Sulfonylation of Amines
2779
7
2
.25 (d, J ¼ 8.81 Hz, 2H), 6.97 (d, J ¼ 8.81 Hz, 2H), 2.73 (q, J ¼ 6.81 Hz,
1
3
H), 1.29 (m, 2H), 1.21 (m, 2H), 0.77 (t, J ¼ 7.21 Hz, 3H); C NMR
(DMSO-d ): d 163.5, 153.5, 150.9, 139.8, 132.3, 130.9 (2C), 130.6 (2C),
6
1
1
5
28.6 (2C), 123.6 (2C), 122.9 (2C), 122.7, 116.2 (2C), 42.0, 30.9, 19.0,
3.3; HRMS (EI): calcd for C H NO S [M þ H]þ 542.0607, found
2
2
24
9 3
42.0613.
N-sec-Butyl-4-hydroxybenzenesulfonamide (8a). Yellow oil; IR
2
neat): 3282, 2979, 2932, 2880, 1651, 1583, 1501 cm ; H NMR (DMSO-
1 1
(
d ): d 10.29 (s, 1H), 7.60 (d, J ¼ 8.79 Hz, 2H), 7.22 (t, J ¼ 8.01 Hz, 1H),
6
6
.89 (d, J ¼ 8.79 Hz, 2H), 2.97 (sep, J ¼ 6.41 Hz, 1H), 1.28 (qn,
1
3
J ¼ 7.21 Hz, 2H), 0.85 (d, J ¼ 6.81 Hz, 3H), 0.70 (t, J ¼ 7.21 Hz, 3H); C
NMR (DMSO-d ): d 160.5, 131.9, 128.5 (2C), 115.2 (2C), 50.4, 29.4, 20.4,
6
2
9
.9; HRMS (EI): calcd for C H NO S [M 2 H] 228.0700, found 228.0698.
10 14 3
N-Hexyl-4-hydroxybenzenesulfonamide (9a). Yellow oil; IR (neat):
2
286, 2955, 2926, 2861, 1655, 1587, 1501 cm ; H NMR (DMSO-d ): d
1 1
3
1
6
0.33 (s, 1H), 7.60 (d, J ¼ 8.81 Hz, 2H), 7.26 (t, J ¼ 8.01 Hz, 1H), 6.90
(
d, J ¼ 8.81 Hz, 2H), 2.67 (q, J ¼ 7.20 Hz, 2H), 1.32 (m, 2H), 1.18 (m, 3H),
1
3
0
1
.82 (t, J ¼ 6.81 Hz, 3H); C NMR (DMSO-d ): d 161.1, 130.9, 129.1 (2C),
6
15.8 (2C), 42.8, 31.1, 29.2, 26.1, 22.3, 14.2; HRMS (EI): calcd for
þ
C H NO S [M þ H] 258.1158, found 258.1168.
1
2
20
3
N-Cyclobutyl-4-hydroxybenzenesulfonamide (10a). White solid; m.p.
1 1
2
1–938C; IR (neat): 3281, 2978, 1644, 1587, 1501 cm ; H NMR (DMSO-
9
d ): d 10.32 (s, 1H), 7.66 (d, J ¼ 8.01 Hz, 1H), 7.58 (d, J ¼ 8.81 Hz, 2H), 6.89
6
(
d, J ¼ 8.81 Hz, 2H), 2.97 (six, J ¼ 8.41 Hz, 1H), 1.88 (m, 2H), 1.70 (m, 2H),
1
.47 (m, 2H); C NMR (DMSO-d ): d 160.7, 131.4, 128.6 (2C), 115.3 (2C),
3
1
4
2
6
2
7.4, 30.4 (2C), 14.4; HRMS (EI): calcd for C H NO S [M 2 H]
3
1
0
12
26.0543, found 226.0542.
0b. Pale yellow solid; IR (neat): 3281, 3102, 2971, 2935, 1651,
1
2
1 1
1
580 cm ; H NMR (DMSO-d ): d 10.94 (bs, 1H), 8.00 (d, J ¼ 8.01 Hz,
6
1
H), 7.78 (d, J ¼ 8.81 Hz, 2H), 7.64 (d, J ¼ 8.81 Hz, 2H), 7.23
(
d, J ¼ 8.81 Hz, 2H), 6.93 (d, J ¼ 8.81 Hz, 2H), 3.59 (six, J ¼ 8.01 Hz, 1H),
1
.81 (m, 2H), 1.63 (m, 2H), 1.47 (m, 2H); C NMR (DMSO-d ): d 163.3,
3
1
6
1
51.5, 140.2, 130.9 (2C), 128.5 (2C), 122.9 (2C), 122.8, 116.2 (2C), 47.4,
2
0.3 (2C), 14.4; HRMS (EI): calcd for C H NO S [M 2 H] 382.0425,
3
found 382.0425.
1
6
16
6 2
1
0c. Pale yellow solid; IR (neat): 3285, 3101, 2987, 2941, 1648,
1 1
2
1
1
586 cm ; H NMR (DMSO-d ): d 11.02 (s, 1H), 8.03 (d, J ¼ 8.01 Hz,
6
H), 7.90 (d, J ¼ 8.81 Hz, 2H), 7.79 (d, J ¼ 8.81 Hz, 2H), 7.68
(
d, J ¼ 8.81 Hz, 2H), 7.30 (d, J ¼ 8.81 Hz, 2H), 7.22 (d, J ¼ 8.81 Hz, 2H),
6
.98 (d, J ¼ 8.81 Hz, 2H), 3.62 (six, J ¼ 8.41 Hz, 1H), 1.81 (m, 2H), 1.63
6
1
m, 2H), 1.46 (m, 2H); C NMR (DMSO-d ): d 163.5, 153.5, 151.0, 140.7,
3
(
1
32.1, 130.9 (2C), 130.7 (2C), 128.6 (2C), 123.6 (2C), 122.8 (2C), 122.6,