126.98, 126.19, 113.52, 55.36, 21.35; MS: m/z = 364, 210, 195,
167, 135, 91, 77, 65, 44; E. A. Anal. Calcd: C, 69.02; H, 5.24; N,
3.83; Found: C, 68.99; H, 5.39; N, 3.73.
137.99, 130.41, 129.34, 128.22, 127.24, 61.24, 21.46, 14.15; MS:
m/z = 407, 343, 252, 224, 155, 104, 91, 77, 65, 44; Anal. Calcd: C,
67.79; H, 5.19; N, 3.44; Found: C, 67.84; H, 5.32; N, 3.18.
4-Methyl-N-(phenyl(4-(trifluoromethyl)phenyl)methylene)ben-
zenesulfonamide (3d). White solid; mp 129–131 ◦C; Rf 0.08
4-Methyl-N-(phenyl(m-tolyl)methylene)benzenesulfonamide(3j).
White solid; mp 99–101 ◦C; Rf 0.46 (hexane–EtOAc = 5 : 1);
1H NMR (300 MHz, CDCl3, 25 ◦C, TMS): d = 7.81 (d, J =
7.8 Hz, 2H), 7.53–7.28 (m, 9H), 7.26 (d, J = 8.1 Hz, 2H), 2.42 (s,
3H), 2.35 (s, 3H); 13C NMR (75 MHz, CDCl3, 25 ◦C, TMS): d =
178.96, 143.18, 138.34, 129.24, 127.94, 127.21, 21.47, 21.28; MS:
m/z = 349, 285, 242, 194, 155, 91, 77, 65; Anal. Calcd: C, 72.18;
H, 5.48; N, 4.01; Found: C, 72.17; H, 5.53; N, 4.16.
(hexane–EtOAc = 2 : 1); H NMR (300 MHz, CDCl3, 25 ◦C,
1
TMS): d = 7.81 (d, J = 8.4 Hz, 2H), 7.70–7.42 (m, 9H), 7.30 (d,
J = 8.4 Hz, 2H), 2.44 (s, 3H); 13C NMR (75 MHz, CDCl3, 25 ◦C,
TMS): d = 176.77, 143.70, 137.81, 133.83, 130.47, 129.41, 128.43,
127.27, 125.35, 124.97, 121.73, 21.48; IR(KBr): MS: m/z = 402,
338, 248, 155, 91, 77, 65; Anal. Calcd: C16H21NF3O2S: C, 62.52;
H, 4.00; N, 3.47; Found: C, 62.77; H, 4.05; N, 3.42.
N-((2-Methoxyphenyl)(phenyl)methylene)-4-methylbenzenesul-
fonamide (3k). White solid; mp 89–91 ◦C; Rf 0.25 (hexane–
EtOAc = 5 : 1); 1H NMR (300 MHz, CDCl3, 25 ◦C, TMS): d = 7.73
(m, 4H), 7.50–7.19 (m, 7H), 7.06 (t, J = 7.2 Hz, 1H), 6.84 (d, J =
8.1 Hz, 1H), 3.58 (s, 3H), 2.39 (s, 3H); 13C NMR (75 MHz, CDCl3,
25 ◦C, TMS): d = 176.51, 155.65, 143.06, 137.49, 136.77, 133.27,
131.32, 131.27, 129.74, 128.91, 128.22, 127.38, 124.15, 119.92,
55.25, 21.42; Anal. Calcd: C, 69.02; H, 5.24; N, 3.83; Found: C,
68.84; H, 5.31; N, 3.46.
4-Methyl-N-(phenyl(3-(trifluoromethyl)phenyl)methylene)ben-
zenesulfonamide (3e). White solid; mp 88–90 ◦C; Rf 0.08
(hexane–EtOAc = 2 : 1); H NMR (300 MHz, CDCl3, 25 ◦C,
1
TMS): d = 7.80–7.73 (m, 4H), 7.57–7.45 (m, 7H), 7.29 (s, J =
7.5 Hz, 2H), 2.43 (s, 3H); 13C NMR (75 MHz, CDCl3, 25 ◦C, TMS):
d = 176.87, 143.77, 137.75, 130.57, 129.45, 128.74, 128.39, 127.32,
125.30, 21.55; 19F NMR (75 MHz, CDCl3, 25 ◦C, TMS): −63.10;
IR (KBr): MS: m/z = 338, 248, 155, 91, 77, 65, 51, 44; Anal. Calcd:
C, 62.52; H, 4.00; N, 3.47; Found: C, 62.55, H, 3.96, N, 3.25.
N-((3-Chlorophenyl)(phenyl)methylene)-4-methylbenzenesulfon-
amide (3f). White solid; mp 83–85 ◦C; Rf 0.35 (hexane–EtOAc =
5 : 1); 1H NMR (300 MHz, CDCl3, 25 ◦C, TMS): d = 7.79 (d, J =
8.4 Hz, 2H), 7.56–7.41 (m, 9H), 7.28 (d, J = 8.1 Hz, 2H), 2.42
(s, 3H); 13C NMR (75 MHz, CDCl3, 25 ◦C, TMS): d = 176.90,
143.60, 137.89, 134.25, 139,67, 129.38, 128.27, 109.64, 21,52; MS:
m/z = 370, 368, 305, 214, 155, 91, 77, 65, 51; Anal. Calcd: C,
64.95; H, 4.36; N, 3.79; Found: C, 64.90, H, 4.20, N, 3.45.
N-((4-Fluorophenyl)(phenyl)methylene)-4-methylbenzenesulfon-
amide (3l). Prepared as N-(diphenylmethylene)-4-methylben-
zenesulfonamide 3a to give a colorless oil; Rf 0.12 (hexane–
◦
EtOAc = 5 : 1); 1H NMR (300 MHz, CDCl3, 25 C, TMS): d =
7.83 (d, J = 8.1 Hz, 2H), 7.60–7.51 (m, 7H), 7.29 (d, J = 8.1 Hz,
2H), 7.09 (m, 2H), 2.42 (s, 3H); 13C NMR (75 MHz, CDCl3, 25 ◦C,
TMS): d = 177.26, 143.28, 138.17, 133.11, 130.60, 129.22, 127.97,
127.06, 115.29, 21.33; MS: m/z = 270, 238, 223, 152, 104, 76, 43;
HRMS Calcd: 353.0880; Found: 353.0874.
N-((2-Chlorophenyl)(phenyl)methylene)-4-methylbenzenesulfon-
amide (3g). White solid; mp 94–95 ◦C; Rf 0.35 (hexane–EtOAc =
N-((4-Chlorophenyl)(phenyl)methylene)-4-methylbenzenesulfon-
amide (3m). White solid; mp 106–108 ◦C; Rf 0.38 (hexane–
5 : 1); H NMR (300 MHz, CDCl3, 25 ◦C, TMS): d = 7.84 (d,
1
J = 8.4 Hz, 2H), 7.68 (m, 2H), 7.56–7.51 (m, 1H), 7.56–7.51 (m,
1H), 7.45–7.34 (m, 6H), 2.28 (d, J = 8.7 Hz, 2H), 2.43 (s, 3H);
13C NMR (75 MHz, CDCl3, 25 ◦C, TMS): d = 174.73, 143.79,
137.36, 135.78, 134.59, 133.83, 131.01, 129.91, 129.38, 129.28,
128.64, 127.60, 1126.51, 21.60; MS: m/z = 333, 214, 155, 111,
91, 77, 65, 51; Anal. Calcd: C, 64.95; H, 4.36; N, 3.79; Found: C,
64.97, H, 4.34, N, 3.60.
◦
EtOAc = 5 : 1); 1H NMR (300 MHz, CDCl3, 25 C, TMS): d =
7.82 (d, J = 8.4 Hz, 2H), 7.56–7.41 (m, 9H), 7.28 (d, J = 8.1 Hz,
2H), 2.42 (s, 3H); 13C NMR (75 MHz, CDCl3, 25 ◦C, TMS): d =
177.29, 143.43, 138.09, 129.31, 128.37, 128.12, 127.18, 21.46; MS:
m/z = 371, 369, 305, 214, 155, 111, 91, 77, 65, 51; Anal. Calcd:
C, 64.95; H, 4.36; N, 3.79; Found: C, 64.87; H, 4.49; N, 3.68.
N-((2-Fluorophenyl)(phenyl)methylene)-4-methylbenzenesulfon-
amide (3n). White solid; mp 74–76 ◦C; Rf 0.10 (hexane–EtOAc =
5 : 1); 1H NMR (300 MHz, CDCl3, 25 ◦C, TMS): d = 7.82 (d, J =
8.1 Hz, 2H), 7.69 (d, J = 7.8 Hz, 2H), 7.53–7.29 (m, 8H), 7.12 (t,
J = 9.1 Hz, 1H), 2.41 (s, 3H); 13C NMR (75 MHz, CDCl3, 25◦C,
TMS): d = 173.10, 143.64, 137.50, 136.31, 133.85, 132.12, 132.03,
129.81, 129.32, 128.53, 127.85, 127.36, 123.80, 115,58, 115,31,
21.47; MS: m/z = 353, 289, 198, 155, 91, 77, 65, 51; Anal. Calcd:
C, 67,97; H, 4.56; N, 3.96; Found: C, 67.94; H, 4.54; N, 3.73.
N-((4-Methoxyphenyl)(phenyl)methylene)-4-methylbenzenesul-
fonamide (3h). White solid; mp 120–122 ◦C; Rf 0.26 (hexane–
◦
EtOAc = 2 : 1); 1H NMR (300 MHz, CDCl3, 25 C, TMS): d =
8.10 (d, J = 7.5 Hz, 1H), 8.02 (br, 1H), 7.79 (d, J = 8.1 Hz, 2H),
7.73–7.72 (m, 1H), 7.57–7.72 (m, 6H), 7.27 (d, J = 8.1 Hz, 2H),
2.57 (s, 1H), 2.40 (s, 3H); 13C NMR (75 MHz, CDCl3, 25 ◦C,
TMS): d = 196.82, 177.50, 143.48, 137.97, 132.80, 130.47, 129.31,
128.28, 127.15, 26.49, 21.41; IR (KBr): m = 3063, 2924, 1686, 1598,
1561, 1322, 1154, 1090, 833, 685, 554 cm−1; MS (m/z) 378.2; Anal.
Calcld: C, 70.00; H, 5.07; N, 3.71; Found: C, 69.85; H, 5.42; N,
3.62.
(E)-N-(1,3-Diphenylallylidene)-4-methylbenzenesulfonamide (3o).
White solid; mp 147–149 ◦C; Rf 0.69 (hexane–EtOAc = 5 : 1);
1H NMR (300 MHz, CDCl3, 25 ◦C, TMS): d = 8.12–8.07 (m,
1H), 7.94 (s, J = 6.9 Hz, 2H), 7.65–7.30 (m, 12H), 7.05 (d, J =
15.9 Hz, 1H), 2.42 (s, 3H); 13C NMR (75 MHz, CDCl3, 25 ◦C,
TMS): d = 177.52, 148.82, 143.39, 138.56, 134.41, 131.93, 131.12,
129.36, 128.95, 128.65, 127.09, 122.47, 21.50; MS: m/z = 361, 296,
206,103, 91, 77, 65.
Ethyl 3-(phenyl(tosylimino)methyl)benzoate (3i). White solid;
mp 104–105 ◦C; Rf 0.14 (hexane–EtOAc = 2 : 1); 1H NMR
◦
(300 MHz, CDCl3, 25 C, TMS): d = 8.20 (d, J = 7.8 Hz, 1H),
7.82–7.75 (m, 4H), 7.57–7.42 (m, 6H), 7.28 (d, J = 8.1 Hz, 2H),
4.36 (d, q = 6.9 Hz, 2H), 2.41 (s, 1H), 1.36 (t, J = 6.9 Hz, 3H); 13
C
NMR (75 MHz, CDCl3, 25 ◦C, TMS): d = 177.50, 165.48, 143.47,
2136 | Org. Biomol. Chem., 2008, 6, 2133–2137
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