KHAN ET AL.
1099
0
0
str. of aromatic ring), 2923 ( CH2 str.), 1673 (C O str.),
2H, CH -6), 3.82 (q, J = 7.2 2H, H-1 ), 2.16 (br.s, 6H, CH -
2
0000
3
0
000
00 13
1
561 (C C str. of aromatic ring), 1517 (C N str.), 1169
2
& 5 ), 1.00 (t, J = 7.2, 3H, H-2 ); C-NMR (150 MHz,
1
000
(C N C bond str.), 623 (C S str.); H-NMR (600 MHz,
DMSO-d , δ/ppm): 168.58 (C-2), 164.60 (C-7 ), 153.19 (C-
6
0
000
0
0
000
0000
DMSO-d , δ/ppm): 9.80 (s, 1H, CO NH-1 ), 7.94 (br.d,
J = 7.9, 2H, H-2 and H-6 ), 7.52 (br.d, J = 8.1, 2H, H-3
5 ), 148.04 (C-3 ), 146.18 (C-4), 141.07 (C-4 ), 135.60 (C-2
6
0
00
000
000
0000 000 000 000
and C-6 ), 133.38 (C-1 ), 128.94 (C-3 & C-5 ), 127.65 (C-
0
00
0000
000 000 0000 0000 0000
and 6 ), 127.59 (C-3 and C-5 ), 126.62 (C-4 ),
and H-5 ), 7.23 (br.d, J = 7.8, 1H, H-6 ), 7.12 (br.s, 1H, H-
2
0
000
0000
00 000
3
), 7.05 (br.d, J = 7.7 1H, H-5 ), 6.96 (br.s, 2H, H N-2),
102.35 (C-5), 38.58 (C-1 ), 36.32 (C-8 ), 27.53 (C-6), 18.00
2
0
00
0000 0000 00
and CH -2 ), 14.64 (C-2 ).. Anal. Calc. for
3
6.27 (s, 1H, H-5), 4.49 (s, 2H, CH -8 ), 3.99 (s, 2H, CH -6),
(CH -2
2
2
3
0
0
0000
3.86 (q, J = 7.0, 2H, CH -1 ), 2.32 (s, 3H, CH -4 ), 2.22 (s,
C H N OS (478.63): C, 60.23; H, 5.48; N, 17.56. Found: C,
24 26 6 2
2
3
0
000
00
13
3H, CH -2 ), 1.05 (br.t, J = 7.2 3H, CH -2 ); C-NMR
60.25; H, 5.47; N, 17.59.
3
3
0
00
(150 MHz, DMSO-d , δ/ppm): 168.59 (C-2), 164.87 (C-7 ),
4-[({5-[(2-Amino-1,3-thiazol-4-yl)methyl]-4-ethyl-
4H-1,2,4-triazol-3-yl}sulfanyl)methyl]-N-(3,4-dimethyl
phenyl)benzamide (9d). Orange solid; Yield: 94%;
6
0 0 000
0000 000 0000 0000
153.18 (C-5 ), 148.03 (C-3 ), 146.17 (C-4), 141.02 (C-4 ),
135.02 (C-1 ), 133.72 (C-1 ), 133.58 (C-2 ), 133.47 (C-4 ),
0
000
000
000
000
ꢀ
1
6
30.77 (C-5 ), 128.86 (C-3 & C-5 ), 127.69 (C-2 and C-
m.p. 192–194 C Mol. Formula: C H N OS ; Mol. Mass:
2
4
26
6
2
0
00
0
000
0000
0000
−1
−1
), 126.49 (C-3 ), 126.45 (C-6 ), 102.36 (C-5), 38.57 (C-
478 gmol ; IR (KBr, ʋ/cm ): 3353 (N H str.), 3039 (C H
str. of aromatic ring), 2910 ( CH2 str.), 1649 (C O str.),
1549 (C C str. of aromatic ring), 1515 (C N str.), 1145
0
000
0000
1
), 36.44 (C-8 ), 27.53 (C-6), 20.50 (CH -4 ), 17.77 (CH -
00
), 14.64 (C-2 ) Anal. Calc. for C H N OS (478.63): C,
24 26 6 2
3
3
0
2
1
60.23; H, 5.48; N, 17.56. Found: C, 60.28; H, 5.44; N, 17.57.
(C N C bond str.), 610 (C S str.); H-NMR (600 MHz,
0000
DMSO-d , δ/ppm): 10.03 (s, 1H, CO NH-1 ), 7.87 (br.d,
6
4
-[({5-[(2-Amino-1,3-thiazol-4-yl)methyl]-4-ethyl-
000 000 0000
J = 8.1, 2H, H-2 and H-6 ), 7.53 (s, 1H, H-2 ), 7.47 (br.d,
4
H-1,2,4-triazol-3-yl}sulfanyl)methyl]-N-(2,5-dimethyl
0
00
000
0000
phenyl)benzamide (9b). Light Brown solid; Yield: 94%;
J = 8.0, 3H, H-3 , H-5 and H-6 ), 7.09 (br.d, J = 8.1, 1H,
ꢀ
0000
m.p. 82–84 C Mol. Formula: C H N OS ; Mol. Mass.:
H-5 ), 6.91 (br.s, 2H, H N-2), 6.22 (s, 1H, H-5), 4.44 (s, 2H,
24
26
6
2
2
−1
−1
000 00
CH -8 ), 3.94 (s, 2H, CH -6), 3.80 (q, J = 7.1 2H, H-1 ) 2.21
2 2
4
78 gmol ; IR (KBr, ʋ/cm ): 3351 (N H str.), 3055 (C H
0000 0000
(br.s, 3H, CH -4 ), 2.18 (s, 3H, CH -3 ), 0.98 (t, J = 7.2
3 3
str. of aromatic ring), 2927 ( CH2 str.), 1671 (C O str.),
566 (C C str. of aromatic ring), 1523 (C N str.), 1169
00
3H, H-2 ); C-NMR (150 MHz, DMSO-d , δ/ppm): 168.58
6
13
1
1
000 0 0
(C-2), 164.77 (C-7 ), 153.17 (C-5 ), 148.00 (C-3 ), 146.17 (C-
(C N C bond str.), 638 (C S str.); H-NMR (600 MHz,
0
000
000 0000 0000
4), 141.00 (C-4 ), 136.76 (C-3 ), 136.07 (C-1 ), 133.98 (C-
DMSO-d , δ/ppm): 9.82 (s, 1H, CO NH-1 ), 7.94 (br.d,
J = 8.1, 2H, H-2 and H-6 ), 7.53 (br.d, J = 8.1, 2H, H-3
and H-5 ), 7.20–7.18 (m, 2H, H-3 and H-6 ), 7.02 (br.d,
J = 7.5, 1H, H-4 ), 6.97 (br.s, 2H, H N-2), 6.28 (s, 1H, H-5),
6
0
00
000
000
000 0000 0000 000 000
1 ), 131.37 (C-4 ), 129.40 (C-5 ), 128.31 (C-3 & C-5 ),
0
00
0000
0000
000 000 0000 0000
127.68 (C-2 and C-6 ), 121.61 (C-2 ), 117.91 (C-6 ),
0
000
00 000
102.37 (C-5), 38.56 (C-1 ), 36.50 (C-8 ), 27.53 (C-6), 19.59
2
0
00
0000 0000 00
(CH -3 ), 18.77 (CH -4 ), 14.65 (C-2 ). Anal. Calc. for
3 3
4.50 (s, 2H, CH -8 ), 4.00 (s, 2H, CH -6), 3.87 (q, J = 7.1,
2
2
0
0
0000
2
5
H, CH -1 ) 2.32 (br.s, 3H, CH -2 ), 2.24 (br.s, 3H, CH3-
C H N OS (478.63): C, 60.23; H, 5.48; N, 17.56. Found: C,
24 26 6 2
2
3
0
000
00 13
), 1.04 (t, J = 7.1, CH -2 ); C-NMR (150 MHz, DMSO-
60.30; H, 5.42; N, 17.58.
3
0
00
0
d , δ/ppm): 168.60 (C-2), 164.84 (C-7 ), 153.18 (C-5 ), 148.04
4-[({5-[(2-Amino-1,3-thiazol-4-yl)methyl]-4-ethyl-
4H-1,2,4-triazol-3-yl}sulfanyl)methyl]-N-(3,5-dimethyl
phenyl)benzamide (9e). Brick Red solid; Yeld: 90%;
6
0 000 0000
000 0000 0000 000
(C-3 ), 146.15 (C-4), 141.06 (C-4 ), 136.10 (C-1 ), 133.58
(
C-1 ), 130.44 (C-2 ), 130.05 (C-3 ), 128.88 (C-3 & C-
0
00
000
000
0
0000
0000
ꢀ
−1
5
1
), 127.70 (C-2 and 6 ), 127.03 (C-4 ), 126.58 (C-6 ),
m.p. 102–104 C; Mol. Formula: C H N OS ; Mol. Mass.:
24
26
6
2
0
000
−1
02.38 (C-5), 38.58 (C-1 ), 36.43 (C-8 ), 27.53 (C-6), 20.46
478.16 gmol ; IR (KBr, ʋ/cm ): 3340 (N H str.), 3041
(C H str. of aromatic ring), 2930 ( CH2 str.), 1674 (C O
str.), 1561 (C C str. of aromatic ring), 1510 (C N str.), 1160
0000 0000 00
CH -5 ), 17.41 (CH -2 ), 14.64 (C-2 ). Anal. Calc. for
3 3
(
C H N OS (478.63): C, 60.23; H, 5.48; N, 17.56. Found: C,
24
26
6
2
1
6
0.24; H, 5.46; N, 17.58.
-[({5-[(2-Amino-1,3-thiazol-4-yl)methyl]-4-ethyl-
H-1,2,4-triazol-3-yl}sulfanyl)methyl]-N-(2,6-dimethyl
(C N C bond str.), 618 (C S str.); H-NMR (600 MHz,
0000
DMSO-d , δ/ppm): 10.03 (s, 1H, CO NH-1 ), 7.87 (br.d,
6
J = 8.1, 2H, H-2 and H-6 ), 7.47 (br.d, J = 8.0, 2H, H-3
and H-5 ), 7.39 (br.s, 2H, H-2 and H-6 ), 6.91 (br.s, 2H,
4
0
00
000
000
4
0
00
0000
0000
phenyl)benzamide (9c). Light Brown solid; Yield: 94%;
ꢀ
0000
m.p. 132–134 C; Mol. Formula: C H N OS ; Mol. Mass.:
H N-2), 6.74 (br.s, 1H, H-4 ), 6.22 (s, 1H, H-5), 4.44 (s, 2H,
24
26
6
2
2
−1
000 00
CH -8 ), 3.94 (s, 2H, CH -6), 3.81 (q, J = 7.1 2H, H-1 ) 2.26
2 2
4
78 gmol-1; IR (KBr, ʋ/cm ): 3353 (N H str.), 3057 (C H
0000 0000 00
(br,s, 6H, CH -3 and CH -5 ), 0.98 (t, J = 7.1, 3H, H-2 );
3 3
str. of aromatic ring), 2930 ( CH2 str.), 1662 (C O str.),
575 (C C str. of aromatic ring), 1529 (C N str.), 1171
13
1
C-NMR (150 MHz, DMSO-d , δ/ppm): 168.58 (C-2), 164.92
6
1
000 0 0
(C-7 ), 153.18 (C-5 ), 148.00 (C-3 ), 146.16 (C-4), 141.07 (C-
(C N C bond str.), 637 (C S str.); H-NMR (600 MHz,
0
000
000 0000 0000 0000
4 ), 138.90 (C-1 ), 137.46 (C-3 and C-5 ), 133.97 (C-
DMSO-d , δ/ppm): 9.71 (s, 1H, CO NH-1 ), 7.92 (br.d,
J = 8.1, 2H, H-2 and H-6 ), 7.49 (br.d, J = 8.1, 2H, H-3
and H-5 ), 7.11 (br.s, 3H, H-3 , H-4 & H-5 ), 6.91 (br.s,
6
0
00
000
000
000 000 000 000 000
1 ), 128.83 (C-3 & C-5 ), 127.81 (C-2 and 6 ), 125.15
0
00
0000
0000
0000
0000 0000 0000
(C-4 ), 118.12 (C-2 and C-6 ), 102.38 (C-5), 38.56 (C-
0
00
00 000 0000 0000
1 ), 36.45 (C-8 ), 27.52 (C-6), 21.08 (CH -3 and 5 ),
3
2H, H N-2), 6.23 (s, 1H, H-5), 4.45 (s, 2H, CH -8 ), 3.94 (s,
2
2