E. A. A. El-Meguid, M. M. Ali
7
.58 (dd, 2H, H ? H chlorophenyl); 7.61 (s, 1H, pyrazole); 7.67 (dd, 2H,
2
6
H ? H benzene); 7.87 (dd, 2H, H ? H benzene); 8.12–8.23 (dd, 2H, H ? H
7
2
6
3
5
4
benzothiazole); 8.84 (s, 2H, NH ); 10.46 (s, 1H, NH).
2
5
-{5-Amino-1-[4-(1,3-benzothiazol-2-yl)benzoyl]-1H-pyrazole}-4-phenyl-2,4-dihy-
dro-[1,2,4]-triazol-3-thione (14b) Yield = 0.7 g (72 %), mp = 257–9 °C. Ana-
lysis for C H N OS (495.6): Calcd.: C, 60.6; H, 3.5; N, 19.8; S, 12.9; Fd.: C,
-
2
5
17
7
2
1
6
0.6; H, 3.4; N, 19.6; S, 13.0. IR (cm ): 3395 (NH), 3228 (NH ), 1667 (CO). MS:
2
?
Á
?
1
m/z (%): 496 (M , 9.8); 495 (M , 22). H NMR: d, ppm (DMSO-d ); 4.30 (s, 2H,
6
NH ); 6.45 (dd, 2H, H ? H phenyl); 6.68 (m, 1H, H phenyl); 7.08 (mm, 2H,
H ? H phenyl); 7.55 (mm, 2H, H ? H benzothiazole); 7.61 (s, 1H, pyrazole);
2
2
6
4
3
5
5
6
7
.67 (dd, 2H, H ? H benzene); 7.87 (dd, 2H, H ? H benzene); 8.12–8.23 (dd,
2 6 3 5
2
H, H ? H benzothiazole); 8.57 (s, 1H, NH).
4
7
General procedure for preparation of 5-{5-amino-1-[4-(1,3-benzothiazol-2-yl)ben-
zoyl]-1H-pyrazole}-4-(4-chlorophenyl)-2-substituted-2,4-dihydro-[1,2,4]-triazol-3-
one (15a–e) A mixture of compound 14a (2 g; 0.067 mol), the appropriate
organohalogen compound (methyl iodide, ethyl chloroformate, methyl 2-bromoac-
etate, ethyl 2-bromoacetate, or ethyl 2-bromopropanoate) (0.067 mol), anhydrous
sodium carbonate (4 g), and acetone (30 ml) was heated under reflux for 8 h. Most
of the solvent was removed by distillation, the residue was diluted with water, and
the product obtained was collected.
5
2
1
-{5-Amino-1-[4-(1,3-benzothiazol-2-yl)benzoyl]-1H-pyrazole}-4-(4-chlorophenyl)-
-methyl-2,4-dihydro-[1,2,4]-triazol-3-one (15a) Yield = 0.8 g (78 %), mp =
42–5 °C. Analysis for C H ClN O S (527.9): Calcd.: C, 59.2; H, 3.4; N, 18.6;
2
6
18
7 2
-
1
S, 6.1; Fd.: C, 59.3; H, 3.6; N, 18.5; S, 6.1. IR (cm ): 3290 (NH ), 1685 (CO),
2
?
?
1
1
d ); 2.71 (s, 3H, CH ); 7.25 (dd, 2H, H ? H chlorophenyl); 7.55 (mm, 2H,
666 (CO). MS: m/z (%): 529 (M , 33); 527 (M , 100). H NMR: d, ppm (DMSO-
6
3
3
5
H ? H benzothiazole); 7.58 (dd, 2H, H ? H chlorophenyl); 7.61 (s, 1H,
2
5
6
6
pyrazole); 7.67 (dd, 2H, H ? H benzene); 7.87 (dd, 2H, H ? H benzene);
2
6
3
5
8
.12–8.23 (dd, 2H, H ? H benzothiazole); 9.72 (s, 2H, NH ).
4 7 2
3
5
0
5
-{5-Amino-1-[4-(1,3-benzothiazol-2-yl)benzoyl]-1H-pyrazole}-4-(4-chlorophenyl)-
-oxo-4,5-dihydro-[1,2,4]-triazole-1-carboxylic acid ethyl ester (15b) Yield =
.9 g (79 %), mp = 92–5 °C. Analysis for C H ClN O S (585.5): Calcd.: C,
2
8
20
7 4
-
1
7.4; H, 3.4; N, 16.7; S, 5.5; Fd.: C, 57.5; H, 3.6; N, 16.6; S, 5.5. IR (cm ): 3220
?
?
(
NH ), 1710 (CO), 1685 (CO), 1662 (CO). MS: m/z (%): 587 (M , 3.3); 585 (M ,
2
1
1
0). H NMR: d, ppm (DMSO-d ); 1.31 (t, 3H, CH ); 4.11 (q, 2H, CH ); 7.25 (dd,
6
3
2
2
H ? H chlorophenyl); 7.61 (s, 1H, pyrazole); 7.67 (dd, 2H, H ? H benzene);
H, H ? H chlorophenyl); 7.55 (mm, 2H, H ? H benzothiazole); 7.58 (dd, 2H,
3
5
5
6
2
6
2
6
7
.87 (dd, 2H, H ? H benzene); 8.12–8.23 (dd, 2H, H ? H benzothiazole); 9.72
3 5 4 7
(
s, 2H, NH2).
1
23