TURKY ET AL.
11 of 13
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1
27.55, (N‐phenyl C‐4), 127.11, (N‐phenyl C‐2, C‐6), 125.44, (NH‐
phenyl C‐2, C‐6), 120.67, (phenyl C‐2, C‐6), 36.80, (SCH ); MS (m/z,
): 420 (M+, 24.62%), 422 (M+2, 7.17%). Anal. calc. for
17ClN OS (M.W. = 420): C, 62.78; H, 4.07; N, 13.31; found: C,
2.80; H, 4.15; N, 13.50%.
20 4
4.09%). Anal. calc. for C26H N OS (M.W. = 436): C, 71.54; H, 4.62; N,
2
12.83; found: C, 71.59; H, 4.70; N, 12.79%.
%
C
22
H
4
N‐(4‐Bromophenyl)‐2‐[(5‐(4‐chlorophenyl)‐4‐phenyl‐4H‐1,2,4‐
triazol‐3‐yl)thio]acetamide (17)
6
−1
White solid (0.40 g, 84%); mp: 254–256°C; IR (KBr) νmax cm : 3,438
2
‐[(4,5‐Diphenyl‐4H‐1,2,4‐triazol‐3‐yl)thio]‐N‐(p‐tolyl)‐
acetamide (14)
White solid (0.26 g, 66%); mp: 223–225°C; IR (KBr) νmax cm : 3,452
(NH), 3,052 (CH aromatic), 2,987 (CH aliphatic), 1,675 (C═O), 1,490
1
(C═C); H NMR (DMSO‐d
6
) δ: 10.47 (brs, 1H, NH), 7.58 (d, J = 1.8 Hz,
−
1
2H), 7.56 (t, J = 1.8 Hz, 1H), 7.53 (d, J = 1.8 Hz, 2H), 7.48 (d, J = 1.8 Hz,
(
(
NH), 3,078 (CH aromatic), 2,979 (CH aliphatic), 1,672 (C═O), 1,454
2H), 7.43 (t, J = 1.8 Hz, 2H), 7.41 (d, J = 1.8 Hz, 2H), 7.34 (d, J = 1.8 Hz,
13
1
C═C); H NMR (DMSO‐d
6
) δ: 10.36 (brs, 1H, NH), 7.56–7.35 (m,
), 2.49 (s,
) δ: 166.51, (C═O), 154.42, (triazole C‐
), 151.67, (triazole C‐3), 151.17, (N‐phenyl C‐1), 148.02, (NH‐phenyl
2H), 4.19 (s, 2H, SCH
2
6
); C NMR (DMSO‐d ) δ: 165.59, (C═O),
J = 1.8 Hz, 12H), 7.12 (d, J = 1.8 Hz, 2H), 4.18 (s, 2H, SCH
2
153.44, (triazole C‐5), 151.78, (triazole C‐3), 137.69, (N‐phenyl C‐1),
134.61, (NH‐phenyl C‐1), 133.46, (phenyl C‐4, N‐phenyl C‐4), 130.22,
(phenyl C‐1), 130.05, (NH‐phenyl C‐3, C‐5), 129.58, (phenyl C‐3, C‐5),
128.71, (N‐phenyl C‐3, C‐5), 127.52, (N‐phenyl C‐4), 127.03, (N‐
phenyl C‐2, C‐6), 125.36, (NH‐phenyl C‐2, C‐6), 120.60, (phenyl C‐2,
13
3
H, CH
3
); C NMR (DMSO‐d
6
5
C‐1), 139.51, (phenyl C‐4, N‐phenyl C‐4), 138.26, (phenyl C‐1),
33.82, (NH‐phenyl C‐3, C‐5), 130.02, (phenyl C‐3, C‐5), 129.94, (N‐
phenyl C‐3, C‐5), 129.11, (N‐phenyl C‐4), 127.77, (N‐phenyl C‐2, C‐6),
27.63, (NH‐phenyl C‐2, C‐6), 123.69, (phenyl C‐6), 119.62, (phenyl
C‐2), 36.74, (SCH ), 20.78, (CH ), 18.02, (CH ); MS (m/z, %): 400 (M+,
.15%). Anal. calc. for C23 OS (M.W. = 400): C, 68.98; H, 5.03; N,
3.99; found: C, 79.98; H, 5.18; N, 14.16%.
1
2
C‐6), 36.74, (SCH ); MS (m/z, %): 499 (M+, 04.62%), 501 (M+2,
1
3.98%). Anal. calc. for C22
H
16BrClN OS (M.W. = 499): C, 52.87; H,
4
2
3
3
3.23; N, 11.21; found: C, 52.80; H, 3.36; N, 11.30%.
6
1
20 4
H N
N‐(4‐Chlorophenyl)‐2‐{[5‐(4‐chlorophenyl)‐4‐phenyl‐4H‐1,2,4‐
triazol‐3‐yl]thio}acetamide (18)
−1
2
‐[(4,5‐Diphenyl‐4H‐1,2,4‐triazol‐3‐yl)thio]‐N‐(4‐methoxyphenyl)‐
White solid (0.37 g, 82%); mp: 248–250°C; IR (KBr) νmax cm : 3,444
acetamide (15)
(NH), 3,074 (CH aromatic), 2,984 (CH aliphatic), 1,674 (C═O), 1,488
−
1
1
White solid (0.27 g, 66%); mp: 226–228°C; IR (KBr) νmax cm
:
(C═C); H NMR (DMSO‐d
6
) δ: 10.48 (brs, 1H, NH), 7.61 (d, J = 1.8 Hz,
3
,422 (NH), 3,072 (CH aromatic), 2,990 (CH aliphatic), 1,672
2H), 7.58 (t, J = 1.8 Hz, 1H), 7.55 (d, J = 1.8 Hz, 2H), 7.45 (d, J = 1.8 Hz,
1
(
C═O), 1,449 (C═C); H NMR (DMSO‐d
6
) δ: 10.19 (brs, 1H, NH),
.58 (d, J = 1.8 Hz, 2H), 7.56 (t, J = 1.8 Hz, 1H), 7.46 (d, J = 1.8 Hz,
H), 7.43 (d, J = 1.8 Hz, 2H), 7.36 (t, J = 1.8 Hz, 2H), 7.34
), 3.72
) δ: 164.90, (C═O), 155.36,
triazole C‐5), 151.60, (triazole C‐3), 133.74, (N‐phenyl C‐1),
2H), 7.43 (t, J = 1.8 Hz, 2H), 7.39 (d, J = 1.8 Hz, 2H), 7.36 (d, J = 1.8 Hz,
1
3
7
2
2H), 4.20 (s, 2H, SCH
2
6
); C NMR (DMSO‐d ) δ: 165.61, (C═O),
153.46, (triazole C‐5), 151.80, (triazole C‐3), 137.71, (N‐phenyl C‐1),
134.63, (NH‐phenyl C‐1), 133.48, (phenyl C‐4, N‐phenyl C‐4), 130.24,
(phenyl C‐1), 130.07, (NH‐phenyl C‐3, C‐5), 129.60, (phenyl C‐3, C‐5),
128.73, (N‐phenyl C‐3, C‐5), 127.54, (N‐phenyl C‐4), 127.05, (N‐
phenyl C‐2, C‐6), 125.38, (NH‐phenyl C‐2, C‐6), 120.62, (phenyl C‐2,
(
(
(
d, J = 1.8 Hz, 2H), 6.90 (d, J = 1.8 Hz, 2H), 4.16 (s, 2H, SCH
2
1
3
s, 3H, OCH
3
); C NMR (DMSO‐d
6
1
31.91, (NH‐phenyl C‐1), 130.09, (phenyl C‐4, N‐phenyl C‐4),
29.97, (phenyl C‐1), 129.74, (NH‐phenyl C‐3, C‐5), 128.55, (phe-
1
2
C‐6), 36.76, (SCH ); MS (m/z, %): 454 (M+, 44.97%), 456 (M+2,
nyl C‐3, C‐5), 127.86, (N‐phenyl C‐3, C‐5), 127.61, (N‐phenyl C‐4),
26.53, (N‐phenyl C‐2, C‐6), 120.64, (NH‐phenyl C‐2, C‐6), 113.90,
14.08%). Anal. calc. for C22
H
16Cl OS (M.W. = 454): C, 58.03; H,
2 4
N
1
3.54; N, 12.30; Found: C, 58.12; H, 3.56; N, 12.36%.
(
phenyl C‐2, C‐6), 55.14, (OCH
3
), 36.80, (SCH
2
); MS (m/z, %): 416
(
M+, 14.12%). Anal. calc. for C23
H
20
N
4
O
2
S (M.W. = 416): C, 66.33;
2‐{[5‐(4‐Chlorophenyl)‐4‐phenyl‐4H‐1,2,4‐triazol‐3‐yl]thio}‐N‐(p‐
tolyl)acetamide (19)
H, 4.84; N, 13.45; found: C, 66.38; H, 4.91; N, 13.37%.
−
1
White solid (0.29 g, 68%); mp: 235–37°C; IR (KBr) νmax cm : 3,439
2
‐[(4,5‐Diphenyl‐4H‐1,2,4‐triazol‐3‐yl)thio]‐N‐(naphthalen‐1‐yl)‐
acetamide (16)
White solid (0.31 g, 72%); mp: 222–224°C; IR (KBr) νmax cm : 3,451
(NH), 3,078 (CH aromatic), 2,979 (CH aliphatic), 1,672 (C═O), 1,507
1
(C═C); H NMR (DMSO‐d
6
) δ: 10.24 (brs, 1H, NH), 757 (d, J = 1.8 Hz,
−
1
2H), 7.54 (t, J = 1.8 Hz, 1H), 7.45 (d, J = 1.8 Hz, 2H), 7.42 (d, J = 1.8 Hz,
(
(
NH), 3,031 (CH aromatic), 2,924 (CH aliphatic), 1,674 (C═O), 1,553
2H), 7.37 (t, J = 1.8 Hz, 2H), 7.34 (d, J = 1.8 Hz, 2H), 7.10 (d, J = 1.8 Hz,
13
1
C═C); H NMR (DMSO‐d
6
) δ: 10.38 (brs, 1H, NH), 7.68–7.36 (m,
2H), 4.18 (s, 2H, SCH
2
), 2.25 (s, 3H, CH
3 6
); C NMR (DMSO‐d ) δ:
1
3
1
1
1
1
3
7H), 4.19 (s, 2H, SCH
2
); C NMR (DMSO‐d
6
) δ: 170.20, (C═O),
170.23, (C═O), 155.49, (triazole C‐5), 149.60, (triazole C‐3), 145.33,
(N‐phenyl C‐1), 138.88, (NH‐phenyl C‐4), 137.57, (NH‐phenyl C‐1),
136.30, (phenyl C‐4), 134.52, (phenyl C‐1), 131.36, (phenyl C‐3, C‐5),
131.26, (NH‐phenyl C‐3, C‐5), 130.95, (phenyl C‐2, C‐6), 130.70, (N‐
phenyl C‐3, C‐5), 130.51, (N‐phenyl C‐4), 127.61, (N‐phenyl C‐2, C‐6),
55.51, (triazole C‐5), 149.62, (triazole C‐3), 145.34, (N‐phenyl C‐1),
37.23, (N‐phenyl C‐1), 134.45, (phenyl C‐4), 134.37, (naphthyl C‐4a),
31.18, (phenyl C‐4), 129.24, (phenyl C‐3, C‐5), 128.74, (N‐phenyl C‐
, C‐5), 128.55, (N‐phenyl C‐6), 127.65, (naphthyl C‐3), 127.54,
(
phenyl C‐2, C‐6), 126.61, (N‐phenyl C‐2, C‐6), 126.10, (naphthyl C‐7),
123.54, (NH‐phenyl C‐2, C‐6), 38.80, (SCH
(CH ). Anal. calc. for C23 19ClN OS (M.W. = 434): C, 63.51; H, 4.40;
N, 12.88; found: C, 63.60; H, 4.52; N, 13.01%.
2 3
), 21.33, (CH ), 18.02,
1
4
25.70, (naphthyl C‐8), 124.64, (naphthyl C‐8a), 121.91, (naphthyl C‐
), 107.13, (naphthyl C‐2), 40.84, (SCH ); MS (m/z, %): 436 (M+,
3
H
4
2