yellow powder;yield: 68 %; m.p: 150–152 °C; Rf:
0.57; FT-IR (KBr) mmax: 3497, 3103, 2931, 1710, 1265,
1484, 1463,1323, 1150, 1031, 790, 749, 671 cm-1; 1H
NMR (CDCl3, 300 MHz): d = 6.4–8.1 (m, 10H,ArH), 5.3
and 5.4 (s, 2H, 2(OH)), 5.1 (s, 2H, –COOCH2–), 4.35 (s,
1H, NH), 3.7 (s, 2H, –CH2COO–); 13C-NMR d (CDCl3,
ppm):146.3 (C-1), 123.8 (C-2), 130.7 (C-3), 123.1 (C-4),
131.3 (C-5), 124.6 (C-6), 151.2 (C-7), 118.9 (C-8), 126.1
(C-9), 141.4 (C-10), 130.0 (C-11), 120.6 (C-12), 158.5 (C-
13), 103.4 (C-14), 103.9 (C-15), 155.3 (C-16), 108.0 (C-
17), 113.2 (C-18), 161.5 (C-19), 171.2 (C-20), 174.1 (C-
21), 35.9 (C-22), 174.1 (C-23), 51.8 (C-24); m/z: 542
(M?1,52 %); Anal. Calcd. for C24H17Cl2N5O4S (541): C,
54.55; H, 3.12; N, 14.46. Found: C, 54.63; H, 3.19; N,
14.50.
3-[2-(20,60-Dichloro phenyl)amino phenyl acetoxy methyl]-
6-(3-hydroxy phenyl)- 1,2,4 triazolo-[3,4-b]-1,3,4-
thiadiazole (6f)
White crystals;yield: 57 %; m.p:138–139 °C; Rf: 0.73; FT-
IR (KBr) mmax: 3572, 3078, 2977, 1737, 1539, 1306, 1209,
1172, 1107, 1052, 783, 747, 671 cm-1; 1H NMR (CDCl3,
300 MHz): d = 6.7–8.1 (m, 11H,ArH), 6.1 (s, 1H, –OH),
5.4 (s, 2H, –COOCH2–), 4.8 (s, 1H, NH), 3.45 (s, 2H, –
CH2COO–);13C-NMR d (CDCl3, ppm):148.6 (C-1), 125.4
(C-2), 130.9 (C-3), 123.8 (C-4), 129.0 (C-5), 123.0 (C-6),
152.5 (C-7), 119.7 (C-8), 127.8 (C-9), 140.7 (C-10), 129.8
(C-11), 121.2 (C-12), 130.6 (C-13), 115.8 (C-14), 152.5
(C-15), 114.5 (C-16), 130.3 (C-17), 127.2 (C-18), 163.1
3-[2-(20,60-Dichloro phenyl)amino phenyl acetoxy methyl]-
6-(2,4-dimethoxy phenyl)-1,2,4 triazolo-[3,4-b]-1,3,4-
thiadiazole (6i)
White powder; yield: 71 %; m.p: 121–122 °C; Rf: 0.5; FT-
IR (KBr) mmax: 3434, 3094, 2961, 1730, 1548, 1391, 1360,
1240,1053, 1019, 789, 749, 670 cm-1; 1H NMR (CDCl3,
300 MHz): d = 6.9–8.0 (m, 10H, ArH), 5.1 (s, 2H, –
COOCH2–), 4.3 (s, 1H, NH), 3.5 (s, 2H, –CH2COO–), 3.2
123