Article
J. Agric. Food Chem., Vol. 58, No. 20, 2010 11001
202-205 °C; 1H NMR (500 MHz, DMSO-d6) δ 1.30 (s, 6H, CH3-C-CH3),
2.00 (s, 3H, CH3-S-CH2), 2.85 (s, 2H, CH3-S-CH2), 7.20 (t, J = 7.8 Hz,
1H, 5-ArH), 7.65 (dd, J1 = 7.6 Hz, J2 = 1.0 Hz, 1H, 4-ArH), 8.02-8.03 (m,
2H, 6-ArH, OdC-NH-C-CH3), 8.09 (dd, J1 = 8.1 Hz, J2 = 1.9 Hz, 1H,
N1-5-ArH), 8.15 (d, J = 8.6 Hz, 1H, N1-6-ArH), 8.35 (d, J = 1.8 Hz, 1H,
N1-2-ArH), 10.84 (s, 1H, OdC-NH-Ar); 13C NMR (500MHz, DMSO-d6)
δ 17.22, 25.31, 44.30, 54.88, 95.18, 101.90, 110.72, 115.62, 116.84, 122.35,
126.95, 129.92, 135.29, 136.27, 136.48, 140.96, 141.63, 143.46, 166.22, 166.96.
Data for N2-[1,1-Dimethyl-2-(methylthio)ethyl]-3-iodo-N1-[4-methoxy-3-(tri-
fluoromethyl)phenyl]-1,2-benzenedicarboxamide 4Ie. Yield: 81%; mp 164-
167 °C; 1H NMR (500 MHz, DMSO-d6) δ 1.26 (s, 6H, CH3-C-CH3), 2.02
(s, 3H, CH3-S-CH2), 2.86 (s, 2H, CH3-S-CH2), 3.87 (s, 3H, CH3OAr),
7.23 (t, 1H, J = 7.8, 5-ArH), 7.28 (d, 1H, J = 9.0, N1-5-ArH), 7.59 (d, 1H,
J = 7.5, 4-ArH), 7.85 (dd, 1H, J1 = 9.0, J2 = 2.0, N1-6-ArH), 7.95 (s, 1H,
OdC-NH-C-CH3), 7.98 (d, 1H, J = 8.0, 6-ArH), 8.02 (d, 1H, J = 2.5,
N1-2-ArH), 10.13 (s, 1H, OdC-NH-Ar); 13C NMR (500 MHz, DMSO-
d6) δ 17.25, 25.26, 44.33, 54.83, 56.21, 95.01, 113.30, 116.41, 116.65, 117.97,
124.90, 126.88, 129.87, 131.79, 136.19, 140.36, 141.41, 152.95, 165.17, 167.12.
Data for N2-[1,1-Dimethyl-2-(methylthio)ethyl]-3-iodo-N1-[3-fluoro-
5-(trifluoromethyl)phenyl]-1,2-benzenedicarboxamide 4If. Yield: 85%;
(s, 3H, CH2-O-CH3), 3.32 (s, 2H, CH2-O-CH3), 7.24 (t, J = 7.8 Hz,
1H, 5-ArH), 7.44 (d, J = 7.8 Hz, 1H, N1-4-ArH), 7.58-7.61 (m, 2H, N1-5-
ArH, 4-ArH), 7.78 (s, 1H, OdC-NH-C-CH3), 7.85 (d, J = 8.4 Hz, 1H,
N1-6-ArH), 7.99 (dd, J1 = 7.9 Hz, J2 = 1.0 Hz, 1H, 6-ArH), 8.16 (s, 1H,
N1-2-ArH), 10.34 (s, 1H, OdC-NH-Ar); 13C NMR (500 MHz, DMSO-
d6) δ 23.40, 53.85, 58.35, 77.79, 94.90, 115.51, 119.88, 122.96, 125.11,
126.87, 129.23, 129.48, 129.88, 136.02, 139.61, 140.45, 141.49, 165.73,
167.03.
Data for N2-[1,1-Dimethyl-2-(methoxy)ethyl]-3-iodo-N1-[4-chloro-3-(tri-
fluoromethyl)phenyl]-1,2-benzenedicarboxamide 4IIb. Yield: 85%; mp
183-186 °C; 1H NMR (500 MHz, DMSO-d6) δ 1.23 (s, 6H, CH3-C-
CH3), 3.16 (s, 3H, CH3-O-CH2), 3.33 (s, 2H, CH3-O-CH2), 7.24 (t,
J = 7.8 Hz, 1H, 5-ArH), 7.61 (d, J = 7.6 Hz, 1H, 4-ArH), 7.71 (d,
J = 8.8 Hz, 1H, N1-5-ArH), 7.79 (s, 1H, OdC-NH-C-CH3), 7.86 (d,
J = 8.7 Hz, 1H, N1-6-ArH), 8.00 (dd, J1 = 7.9 Hz, J2 = 0.8 Hz, 1H,
6-ArH), 8.26 (d, 1H, J = 2.3 Hz, N1-2-ArH), 10.47 (s, 1H, OdC-
NH-Ar); 13C NMR (300 MHz, DMSO-d6) δ 23.43, 53.87, 58.37, 77.80,
95.01, 118.13, 120.84, 124.22, 126.87, 129.89, 132.09, 132.79, 135.75,
137.15, 138.35, 140.62, 141.61, 165.80, 167.03.
Data for N2-[1,1-Dimethyl-2-(methoxy)ethyl]-3-iodo-N1-[4-cyano-3-(tri-
fluoromethyl)phenyl]-1,2-benzenedicarboxamide 4IId. Yield: 83%; mp
mp 184-187 °C; 1H NMR (300 MHz, CDCl3)
δ 1.56 (s, 6H,
1
CH3-C-CH3), 2.10 (s, 3H, CH3-S-CH2), 2.91 (s, 2H, CH3-S-CH2),
6.06 (s, 1H, OdC-NH-C-CH3), 6.95 (d, J = 7.3 Hz, 1H, N1-4-ArH),
7.21 (t, J = 7.8 Hz, 1H, 5-ArH), 7.54 (s, 1H, N1-6-ArH), 7.65 (d, J = 7.8
Hz, 1H, 4-ArH), 7.74-7.82 (m, 2H, 6-ArH, N1-2-ArH), 10.18 (s, 1H,
OdC-NH-Ar). Anal. Calcd for C20H19F4IN2O2S: C, 43.33; H, 3.45; N,
5.05. Found: C, 43.16; H, 3.69; N, 4.87.
216-218 °C; H NMR (500 MHz, DMSO-d6) δ 1.23 (s, 6H, C(CH3)2),
3.16 (s, 3H, CH2-O-CH3), 3.34 (s, 2H, CH2-O-CH3), 7.26 (t, 1H, J =
7.8 Hz, 5-ArH), 7.64 (dd, J1 = 7.7 Hz, J2 = 1.1 Hz, 1H, 4-ArH), 7.84 (s,
1H, OdC-NH-C-CH3), 8.02 (dd, J1 = 8.0 Hz, J2 = 1.1 Hz, 1H,
6-ArH), 8.08 (dd, J1 = 8.6 Hz, J2 = 1.9 Hz, 1H, N1-5-ArH), 8.10 (d, J =
8.6 Hz, 1H, N1-6-ArH), 8.34 (d, J = 1.9 Hz, 1H, N1-2-ArH), 10.84 (s, 1H,
OdC-NH-Ar); 13C NMR (500 MHz, DMSO-d6) δ 23.42, 53.90, 58.37,
77.74, 95.08, 101.93, 115.62, 116.79, 122.33, 126.91, 129.90, 131.49, 131.74,
135.29, 136.49, 140.92, 141.73, 143.42, 166.28, 166.94.
Data for N2-[1,1-Dimethyl-2-(methylthio)ethyl]-3-iodo-N1-[3,5-(ditri-
fluoromethyl)phenyl]-1,2-benzenedicarboxamide 4Ig. Yield: 86%; mp 232-
1
235 °C; H NMR (500 MHz, DMSO-d6) δ 1.31 (s, 6H, CH3-C-CH3),
Data for N2-[1,1-Dimethyl-2-(methoxy)ethyl]-3-iodo-N1-[4-methoxy-3-(tri-
fluoromethyl)phenyl]-1,2-benzenedicarboxamide 4IIe. Yield: 83%; mp
2.08 (s, 3H, CH3-S-CH2), 2.86 (s, 2H, CH3-S-CH2), 7.27 (t, J = 7.8
Hz, 1H, 5-ArH), 7.66 (dd, J1 = 7.1 Hz, J2 = 1.0 Hz, 1H, 4-ArH), 7.82 (s,
1H, N1-4-ArH), 8.01-8.03 (t, 2H, 6-ArH, OdC-NH-C-CH3), 8.36 (s,
2H, N1-2,6-ArH), 10.73 (s, 1H, OdC-NH-Ar); 13C NMR (300 MHz,
DMSO-d6) δ 17.18, 25.32, 44.30, 54.86, 95.25, 119.26, 121.34, 124.95,
126.85, 129.94, 130.46, 130.92, 135.42, 140.76, 140.88, 166.08, 167.04.
Data for N2-[1,1-Dimethyl-2-(methylthio)ethyl]-3-iodo-N1-[3-meth-
oxy-5-(trifluoromethyl)phenyl]-1,2-benzenedicarboxamide 4Ih. Yield: 89%;
mp 200-204 °C; 1H NMR (300 MHz, DMSO-d6) δ 1.30 (s, 6H,
CH3-C-CH3), 2.00 (s, 3H, CH3-S-CH2), 2.85 (s, 2H, CH3-S-CH2),
3.82 (s, 3H, CH3OAr), 6.98 (s, 1H, N1-4-ArH), 7.24 (t, J = 7.8 Hz, 1H,
5-ArH), 7.53 (s, 1H, N1-6-ArH), 7.60 (d, J = 7.3 Hz, 1H, 4-ArH), 7.69 (s,
1H, N1-2-ArH), 8.03-7.98 (t, 2H, 6-ArH, OdC-NH-C-CH3), 10.33
(1H, s, OdC-NH-Ar); 13C NMR (300 MHz, DMSO-d6) δ 17.26, 25.26,
44.31, 54.86, 55.58, 95.07, 105.33, 107.37, 108.19, 108.70, 126.87, 129.93,
130.18, 136.01, 140.55, 140.87, 141.47, 160.39, 165.71, 167.06.
1
169-172 °C; H NMR (300 MHz, DMSO-d6) δ 1.24 (s, 6H, C(CH3)2),
3.17 (s, 3H, CH2-O-CH3), 3.34 (s, 2H, CH2-O-CH3), 3.87 (s, 3H,
CH3OAr), 7.26 (t, J = 7.8 Hz, 1H, 5-ArH), 7.28 (d, J = 9.0 Hz, 1H, N1-5-
ArH), 7.58 (t, J = 6.8 Hz, 1H, 4-ArH), 7.77 (s, 1H, OdC-NH-C-CH3),
7.84 (dd, J1 = 9.0 Hz, J2 = 2.3 Hz, 1H, N1-6-ArH), 7.97 (dd, J1 = 7.9 Hz,
J2 = 0.9 Hz, 1H, 6-ArH), 8.02 (d, J = 2.4 Hz, 1H, N1-2-ArH), 10.12 (s,
1H, OdC-NH-Ar); 13C NMR (300 MHz, DMSO-d6) δ 23.45, 53.85,
56.22, 58.41, 77.86, 94.96, 113.31, 116.32, 116.72, 117.96, 124.88, 126.88,
129.86, 131.80, 136.18, 140.33, 141.51, 152.97, 165.22, 167.13.
Data for N2-[1,1-Dimethyl-2-(methoxy)ethyl]-3-iodo-N1-[3-fluoro-5-(tri-
fluoromethyl)phenyl]-1,2-benzenedicarboxamide 4IIf. Yield: 87%; mp
1
162-167 °C; H NMR (300 MHz, DMSO-d6) δ 1.23 (s, 6H, C(CH3)2),
3.17 (s, 3H, CH2-O-CH3), 3.34 (s, 2H, CH2-O-CH3), 7.25 (t, J = 7.8
Hz, 1H, 5-ArH), 7.39 (d, J = 8.5 Hz, 1H, N1-4-ArH), 7.61 (dd, J1 = 7.2
Hz, J2 = 0.9 Hz, 1H, 4-ArH), 7.81-7.84 (d, 2H, N1-2,6-ArH), 7.91 (s, 1H,
OdC-NH-C-CH3), 8.00 (dd, J1 = 7.4 Hz, J2 = 0.9 Hz, 1H, 6-ArH),
10.58 (s, 1H, OdC-NH-Ar); 13C NMR (300 MHz, DMSO-d6) δ 23.41,
53.89, 58.36, 77.79, 95.06, 107.13, 107.42, 109.52, 109.87, 111.89, 126.84,
129.90, 135.61, 140.72, 141.63, 141.64, 163.59, 165.96, 167.00.
Data for N2-[1,1-Dimethyl-2-(methylthio)ethyl]-3-iodo-N1-[2-methoxy-5-
(trifluoromethyl)phenyl]-1,2-benzenedicarboxamide 4Ii. Yield: 83%; mp
150-154 °C; 1H NMR (500 MHz, DMSO-d6) δ 1.26 (s, 6H, CH3-
C-CH3), 1.92 (s, 3H, CH3-S-CH2), 2.80 (s, 2H, CH3-S-CH2), 3.92 (s,
3H, CH3OAr), 7.24-7.28 (m, 2H, 5-ArIH, N1-3-ArH), 7.48 (dd, J1 = 8.6
Hz, J2 = 1.8 Hz, 1H, N1-4-ArH), 7.62 (d, J = 7.7 Hz, 1H, 4-ArIH), 8.01
(d, J = 7.6 Hz, 1H, 6-ArIH), 8.25 (s, 1H, OdC-NH-C-CH3), 8.58 (d,
J = 1.0 Hz, 1H, N1-6-ArH), 9.34 (s, 1H, OdC-NH-Ar); 13C NMR (300
MHz, DMSO-d6) δ 17.11, 25.18, 44.15, 54.85, 56.24, 94.80, 111.36, 116.60,
120.55, 120.98, 121.60, 127.47, 127.85, 130.10, 135.54, 140.72, 140.88,
151.50, 165.47, 167.52.
Data for N2-[1,1-Dimethyl-2-(methylthio)ethyl]-3-iodo-N1-[2-fluoro-
5-(trifluoromethyl)phenyl]-1,2-benzenedicarboxamide 4Ij. Yield: 89%;
mp 213-215 °C; 1H NMR (300 MHz, DMSO-d6) δ 1.30 (s, 6H,
CH3-C-CH3), 1.97 (s, 3H, CH3-S-CH2), 2.86 (s, 2H, CH3-S-CH2),
7.25 (t, J = 7.8 Hz, 1H, 5-ArH), 7.65-7.52 (m, 3H, N1-3-ArH, N1-4-ArH,
4-ArH), 8.01 (dd, J1 = 7.9 Hz, J2 = 1.1 Hz, 1H, 6-ArH), 8.09 (s, 1H,
OdC-NH-C-CH3), 8.46 (dd, 1H, N1-6-Ar), 10.06 (s, 1H, OdC-
NH-Ar); 13C NMR (300 MHz, DMSO-d6) δ 17.18, 25.25, 44.22, 54.86,
94.98, 116.66, 116.94, 120.13, 122.62, 126.97, 127.13, 127.28, 129.99,
135.25, 140.79, 141.23, 156.78, 165.90, 167.30.
Data for N2-[1,1-Dimethyl-2-(methoxy)ethyl]-3-iodo-N1-[3,5-
(ditrifluoromethyl)phenyl]-1,2-benzenedicarboxamide 4IIg. Yield: 89%; mp
1
179-183 °C; H NMR (300 MHz, DMSO-d6) δ 1.23 (s, 6H, C(CH3)2),
3.14 (s, 3H, CH2-O-CH3), 3.33 (s, 2H, CH2-O-CH3), 7.26 (t, J = 7.8
Hz, 1H, 5-ArH), 7.65 (d, J = 7.4 Hz, 1H, 4-ArH), 7.81-7.84 (d, 2H,
OdC-NH-C-CH3, N1-4-ArH), 8.02 (d, J = 7.8 Hz, 1H, 6-ArH), 8.35
(s, 2H, N1-2,6-ArH), 10.71 (s, 1H, OdC-NH-Ar); 13C NMR (300 MHz,
DMSO-d6) δ 23.41, 53.87, 58.29, 77.73, 95.13, 116.42, 119.25, 124.27,
126.81, 129.92, 132.51, 135.41, 140.73, 140.83, 141.74, 166.14, 167.03.
Data for N2-[1,1-Dimethyl-2-(methoxy)ethyl]-3-iodo-N1-[2-methoxy-
5-(trifluoromethyl)phenyl]-1,2-benzenedicarboxamide 4IIi. Yield: 80%;
mp 154-156 °C; 1H NMR (300 MHz, DMSO-d6) δ 1.19 (s, 6H, C(CH3)2),
3.06 (s, 3H, CH2-O-CH3), 3.28 (s, 2H, CH2-O-CH3), 3.92 (3H, s,
CH3OAr), 7.22-7.28 (m, 2H, 5-ArH, N1-3-ArH), 7.48 (d, J = 8.5 Hz, 1H,
N1-4-ArH), 7.61 (d, J = 7.7 Hz, 1H, 4-ArH), 8.00 (d, J = 7.9 Hz, 1H,
6-ArH), 8.12 (s, 1H, OdC-NH-C-CH3), 8.58 (s, 1H, N1-6-ArH), 9.37
(s, 1H, OdC-NH-Ar); 13C NMR (300 MHz, DMSO-d6) δ 23.29, 53.89,
56.22, 58.29, 77.58, 94.71, 111.36, 116.53, 120.55, 120.98, 121.56, 127.42,
127.86, 130.03, 135.50, 140.68, 141.07, 151.53, 165.53, 167.55.
Data for N2-[1,1-Dimethyl-2-(methoxy)ethyl]-3-iodo-N1-[3-(trifluoro-
methyl)phenyl]-1,2-benzenedicarboxamide 4IIa. Yield: 87%; mp 113-
116 °C; 1H NMR (500 MHz, DMSO-d6) δ 1.22 (s, 6H, C(CH3)2), 3.15