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EL‐SHERSHABY ET AL.
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2‐chloro‐N‐arylacetamide
or
3‐chloro‐N‐arylpropanamide
(s, 1H, quinoline‐H4), 7.90 (d, 1H, J = 9 Hz, quinoline‐H8), 7.72 (d, 2H,
J = 6 Hz, phenyl‐H3, H5), 7.43 (d, 1H, J = 9.0 Hz, quinoline‐H7), 7.31
(t, 1H, J = 6 Hz, phenyl‐H4) 7.50 (s, 1H, quinoline‐H5), 4.31 (s, 2H,
S–CH2), 2.5 (s, 3H, CH3). 13C NMR (DMSO‐d6, 100 MHz) δ (ppm):
18.06 (CH3), 34.70 (S–CH2), 104.51, 115.85, 126.48, 127.27, 127.48,
127.57, 134.99, 135.25, 135.62, 135.78, 143.46, 146.41, and 156.12
(aromatic carbons), 123.82 (C≡N), and 165.52 (C═O). MS (m/z): 403
(C19H13Cl2N3OS, 2.1%, M+2), 401 (C19H13Cl2N3OS, 3.8%, M+), 241
(C13H9N2OS, 100%), 199 (C11H7N2S, 13.9%), 167 (C11H7N2, 34.7%).
Anal. calc. for C19H13Cl2N3O2S (M.W. = 401): C, 56.73; H, 3.26;
N, 10.45%; found: C, 56.91; H, 3.39; N, 10.66%.
derivative[36–38] (0.011 mol) was added, and the reaction mixture was
heated to 120°C for 7 hr with continuous stirring. After the reaction was
completed (monitored by TLC), the mixture was allowed to stand
overnight. Later, after adding distilled cold water (100 ml), the obtained
solid products were collected through filtration, washed with three
repetitive portions of cold water (100 ml each) to remove the side salt
product triethylammonium chloride, dried, crystallized from ethanol, and
finally purified by using the column chromatography technique using
hexane ethyl acetate as an eluent to afford the pure amide derivatives
(12–29) in reasonable yields.
N‐(4‐Chlorophenyl)‐2‐[(3‐cyano‐6‐methylquinolin‐2‐yl)thio]-
acetamide (12)
Yellowish white solid. Yield: 85%; m.p. 230°C. IR (KBr) cm−1: 3,295
2‐[(3‐Cyano‐6‐methylquinolin‐2‐yl)thio]‐N‐(2,6‐dimethylphenyl)-
acetamide (15)
White solid. Yield: 70%; m.p. 270°C. IR (KBr) cm−1: 3,249 (NH), 3,028
(CH aromatic), 2,984 (CH aliphatic), 2,222 (C≡N), 1,660 (C═O). 1H
NMR (DMSO‐d6) δ ppm: 9.6 (s, 1H, NH, D2O‐exchangeable), 8.9 (s, 1H,
quinoline‐H4), 7.91 (d, 1H, J = 9 Hz, quinoline‐H8), 7.83 (d, 2H, J = 6 Hz,
phenyl‐H3, H5), 7.72 (d, 1H, J = 9.0 Hz, quinoline‐H7), 7.02 (t, 1H,
J = 6 Hz, phenyl‐H4), 7.54 (s, 1H, quinoline‐H5), 4.33 (s, 2H, S–CH2),
2.50 (s, 3H, quinoline‐CH3), 2.08 (s, 6H, phenyl‐2CH3). 13C NMR
(DMSO‐d6, 100 MHz) δ (ppm): 18.06, 20.26, 33.71 (aliphatic carbons),
104.52, 115.86, 126.49, 127.28, 127.49, 127.58, 135.00, 135.26,
135.63, 136.78, 143.47, 146.42, and 156.13 (aromatic carbon atoms),
123.83 (C≡N), and 165.53 (C═O). MS (m/z), 361 (C21H19N3OS, .85%,
M+), 241 (C13H9N2OS, 90.6%), 213 (C12H9N2S, 100%), 199 (C11H7N2S,
18.3%). Anal. calc. for C21H19N3OS (M.W. = 361): C, 69.78; H, 5.3;
N, 11.63%; found: C, 69.91; H, 5.39; N, 11.76%.
(NH), 3,051 (CH aromatic), 2,904 (CH aliphatic), 2,221 (C≡N), 1,689
(C═O). 1H NMR (DMSO‐d6)
δ ppm: 9.89 (s, 1H, NH, D2O‐
exchangeable), 8.9 (s, 1H, quinoline‐H4), 7.8 (d, 1H, J = 9.0 Hz,
quinoline‐H8), 7.5 (d, 1H, J = 9.0 Hz, quinoline‐H7), 7.4 (d, 2H,
J = 9.6 Hz, phenyl‐H2, H6), 7.1 (d, 2H, J = 9.6 Hz, phenyl‐H3, H5), 7.3
(s, 1H, quinoline‐H5), 4.37 (s, 2H, S–CH2), 2.49 (s, 3H, CH3). 13C NMR
(DMSO‐d6, 100 MHz) δ (ppm): 18.11 (CH3), 34.75 (S–CH2), 104.56,
115.90, 126.53, 127.32, 127.53, 127.62, 135.04, 135.30, 135.67,
135.83, 143.51, 146.45, and 156.17 (aromatic carbons), 123.84
(C≡N), and 165.57 (C═O). MS (m/z): 369 (C19H14ClN3OS, 1.53%, M
+2), 367 (C19H14ClN3OS, 4.17%, M+), 241 (C13H9N2OS, 100%), 213
(C12H9N2S, 46.37%), 199 (C11H7N2S, 1.52%), 167 (C11H7N2, 15.69%),
90 (C7H6, 4%). Anal. calc. for C19H14ClN3OS (M.W. = 367): C, 62.04;
H, 3.42; N, 11.42%; found: C, 62.16; H, 3.91; N, 11.53%.
2‐[(3‐Cyano‐6‐methylquinolin‐2‐yl)thio]‐N‐(4‐methoxyphenyl)-
acetamide (16)
Greyish white solid. Yield: 85%; m.p. 225°C. IR (KBr) cm−1: 3,257
2‐[(3‐Cyano‐6‐methylquinolin‐2‐yl)thio]‐N‐(m‐tolyl)acetamide (13)
Yellowish solid. Yield: 85%; m.p. 210°C. IR (KBr) cm−1: 3,254 (NH),
3,043 (CH aromatic), 2,976 (CH aliphatic), 2,223 (C≡N), 1,662 (C═O).
1H NMR (DMSO‐d6) δ ppm: 10.30 (s, 1H, NH, D2O‐exchangeable),
8.81 (s, 1H, quinoline‐H4), 7.82 (d, 1H, J = 9.0 Hz, quinoline‐H8), 7.77
(d, 1H, J = 9.0 Hz, quinoline‐H7), 7.53 (s, 1H, phenyl‐H2), 7.44 (s, 1H,
quinoline‐H5), 7.32 (d, 1H, J = 7.8 Hz, phenyl‐H6), 7.25 (t, 1H,
J = 10.80 Hz, phenyl‐H5), 6.80 (d, 1H, J = 6 Hz, phenyl‐H4), 4.29
(s, 2H, S–CH2), 2.26 (s, 3H, quinoline‐CH3), 2.26 (s, 3H, phenyl‐CH3).
13C NMR (DMSO‐d6, 100 MHz) δ (ppm): 18.09 (CH3), 19.17 (CH3),
34.73 (S–CH2), 104.54, 115.90, 126.51, 127.30, 127.54, 127.60,
135.05, 135.32, 135.69, 135.85, 143.51, 146.43, and 156.16 (aro-
matic carbons), 123.86 (C≡N), and 165.55 (C═O). MS (m/z): 347
(C20H17N3OS, 9.6%, M+), 241 (C13H9N2OS, 100%), 213 (C12H9N2S,
70.6%), 199 (C11H7N2S, 2.5%), 167 (C11H7N2, 28.1%), 90 (C7H6,
2.8%). Anal. calc. for C20H17N3OS (M.W. = 347): C, 69.14; H, 4.93;
N, 12.09%; found: C, 69.36; H, 5.1; N, 12.26%.
(NH), 3,049 (CH aromatic), 2,922 (CH aliphatic), 2,223 (C≡N), 1,662
(C═O). 1H NMR (DMSO‐d6)
δ ppm: 10.26 (s, 1H, NH, D2O‐
exchangeable), 8.82 (s, 1H, quinoline‐H4), 7.85 (d, 1H, J = 9.0 Hz,
quinoline‐H8), 7.7 (d, 1H, J = 9.0 Hz, quinoline‐H7), 7.51 (d, 2H,
J = 9.6 Hz, phenyl‐H2, H6), 6.82 (d, 2H, J = 9.6 Hz, phenyl‐H3, H5),
7.43 (s, 1H, quinoline‐H5), 4.24 (s, 2H, S–CH2), 3.34 (s, 3H, phenyl‐
OCH3), 2.40 (s, 3H, quinoline‐CH3). 13C NMR (DMSO‐d6, 100 MHz)
δ (ppm): 18.19 (CH3), 34.83 (S–CH2), 57.26 (OCH3), 104.64, 115.98,
126.61, 127.40, 127.64, 127.70, 135.15, 135.42, 135.79, 135.95,
143.61, 146.53, and 156.26 (aromatic carbons), 123.88 (C≡N), and
165.65 (C═O). MS (m/z): 363 (C20H17N3O2S, 9.4%, M+), 241
(C13H9N2OS, 21.54%), 213 (C12H9N2S, 14.9%), 123 (C7H9NO, 100%).
Anal. calc. for C20H17N3O2S (M.W. = 363): C, 66.10; H, 4.71; N,
1.56%; found: C, 66.19; H, 4.74; N, 11.61%.
2‐[(3‐Cyano‐6‐methylquinolin‐2‐yl)thio]‐N‐(4‐nitrophenyl)-
acetamide (17)
Yellowish white solid. Yield: 85%; m.p. 230°C. IR (KBr) cm−1: 3,227
2‐[(3‐Cyano‐6‐methylquinolin‐2‐yl)thio]‐N‐(2,6‐dichlorophenyl)-
acetamide (14)
White solid. Yield: 85%; m.p. 250°C. IR (KBr) cm−1: 3,241 (NH), 3,022
(CH aromatic), 2,957 (CH aliphatic), 2,226 (C≡N), 1,673 (C═O). 1H
NMR (DMSO‐d6) δ ppm: 10.20 (s, 1H, NH, D2O‐exchangeable), 8.9
(NH), 3,043 (CH aromatic), 2,929 (CH aliphatic), 2,221 (C≡N), 1,675
(C═O). 1H NMR (DMSO‐d6)
exchangeable), 8.9 (s, 1H, quinoline‐H4), 8.21 (d, 1H, J = 9.0 Hz,
δ ppm: 11.02 (s, 1H, NH, D2O‐