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K. C. Majumdar et al.
PAPER
IR (neat): 1624, 1687, 1710, 2960 cm–1.
Anal. Calcd for C24H21NO3: C, 77.61; H, 5.70; N, 3.77. Found: C,
77.79; H, 5.72; N, 3.65.
1H NMR (400 MHz, CDCl3): d = 0.96 (t, J = 7.2 Hz, 3 H, CH2CH3),
1.16 (t, J = 7.2 Hz, 3 H, NCH2CH3), 1.40–1.49 (m, 2 H, CH2CH3),
1.65–1.72 (m, 2 H, COCH2CH2), 3.04 (t, J = 7.2 Hz, 2 H, COCH2),
3.92 (q, J = 7.2 Hz, 2 H, NCH2), 6.82 (d, J = 7.2 Hz, 1 H, HAr),
7.07–7.11 (m, 1 H, HAr), 7.21–7.24 (m, 1 H, HAr), 7.29–7.35 (m, 3
H, HAr), 7.46 (d, J = 7.6 Hz, 2 H, HAr), 7.67 (d, J = 7.6 Hz, 1 H, HAr).
2-(1,2-Dioxopentyl)-N-ethyl-N-(4-methylphenyl)benzamide
(3g)
White solid; yield: 67%; mp 58–59 °C.
IR (KBr): 1623, 1685, 1710, 2960 cm–1.
13C NMR (100 MHz, CDCl3): d = 12.6, 13.9, 22.4, 25.0, 37.1, 45.7,
112.3, 127.2, 127.8, 128.5, 129.4, 130.0, 130.4, 136.3, 137.0, 143.0,
168.6, 192.7, 200.8.
1H NMR (400 MHz, CDCl3): d = 1.03 (t, J = 7.2 Hz, 3 H, CH2CH3),
1.15 (t, J = 7.2 Hz, 3 H, NCH2CH3), 1.68–1.78 (m, 2 H, CH2CH3),
2.31 (s, 3 H, CH3), 3.02 (t, J = 7.2 Hz, 2 H, COCH2), 3.88 (q,
J = 7.2 Hz, 2 H, NCH2), 6.84 (d, J = 7.6 Hz, 1 H, HAr), 7.08–7.12
(m, 3 H, HAr), 7.27 (d, J = 8.0 Hz, 2 H, HAr), 7.31–7.35 (m, 1 H,
HAr), 7.66 (d, J = 7.6 Hz, 1 H, HAr).
13C NMR (100 MHz, CDCl3): d = 12.6, 13.8, 16.4, 21.0, 39.2, 45.7,
127.6, 128.5, 129.8, 130.0, 130.4, 136.3, 137.1, 140.3, 168.5, 192.8,
200.6.
MS (ESI): m/z = 360 [M + Na]+.
Anal. Calcd for C21H23NO3: C, 74.75; H, 6.87; N, 4.15. Found: C,
74.58; H, 6.99; N, 4.25.
2-(1,2-Dioxopentyl)-N-methyl-N-phenylbenzamide (3d)
White solid; yield: 78%; mp 64–65 °C.
IR (KBr): 1625, 1687, 1709, 2964 cm–1.
MS (ESI): m/z = 360 [M + Na]+.
Anal. Calcd for C21H23NO3: C, 74.75; H, 6.87; N, 4.15. Found: C,
74.77; H, 6.86; N, 4.24.
1H NMR (400 MHz, CDCl3): d = 1.03 (t, J = 7.2 Hz, 3 H, CH2CH3),
1.69–1.77 (m, 2 H, CH2CH3), 3.0 (t, J = 7.2 Hz, 2 H, COCH2), 3.43
(s, 3 H, NCH3), 6.83 (br s, 1 H, HAr), 7.13 (br s, 1 H, HAr), 7.20–7.23
(m, 1 H, HAr), 7.28–7.34 (m, 2 H, HAr), 7.36–7.40 (m, 3 H, HAr),
7.70 (d, J = 7.2 Hz, 1 H, HAr).
13C NMR (100 MHz, CDCl3): d = 13.7, 16.4, 38.5, 39.2, 126.8,
127.1, 128.5, 129.4, 130.0, 130.4, 130.6, 136.9, 138.9, 144.6, 169.4,
192.8, 201.0.
2-(1,2-Dioxo-2-phenylethyl)-N-ethyl-N-(4-methoxyphe-
nyl)benzamide (3h)
White solid; yield: 72%; mp 88–89 °C.
IR (KBr): 1625, 1662, 1684, 2947 cm–1.
1H NMR (400 MHz, CDCl3): d = 1.05 (t, J = 7.3 Hz, 3 H,
NCH2CH3), 3.25–3.32 (m, 1 H, NCHaHb), 3.79 (s, 3 H, OCH3),
4.26–4.33 (m, 1 H, NCHaHb), 6.83–6.88 (m, 1 H, HAr), 6.91 (dd,
J = 8.5, 3.0 Hz, 1 H, HAr), 7.06 (dd, J = 8.5, 3.0 Hz, 1 H, HAr), 7.21–
7.29 (m, 2 H, HAr), 7.35–7.38 (m, 1 H, HAr), 7.42–7.55 (m, 2 H,
HAr), 7.59–7.72 (m, 2 H, HAr), 7.82–7.88 (m, 1 H, HAr), 8.01 (d,
J = 7.3 Hz, 1 H, HAr), 8.15 (d, J = 8.5 Hz, 1 H, HAr).
13C NMR (100 MHz, CDCl3): d = 12.6, 45.7, 55.4, 125.7, 127.9,
128.3, 128.8, 129.1, 129.8, 130.5, 131.5, 132.4, 134.7, 136.4, 138.7,
144.2, 150.2, 168.8, 191.4, 193.2.
MS (ESI): m/z = 332 [M + Na]+.
Anal. Calcd for C19H19NO3: C, 73.77; H, 6.19; N, 4.53. Found: C,
74.03; H, 6.12; N, 4.39.
2-(1,2-Dioxopentyl)-N-ethyl-N-phenylbenzamide (3e)
Gummy; yield: 63%.
IR (neat): 1620, 1695, 1714, 2936 cm–1.
1H NMR (400 MHz, CDCl3): d = 1.03 (t, J = 7.6 Hz, 3 H, CH2CH3),
1.16 (t, J = 7.2 Hz, 3 H, NCH2CH3), 1.69–1.78 (m, 2 H, CH2CH3),
3.02 (t, J = 7.2 Hz, 1 H, COCH2), 3.92 (q, J = 7.2 Hz, 2 H, NCH2),
6.82 (d, J = 7.2 Hz, 1 H, HAr), 7.07–7.11 (m, 1 H, HAr), 7.20–7.25
(m, 1 H, HAr), 7.29–7.35 (m, 3 H, HAr), 7.40 (d, J = 7.6 Hz, 2 H,
HAr), 7.67 (d, J = 7.6 Hz, 1 H, HAr).
13C NMR (100 MHz, CDCl3): d = 12.6, 13.8, 16.4, 39.2, 45.7,
114.5, 127.2, 127.8, 128.5, 129.4, 130.0, 130.4, 134.2, 136.3, 144.3,
168.3, 192.8, 201.3.
MS (ESI): m/z = 410 [M + Na]+.
Anal. Calcd for C24H21NO4: C, 74.40; H, 5.46; N, 3.62. Found: C,
74.63, H, 5.58; N, 3.34.
N-(1,2-Dimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)-
2-(1,2-dioxo-2-phenylethyl)-N-methylbenzamide (3i)
Yellow solid; yield: 92%; mp 208–209 °C.
IR (KBr): 1623, 1662, 1677, 1709, 2944 cm–1.
1H NMR (400 MHz, CDCl3): d = 3.19 (s, 3 H, NCH3), 3.31 (s, 3 H,
NCH3), 3.36 (s, 3 H, NCH3), 7.31–7.33 (m, 1 H, HAr), 7.45–7.49 (m,
2 H, HAr), 7.52–7.56 (m, 2 H, HAr), 7.65–7.69 (m, 1 H, HAr), 7.72 (s,
1 H, uracil C6-H), 7.84–7.86 (m, 1 H, HAr), 8.07 (d, J = 8.0 Hz, 2 H,
HAr).
13C NMR (100 MHz, CDCl3): d = 28.4, 36.1, 37.3, 118.4, 126.7,
128.9, 129.9, 130.4, 131.4, 132.7, 132.9, 133.4, 134.8, 137.7, 143.0,
150.9, 160.7, 170.2, 192.7, 194.0.
MS (ESI): m/z = 346 [M + Na]+.
Anal. Calcd for C20H21NO3: C, 74.28; H, 6.55; N, 4.33. Found: C,
74.43; H, 6.47; N, 4.27.
2-(1,2-Dioxo-2-phenylethyl)-N-ethyl-N-(4-methylphenyl)benz-
amide (3f)
White solid; yield: 75%; mp 118–119 °C.
IR (KBr): 1647, 1669, 1679, 2974 cm–1.
1H NMR (400 MHz, CDCl3): d = 1.0 (t, J = 7.2 Hz, 3 H,
NCH2CH3), 2.30 (s, 3 H, CH3), 3.80 (q, J = 6.8 Hz, 2 H, NCH2),
6.96 (d, J = 7.2 Hz, 1 H, HAr), 7.07 (d, J = 8.0 Hz, 2 H, HAr), 7.19–
7.26 (m, 3 H, HAr), 7.31–7.35 (m, 1 H, HAr), 7.52 (t, J = 7.6 Hz, 2 H,
HAr), 7.63 (t, J = 7.2 Hz, 1 H, HAr), 7.80 (d, J = 7.6 Hz, 1 H, HAr),
8.81 (d, J = 7.6 Hz, 2 H, HAr).
13C NMR (100 MHz, CDCl3): d = 12.8, 21.1, 44.4, 127.3, 127.9,
128.3, 128.6, 129.5, 129.6, 129.9, 130.6, 131.1, 131.6, 134.1, 137.3,
139.0, 142.6, 169.7, 191.3, 193.3.
MS (ESI): m/z = 428 [M + Na]+.
Anal. Calcd for C22H19N3O5: C, 65.18; H, 4.72; N, 10.37. Found: C,
65.15; H, 4.73; N, 10.41.
N-(1,2-Dimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)-
2-(1,2-dioxo-2-phenylethyl)-N-ethylbenzamide (3j)
Yellow solid; yield: 90%; mp 191–192 °C.
IR (KBr): 1624, 1663, 1680, 1709, 2940 cm–1.
1H NMR (400 MHz, CDCl3): d = 1.00 (t, J = 7.2 Hz, 3 H,
NCH2CH3), 3.11–3.20 (m, 1 H, NCHaHb), 3.30 (s, 3 H, NCH3), 3.37
(s, 3 H, NCH3), 4.02–411 (m, 1 H, NCHaHb), 7.29–7.31 (m, 1 H,
MS (ESI): m/z = 394 [M + Na]+.
Synthesis 2011, No. 18, 2951–2958 © Thieme Stuttgart · New York