Y. Kawano et al.
sulfonamide (38c):8 Colorless granulars; mp 186–188 C; IR
Bull. Chem. Soc. Jpn. Vol. 79, No. 7 (2006) 1143
ꢁ
Hz, 2H), 7.54 (d, J ¼ 8:1 Hz, 2H), 7.40 (d, J ¼ 8:1 Hz, 2H), 7.19
ꢂ1
1
13
(
ATR) 3256, 1457, 1325, 1263, 1181 cm ; H NMR (270 MHz,
CDCl3) ꢂ 7.61 (d, J ¼ 8:1 Hz, 2H), 7.16 (d, J ¼ 8:1 Hz, 2H),
.05 (s, 4H), 5.73 (d, J ¼ 9:5 Hz, 1H), 4.93–4.79 (m, 1H), 2.37
(d, J ¼ 5:1 Hz, 2H), 5.52–5.36 (m, 1H), 2.27 (s, 3H); C NMR
(68 MHz, DMSO-d6) ꢂ 149.4, 142.8, 140.7, 137.5, 129.1, 126.2,
123.8 (q, JC{F ¼ 281 Hz), 123.0, 56.8 (q, JC{C{F ¼ 31 Hz), 20.9;
Anal. Calcd for C14H13F3N2O2S: C, 50.90; H, 3.97; N, 8.48%.
Found: C, 50.83; H, 3.98; N, 8.39%.
7
1
3
(
s, 3H), 2.30 (s, 3H); C NMR (68 MHz, CDCl3) ꢂ 143.6, 139.2,
1
36.9, 129.4, 129.3, 128.9, 127.5 (d, JC{C{C{F ¼ 1 Hz), 126.9,
1
23.9 (q, JC{F ¼ 281 Hz), 58.9 (q, JC{C{F ¼ 32 Hz), 21.6, 21.2.
4-Methyl-N-(1,1,1-trifluoro-4-phenylbut-3-en-2-yl)benzene-
sulfonamide (38j):8 Colorless granulars; mp 116–118 C; IR
ꢁ
Anal. Calcd for C16H16F3NO2S: C, 55.97; H, 4.70; N, 4.08%.
Found: C, 55.70; H, 4.60; N, 3.68%.
N-[1-(4-Chlorophenyl)-2,2,2-trifluoroethyl]-4-methylbenzene-
sulfonamide (38d):22 Colorless granulars; mp 196–198 C; IR
ATR) 3250, 1603, 1499, 1336, 1185, 1091 cm ; 1H NMR (270
ꢂ1
;
1H NMR
(ATR) 3253, 1598, 1452, 1265, 1185, 1127 cm
(270 MHz, CDCl3) ꢂ 7.76 (d, J ¼ 8:1 Hz, 2H), 7.34–7.16 (m,
7H), 6.49 (d, J ¼ 15:9 Hz, 1H), 5.90 (dd, J ¼ 15:9, 7.0 Hz, 1H),
5.26 (d, J ¼ 9:2 Hz, 1H), 4.65–4.50 (m, 1H), 2.34 (s, 3H);
ꢁ
ꢂ1
(
1
3
MHz, CDCl3) ꢂ 7.59 (d, J ¼ 7:8 Hz, 2H), 7.28–7.08 (m, 6H), 6.06
C NMR (68 MHz, CDCl3) ꢂ 143.9, 137.2, 136.8, 134.8, 129.6
1
3
(
(
d, J ¼ 9:5 Hz, 1H), 4.97–4.82 (m, 1H), 2.39 (s, 3H); C NMR
(d, JC{C{C{F ¼ 1 Hz), 128.7, 128.5, 127.0, 126.7, 123.8 (q, JC{F ¼
281 Hz), 118.1 (q, JC{C{C{F ¼ 2 Hz), 57.5 (q, JC{C{F ¼ 32 Hz),
21.5; Anal. Calcd for C17H16F3NO2S: C, 57.46; H, 4.54; N,
3.94%. Found: C, 57.35; H, 4.50; N, 3.56%.
68 MHz, DMSO-d6) ꢂ 142.6, 137.7, 131.1, 130.0, 129.1, 128.0,
126.2, 125.4, 123.7 (q, JC{F ¼ 281 Hz), 57.1 (q, JC{C{F ¼ 31 Hz),
20.8. Anal. Calcd for C15H13ClF3NO2S: C, 49.52; H, 3.60; N,
3.85%. Found: C, 49.26; H, 3.61; N, 4.07%.
N-[1-(t-Butyl)-2,2,2-trifluoroethyl]-4-methylbenzenesulfon-
ꢁ
N-[1-(4-Bromophenyl)-2,2,2-trifluoroethyl]-4-methylbenzene-
amide (38k): Colorless needles; mp 178–179 C; IR (ATR)
sulfonamide (38e):22 Colorless granulars; mp 221–223 C; IR
ꢁ
3296, 2985, 1477, 1327, 1265, 1173, 1094 cm ; H NMR (270
MHz, CDCl3) ꢂ 7.74 (d, J ¼ 8:1 Hz, 2H), 7.28 (d, J ¼ 8:1 Hz,
2H), 5.13 (d, J ¼ 10:0 Hz, 1H), 3.84–3.66 (m, 1H), 2.42 (s, 3H),
ꢂ1
1
ꢂ1
(
ATR) 3250, 1600, 1495, 1333, 1183, 1135 cm ; 1H NMR (270
MHz, DMSO-d6) ꢂ 9.20 (d, J ¼ 9:7 Hz, 1H), 7.51 (d, J ¼ 8:1 Hz,
H), 7.43 (d, J ¼ 8:6 Hz, 2H), 7.32 (d, J ¼ 8:6 Hz, 2H), 7.18 (d,
13
2
1.05 (s, 9H); C NMR (68 MHz, CDCl3) ꢂ 143.4, 138.0, 129.4,
126.7, 125.2 (q, JC{F ¼ 283 Hz), 62.7 (q, JC{C{F ¼ 28 Hz), 34.0,
27.2 (q, JC{C{C{F ¼ 2 Hz), 21.6; Anal. Calcd for C13H18F3NO2S:
C, 50.47; H, 5.86; N, 4.53%. Found: C, 50.16; H, 5.62; N, 4.27%.
N-(1-Cyclohexyl-2,2,2-trifluoroethyl)-4-methylbenzenesul-
1
3
J ¼ 8:1 Hz, 2H), 5.40–5.24 (m, 1H), 2.29 (s, 3H); C NMR
(
68 MHz, DMSO-d6) ꢂ 142.6, 137.6, 131.5, 131.0, 130.3, 129.1,
126.2, 123.9 (q, JC{F ¼ 281 Hz), 122.1, 57.2 (q, JC{C{F ¼ 31 Hz),
20.9; Anal. Calcd for C15H13BrF3NO2S: C, 44.13; H, 3.21; N,
3.43%. Found: C, 44.01; H, 3.10; N, 3.50%.
ꢁ
fonamide (38l): White solid; mp 130–132 C; IR (ATR) 3279,
ꢂ1
1
4
-Methyl-N-[2,2,2-trifluoro-1-(4-nitrophenyl)ethyl]benzene-
ꢁ
2936, 1454, 1332, 1175, 1122 cm ; H NMR (270 MHz, CDCl3)
ꢂ 7.74 (d, J ¼ 8:1 Hz, 2H), 7.29 (d, J ¼ 8:1 Hz, 2H), 4.94 (d,
J ¼ 10:3 Hz, 1H), 3.88–3.72 (m, 1H), 2.42 (s, 3H), 1.85–1.55
(m, 6H), 1.35–0.95 (m, 5H); 13C NMR (68 MHz, CDCl3) ꢂ 143.5,
137.9, 129.4, 126.9, 124.8 (q, JC{F ¼ 283 Hz), 59.5 (q, JC{C{F ¼
29 Hz), 37.7, 29.9, 27.0 (q, JC{C{C{F ¼ 1 Hz), 26.0, 25.8, 25.7,
21.6; Anal. Calcd for C15H20F3NO2S: C, 53.72; H, 6.01; N,
4.18%. Found: C, 53.37; H, 5.78; N, 3.96%.
sulfonamide (38f):
ATR) 3254, 1537, 1349, 1263, 1183, 1166, 1086 cm ; 1H NMR
Colorless granulars; mp 164–165 C; IR
ꢂ1
(
(
270 MHz, CDCl3) ꢂ 8.12 (d, J ¼ 8:4 Hz, 2H), 7.62 (d, J ¼ 8:4
Hz, 2H), 7.43 (d, J ¼ 8:4 Hz, 2H), 7.19 (d, J ¼ 8:4 Hz, 2H), 6.05
1
3
(
(
d, J ¼ 8:9 Hz, 1H), 5.12–4.95 (m, 1H), 2.38 (s, 3H); C NMR
68 MHz, CDCl3) ꢂ 148.3, 144.4, 138.5, 136.4, 129.7, 129.0,
126.9, 123.8, 123.3 (q, JC{F ¼ 281 Hz), 58.6 (q, JC{C{F ¼ 32 Hz),
21.6; Anal. Calcd for C15H13F3N2O4S: C, 48.13; H, 3.50; N,
7.48%. Found: C, 47.93; H, 3.34; N, 7.32%.
4-Methyl-N-(3-phenyl-1-trifluoromethylpropyl)benzenesul-
ꢁ
fonamide (38m): White solid; mp 109–111 C; IR (ATR) 3255,
ꢂ1
1
4
-Methyl-N-[2,2,2-trifluoro-1-(2-naphthyl)ethyl]benzenesul-
ꢁ
2938, 1454, 1342, 1129 cm ; H NMR (270 MHz, CDCl3) ꢂ 7.74
(d, J ¼ 8:4 Hz, 2H), 7.33–7.05 (m, 7H), 4.93 (d, J ¼ 9:7 Hz, 1H),
4.04–3.84 (m, 1H), 2.86–2.57 (m, 2H), 2.43 (s, 3H), 2.16–2.02 (m,
1H), 1.86–1.66 (m, 1H); 13C NMR (68 MHz, CDCl3) ꢂ 143.8,
139.7, 137.5, 129.6, 128.5, 128.3, 126.9, 126.3, 124.6 (q, JC{F ¼
281 Hz), 55.0 (q, JC{C{F ¼ 29 Hz), 31.1 (q, JC{C{C{F ¼ 2 Hz), 31.0,
fonamide (38g):3g
(
(
4
1
1
1
3
Colorless granulars; mp 154–155 C; IR
ATR) 3252, 1598, 1454, 1336, 1267, 1191, 1126 cm ; 1H NMR
ꢂ1
270 MHz, DMSO-d6) ꢂ 9.28 (d, J ¼ 10:3 Hz, 1H), 7.89–7.72 (m,
H), 7.55–7.46 (m, 5H), 7.03 (d, J ¼ 8:6 Hz, 2H), 5.46–5.30 (m,
13
H), 2.07 (s, 3H); C NMR (68 MHz, DMSO-d6) ꢂ 142.4, 137.7,
32.5, 132.0, 129.4, 128.9, 128.0, 127.8, 127.3, 126.5, 126.4,
26.3, 126.1, 125.0, 124.3 (q, JC{F ¼ 281 Hz), 58.1 (q, JC{C{F ¼
1 Hz), 20.9; Anal. Calcd for C19H16F3NO2S: C, 60.15; H, 4.25;
þ
21.7; HRMS (FAB+) calcd for C17H19F3NO2S ½M þ Hꢃ
358.1089, found 358.1082.
4-Chloro-N-(2,2,2-trifluoro-1-phenylethyl)benzenesulfon-
amide (45): Colorless needles; mp 172–174 C; IR (ATR) 3251,
1461, 1346, 1265, 1174, 1127 cm ; H NMR (270 MHz, DMSO-
d6) ꢂ 9.40 (brs, 1H), 7.64 (d, J ¼ 8:6 Hz, 2H), 7.44 (d, J ¼ 8:6 Hz,
2H), 7.40–7.34 (m, 2H), 7.32–7.18 (m, 3H), 5.35–5.22 (m, 1H);
ꢁ
N, 3.69%. Found: C, 59.86; H, 4.23; N, 3.68%.
4-Methyl-N-[2,2,2-trifluoro-1-(2-furyl)ethyl]benzenesulfon-
amide (38h): Colorless granulars; mp 140–142 C; IR (ATR)
ꢂ1
1
ꢁ
ꢂ1
1H NMR
3
244, 1454, 1330, 1268, 1184, 1167, 1091 cm
;
13
(
270 MHz, CDCl3) ꢂ 7.66 (d, J ¼ 8:4 Hz, 2H), 7.27 (d, J ¼ 7:8
C NMR (68 MHz, DMSO-d6) ꢂ 139.4, 137.1, 131.8, 128.7,
Hz, 1H), 7.23 (d, J ¼ 8:4 Hz, 2H), 6.27 (s, 2H), 5.39 (d,
128.6, 128.1, 126.6, 124.1 (q, JC{F ¼ 281 Hz), 57.8 (q, JC{C{F ¼
31 Hz); Anal. Calcd for C14H11ClF3NO2S: C, 48.08; H, 3.17; N,
4.00%. Found: C, 48.01; H, 3.27; N, 3.80%.
1
3
J ¼ 9:7 Hz, 1H), 5.12–4.98 (m, 1H), 2.40 (s, 3H); C NMR (68
MHz, CDCl3) ꢂ 144.2, 143.8, 143.5, 136.7, 129.5, 126.8, 122.8
(
q, JC{F ¼ 281 Hz), 110.6, 110.4, 53.3 (q, JC{C{F ¼ 34 Hz), 21.6;
4-Nitro-N-(2,2,2-trifluoro-1-phenylethyl)benzenesulfonamide
ꢁ
Anal. Calcd for C13H12F3NO3S: C, 48.90; H, 3.79; N, 4.39%.
Found: C, 48.84; H, 3.56; N, 4.22%.
(46): Colorless granulars; mp 153–154 C; IR (ATR) 3268, 1524,
ꢂ1
1
1351, 1190, 1134 cm ; H NMR (270 MHz, DMSO-d6) ꢂ 9.71 (d,
J ¼ 10:0 Hz, 1H), 8.21 (d, J ¼ 8:6 Hz, 2H), 7.89 (d, J ¼ 8:6 Hz,
2H), 7.48–7.36 (m, 2H), 7.28–7.16 (m, 3H), 5.48–5.32 (m, 1H);
4-Methyl-N-[2,2,2-trifluoro-1-(4-pyridyl)ethyl]benzenesulfon-
amide (38i): Colorless granulars; mp 194–197 C (dec.); IR
ꢁ
ATR) 3045, 2738, 1607, 1339, 1183, 1164 cm ; 1H NMR (270
ꢂ1
13
C NMR (68 MHz, DMSO-d6) ꢂ 149.1, 146.0, 131.7, 129.0,
128.1, 128.1, 127.8, 124.1 (q, JC{F ¼ 281 Hz), 124.0, 57.9 (q,
(
MHz, DMSO-d6) ꢂ 9.37 (d, J ¼ 10:3 Hz, 1H), 8.44 (d, J ¼ 5:1