Med Chem Res
N-(2-(2-methoxyphenylamino)-2-oxoethyl)benzamide (4)
HCl (15 mL), 10 % NaOH (15 mL), and water (20 mL).
The organic phase was dried over anhydrous Na2SO4 and
then evaporated under reduced pressure. The precipitate
was crystallized from ethanol:water (1:1) to furnish title
compounds.
Yield 67 %; mp 106 °C; IR tmaks (KBr): 3330, 3056, 1681,
1648, 1538, 1486 cm-1; 1H NMR (DMSO-d6): d 3.78 (3H,
s, OCH3), 4.09 (2H, d, J = 5.5 Hz, CH2), 6.89 (1H, t,
J = 7.4 Hz, H-4), 7.01–7.05 (2H, m, H-3 and H-5),
7.47–7.55 (3H, m, H-30, H-40 and H-50), 7.90 (2H, dd,
J = 1.2; 7.6 Hz, H-20 and H-60), 8.02 (1H, d, J = 7.8 Hz,
H-6), 8.92 (1H, bs, NH–CH2), 9.14 (1H, bs, NH–phenyl);
13C NMR (DMSO-d6): d 44.3, 56.4, 111.8, 121.1, 124.9,
127.8, 128.0, 129.1, 132.2, 134.6, 150.0, 167.6, 168.5 ppm;
MS (API-ES) m/z (%):285 (M?H?, 73); Anal. calcd. for
C16H16N2O3: C, 67.59; H, 5.67; N, 9.85. Found: C, 67.37;
H, 5.61; N, 9.79.
N-(2-oxo-2-(phenylamino)ethyl)benzamide (1)
Yield 26 %; mp 216 °C (lit.24 213–215 °C); IR tmaks
(KBr): 3274, 3139, 1683, 1639, 1540, 1492 cm-1
;
1H NMR (DMSO-d6): d 4.05 (2H, d, J = 5.6 Hz, CH2),
7.03 (1H, td, J = 1.2; 7.4 Hz, H-4), 7.29 (2H, td, J = 2.0;
8.0 Hz, H-3 and H-5), 7.45–7.49 (2H, m, H-2 and H-6),
7.52–7.56 (1H, m, H-40), 7.58–7.60 (2H, m, H-30 and H-50),
7.90 (2H, dd, J = 1.6; 7.0 Hz, H-20 and H-60), 8.79 (1H,
t, J = 5.5 Hz, NH–CH2), 10.01 (1H, bs, NH–phenyl);
13C NMR (DMSO-d6): d 43.6, 119.9, 123.9, 128.0, 129.0,
129.4, 132.1, 134.7, 139.6, 167.3, 168.5 ppm; (MS
(API-ES) m/z (%): 255 (M?H?, 70); Anal. calcd. for
C15H14N2O2: C, 70.85; H, 5.55; N, 11.02. Found: C, 70.69;
H, 5.32; N, 11.05.
N-(2-(2-ethylphenylamino)-2-oxoethyl)benzamide (5)
Yield 32 %; mp 187 °C; IR tmaks (KBr): 3255, 3089, 1668,
1
1639, 1536, 1490 cm-1; H NMR (CDCl3): d 1.09 (3H, t,
J = 7.4 Hz, CH3), 2.57 (2H, q, J = 7.4; 15.0 Hz,
CH2CH3), 4.08 (2H, d, J = 5.1 Hz, CH2), 7.11–7.22 (3H,
m, H-4, H-5 and H-6), 7.39–7.53 (4H, m, H-3, H-30, H-40
and H-50), 7.90 (2H, dd, J = 1.2; 7.6 Hz, H-20 and H-60),
8.83 (1H, t, J = 5.5 Hz, NH–CH2), 9.29 (1H, bs, NH–
phenyl); 13C NMR (DMSO-d6): d 14.9, 24.4, 43.9, 126.1,
126.2, 126.6, 128.0, 129.0, 129.2, 132.1, 134.7, 136.1,
138.2, 167.4, 168.9 ppm; MS (API-ES) m/z (%):281
(M-H-, 100); Anal. calcd. for C17H18N2O2: C, 72.32; H,
6.43; N, 9.92. Found: C, 72.34; H, 6.31; N, 9.95.
N-(2-(2-chlorophenylamino)-2-oxoethyl)benzamide (2)
Yield 77 %; mp 179 °C; IR tmaks (KBr): 3274, 3110, 1679,
1643, 1538, 1488 cm-1; 1H NMR (DMSO-d6): d 4.12 (2H,
d, J = 6.2 Hz, CH2), 7.16 (1H, td, J = 1.6; 7.7 Hz, H-4),
7.32 (1H, td, J = 1.4; 7.7 Hz, H-5), 7.46–7.56 (4H, m,
H-3, H-30, H-40 and H-50), 7.82 (1H, dd, J = 1.6; 8.2 Hz,
H-6), 7.88 (2H, dd, J = 1.2; 7.0 Hz, H-20 and H-60), 8.90
(1H, t, J = 5.9 Hz, NH–CH2), 9.49 (1H, bs, NH–phenyl);
13C NMR (DMSO-d6): d 44.0, 125.7, 126.3, 126.7, 128.0,
128.2, 129.0, 130.1, 132.2, 134.5, 135.4, 167.5, 169.0 ppm;
MS (API-ES) m/z (%): 287(M-H-, 100), 289(M-H?2,
35); Anal. calcd. for C15H13ClN2O2: C, 62.40; H, 4.54; N,
9.70. Found: C, 62.25; H, 4.54; N, 9.76.
N-(2-(2-isopropylphenylamino)-2-oxoethyl)benzamide (6)
Yield 17 %; mp 120 °C; IR tmaks (KBr): 3262, 3089, 1666,
1639, 1527, 1486 cm-1; 1H NMR (DMSO-d6): d 1.11 (6H,
d, J = 6.6 Hz, 2 9 CH3), 3.13-3.17 (1H, m, CH), 4.08
(2H, d, J = 5.5 Hz, CH2), 7.14–7.17 (2H, m, H-4 and H-5),
7.28–7.30 (2H, m, H-3 and H-6), 7.45–7.49 (2H, m, H-30
and H-50), 7.51–7.55 (1H, m, H-40), 7.89 (2H, dd, J = 1.6;
7.0 Hz, H-20 and H-60), 8.82 (1H, t, J = 5.6 Hz, NH–CH2),
9.35 (1H, bs, NH–phenyl); 13C NMR (DMSO-d6): d 23.9,
27.7, 43.8, 126.2, 126.4, 126.8, 127.1, 128.0, 129.0, 132.1,
134.7, 135.3, 143.6, 167.4, 169.1 ppm; MS (API-ES)
m/z (%):295 (M-H-, 100); Anal. calcd. for C18H20N2O2:
C, 72.95; H, 6.80; N, 9.45. Found: C, 73.16; H, 6.77; N,
9.50.
N-(2-oxo-2-(o-tolylamino)ethyl)benzamide (3)
Yield 22 %; mp 195 °C; IR tmaks (KBr): 3268, 3050, 1673,
1641, 1542, 1490 cm-1; 1H NMR (DMSO-d6): d 2.19 (3H,
s, CH3), 4.02 (2H, d, J = 5.6 Hz, CH2), 7.06 (1H, t,
J = 7.4 Hz, H-4), 7.13–7.20 (2H, m, H-5 and H-6),
7.41–7.55 (4H, m, H-3, H-30, H-40 and H-50), 7.89 (2H, dd,
J = 1.2; 8.2 Hz, H-20 and H-60), 8.90 (1H, t, J = 5.9 Hz,
NH–CH2), 9.49 (1H, bs, NH–phenyl); 13C NMR (DMSO-
d6): d 18.4, 43.9, 125.4, 125.8, 126.6, 128.0, 129.0, 131.0,
132.1, 132.5, 134.7, 136.8, 167.4, 168.6 ppm; MS
(API-ES) m/z (%):267 (M-H-, 100); Anal. calcd. for
C16H16N2O2: C, 71.62; H, 6.01; N, 910.44. Found: C,
71.50; H, 5.89; N, 10.39.
N-(2-(2,6-dimethylphenylamino)-2-oxoethyl)benzamide (7)
Yield 80 %; mp 224 °C; IR tmaks (KBr): 3417, 3249, 1668,
1627, 1569, 1536 cm-1; 1H NMR (DMSO-d6): d 2.13 (6H,
s, 2 9 CH3), 4.05 (2H, d, J = 5.9 Hz, CH2), 7.03–7.04
(3H, m, H-3, H-4 and H-5), 7.45 (2H, d, J = 7.0 Hz, H-30
and H-50), 7.48–7.55 (1H, m, H-40), 7.89 (2H, dd, J = 1.6;
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