Molecules 2010, 15
1119
4-Dimethylaminopyridinium (4-chloropyridin-3-ylsulfonyl carbamoylide (3d). Yield: 39%; m.p.
151–153 °C (dec); IR (KBr) ν = 3097, 2934, 1702, 1645, 1572, 1559, 1449, 1395, 1296, 1260, 1089,
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842, 824, 766, 596 cm-1; H-NMR (DMSO-d6) δ = 3.25 (s, 6H, CH3), 7.00 (d, 2H, CH, J = 8.1 Hz),
7.64 (d, 1H, CH, J = 5.2 Hz), 8.64 (d, 1H, CH, J = 5.2 Hz), 8.73 (d, 2H, CH, J = 8.1 Hz), 9.07 (s, 1H,
CH); Anal. Calcd. for C13H13ClN4O3S (340.79) C, 45.82%; H, 3.85%; N, 16.44%; Found C, 45.61%;
H, 3.90%; N, 16.16%.
4-(Dimethylamino)pyridinium (5-chlorothiophen-2-ylsulfonyl)(phenoxycarbonyl)amide (4a). Yield:
54%; m.p. 144–146 °C (dec); IR (KBr) ν = 3077, 2924, 2611, 1964, 1645, 1562, 1409, 1295, 1262,
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1210, 1186, 1173, 1024, 988, 924, 887, 807, 626 cm-1; H-NMR (DMSO-d6) δ = 3.18 (s, 6H, CH3),
6.96-7.38 (m, 8H, CH), 7.42 (d, 1H, CH, J = 3.9 Hz), 8.21 (d, 2H, CH, J = 7.6 Hz), 12.6 (bs, 1H, NH);
Anal. Calcd. for C18H18ClN3O4S2 (439.94) C, 49.14%; H, 4.12%; N, 9.55%; Found C, 48.93%; H,
4.26%; N, 9.19%.
4-(Dimethylamino)pyridinium (benzothiazol-2-ylsulfonyl)(phenoxycarbonyl)amide (4b). Yield: 73%;
m.p. 135–138 °C (dec); IR (KBr) ν = 3060, 2924, 1685, 1646, 1559, 1271 cm-1; 1H-NMR (DMSO-d6)
δ = 3.14 (s, 6H, CH3), 6.92-6.96 (m, 4H, CH), 7.02-7.12 (t, 1H, J = 7.4 Hz), 7.25-732 (t, 2H, CH,
J = 7.4 Hz), 7.45-7.62 (m, 2H, CH), 8.04-8.16 (m, 2H, CH), 8.29 (d, 2H, CH, J = 7.6 Hz); Anal. Calcd.
for C21H20N4O4S2 (456.54) C, 55.25%; H, 4.42%; N, 12.27%; Found C, 55.21%; H, 4.62%; N,
11.92%. Upon treatment of the above pyridinium salt with aqueous 1% HCl at room temperature the
free carbamate 4b’ was obtained; m.p. 206-208 °C; IR (KBr) ν = 3007, 2851, 2799, 1758, 1458, 1222,
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1096, 922, 767, 634 cm-1; H-NMR (DMSO-d6) δ = 6.75 (d, 2H, CH, J = 7.8 Hz), 7.16 (t, 1H, CH,
J = 7.8 Hz), 7.35 (t, 2H, CH, J = 7.8 Hz), 7.60-7.72 (m, 2H, CH), 8.16-8.30 (m, 2H, CH), 8.35 (s, 1H,
NH); Anal. Calcd. for C14H10N2O4S2 (334.37) C, 50.29%; H, 3.01%; N, 8.38%; Found C, 50.22%; H,
3.32%; N, 8.61%.
4-(Dimethylamino)pyridinium (6-ethoxybenzothiazol-2-ylsulfonyl)(phenoxy-carbonyl)amide (4c).
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Yield: 29.7%; m.p. 251–255 °C; IR (KBr) ν = 3223, 3066, 2924, 1681, 1645, 1557, 1296 cm-1; H-
NMR (DMSO-d6) δ = 1.35 (t, 3H, CH3, J = 8.1 Hz), 3.14 (s, 6H, CH3), 4.09 (q, 2H, CH2, J = 8.1 Hz),
6.92-6.96 (m, 4H, CH), 7.05-7.15 (dd, 1H, CH, Jortho = 6.75, Jmeta = 2.3 Hz), 7.22-7.30 (t, 2H, CH,
J = 7.4 Hz), 7.65 (d, 1H, CH, Jmeta = 2.3 Hz), 7.93 (d, 1H, CH, Jortho = 6.75 Hz), 8.19 (d, 2H, CH,
J = 7.7 Hz); Anal. Calcd. for C23H24N4O5S2 (500.59) C, 55.18%; H, 4.83%; N, 11.19%; Found C,
54.97%; H, 5.11%; N, 10.98%. Upon treatment of the above pyridinium salt with aqueous 1% HCl the
free carbamate 4c’ was obtained; m.p. 206-208 °C; IR (KBr) ν = 2989, 2859, 2787, 2663, 1756, 1599,
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1485, 1375, 1262, 1217, 1168, 1080, 1042, 842, 759, 688, 627 cm-1; H-NMR (DMSO-d6) δ = 1.37
(t, 3H, CH3, J = 8.2 Hz), 4.12 (q, 2H, CH2, J = 8.2 Hz), 6.75 (m, 1H, CH), 7.00-7.45 (m, 5H, CH),
7.80-7.95 (m, 1H, CH), 8.00-8.15 (m, 1H, CH), 8.75 (bs, 1H, NH); Anal. Calcd. for C16H14N2O5S2
(378.42) C, 50.78%; H, 3.73%; N, 7.40%; Found C, 50.53%; H, 3.89%; N, 7.06%.
4-(Dimethylamino)pyridinium (4-chloropyridin-3-ylsulfonyl)(phenoxycarbonyl)amide (4d). Yield:
48%; m.p. 191–193 °C; IR (KBr) ν = 3215, 3082, 2922, 1688, 1646, 1561, 1397, 1263, 1191, 1149,
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1028, 916, 887, 806, 797 cm-1; H-NMR (DMSO-d6) δ = 3.16 (s, 6H, CH3), 6.88-6.93 (m, 2H, CH),