JOURNAL OF CHEMICAL RESEARCH 2015 143
3.79 (3HOMe, s), 6.80–6.87 (2Harom, 1Hvinyl, 1HN–H, m), 7.21 (2Harom, d,
J=8.0 Hz), 7.36–7.44 (5Harom, 1Hvinyl, m); 13C NMR (CDCl3) δ (ppm)
50.7, 121.8, 125.6, 128.1, 129.7, 130.9, 131.5, 132.2, 133.5, 135.6, 142.9.
Anal. calcd for C15H15NO3S: C, 62.26; H, 5.23; N, 4.84; found: C, 62.31;
H, 5.29; N, 4.78%.
(E)-N-(2-Methoxyphenyl)-2-phenylethenesulfonamide (3c): Grey
powder, m.p. 106–108 °C; Rf =0.41 (20% ethyl acetate, 80% n-hexane);
IR (KBr, cm–1) 3254 (NH), 1605 (C=C), 1337, 1149 (SO2);1H NMR
(CDCl3) δ (ppm) 3.86 (3HOMe, s), 6.79 (1Hvinyl, d, J=15.2 Hz), 6.87
(1Harom, d, J=8.0 Hz), 6.96 (2Harom, t, J=7.8 Hz), 7.01 (1HN–H, s), 7.10
(1Harom, t, J=7.6 Hz), 7.37–7.45 (5Harom, m), 7.49 (1Hvinyl, d, J=15.2 Hz),
7.56 (1Harom, d, J=7.6 Hz); 13C NMR (CDCl3) δ (ppm) 55.8, 110.6,
120.4, 121.2, 124.3, 125.2, 125.9, 128.3, 129.0, 130.9, 132.4, 142.7,
149.3. Anal. calcd for C15H15NO3S: C, 62.26; H, 5.23; N, 4.84; found: C,
62.20; H, 5.19; N, 4.80%.
(E)-N-(2,4-Dichlorophenyl)-2-phenylethenesulfonamide (3j): Light
yellow needles; m.p. 121–124°C; Rf =0.46 (20% ethyl acetate, 80%
n-hexane); IR (KBr, cm–1) 3270 (NH), 1616 (C=C), 1334, 1153 (SO2);
1H NMR (CDCl3) δ (ppm) 6.78 (1Hvinyl, d, J=15.2 Hz), 6.87 (1HN–H
,
br), 7.27 (1Harom, d, J=7.4 Hz), 7.40–7.48 (6Harom, m), 7.51 (1Hvinyl, d,
J=15.2 Hz), 7.62 (1Harom, d, J=8.8); 13C NMR (CDCl3) δ (ppm) 123.2,
123.7, 125.8, 126.7, 128.3, 128.5, 129.2, 129.4, 131.0, 131.4, 132.0,
132.1, 143.8. Anal. calcd for C14H11Cl2NO2S: C, 51.23; H, 3.38; N, 4.27;
found: C, 51.26; H, 3.36; N, 4.31%.
(E)-N-(3-Nitrophenyl)-2-phenylethenesulfonamide (3k): Oil;
Rf =0.64 (40% ethyl acetate, 60% n-hexane); IR (KBr, cm–1) 3269
1
(NH), 1615 (C=C), 1347, 1148 (SO2); H NMR (CDCl3) δ (ppm) 6.86
(1Hvinyl, d, J=15.6 Hz), 7.33–7.48 (5Harom, 1Hvinyl, m), 7.59–7.62 (2Harom
,
m), 7.92 (1Harom, d, J=8.0 Hz), 8.11–8.13 (1Harom, m), 8.33 (1HN–H, br).
Anal. calcd for C14H12N2O4S: C, 55.25; H, 3.97; N, 9.21; found: C,
55.28; H, 4.01; N, 9.18%.
(E)-2-Phenyl-N-p-tolylethenesulfonamide (3d): Oil; Rf =0.33 (20%
ethyl acetate, 80% n-hexane);IR (KBr, cm–1) 3264 (NH), 1615 (C=C),
(E)-N-(6-Methylpyridin-2-yl)-2-phenylethenesulfonamide (3l): Oil;
Rf =0.63 (100% ethyl acetate); IR (KBr, cm–1) 3241 (NH), 1607 (C=C),
1332, 1146 (SO2); 1H NMR (CDCl3) δ (ppm) 2.32 (3HMe, s), 6.84 (1Hvinyl
d, J=15.2 Hz), 6.97 (1HN–H, br), 7.11–7.19 (4Harom, m), 7.36–7.46 (5Harom
,
,
1362, 1116 (SO2); 1H NMR (CDCl3) δ (ppm) 2.52 (3HMe, s), 6.74 (1Harom
,
m), 7.50 (1Hvinyl, d, J=15.2 Hz); 13C NMR (CDCl3) δ (ppm) 20.9, 121.8,
124.3, 128.4, 129.1, 130.0, 131.0, 132.4, 133.7, 135.3, 142.9. Anal. calcd
for C15H15NO2S: C, 65.91; H, 5.53; N, 5.12; found: C, 65.84; H, 5.58; N,
5.06%.
d, J=7.2 Hz), 6.96 (1Hvinyl, d, J=15.2 Hz), 7.14–7.23 (1HN–H, 1Harom, m),
7.40–7.44 (3Harom, m), 7.48–7.52 (2Harom, m), 7.59–7.65 (1Hvinyl, 1Harom
,
m); 13C NMR (CDCl3) δ (ppm) 23.6, 112.3, 120.5, 125.6, 128.4, 129.3,
132.5, 133.4, 135.7, 142.9, 149.5, 153.6. Anal. calcd for C14H14N2O2S: C,
61.29; H, 5.14; N, 10.21; Found: C, 61.34; H, 5.09; N, 10.25%.
(E)-N-(4-Hydroxyphenyl)-2-phenylethenesulfonamide (3m): Yellow
mustard needles; m.p. 173 °C; Rf =0.76 (100% ethyl acetate); IR (KBr,
cm–1) 3392 (OH), 3206 (NH), 1614 (C=C), 1317, 1140 (SO2); 1H NMR
(DMSO) δ (ppm) 6.67 (2Harom, d, J=7.2 Hz), 7.01 (2Harom, d, J=7.2 Hz),
7.15 (1Hvinyl, d, J=15.2 Hz), 7.28 (1Hvinyl, d, J=15.2 Hz), 7.38–7.69
(5Harom, 1HN–H, m), 9.52 (1HOH, s); 13C NMR (DMSO) δ (ppm) 115.4,
124.0, 126.1, 126.2, 128.4, 128.9, 130.6, 132.5, 140.4, 140.5. Anal. calcd
for C14H13NO3S: C, 61.07; H, 4.76; N, 5.09; found: C, 61.37; H, 4.45; N,
5.14%.
(E)-2-Phenyl-N-o-tolylethenesulfonamide (3e): Cream powder, m.p.
126–128 °C; Rf =0.44 (80% ethyl acetate, 20% n-hexane); IR (KBr,
1
cm–1) 3278 (NH), 1612 (C=C), 1327, 1146 (SO2); H NMR (CDCl3)
δ (ppm) 2.23 (3HCH3, s), 6.27 (1HN–H, S), 6.75 (1Hvinyl, d, J=15.2 Hz),
7.01–7.05(1Harom, m), 7.11 (2Harom, d, J= 7.2), 7.18–7.20 (1Harom, m),
7.31–7.33 (2Harom, m), 7.34–7.36 (3Harom, m), 7.39 (1Hvinyl, d, J=15.2 Hz);
13C NMR (CDCl3) δ (ppm) 8.0, 123.4, 124.6, 126.1, 127.2, 128.3, 128.7,
129.1, 130.7, 131.0, 132.3, 134.4, 142.7. Anal. calcd for C15H15NO2S: C,
65.91; H, 5.53; N, 5.12; found: C, 65.82; H, 5.49; N, 5.18%.
(E)-N-(2,4-Dimethylphenyl)-2-phenylethenesulfonamide (3f): Light
yellow powder, m.p. 140–141 °C; Rf =0.53 (20% ethyl acetate, 80%
n-hexane); IR (KBr, cm–1) 3279 (NH), 1615 (C=C), 1326, 1147 (SO2);
(E)-N-(2-Hydroxyphenyl)-2-phenylethenesulfonamide (3n): Oil;
Rf =0.66 (100% ethyl acetate); IR (KBr, cm–1) 3251 (OH, NH), 1601
1H NMR (CDCl3) δ (ppm) 2.31 (6H, s), 6.30 (1HN–H, s), 6.85 (1Hvinyl
,
1
(C=C), 1330, 1145 (SO2); H NMR (DMSO) δ (ppm) 6.37 (1HN–H, b),
d, J=15.2 Hz), 6.99–7.05 (2Harom, m), 7.28–7.34 (1Harom, m), 7.39–7.48
(5Harom, 1Hvinyl, m);13C NMR (CDCl3) δ (ppm) 18.1, 20.9, 124.7, 124.8,
127.7, 128.3, 129.1, 131.0, 131.6, 131.7, 132.5, 136.4, 142.3. Anal. calcd
for C16H17NO2S: C, 66.87; H, 5.96; N, 4.87; found: C, 66.82; H, 5.90; N,
4.89%.
6.72 (1Hvinyl, d, J=15.6 Hz), 6.80 (1Harom, dt, J1 =7.6, J2 =1.2), 6.86
(1Harom, dd, J1 =8.0, J2 =1.2), 7.04 (1Harom, dt, J1 =7.6, J2 =1.2), 7.16
(1Harom, dd, J1 =8.0, J2 =1.2), 7.19 (1HOH, s), 7.30–7.39 (5Harom, 1Hvinyl
,
m); 13C NMR (CDCl3) δ (ppm) 111.2, 116.9, 121.3, 123.2, 125.3, 128.0,
128.4, 128.5, 129.1, 131.2, 143.7, 149.9. Anal. calcd for C14H13NO3S: C,
61.07; H, 4.76; N, 5.09; found: C, 61.44; H, 4.46; N, 5.08%.
(E)-N-(4-Bromophenyl)-2-phenylethenesulfonamide (3g): Oil;
Rf =0.45 (20% ethyl acetate, 80% n-hexane); IR (KBr, cm–1)
(E)-N-Cyclohexyl-2-phenylethenesulfonamide (3o): Oil; Rf =0.28
(20% ethyl acetate, 80% n-hexane); IR (KBr, cm–1) 3283 (NH), 1602
1
3248(NH), 1611 (C=C), 1329, 1147 (SO2); H NMR (CDCl3) δ (ppm)
6.84 (1Hvinyl, d, J=15.6 Hz), 7.13–7.18 (2Harom, m), 7.39–7.46 (6Harom
,
(C=C), 1322, 1143 (SO2); 1H NMR (CDCl3) δ (ppm) 1.25–1.34 (4HCH2–
m), 1.50–1.60 (2HCH2–, m), 1.66–1.75 (4HCH2–, m), 3.16–3.28 (1HCH–
,
,
1HN-H, m), 7.53 (1Hvinyl, d, J=15.6 Hz); 13C NMR (CDCl3) δ (ppm)
118.4, 122.5, 123.8, 128.5, 129.1, 131.3, 132.0, 132.5, 135.6, 143.7. Anal.
calcd for C14H12BrNO2S: C, 49.72; H, 3.58; N, 4.14; found: C, 49.79; H,
3.61; N, 4.12%.
m), 6.84 (1Hvinyl, d, J=15.6 Hz), 7.40–7.43 (4Harom, m), 7.47 (1HN–H, s),
7.48–7.51 (1Harom, 1Hvinyl, m); 13C NMR (CDCl3) δ (ppm) 24.8, 25.2,
34.3, 52.7, 126.6, 128.2, 129.1, 130.6, 132.8, 140.4. Anal. calcd for
C14H19NO2S: C, 63.32; H, 7.26; N, 5.28; found: C, 63.39; H, 7.19; N,
5.31%.
(E)-N-(3-Chlorophenyl)-2-phenylethenesulfonamide (3h): Oil;
Rf =0.35 (20% ethyl acetate, 80% n-hexane); IR (KBr, cm–1) 3257
1
(NH), 1618 (C=C), 1323, 1147 (SO2); H NMR (CDCl3) δ (ppm) 6.85
1,4-Bis(styrylsulfonyl)piperazine (3p): Light brown powder, m.p.
253–256 °C; Rf =0.64 (40% ethyl acetate, 60% n-hexane); IR (KBr,
(1Hvinyl, d, J=15.6 Hz), 7.11–7.16 (2Harom, m), 7.25 (1Harom, t, J=8.0 Hz),
7.29–7.38 (1Harom, 1HN–H, m), 7.38–7.48 (5Harom, m), 7.58 (1Hvinyl, d,
J=15.2 Hz); 13C NMR (CDCl3) δ (ppm) 118.4, 120.4, 123.8, 125.1,
128.5, 129.1, 130.5, 131.3, 132.0, 135.1, 137.9, 143.8. Anal. calcd for
C14H12ClNO2S: C, 57.24; H, 4.12; N, 4.77; found: C, 57.20; H, 4.09; N,
4.71%.
(E)-N-(2-Chlorophenyl)-2-phenylethenesulfonamide (3i): Oil;
Rf =0.43 (20% ethyl acetate, 80% n-hexane); IR (KBr, cm–1) 3280 (NH),
1613 (C=C), 1336, 1151 (SO2); 1H NMR (CDCl3) δ (ppm) 6.83 (1Hvinyl, d,
J=15.6 Hz), 7.11–7.17 (2Harom, m), 7.25 (1Harom, t, J=8.1 Hz), 7.30–7.35
(1Harom, 1HN–H, m), 7.37–7.49 (5Harom, m), 7.59 (1Hvinyl, d, J=15.6 Hz);
13C NMR (CDCl3) δ (ppm) 119.0, 120.4, 123.7, 125.1, 128.4, 129.0,
130.5, 131.3, 132.0, 135.2, 137.8, 143.9. Anal. calcd for C14H12ClNO2S:
C, 57.24; H, 4.12; N, 4.77; found: C, 57.29; H, 4.19; N, 4.74%.
1
cm–1) 1606 (C=C), 1155, 1335 (SO2); H NMR (DMSO) δ (ppm) 3.50
(8H, t, J=5.6 Hz), 6.89 (2Hvinyl, d, J=15.2 Hz), 7.45–7.51 (10Harom, m),
7.76 (2Hvinyl, d, J=15.2 Hz); 13C NMR (DMSO) δ (ppm) 44.9, 122.2,
127.0, 128.8, 129.0, 130.9, 132.5. Anal. calcd for C20H22N2O4S2: C,
57.39; H, 5.30; N, 6.69; found: C, 57.42; H, 5.25; N, 6.71%.
We appreciate the financial support of the Shahreza Branch,
Islamic Azad University (IAUSH) Research Council.
Received 28 November 2014; accepted 3 February 2015
Paper 1403049 doi: 10.3184/174751915X14241022318075
Published online: 18 March 2015