Job/Unit: O43531
/KAP1
Date: 22-01-15 13:25:06
Pages: 9
C. Buathongjan, D. Beukeaw, S. Yotphan
FULL PAPER
1-Tosylpyrrolidine (3c):[9] White solid. 1H NMR (400 MHz,
CDCl3): δ = 7.69 (d, J = 8.2 Hz, 2 H), 7.30 (d, J = 8.0 Hz, 2 H),
J = 8.0 Hz, 2 H), 7.32–7.27 (m, 5 H), 4.10 (s, 2 H), 2.56 (s, 3 H),
2.44 (s, 3 H) ppm. 13C NMR (100 MHz, CDCl3): δ = 143.7, 135.9,
134.5, 130.0, 128.8, 128.6, 128.1, 127.7, 54.4, 34.5, 21.8 ppm.
HRMS (ESI): calcd. for C15H17NO2SNa [M + Na]+ 298.0872;
found 298.0877.
3.22 (t, J = 6.8 Hz, 4 H), 2.41(s, 3 H), 1.74–1.71 (m, 4 H) ppm. 13
C
NMR (100 MHz, CDCl3): δ = 143.5, 134.1, 129.8, 127.8, 48.1, 25.4,
21.7 ppm. HRMS (ESI): calcd. for C11H17NO2SNa [M + Na]+
248.0716; found 248.0727.
N-Benzyl-4-methylbenzenesulfonamide (3m):[9] White solid. 1H
NMR (400 MHz, CDCl3): δ = 7.74 (d, J = 8.2 Hz, 2 H), 7.29 (d,
J = 8.0 Hz, 2 H), 7.26–7.17 (m, 5 H), 4.64 (br., 1 H), 4.10 (d, J =
6.2 Hz, 2 H), 2.42 (s, 3 H) ppm. 13C NMR (100 MHz, CDCl3): δ
1-Tosylpiperidine (3d):[19] White solid. 1H NMR (400 MHz,
CDCl3): δ = 7.61 (d, J = 8.1 Hz, 2 H), 7.29 (d, J = 8.0 Hz, 2 H),
2.94 (t, J = 5.4 Hz, 4 H), 2.40 (s, 3 H), 1.64–1.58 (m, 4 H), 1.41–
1.35 (m, 2 H) ppm. 13C NMR (100 MHz, CDCl3): δ = 143.5, 133.4, = 143.8, 137.1, 136.5, 130.0, 128.9, 128.2, 128.1, 127.4, 47.5,
129.7, 127.9, 47.1, 25.4, 23.7, 21.7 ppm. HRMS (ESI): calcd. for
21.8 ppm. HRMS (ESI): calcd. for C14H15NO2SNa [M + Na]+
284.0716; found 284.0717.
C12H17NO2SNa [M + Na]+ 262.0872; found 262.0869.
1
1-Tosylazepane (3e):[19] White solid. H NMR (400 MHz, CDCl3): N-Cyclohexyl-4-methylbenzenesulfonamide (3n):[21] Yellow solid. 1H
δ = 7.64 (d, J = 8.2 Hz, 2 H), 7.25 (d, J = 8.1 Hz, 2 H), 3.24–3.21
NMR (400 MHz, CDCl3): δ = 7.75 (d, J = 8.0 Hz, 2 H), 7.26 (d,
J = 8.0 Hz, 2 H), 4.87–4.85 (m, 1 H), 3.08–3.07 (m, 1 H), 2.39 (s,
(m, 4 H), 2.39 (s, 3 H), 1.68–1.67 (m, 4 H), 1.56–1.53 (m, 4 H) ppm.
13C NMR (100 MHz, CDCl3): δ = 143.0, 136.8, 129.8, 127.1, 48.4, 3 H), 1.72–1.45 (m, 5 H), 1.19–1.05 (m, 5 H) ppm. 13C NMR
29.3, 27.1, 21.7 ppm. HRMS (ESI): calcd. for C11H17NO2SNa [M
(100 MHz, CDCl3): δ = 143.2, 138.7, 129.8, 127.1, 52.7, 34.0, 25.3,
24.8, 21.7 ppm. HRMS (ESI): calcd. for C13H19NO2SNa [M +
Na]+ 276.1029; found 276.1036.
+ Na]+ 276.1029; found 276.1031.
4-Tosylmorpholine (3f):[9] White solid. 1H NMR (400 MHz,
CDCl3): δ = 7.59 (d, J = 8.2 Hz, 2 H), 7.30 (d, J = 8.2 Hz, 2 H),
3.69 (t, J = 4.6 Hz, 4 H), 2.94 (t, J = 4.6 Hz, 4 H), 2.40 (s, 3
H) ppm. 13C NMR (100 MHz, CDCl3): δ = 144.1, 132.2, 129.9,
128.0, 66.2, 46.1, 21.7 ppm. HRMS (ESI): calcd. for
C11H15NO3SNa [M + Na]+ 264.0665; found 264.0666.
N-Isopropyl-4-methylbenzenesulfonamide (3o): White solid, m.p.
45.0–46.0 °C. 1H NMR (400 MHz, CDCl3): δ = 7.75 (d, J = 8.2 Hz,
2 H), 7.26 (d, J = 8.1 Hz, 2 H), 4.79 (br., 1 H), 3.44–3.35 (m, 1 H),
2.39 (s, 3 H), 1.03 (d, J = 6.6 Hz, 6 H) ppm. 13C NMR (100 MHz,
CDCl ): δ = 143.3, 138.3, 129.8, 127.2, 46.2, 23.9, 21.7 ppm. IR: ν
˜
3
= 3276, 2974, 1598, 1424, 1301, 1140, 1091, 813, 660 cm–1. HRMS
(ESI): calcd. for C10H15NO2SNa [M + Na]+ 236.0716; found
236.0718.
4-Tosylthiomorpholine (3g):[20] White solid. 1H NMR (400 MHz,
CDCl3): δ = 7.60 (d, J = 8.2 Hz, 2 H), 7.30 (d, J = 8.0 Hz, 2 H),
3.31–3.28 (m, 4 H), 2.69–2.67 (m, 4 H), 2.42 (s, 3 H) ppm. 13C
NMR (100 MHz, CDCl3): δ = 144.0, 134.0, 130.0, 127.7, 48.1, 27.5,
21.7 ppm. HRMS (ESI): calcd. for C11H15NO2S2Na [M + Na]+
280.0436; found 280.0434.
N-(tert-Butyl)-4-methylbenzenesulfonamide (3p):[9] White solid. 1H
NMR (400 MHz, CDCl3): δ = 7.80 (d, J = 8.2 Hz, 2 H), 7.29 (d,
J = 8.0 Hz, 2 H), 5.06 (br., 1 H), 2.43 (s, 3 H), 1.22 (s, 9 H) ppm.
13C NMR (100 MHz, CDCl3): δ = 142.9, 140.8, 129.6, 127.2, 54.7,
30.3, 21.7 ppm. HRMS (ESI): calcd. for C11H17NO2SNa [M +
Na]+ 250.0872; found 250.0873.
1-Tosylpiperazine (3h): White solid, m.p. 96.2–97.1 °C. 1H NMR
(400 MHz, CDCl3): δ = 7.60 (d, J = 8.2 Hz, 2 H), 7.30 (d, J =
8.0 Hz, 2 H), 2.94–2.88 (m, 8 H), 2.40 (s, 3 H), 1.57 (s, 1 H) ppm.
13C NMR (100 MHz, CDCl3): δ = 143.8, 132.7, 129.8, 128.1, 47.1, N-Butyl-4-methylbenzenesulfonamide (3q):[9] Yellow oil. 1H NMR
45.5, 21.7 ppm. IR: ν = 3331, 2911, 2851, 1597, 1495, 1442, 1335,
(400 MHz, CDCl3): δ = 7.73 (d, J = 8.2 Hz, 2 H), 7.26 (d, J =
8.0 Hz, 2 H), 4.97 (br., 1 H), 2.89–2.85 (m, 2 H), 2.38 (s, 3 H),
1.43–1.35 (m, 2 H), 1.28–1.19 (m, 2 H), 0.79 (t, J = 7.3 Hz, 3
H) ppm. 13C NMR (100 MHz, CDCl3): δ = 143.4, 137.1, 129.8,
127.2, 43.0, 31.6, 21.6, 19.8, 13.7 ppm. HRMS (ESI): calcd. for
C11H17NO2SNa [M + Na]+ 250.0872; found 250.0877.
˜
1158, 1092, 722 cm–1. HRMS (ESI): calcd. for C11H17N2O2S [M +
H]+ 241.1005; found 241.1007.
1-Methyl-4-tosylpiperazine (3i):[21] White solid. 1H NMR
(400 MHz, CDCl3): δ = 7.61 (d, J = 8.2 Hz, 2 H), 7.29 (d, J =
8.0 Hz, 2 H), 2.99 (br., 4 H), 2.46–2.43 (m, 4 H), 2.40 (s, 3 H), 2.24
(s, 3 H) ppm. 13C NMR (100 MHz, CDCl3): δ = 143.9, 132.5, 1-Tosyl-1H-imidazole (3t):[23] White solid. 1H NMR (400 MHz,
129.8, 128.1, 54.3, 46.2, 45.9, 21.7 ppm. HRMS (ESI): calcd. for
CDCl3): δ = 7.98 (s, 1 H), 7.80 (d, J = 8.4 Hz, 2 H), 7.33 (d, J =
8.2 Hz, 2 H), 7.26 (s, 1 H), 7.06 (s, 1 H), 2.42 (s, 3 H) ppm. 13C
NMR (100 MHz, CDCl3): δ = 146.5, 136.8, 135.1, 131.6, 130.6,
127.6, 117.6, 21.9 ppm. HRMS (ESI): calcd. for C10H11N2O2S [M
+ H]+ 223.0536; found 223.0544.
C12H19N2O2S [M + H]+ 255.1162; found 255.1165.
tert-Butyl 4-Tosylpiperazine-1-carboxylate (3j): White solid, m.p.
150.0–151.7 °C. 1H NMR (400 MHz, CDCl3): δ = 7.60 (d, J =
8.2 Hz, 2 H), 7.31 (d, J = 8.0 Hz, 2 H), 3.49–3.46 (m, 4 H), 2.94–
2.92 (m, 4 H), 2.41 (s, 3 H), 1.38 (s, 9 H) ppm. 13C NMR 1-Tosyl-1H-pyrazole (3u):[24] White solid. 1H NMR (400 MHz,
(100 MHz, CDCl3): δ = 154.2, 143.9, 132.5, 129.8, 127.8, 80.4, 45.9,
43.0, 28.3, 21.5 ppm. IR: ν = 2973, 1694, 1596, 1416, 1345, 1164,
CDCl3): δ = 8.09–8.08 (m, 1 H), 7.87 (d, J = 8.3 Hz, 2 H), 7.70 (s,
1 H), 7.30 (d, J = 8.2 Hz, 2 H), 6.37–6.36 (m, 1 H), 2.39 (s, 3
˜
1126, 938, 720 cm–1. HRMS (ESI): calcd. for C16H24N2O4SNa [M H) ppm. 13C NMR (100 MHz, CDCl3): δ = 146.1, 145.4, 134.2,
+ Na]+ 363.1349; found 363.1348.
131.3, 130.2, 128.4, 108.9, 21.9 ppm. HRMS (ESI): calcd. for
C10H11N2O2S [M + H]+ 223.0536; found 223.0542.
1
N,N-Dibenzyl-4-methylbenzenesulfonamide (3k):[19] White solid. H
NMR (400 MHz, CDCl3): δ = 7.72 (d, J = 8.2 Hz, 2 H), 7.29 (d,
J = 8.0 Hz, 2 H), 7.20–7.19 (m, 6 H), 7.04–7.02 (m, 4 H), 4.29 (s,
4-Methylbenzenesulfonamide (3v):[25] White solid. 1H NMR
(400 MHz, CDCl3): δ = 7.79 (d, J = 8.3 Hz, 2 H), 7.29 (d, J =
4 H), 2.43 (s, 3 H) ppm. 13C NMR (100 MHz, CDCl3): δ = 143.5, 8.0 Hz, 2 H), 4.91 (s, 2 H), 2.41 (s, 3 H) ppm. 13C NMR (100 MHz,
138.0, 135.9, 129.9, 128.8, 128.6, 127.8, 127.5, 50.7, 21.8 ppm.
CDCl3): δ = 143.8, 139.3, 129.9, 126.7, 21.7 ppm. HRMS (ESI):
HRMS (ESI): calcd. for C21H21NO2SNa [M + Na]+ 374.1185; calcd. for C7H9NO2S [M + Na]+ 194.0246; found 194.0253.
found 374.1187.
4-(Phenylsulfonyl)thiomorpholine (4a): White solid, m.p. 110.6–
N-Benzyl-N,4-dimethylbenzenesulfonamide (3l):[22] White solid. 1H
NMR (400 MHz, CDCl3): δ = 7.71 (d, J = 8.0 Hz, 2 H), 7.34 (d,
111.8 °C. 1H NMR (400 MHz, CDCl3): δ = 7.72–7.70 (m, 2 H),
7.60–7.57 (m, 1 H), 7.53–7.50 (m, 2 H), 3.32–3.30 (m, 4 H), 2.69–
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