2
074
d: Mp 74–76 8C (lit.
IR: 1732, 1613, 1586, 1533, 1447, 1281, 1122, 1023, 837, 804, 764, 724 cm
M. Chakrabarty, T. Kundu, and Y. Harigaya
[
19b]
1
mp 75–76 8C; no spectroscopic data were given);
2
1
;
1
H NMR (CDCl ): d 1.63 (9H, s), 3.79 (3H, s), 6.45 (1H, d, J ¼ 3.5 Hz), 6.91
3
(1H, dd, J ¼ 9 Hz, J ¼ 2 Hz), 6.99 (1H, d, J ¼ 2 Hz), 7.54 (1H, s), 8.02 (1H,
br); C NMR: d 28.6 (NCO CMe ), 56.0 (OCH ), 83.8 (NCO CMe ), 103.9,
1
2
1
3
2
3
3
2
3
1
07.5, 113.4, 116.2, 126.9 (all Ar-CH), 130.3, 131.1, 156.3 (all Ar-C), 150.1
þ
(
carbamate CO); EI-MS: m/z (%) 247 (M ; 34), 191 (100), 147 (47), 132 (38),
þ
57 (48), 41 (12); HR EI-MS: m/z 247.1211 (M ). Calcd. for C H NO :
1
4
17
3
247.1209.
1
e: Mp 58–60 8C; IR: 1739, 1573, 1533, 1275, 1248, 1162, 1082, 1023,
2
1 1
7
64 cm ; H NMR (CDCl ): d 1.66 (9H, s), 6.49 (1H, d, J ¼ 3.5 Hz), 7.38
3
(
1H, dd, J ¼ 9 Hz, J ¼ 1.5 Hz), 7.57 (1H, d, J ¼ 3.5 Hz), 7.67 (1H, d,
2 3
1
2
1
3
J ¼ 1.5 Hz), 8.01 (1H, br d, J ¼ 8 Hz); C NMR: d 28.5 (NCO CMe ),
8
1
4.5 (NCO CMe ), 106.8, 116.9, 123.9, 127.4 (ꢀ2) (all Ar-CH), 116.3,
2
3
32.6, 134.3 (all Ar-C), 149.8 (carbamate CO); EI-MS: m/z (%) 297
þ
(
M þ 2; 18), 295 (M ; 18), 241 (40), 239 (40), 224 (10), 222 (10), 197
(63), 195 (66), 116 (27), 115 (27), 57 (100), 41 (53); HR EI-MS: m/z
þ
95.0197 (M ). Calcd. for C H NO Br: 295.0208.
13 14 2
79
2
1
f: Mp 172–174 8C (dec.); IR: 3363, 3169, 1719, 1547, 1469, 1327, 1299,
21 1
1
155, 1049, 764 cm ; H NMR (DMSO-d ): d 1.61 (9H, s), 2.89 (3H, d,
6
J ¼ 4.5 Hz), 6.68 (1H, d, J ¼ 3.5 Hz), 7.19 (1H, d, J ¼ 8.5 Hz), 7.49 (1H, br
s), 7.56 (1H, s), 7.65 (1H, d, J ¼ 3.5 Hz), 7.96 (1H, d, J ¼ 8.5 Hz), 9.50
1
3
(
1H, br s);
C NMR: d 27.6 (NCO CMe ), 31.3 (N-CH ), 83.8
2 3 3
(
NCO CMe ), 107.5, 114.7, 116.7, 121.5, 126.6 (all Ar-CH), 130.4, 131.9,
2 3
1
3
1
33.7 (all Ar-C), 149.0 (carbamate CO), 181.3 (C 55 S); EI-MS: m/z (%)
þ
05 (M ; 100), 249 (45), 216 (29), 215 (28), 205 (26), 193 (48), 176 (69),
32 (76), 131 (32), 74 (25), 57 (86), 41 (25). Anal. calcd. for C H N O S:
1
5 19 3 2
C, 59.01; H, 6.23; N, 13.77. Found: C, 59.07; H, 6.21; N, 13.80.
1
k: Mp 180–182 8C (dec.); IR (KBr): 3232, 1733, 1621, 1562, 1426, 1367,
2
1
1
1
278, 1154, 763 cm ; H NMR (CDCl ): d 1.68 (9H, s), 3.12 (3H, d,
3
J ¼ 5.5 Hz), 5.92 (1H, br s), 6.50 (1H, d, J ¼ 3.5 Hz), 7.51 (1H, d,
1
3
J ¼ 8.5 Hz), 7. 64 (1H, d, J ¼ 3.5 Hz), 8.10 (1H, d, J ¼ 8.5 Hz); C NMR:
d 27.2 (NCO CMe ), 31.3 (N-CH ), 83.3 (NCO CMe ), 104.7, 112.8, 114.9,
2
3
3
2
3
1
26.0 (all Ar-CH), 120.5, 123.4, 130.3, 148.1, 166.9 (all Ar-C), 149.1
þ
(
carbamate CO); EI-MS: m/z (%) 303 (M ; 28), 247 (100), 203 (35), 202
17), 175 (13), 174 (25), 57 (26), 41 (11). Anal. calcd. for C H N O S: C,
(
1
5 17 3 2
59.40; H, 5.61; N, 13.86. Found: C, 59.33; H, 5.60; N, 13.89.
2
1
1
l: Mp 128–130 8C; IR: 1765, 1613, 1527, 1341, 1295, 1149, 1029, 830 cm
;
1
H NMR (DMSO-d ): d 1.45 (9H, s), 7.98 (1H, d, J ¼ 9 Hz), 8.17 (1H, dd,
6
1
3
J ¼ 9 Hz, J ¼ 2 Hz), 8.40 (1H, s), 8.60 (1H, d, J ¼ 2 Hz); C NMR: d
1
2
2
8.4 (NCO CMe ), 86.5 (NCO CMe ), 115.6, 119.5, 124.5, 141.8 (all
2 3 2 3