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HETEROCYCLES, Vol. 76, No. 2, 2008
(CDCl3, 500 MHz): δ = 3.16 (t, J = 7.2Hz, 2H, CH2 ), 3.52 (t, J = 7.2Hz, 2H, CH2), 7.18 – 8.02 (m, 20H,
phenyl). 13C NMR (CDCl3, 125 MHz):δ = 198.6, 136.9, 133.2, 129.6, 128.6, 128.1, 127.5, 126.8, 82.0, 53.4,
37.4 RMS: m/z [M+] calcd for C28H24NOClNa: 448.1439; found: 448.145. Anal. Calcd for C29H24ClNO: C,
78.95; H, 5.68; N, 3.29; Cl, 8.32. Found: C, 78.93; H, 5.76; N, 3.20; Cl, 8.22.
N-t-Butyl-2-N-chloroaminoethyl phenyl sulfone (2i): oil; IR (film): 3066, 2979, 2938, 1979, 1905, 1818,
1586, 1478, 1447, 1394, 1366, 1320, 1294, 1229, 1201, 1172, 1142, 1087, 1069, 988, 904, 808, 762, 737,
688, 627, 579, 559, 543, 526, 483, 461, 437. 1H NMR (CDCl3, 500 MHz): δ = 1.17 (s, 9H, C(CH3)3), 3.33 (t,
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J = 6.9Hz, 2H, CH2), 3.52 (t, J = 6.9Hz, 2H, CH2), 7.54 – 7.95 (m, 5H, phenyl). C NMR (CDCl3, 125
MHz):δ = 139.9, 133.7, 129.1, 127.9, 62.5, 55.5, 49.8, 26.2. HRMS: m/z [MH+] calcd for C12H18ClNO2S:
275.0747 found: 275.0753. Anal. Calcd for C12H18ClNO2S: C, 52.26; H, 6.58; Cl, 12.85; N, 5.08; S, 11.63.
Found: C, 52.35; H, 6.46; Cl, 12.98; N, 5.09; S, 11.50.
N-Chloro-2-N-methylaminoethyl phenyl sulfone (2j): oil; IR (film): 3627, 3555, 3065, 2994, 2958, 2925,
2881, 2800, 1585, 1447, 1412, 1369, 1318, 1309, 1294, 1245, 1146, 1086, 1070, 1024, 998, 944, 805, 748,
729, 689, 608, 564, 535, 438. 1H NMR (CDCl3, 500 MHz): δ = 2.91 (s, 3H, CH3), 3.27 (t, J = 7.3Hz, 2H,
CH2), 3.48 (t, J = 7.3Hz, 2H, CH2), 7.57 – 7.94 (m, 5H, phenyl). 13C NMR (CDCl3, 125 MHz):δ = 139.6,
133.9, 129.3, 127.9, 58.6, 54.6, 53.0. HRMS: m/z [MNa+] calcd for C9H12ClNO2SNa: 256.0170 found:
256.0181. Anal. Calcd for C9H12ClNO2S: C, 46.25; H, 5.18; Cl, 15.17; N, 5.99; S, 13.72. Found: C, 46.26;
H, 4.99; Cl, 15.36; N, 5.81; S, 13.57.
N-Chloro-2-N-benzylaminoethyl phenyl sulfone (2k): pale yellow oil; IR(film):3423, 3064, 3032, 2931,
2900, 1959, 1815, 1735, 1585, 1497, 1447, 1319, 1309, 1296, 1086, 1071, 1025, 999, 911, 841, 806, 770,
741, 688, 594, 580, 569, 535, 436. 1H NMR (CDCl3, 500 MHz): δ = 3.37 (t, J = 7.1Hz, 2H, CH2), 3.55 (t,
J = 7.1Hz, 2H, CH2), 4.07 (s, 2H, CH2), 7.22 – 7.91 (m, 10H, phenyl). 13C NMR (CDCl3, 125 MHz):δ =
139.4, 135.8, 133.8, 129.3, 129.2, 128.5, 128.2, 128.0, 68.4, 56.0, 54.5. HRMS: m/z [MNa+] calcd for
C15H16ClNO2SNa: 332.0483; found: 332.0483. Anal. Calcd for C15H16ClNO2S: C, 58.15; H, 5.21; Cl,
11.40; N, 4.52; S, 10.35. Found: C, 58.06; H, 5.41; Cl, 11.40; N, 4.65; S, 10.42.
Ethyl N-acetyl-3-N-chloroaminopropionate (2l): oil; IR(film): 3519, 2984, 2939, 1733, 1681, 1440,
1372, 1338, 1251, 1187, 1098, 1069, 1032, 981, 857, 784, 639, 585, 505. 1H NMR (CDCl3, 500 MHz): δ
= 1.24 (t, J = 7,1Hz, 3H, CH3), 2.22 (s, 3H, CH3), 2.66 (t, J = 7.0Hz, 2H, CH2), 3.96 (t, J = 7.1Hz, 2H,
CH2), 4.13 (q, J = 7.1Hz, 2H, CH2). 13C NMR (CDCl3, 125 MHz):δ = 170.6, 60.8, 48.4, 32.3, 21.6, 14.1.
RMS: m/z [MNa+] calcd for C7H12NO3NaCl: 216.0398; found: 216.0400. Anal. Calcd for C7H12ClNO3: C,
43.42; H, 6.25; N, 7.23; Cl, 18.31. Found: C, 42.77; H, 6.20; N, 7.28; Cl, 18.48.
Ethyl N-chloro-3-etoxycarbonylaminopropionate (2m): oil; IR(film): 3629, 3550, 3450, 3388, 2984,
2939, 2911, 2876, 1735, 1709, 1512, 1466, 1444, 1400, 1374, 1322, 1252, 1187, 1141, 1095, 1075, 1027,
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970, 876, 857, 788, 754, 615, 569, 474. H NMR (CDCl3, 500 MHz): δ = 1.27 (t, J = 7,1Hz, 3H, CH3),