HETEROCYCLES, Vol. 78, No. 1, 2009
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m/z 244 [M+H]+ (40%). Anal. Calcd for C14H17N3O: C, 69.11; H, 7.04; N, 17.27. Found: C, 68.93; H,
7.20; N, 17.08.
N-(2,5-Dimethyl-1H-pyrrol-1-yl)-3-(phenylamino)propanamide (4). A mixture of 2 (0.54 g, 3 mmol),
2-propanol (75 mL), 2,5-hexanedione (0.69 g, 6 mmol), and acetic acid (1.5 mL) was refluxed for 20 h.
Then cold water (25 mL) was added. The crystals were filtered and recrystallized from EtOH. Yield 0.55
g (71 %), mp. 134–135 ºC. 1H NMR (300 MHz, DMSO-d6): δ 1.96 (s, 6H, 2 CH3), 2.55 (t, 2H, J = 6.9 Hz,
COCH2), 3.36 (t, 2H, J = 6.9 Hz, NHCH2), 5.62 (s, 2H, 2 CH), 5.65 (s, 1H, NH), 6.55 (t, 1H, J = 7.2 Hz,
Har-4), 6.62 (d, 2H, J = 7.2 Hz, Har-2,6), 7.09 (t, 2H, J = 7.2 Hz, Har-3,5), 10.61 (s, 1H, NH). 13C NMR (75.4
MHz, DMSO-d6): δ 170.28 (C-9), 148.50 (C-1), 128.89 (C-3, 5), 126.67 (C-10, 13), 115.77 (C-4), 102.79
(C-11, 12), 112.03 (C-2, 6), 38.38 (C-7), 33.14 (C-8), 10.89 ((С-14, 15). IR (KBr), ν/cm-1: 3368 (NH),
1668 (C=O). MS (ESI, 20V): m/z 258 [M+H]+ (70%). Anal. Calcd for C15H19N3O: C, 70.01; H, 7.44; N,
16.33. Found: C, 69.95; H, 7.9; N, 15.98.
3-(Phenylamino)-N-[(phenylcarbamoyl)amino]propanamide (5). To a solution of 2 (4.48 g, 25 mmol)
in methanol (50 mL) phenyl isocyanate (2.98 g, 2.71 mL, 25 mmol) was added dropwise. The reaction
mixture was refluxed for 1 h, and cooled down. The crystals were filtered, washed with MeOH, and
recrystallized from MeOH. Yield 6.0 g (80 %), mp 133–134 ºC. 1H NMR (300 MHz, DMSO-d6): δ 2.46
(t, 2H, J = 7.2 Hz, CH2CO), 3.30 (t, 2H, J = 7.2 Hz CH2N), 6.55 (t, 1H, J = 7.2 Hz, Har-4), 6.96 (d, 2H, J =
8.5 Hz, Har-2,6), 7.09 (t, 2H, J = 8.5 Hz, Har-3,5), 7.23–7.47 (m, 5H, Har’), 8.06 (s, 1H, NHNHCO), 8.72 (s,
13
1H, NHNHCO), 9.76 (s, 2H, NHAr). C NMR (75.4 MHz, DMSO-d6): δ 170.84 (C-9), 155.35 (C-1),
148.50 (C-10), 139.51 (C-11), 128.88 (C-3, 5), 128.58 (C-13, 15), 121.85 (C-14), 118.43 (C-4), 115.83
(C-12, 16),112.09 (C-2, 6), 43.02 (C-7), 33.17 (C-8). IR (KBr), ν/cm-1: 3375, 3344, 3206 (NH); 1638
(CO). MS (ESI, 20 V): m/z 299 [M+H]+ (85 %). Anal. Calcd for C16H18N4O2: C, 64.41; H, 6.08; N, 18.78.
Found: C, 64.04; H, 6.03; N, 18.30.
3-(Phenylamino)-N-[(phenylthiocarbamoyl)amino]propanamide (6). To a solution of 2 (4.48 g, 25
mmol) in MeOH (50 mL) phenyl isothiocyanate (3.38 g, 2.99 mL, 25 mmol) was added dropwise. The
reaction mixture was refluxed for 5 min. The crystals were filtered, washed with Et2O, and recrystallized
o
1
from DMF – water mixture. Yield 5.97 g (65 %), mp 175–176 C. H NMR (300 MHz, DMSO-d6): δ
2.48 (t, 2H, J = 7.2 Hz, CH2CO), 3.29 (q, 2H, J = 7.2 Hz, CH2NH), 5.56 (s, 1H, NHAr), 6.51 (t, 1H, J =
7.2 Hz, Har-4), 6.57 (d, 2H, J = 8.5 Hz, Har-2,6), 7.08 (t, 2H, J = 7.2 Hz, Har-3,5), 7.16 (t, 1H, J = 7.2 Hz;
Har’-4), 7.33 (t, 2H, J = 7.2 Hz, Har’-3,5), 7.43 (d, 2H, J=7.2 Hz, Har’-2,6), 9.58 (s, 2H, NHNHCS), 10.00 (s,
1H, NHAr’). 13C NMR (75.4 MHz, DMSO-d6): δ 175.17 (C-10), 170.72 (C-9), 148.48 (C-1), 138.99
(C-11), 128.85 (C-3, 5), 127.99 (C-13, 15), 125.69 (C-14), 125.06 (C-4), 115.81 (C-12, 16), 112.06 (C-2,
6), 43.68 (C-7), 33.19 (C-8). IR (KBr), ν/cm-1: 3362, 3266, 3137 (NH), 1678 (CO), 1175 (CS). MS (ESI,
20V): 315 [M+H]+ (80%). Anal. Calcd for C16H18N4OS: C, 61.12; H, 5.77; N, 17.82. Found: C, 61.02; H,