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Organic & Biomolecular Chemistry
Page 4 of 5
DOI: 10.1039/C6OB01208F
ARTICLE
Journal Name
standard]. The following abbreviations were used to explain the 2H), 3.29 (q, J = 7.2 Hz, 4H), 1.16 (t, J = 7.2 Hz, 6H); 13C NMR (CDCl3,
multiplicities: s = singlet, d = doublet, dd = doublet of doublet, t = 100 MHz) δ (ppm) 144.9, 132.9, 127.5, 117.4, 116.0, 42.1, 14.1.
triplet, q = quartet, m = multiplet. High-resolution mass spectra N,N-Diethyl-4-(trifluoromethyl)benzenesulfonamide (3ja).20 Yellow
(HRMS) were obtained with a Waters Q-TOF mass spectrometer. oil. 1H NMR (CDCl3, 400 MHz) δ (ppm) 7.96 (d, J = 8.0 Hz, 2H), 7.78
Melting points are uncorrected.
(d, J = 8.0 Hz, 2H), 3.29 (q, J = 7.2 Hz, 4H), 1.16 (t, J = 7.2 Hz, 6H);13
C
NMR (CDCl3, 100 MHz) δ (ppm) 144.1, 134.0 (q, J = 32.9 Hz), 127.4,
126.2 (q, J = 3.6 Hz), 123.3 (q, J = 271.1 Hz), 42.1, 14.2.
General experimental procedures
N,N-diethylthiophene-2-sulfonamide (3ka).21 Yellow oil. 1H NMR
(CDCl3, 400 MHz) δ (ppm) 7.56 (d, J = 4.4 Hz, 2H), 7.10 (t, J = 4.4 Hz
1H), 3.27 (q, J = 7.2 Hz, 4H), 1.19 (t, J = 7.2 Hz, 6H); 13C NMR (CDCl3,
100 MHz) δ (ppm) 140.9, 131.3, 131.1, 127.2, 42.6, 14.2.
N,N-Diethylpyridine-3-sulfonamide (3la). Yellow oil. 1H NMR (CDCl3,
400 MHz) δ (ppm) 9.05 (s, 1H), 8.80 (d, J = 4.0 Hz, 1H), 8.12 (dd, J =
8.0, 1.6 Hz, 1H), 7.47 (d, J = 8.0 Hz, 1H), 3.30 (q, J = 7.2 Hz, 4H), 1.18
(t, J = 7.2 Hz 6H); 13C NMR (CDCl3, 100 MHz) δ (ppm) 152.8, 147.8,
137.2, 134.6, 123.7, 42.1, 14.2; HRMS-ESI (m/z): calcd for
C9H14N2O2SNa [M + Na]+ 237.0669, found 237.0672.
N,N,4-Trimethylbenzenesulfonamide (3ab).5 Yellow oil. 1H NMR
(CDCl3, 400 MHz) δ (ppm) 7.68 (d, J = 8.4 Hz, 2H), 7.35 (d, J = 8.4 Hz,
2H), 2.71 (s, 6H), 2.46 (s, 3H); 13C NMR (CDCl3, 100 MHz) δ (ppm)
143.5, 132.5, 129.6, 127.8, 38.0, 21.5.
N,4-Dimethyl-N-phenylbenzenesulfonamide (3ac).7b White solid.
Mp: 87-89 oC. 1H NMR (CDCl3, 400 MHz) δ (ppm) 7.45–7.42 (m, 2H),
7.33–7.24 (m, 5H), 7.12–7.10 (m, 2H), 3.18 (s, 3H), 2.43 (s, 3H); 13C
NMR (CDCl3, 100 MHz) δ (ppm) 143.6, 141.6, 133.5, 129.4, 128.8,
127.9, 127.3, 126.6. 38.1, 21.6.
A mixture of 4-methylbenzenesulfonyl chloride 1a (0.5 mmol), Et3N
2a (1.0 mmol), Cu2O (5 mol%) and DCE (2.0 mL) was sealed in a 25
mL tube with a Teflon lined cap under oxygen atmosphere. The
tube was then placed in an oil bath, stirred and heated at 50 oC for
4 h. After cooling to room temperature, the reaction mixture was
quenched with water (20 mL) and extracted with dichloromethane
(25 mL × 3). The combined organic layers were dried with
anhydrous Na2SO4 and the solvent was removed under vacuum.
The crude product was purified over a column of silica gel (eluent:
hexane/ethyl acetate = 10 : 1) to afford the desired product 3aa.
N,N-Diethyl-4-methylbenzenesulfonamide (3aa).8 Yellow oil. 1H
NMR (CDCl3, 400 MHz) δ (ppm) 7.70 (d, J = 8.0 Hz, 2H), 7.29 (d, J =
8.0 Hz, 2H), 3.23 (q, J = 7.2 Hz, 4H), 2.43 (s, 3H) 1.13 (t, J = 7.2 Hz,
6H); 13C NMR (CDCl3, 100 MHz) δ (ppm) 142.9, 137.4, 129.6, 127.0,
42.0, 21.6, 14.1.
1
N,N-Diethylbenzenesulfonamide (3ba).8 Yellow oil. H NMR (CDCl3,
400 MHz) δ (ppm) 7.83–7.80 (m, 2H), 7.57–7.53 (m, 1H), 7.52–7.47
(m, 2H), 3.26 (q, J = 7.2 Hz, 4H), 1.12 (t, J = 7.2 Hz, 6H); 13C NMR
(CDCl3, 100 MHz) δ (ppm) 140.4, 132.2, 129.0, 126.9, 42.0, 14.1.
N,N-Diethyl-4-methoxybenzenesulfonamide (3ca).15 Yellow oil. 1H
NMR (CDCl3, 400 MHz) δ (ppm) 7.75–7.72 (m, 2H), 6.98–6.94 (m,
2H), 3.86 (s, 3H), 3.21 (q, J = 7.2 Hz, 4H), 1.12 (t, J = 7.2 Hz 6H); 13C
NMR (CDCl3, 100 MHz) δ (ppm) 162.6, 132.1, 129.0, 114.1, 55.6,
41.9, 14.1.
4-Chloro-N,N-diethylbenzenesulfonamide (3da).16 Yellow oil. 1H
NMR (CDCl3, 400 MHz) δ (ppm) 7.77–7.74 (m, 2H), 7.49–7.46 (m,
2H), 3.25 (q, J = 7.2 Hz, 4H), 1.14 (t, J = 7.2 Hz, 6H); 13C NMR (CDCl3,
100 MHz) δ (ppm) 139.0, 138.7, 129.3, 128.4, 42.0, 14.1.
3-Chloro-N,N-diethylbenzenesulfonamide (3ea).15 Yellow oil. 1H
NMR (CDCl3, 400 MHz) δ (ppm) 7.81 (s, 1H), 7.72–7.69 (m, 1H),
7.55–7.53 (m, 1H), 7.48–7.44 (m, 1H), 3.27 (q, J = 7.2 Hz, 4H), 1.16
(t, J = 7.2 Hz 6H); 13C NMR (CDCl3, 100 MHz) δ (ppm) 142.2, 135.2,
132.4, 130.3, 127.0, 125.0, 42.2, 14.2.
4-Bromo-N,N-diethylbenzenesulfonamide (3fa).17 Yellow oil. 1H
NMR (CDCl3, 400 MHz) δ (ppm) 7.70–7.63 (m, 4H), 3.25 (q, J = 7.2
Hz, 4H), 1.14 (t, J = 7.2 Hz, 6H);13C NMR (CDCl3, 100 MHz) δ (ppm)
139.6, 132.3, 128.5, 127.1, 42.1, 14.1.
3-Bromo-N,N-diethylbenzenesulfonamide (3ga).18 Yellow oil. 1H
NMR (CDCl3, 400 MHz) δ (ppm) 7.97 (s, 1H), 7.77–7.74 (m, 1H),
7.70–7.68 (m, 1H), 7.41–7.37 (m, 1H), 3.27 (q, J = 7.2 Hz, 4H), 1.16
(t, J = 7.2 Hz, 6H); 13C NMR (CDCl3, 100 MHz) δ (ppm) 142.4, 135.3,
130.6, 129.9, 125.5, 123.0, 42.2, 14.2.
2-Bromo-N,N-diethylbenzenesulfonamide (3ha).19 Yellow oil. 1H
NMR (CDCl3, 400 MHz) δ (ppm) 8.15–8.13 (m, 1H), 7.75–7.72 (m,
1H), 7.46–7.42 (m, 1H), 7.40–7.36 (m, 1H), 3.40 (q, J = 7.2 Hz, 4H),
1.14 (t, J = 7.2 Hz, 6H); 13C NMR (CDCl3, 100 MHz) δ (ppm) 139.8,
135.6, 133.3, 132.1, 127.4, 120.4, 41.2, 13.7.
4-Cyano-N,N-diethylbenzenesulfonamide (3ia).17 Yellow oil. 1H
NMR (CDCl3, 400 MHz) δ (ppm) 7.95–7.93 (m, 2H), 7.83–7.81 (m,
N,4-Dimethyl-N-(p-tolyl)benzenesulfonamide (3ad).22 Yellow oil. 1H
NMR (CDCl3, 400 MHz) δ (ppm) 7.47–7.44 (m, 2H), 7.26 (d, J = 8.0
Hz, 2H), 7.11 (d, J = 8.0 Hz, 2H), 7.00–6.97 (m, 2H), 3.15 (s, 3H), 2.44
(s, 3H), 2.35 (s, 3H); 13C NMR (CDCl3, 100 MHz) δ (ppm) 143.4, 139.0,
137.2, 133.6, 129.5, 129.3, 128.0, 126.5, 38.2, 21.6, 21.0.
N-(4-Bromophenyl)-N,4-dimethylbenzenesulfonamide
(3ae).7b
Yellow oil. 1H NMR (CDCl3, 400 MHz) δ (ppm) 7.45–7.42 (m, 4H),
7.27 (d, J = 8.4 Hz, 2H), 6.99 (dd, J = 6.8, 2.4 Hz, 2H), 3.14 (s, 3H),
2.44 (s, 3H); 13C NMR (CDCl3, 100 MHz) δ (ppm) 143.8, 140.7, 133.1,
132.0, 129.5, 128.1, 127.9, 120.9, 37.9, 21.6.
N-Ethyl-4-methyl-N-phenylbenzenesulfonamide (3af):23 Brown oil.
1H NMR (CDCl3, 400 MHz) δ (ppm) 7.52–7.49 (m, 2H), 7.35–7.25 (m,
5H), 7.08–7.05 (m, 2H), 3.62 (q, J = 7.2 Hz, 2H), 2.44 (s, 3H), 1.09 (t, J
= 7.2 Hz, 3H); 13C NMR (CDCl3, 100 MHz) δ (ppm) 143.3, 138.9,
135.5, 130.9, 129.4, 129.0, 127.8, 127.7, 45.5, 21.5, 14.0.
N-Butyl-4-methyl-N-phenylbenzenesulfonamide (3ag).24 Yellow oil.
1H NMR (CDCl3, 400 MHz) δ (ppm) 7,48 (dd, J = 6.4, 1.6 Hz, 2H),
7.35–7.29 (m,3H), 7.25 (d, J = 7.6 Hz, 2H), 7.07–7.05 (m, 2H), 3.54 (t,
J = 6.8 Hz, 2H), 2.44 (s, 3H), 1.40–1.34 (m, 4H), 0.87 (t, J = 6.8 Hz
3H); 13C NMR (CDCl3, 100 MHz) δ (ppm) 143.2, 139.2, 135.3, 130.9,
129.3, 128.9, 128.8, 127.7, 50.2, 30.2, 21.5, 19.6, 13.6.
1-Tosylpiperidine (3ah).25 Yellow soild. Mp: 71-79 oC. 1H NMR
(CDCl3, 400 MHz) δ (ppm) 7.65 (d, J = 8.0 Hz, 2H), 7.33 (d, J = 8.0 Hz,
2H), 2.98 (t, J = 5.6 Hz, 4H), 2.45 (s, 3H), 1.68–1.62 (m, 4H), 1.45–
1.39 (m, 2H); 13C NMR (CDCl3, 100 MHz) δ (ppm) 143.3, 133.3,
129.5, 127.7, 46.9, 25.2, 23.5, 21.5.
1-((4-Methoxyphenyl)sulfonyl)piperidine (3ch).26 Yellow oil. 1H
NMR (CDCl3, 400 MHz) δ (ppm) 7.70 (d, J = 8.8 Hz, 2H), 7.00 (d, J =
8.8 Hz, 2H), 3,89 (s, 3H), 2.97 (t, J = 5.6 Hz, 4H), 1.68–1.62 (m, 4H),
1.45–1.39 (m, 2H); 13C NMR (CDCl3, 100 MHz) δ (ppm) 162.8, 129.8,
127.9,114.1, 55.6, 46.9, 25.2, 23.5.
4 | J. Name., 2012, 00, 1-3
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