14 JOURNAL OF CHEMICAL RESEARCH 2010
J = 8.0 Hz), 7.32 (2H, d, J = 8.0 Hz), 6.85 (2H, d, J = 8.0 Hz),
5.63 (1H, brs), 5.39 (1H, d, J = 8.0 Hz), 4.05 (2H, q, J = 7.0 Hz), 2.46
(3H, s), 1.43 (3H, t, J = 7.0 Hz); 13C NMR (200 MHz, CDCl3):
δ 160.1, 145.0, 136.5, 130.1, 128.7, 127.3, 123.8, 116.7, 115.2, 63.9,
47.9, 21.6, 14.6; LCMS: m/z 353 [M+Na]+; Anal. Calcd for
C H18N2O S: C, 61.82; H, 5.45; N, 8.48. Found: C, 61.92; H, 5.51;
N1,78.56%. 3
136.3, 130.3, 127.5, 117.3, 45.4, 27.6, 21.4, 9.9; LCMS: m/z 261
[M+Na]+; Anal. Calcd for C11H N O2S: C, 55.46; H, 5.88; N, 11.76.
Found: C, 55.36; H, 5.97; N, 111.4852%.
N-(1-Cyanobutyl)-4-methylbenzenesulfonamide (3m): M.p. 84–
1
86 °C. IR: 3288, 2236, 1600, 1430, 1340, 1156 cm−1; H NMR (200
MHz, CDCl ): δ 7.75 (2H, d, J = 8.0 Hz), 7.40 (2H, d, J = 8.0 Hz),
5.72 (1H, b3rs), 4.24 (1H, q, J = 7.0 Hz), 2.50 (3H, s), 1.80–1.69
(2H, m), 1.49–1.40 (2H, m), 0.94 (3H, t, J = 7.0 Hz); 13C NMR (50
MHz, CDCl3): δ 144.3, 136.2, 130.0, 127.1, 117.4, 44.0, 35.7, 21.5,
18.6, 13.0; LCMS: m/z 275 [M+Na]+; Anal. Calcd for C H16N2O S:
C, 57.14; H, 6.35; N, 11.11. Found: C, 57.23; H, 6.44; N,1121.05%.2
N-[(4-Benzyloxyphenyl)(cyano)methyl]-4-methylbenzenesulfon-
amide (3d): M.p. 165–167 °C., IR: 3265, 2245, 1616, 1518, 1335,
1
1253 cm−1; H NMR(200 MHz, CDCl ): δ 7.80 (2H, d, J = 8.0 Hz),
7.44–7.30 (9H, m), 6.95 (2H, d, J = 8.0 3Hz), 5.40 (1H, d, J = 10.0 Hz),
5.16 (1H, d, J = 10.0 Hz), 5.00 (2H, s), 2.43 (3H, s); 13C NMR (200
MHz, CDCl3): δ 158.6, 145.7, 136.0, 130.3, 130.6, 130.0, 127.4,
124.5, 115.7, 70.0, 48.1, 21.8; LCMS: m/z 415 [M+Na]+; Anal. Calcd
for C22H20N2O3S: C, 67.35; H, 5.10; N, 7.14. Found: C, 67.49; H, 5.05;
N, 7.25%.
The authors thank the Head, NMR division, IICT, Hyderabad
for providing spectral data.
Received 20 August 2009; accepted 11 December 2009
Paper 090752 doi: 10.3184/030823409X12611577711291
Published online: 20 January 2010
N-[(3-Chlorophenyl)cyanomethyl]-4-methylbenzenesulfonamide
(3f): M.p. 101–103 °C., IR: 3270, 2243, 1590, 1445, 1353, 1166 cm−1;
1H NMR(200 MHz, CDCl3): δ 7.75 (2H, d, J = 8.0 Hz), 7.38–7.30
(6H, m), 5.62 (1H, d, J = 10.0 Hz), 5.35 (1H, d, J = 10.0 Hz), 2.46
(3H, s); 13C NMR (200 MHz, CDCl3): δ 144.8, 135.6, 135.5, 133.6,
130.6, 129.5, 130.0, 127.2, 124.8, 116.0, 47.5, 21.9; LCMS: m/z 343
[M+Na]+; Anal. Calcd for C H ClN O2S: C, 56.25; H, 4.06; N, 8.75.
Found: C, 56.35; H, 4.11; N1,58.1634%. 2
N-[Cyano(2,5-dimethylphenyl)methyl]-4-methylbenzenesulfon-
amide (3h): M.p. 135–137 °C. IR: 3259, 2230, 1585, 1340, 1160 cm−
1; 1H NMR(200 MHz, CDCl3): δ 7.85 (2H, d, J = 8.0 Hz), 7.45 (2H, d,
J = 8.0 Hz), 7.25 (1H, dd, J = 8.0, 2.0 Hz), 7.10 (2H, brs), 5.55 (1H, d,
J = 10.0 Hz), 4.93 (1H, d, J = 10.0 Hz), 2.50 (3H, s), 2.32 (3H, s),
2.34 (3H, s); 13C NMR (200 MHz, CDCl ): δ 144.6, 136.6, 136.4,
133.3, 131.4, 130.5, 129.6, 128.0, 127.5, 1136.9, 46.0, 21.3, 21.0, 18.4;
LCMS: m/z 337 [M+Na]+; Anal. Calcd for C17H18N O2S: C, 64.97; H,
5.73; N, 8.91. Found: C, 64.81; H, 5.79; N, 8.82%.2
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N-[Cyano(2,4,6-trimethylphenyl)methyl]-4-methylbenzenesulfon-
amide (3i): M.p. 139–141 °C. IR: 3270, 1611, 1420, 1330, 1165 cm−1;
1H NMR(200 MHz, CDCl3): δ 7.78 (2H, d, J = 8.0 Hz), 7.25 (2H, d,
J = 8.0 Hz), 6.85 (2H, s), 5.68 (1H, d, J = 8.0 Hz), 5.55 (1H, brs), 2.45
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δ 144.6, 139.5, 136.9, 136.2, 130.3, 130.0, 127.0, 126.1, 116.6, 42.6,
21.4, 20.7, 19.9; LCMS: m/z 351 [M+Na]+; Anal. Calcd for
C H20N2O2S: C, 65.85; H, 6.10; N, 8.54. Found: C, 65.75; H, 6.20; N,
8.1681%.
N-[Cyano(thiophene-2-yl)methyl]-4-methylbenzenesulfonamide
(3j): M.p. 112–113 °C. IR: 3241, 2222, 1607, 1335 cm−1; 1H NMR(200
MHz, CDCl3): δ 7.83 (2H, d, J = 8.0 Hz), 7.38–7.30 (3H, m), 7.24
(1H, m), 6.95 (1H, m), 5.81 (1H, d, J = 10.0 Hz), 5.68 (1H, d, J = 10.0
Hz), 2.48 (3H, s); 13C NMR (200 MHz, CDCl3): δ 145.1, 136.4, 134.7,
130.3, 130.2, 128.4, 128.0, 127.1, 127.4, 126.2, 115.6, 43.7, 21.4;
LCMS: m/z 315 [M+Na]+; Anal. Calcd for C H12N2O2S2: C, 53.42;
H, 4.11; N, 9.59. Found: C, 53.54; H, 4.19; N,193.47%.
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N-(1-Cyanopropyl)-4-methylbenzenesulfonamide (3l): M.p. 79–
1
82 °C. IR: 3274, 2253, 1604, 1448, 1345, 1173 cm−1; H NMR (200
MHz, CDCl3): δ 7.82 (2H, d, J = 8.0 Hz), 7.38 (2H, d, J = 8.0 Hz),
5.85 (1H, brs), 4.20 (1H, q, J = 7.0 Hz), 2.43 (3H, s), 1.86–1.74 (2H,
m), 1.03 (3H, t, J = 7.0 Hz); 13C NMR(50 MHz, CDCl3): δ 144.3,