3
870
Chandrasekhar et al.
7
C H N O S 404.522; Found 404.518.
.30 (d, J ¼ 7.8 Hz, 1H), 7.80 (d, J ¼ 7.8 Hz, 2H). HRMS (EI) m/z calcd for
2
1 28 2 4
1-N-(2-Methylanilinocyclopentyl)-4-methyl-1-benzenesulfonamide (2b):
viscous liquid; IR (neat): 3275 cm ; H NMR (CDCl ): d 1.28–1.32 (m, 2H),
2
1 1
3
1
.42–1.47 (m, 2H), 1.72–1.76 (m, 2H), 2.45 (s, 3H), 2.45 (s, 3H), 3.38–3.43
m, 1H), 3.83–3.87 (m, 1H), 5.25 (bs, 1H), 6.58–6.63 (m, 1H), 7.24–7.28
(
(
H, 7.02; N, 6.29; Found: C, 66.35; H, 7.00; N, 6.22.
m, 4H), 7.70 (d, J ¼ 7.9 Hz, 2H). Anal Calcd for C H N O S: C, 66.15;
1
9 24 2 2
1
-N-(1-Ethylaminomethylpentyl)-4-methyl-1-benzenesulfonamide (4b):
2
1 1
viscous liquid; IR (neat) 3288 cm ; H NMR (CDCl ): d 0.75 (t, J ¼ 4.1 Hz,
3
3
H), 1.05 (t, J ¼ 5.58 Hz, 3H), 1.13–1.18 (m, 4H), 1.35–1.45 (m, 2H), 2.45
(
s, 3H), 3.15–3.25 (m, 4H), 3.40–3.50 (m, 1H), 5.15–5.25 (m, 1H),
.55 (d, J ¼ 8.8 Hz, 2H), 6.65–6.75 (m, 1H), 7.10–7.20 (m, 4H), 7.75
6
þ
(
C H N O S: C, 67.34; H, 8.07; N, 7.48; Found: C, 67.36; H, 8.11; N, 7.49.
d, J ¼ 7.5 Hz, 2H). MS: 374 (M ), 239, 155, 120, 91, 57. Anal Calcd for
2
1 30 2 2
4
benzene (5a): viscous liquid; IR (neat) 3282 cm ; H NMR (CDCl ): d
-Fluoro-1-[4-methyl-2-(4-methylphenylsulfonamido)pentylamino]
2
1 1
3
0
1
3
6
.65 (d, J ¼ 5.9 Hz, 3H), 0.85 (d, J ¼ 5.9 Hz, 3H), 1.20–1.30 (m, 2H),
.45–1.55 (m, 1H), 2.40 (s, 3H), 2.93–2.97 (m, 1H), 3.10 (dd, J ¼ 10.8,
.3 Hz, 1H), 3.41–3.48 (m, 1H), 3.80 (bs, 1H), 5.03–5.07 (m, 1H),
.42–6.46 (m, 2H), 6.78–6.83 (m, 2H), 7.25 (d, J ¼ 7.7 Hz, 2H), 7.85
(
d, J ¼ 7.7 Hz, 2H). HRMS (EI) m/z calcd for C H FN O S 364.476,
1
9
25
2 2
found 364.474.
1
viscous liquid; IR (neat) 3275 cm
-N-(1-Ethylanilinomethylnonyl)-4-methyl-1-benzenesulfonamide (7):
2
1
1
;
H NMR (CDCl ): d 0.80
3
(
t, J ¼ 4.2 Hz, 3H), 0.85 (t, J ¼ 5.5 Hz, 3H), 1.23–1.28 (m, 12H), 1.63–
1
4
.68 (m, 2H), 2.45 (s, 3H), 3.43–3.48 (m, 3H), 3.40–3.50 (m, 2H),
.68–4.73 (m, 1H), 6.60–6.70 (m, 2H), 7.20–7.30 (m, 5H), 7.70
(
d, J ¼ 8.1 Hz, 2H). Anal Calcd for C H N O S: C, 69.73; H, 8.89; N,
2
5 38 2 2
6
.50; Found: C, 69.75; H, 8.93; N, 6.55.
-Bromo-1-[1-(4-bromoanilino)-2-(4-ethylphenylsulfonamido)ethyl]-
4
benzene (10): semi solid; IR (KBr) 3279 cm ; H NMR (CDCl ): d
1
1
3
2
.45 (s, 3H), 3.08–3.12 (m, 2H), 4.15–4.25 (m, 2H), 5.55 (bs, 1H), 6.30
(
d, J ¼ 8.4 Hz, 2H), 7.05 (d, J ¼ 8.4 Hz, 2H), 7.18–7.25 (m, 4H), 7.40 (d,
J ¼ 7.1 Hz, 2H), 7.75 (d, J ¼ 8.2 Hz, 2H). Anal Calcd for C H Br N O S:
2
1
20
2 2 2
C, 48.11; H, 3.84; N, 5.34; Found: C, 48.17; H, 3.88; N, 5.36.
ACKNOWLEDGMENTS
Three of us (S.J.P., T.S., and T.R.) are thankful to CSIR, New Delhi for
financial assistance.