Journal of the Iranian Chemical Society
70 eV), m/z (%): 392 (M+, 24.5), 319 (base peak), 291 (4.9),
146 (15.7). Anal. Calcd for C24H28N2O3: C, 73.44; H, 7.19;
N, 7.14; found: C, 73.11; H, 7.16, N, 6.85.
421 (base peak), 342 (6.9), 198 (11.7), 91 (7.8). Anal. Calcd
for C20H18Br2N2O3: C, 48.61; H, 3.67; Br, 32.34; N, 5.67;
found: C, 48.27; H, 3.61, N, 5.34.
Ethyl 1‑(4‑chlorophenyl)‑4‑((4‑chlorophenyl)amino)
Ethyl 2‑methyl‑1‑(3‑nitrophenyl)‑4‑((3‑nitrophenyl)
‑2‑methyl‑5‑oxo‑2,5‑dihdro‑1H‑pyrrole‑2‑carboxylate (3e)
amino)‑5‑oxo‑2,5‑dihydro‑1H‑pyrrole‑2‑carboxylate (3h)
Pale yellow solid, recrystallized from ethanol, mp
218–220 °C. IR (KBr) (cm−1): 3309 (N–H), 3115 (=C–H),
Yellow solid, recrystallized from ethanol, mp 196–198 °C.
IR (KBr) (cm−1): 3316 (N–H), 3121 (=C–H), 1730 (C=O).
1H-NMR (400 MHz, CDCl3): δ (ppm) 1.15–1.45 (m, 3H,
CH3), 1.79 (s, 3H, CH3), 4.15–4.45 (m, 2H, OCH2), 6.22
(s, 1H, = CH), 7.03 (s, 1H, NH), 7.29–7.74 (m, 3H, Ar),
7.80–8.05 (m, 3H, Ar), 8.17–8.47 (m, 2H, Ar). 13C NMR
(100 MHz, CDCl3): δ (ppm) 14.1, 21.2, 63.0, 69.0, 110.2,
110.7, 116.6, 119.7, 121.4, 122.9, 130.1, 130.3, 130.6,
132.5, 136.9, 141.7, 148.7, 149.2, 166.9, 170.4. MS (EI,
70 eV), m/z (%): 426 (M+, 5.9), 353 (base peak), 307 (9.8),
163 (6.8). Anal. Calcd for C20H18N4O7: C, 56.34; H, 4.26;
N, 13.14; found: C, 56.02; H, 4.28, N, 12.83.
1
1731 (C=O). H-NMR (400 MHz, CDCl3): δ (ppm) 1.26
(t, 3H, J=7.2 Hz, CH3), 1.67 (s, 3H, CH3), 4.15–4.30 (m,
2H, OCH2), 5.97 (s, 1H, =CH), 6.74 (s, 1H, NH), 7.02 (d,
2H, J = 8.8 Hz, Ar), 7.30 (d, 2H, J = 8.6 Hz, Ar), 7.36 (d,
2H, J=8.8 Hz, Ar), 7.42 (d, 2H, J=8.8 Hz, Ar). 13C NMR
(100 MHz, CDCl3): δ (ppm) 14.1, 21.2, 62.4, 68.8, 108.0,
118.1, 126.6, 126.7, 129.3, 129.4, 132.6, 133.3, 134.4,
139.4, 167.2, 171.1. MS (EI, 70 eV), m/z (%): 408 (M+4,
2.0), 406 (M+2, 6.9), 404 (M+, 9.8), 331 (base peak), 152
(21.6), 91 (2.9). Anal. Calcd for C20H18Cl2N2O3: C, 59.27;
H, 4.48; Cl, 17.50; N, 6.91; found: C, 58.94; H, 4.51, N,
6.59.
Ethyl 1‑(4‑methoxy‑3‑(N‑phenylsulfamoyl)
phenyl)‑4‑((4‑methoxy‑3‑(N‑phenyl‑sulfamoyl)
phenyl)amino)‑2‑methyl‑5‑oxo‑2,5‑dihdro‑1H‑
pyrrole‑2‑carboxylate (4a)
Ethyl‑1‑(3‑chlorophenyl)‑4‑((3‑chlorophenyl)amino)‑2
‑methyl‑5‑oxo‑2,5‑dihdro‑1H‑pyrrole‑2‑carboxylate (3f)
White Solid, recrystallized from ethanol, mp 213–215 °C,
IR (KBr) ν (cm−1): 3308 (N–H), 3115 (=C–H), 1731
(C=O). 1H-NMR (400 MHz, CDCl3): δ (ppm) 1.26 (t, 3H,
J=7.2 Hz, CH3), 1.66 (s, 3H, CH3), 4.23 (q, 2H, CH2), 5.97
(s, 1H, = CH), 6.75 (s, 1H, NH), 7.11–7.22 (m, 3H, Ar),
7.32 (d, 1H, J = 8.8 Hz, Ar), 7.40 (d, 2H, J = 8.6 Hz, Ar),
7.51–7.55 (m, 1H, Ar), 7.82–7.85 (m, 1H, Ar). 13C NMR
(100 MHz, CDCl3): δ (ppm) 14.1, 21.3, 62.4, 68.8, 108.5,
118.6, 126.6, 126.7, 129.1, 130.2, 132.6, 134.3, 135.4, 136.0,
139.4, 167.2, 171.2. MS (EI, 70 eV): m/z (%)=408 (M+4,
2.1), 406 (M+2, 6.9), 404 (M+, 9.7), 331(base peak), 303
(8.1), 152 (21.7), 91(3.2). Anal. Calcd for C20H18Cl2N2O3:
C, 59.27; H, 4.48; Cl, 17.49; N, 6.91; found: C, 58.94; H,
4.35; N, 6.59.
White solid, recrystallized from ethanol, mp > 250 °C.
1
IR (KBr) (cm−1): 3299 (N–H), 1736 (C=O). H-NMR
(400 MHz, DMSO-d6): δ (ppm) 1.20 (t, 3H, J = 7.2 Hz,
CH3), 1.44 (s, 3H, CH3), 3.85 (s, 3H, OCH3), 3.92 (s,
3H, OCH3), 4.08–4.18 (m, 2H, CH2), 5.98 (s, 1H, = CH),
6.97–7.01 (m, 2H, Ar), 7.08–7.13 (m, 5H, Ar), 7.18–7.23
(m, 4H, Ar), 7.28 (d, 1H, J = 9.2 Hz, Ar), 7.46 (dd, 1H,
J1 =8.8, J2 =2.8 Hz, Ar), 7.54 (dd, 1H, J1 =8.8, J2 =2.8 Hz,
Ar), 7.70 (d, 2H, J=2.8 Hz, Ar), 8.45 (s, 1H, NH), 10.06 (s,
1H, SO2NH), 10.16 (s, 1H, SO2NH). 13C NMR (100 MHz,
DMSO-d6): δ (ppm) 14.3, 21.2, 56.8, 57.0, 62.4, 68.5, 108.0,
114.2, 114.3, 119.7, 119.8, 124.0, 124.1, 124.2, 127.0,
127.3, 128.1, 128.5, 129.4, 129.5, 133.5, 134.6, 135.0,
138.1, 138.4, 151.1, 155.5, 167.2, 171.3. MS (EI, 70 eV),
m/z (%): 706 (M+), 530 (0.1), 438 (0.2), 300 (0.9), 207 (2.9),
93 (base peak), 43 (73). Anal. Calcd for C34H34N4O9S2: C,
57.78; H, 4.85; N, 7.93; S, 9.07; found: C, 57.45; H, 4.81,
N, 7.61.
Ethyl 1‑(4‑bromophenyl)‑4‑((4‑bromophenyl)amino)‑2
‑methyl‑5‑oxo‑2,5‑dihydro‑1H‑pyrrole‑2‑carboxylate (3g)
White solid, recrystallized from ethanol, mp 233–235 °C. IR
(KBr) (cm−1): 3313 (N–H), 3115 (=C–H), 1730 (C=O). 1H-
NMR (400 MHz, CDCl3): δ (ppm) 1.25 (t, 3H, J=7.1 Hz,
CH3), 1.67 (s, 3H, CH3), 4.14–4.30 (m, 2H, OCH2), 5.97 (s,
1H, = CH), 6.74 (s 1H, NH), 6.97 (d, 2H, J= 8.0 Hz, Ar),
7.30 (d, 2H, J = 8.3 Hz, Ar), 7.44 (d, 2H, J = 8.0 Hz, Ar),
7.56 (d, 2H, J=8.3 Hz, Ar). 13C NMR (100 MHz, CDCl3):
δ (ppm) 14.1, 21.2, 62.5, 68.7, 108.2, 113.9, 118.6, 120.5,
126.9, 132.3, 134.9, 139.9, 167.2, 171.1. MS (EI, 70 eV),
m/z (%): 496 (M+4, 4.9), 494 (M+2, 11.8), 492 (M+, 3.9),
Ethyl 1‑(3‑(N‑(4‑chlorophenyl)sulfamoyl)‑4‑
methoxyphenyl)‑4‑((3‑(N‑(4‑chlorophenyl)
sulfamoyl)‑4‑methoxyphenyl)‑amino)
‑2‑methyl‑5‑oxo‑2,5‑dihdro‑1H‑pyrrole‑2‑carboxylate (4b)
White solid, recrystallized from ethanol, mp > 250 °C.
IR (KBr) (cm−1): 3296 (N–H), 1738 (C=O). H-NMR
1
(400 MHz, DMSO-d6): δ (ppm) 1.19 (t, 3H, J = 7.2 Hz,
CH3), 1.46 (s, 3H, CH3), 3.84 (s, 3H, OCH3), 3.92 (s,
1 3