W. Zhang et al. · Efficient One-pot Synthesis of 4-Ethynylbenzenesulfonamides
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CDCl3): δ = 1.04 (6H, t, J = 7.15 Hz), 3.16 (1H, s), 3.15 (500 MHz, CDCl3): δ = 3.16 (1H, s), 6.99 – 7.01 (3H, m),
(4H, q, J = 7.15 Hz), 7.51 (2H, d, J = 8.5 Hz), 7.68 (2H, 7.06 (1H, m), 7.15 – 7.19 (2H, m), 7.45 (2H, d, J = 8.5 Hz),
d, J = 8.5 Hz). – 13C NMR (125 MHz, CDCl3): δ = 14.07, 7.65 (2H, d, J = 8.5 Hz). – 13C NMR (125 MHz, CDCl3):
42.00, 80.36, 82.05, 126.27, 126.88, 132.59, 140.50. – Anal. δ = 80.86, 81.89, 121.99, 125.79, 127.15, 127.19, 129.42,
for C12H15NO2S: calcd. C 60.73, H 6.37; found C 60.64, 132.60, 138.96. – Anal. for C14H11NO2S: calcd. C 63.35,
H 6.45.
H 4.31; found C 63.30, H 4.28.
1-(4-Ethynylphenylsulfonyl)piperidine (4f)
4-Ethynyl-N-p-tolylbenzenesulfonamide (4i)
White solid. M. p. 134.0 – 135.0 ◦C. – IR (KBr): ν =
3448, 3252, 1595, 1552, 1481, 1467, 1161 cm−1. – 1H NMR
(500 MHz, CDCl3): δ = 1.35 – 1.37 (2H, m), 1.55 – 1.59
(4H, m), 2.91 – 2.93 (4H, t, J = 5.5 Hz), 3.19 (1H, s), 7.55
(2H, d, J = 8.3 Hz), 7.64 (2H, d, J = 8.3 Hz). – 13C NMR
(125 MHz, CDCl3): δ = 23.45, 25.13, 46.89, 80.57, 82.00,
126.63, 127.54, 132.52, 138.09. – Anal. for C13H15NO2S:
calcd. C 62.62, H 6.06; found C 62.58, H 6.02.
White solid. M. p. 125.0 – 126.0 ◦C. – IR (KBr): ν = 3435,
3256, 1589, 1512, 1423, 1160 cm−1. – 1H NMR (500 MHz,
CDCl3): δ = 2.28 (3H, s), 3.23 (1H, s), 6.53 (1H, s), 6.93
(2H, d, J = 8.4 Hz), 7.05 (2H, d, J = 8.4 Hz), 7.52 (2H,
d, J = 8.6 Hz), 7.68 (2H, d, J = 8.6 Hz). – 13C NMR
(125 MHz, CDCl3): δ = 20.80, 80.74, 81.94, 122.65, 126.97,
127.21, 129.94, 132.54, 133.26, 135.85, 139.00. – Anal. for
C15H13NO2S: calcd. C 66.40, H 4.83; found C 66.45, H 4.88.
4-Ethynylbenzenesulfonamide (4g)
4-Ethynyl-N-o-tolylbenzenesulfonamide (4j)
White solid. M. p. 175.7 – 176.4 ◦C. – IR (KBr): ν = 3356,
3262, 3090, 1592, 1546, 1486, 1396, 1157 cm−1. – 1HNMR
(500 MHz, CDCl3): δ = 3.26 (1H, s), 4.83 (2H, s), 7.63
(2H, d, J = 8.6 Hz), 7.89 (2H, d, J = 8.6 Hz). – 13C NMR
(125 MHz, CDCl3): δ = 109.17, 126.03, 129.14, 131.31,
138.25, 143.55.
White solid. M. p. 136.0 – 137.0 ◦C. – IR (KBr): ν =
3438, 3309, 1622, 1586, 1489, 1383, 1163 cm−1. – 1H NMR
(500 MHz, CDCl3): δ = 2.00 (3H, s), 3.25 (1H, s), 6.47
(1H, s), 7.09 – 7.30 (4H, m), 7.53 (2H, d, J = 8.6 Hz), 7.68
(2H, d, J = 8.6 Hz). – 13C NMR (125 MHz, CDCl3): δ =
17.54, 80.83, 81.92, 124.75, 126.66, 127.05, 127.08, 130.91,
131.75, 132.57, 134.00, 139.62. – Anal. for C15H13NO2S:
calcd. C 66.40, H 4.83; found C 66.46, H 4.80.
General procedure for the one-pot synthesis of N-aryl-4-
ethynylarylsulfonamides 4h – k
To a solution of 1 (1 mmol) in DMF (2 mL) was added an
arylamine 2 (2.4 mmol). The mixture was kept inside a mi-
crowave oven and was irradiated for 25 s. To the mixture was
then added pyridine (2 mL). The reaction mixture was irradi-
ated for 40 s, removed from the oven and cooled to r. t. To the
reaction mixtures was added NaOEt (4 mmol). The mixture
was stirred at 60 ◦C in an oil bath for 2 h. After cooling to r. t.,
aqueous HCl (5 %) and EtOAc were added, and the organic
layer was separated. The aqueous layer was extracted with
EtOAc. The combined organic layers were washed with brine
and water and dried over anhydrous Na2SO4. Evaporation of
the solvent gave the crude product, which was subjected to
column chromatography (silica gel, EtOAc-petroleum ether)
to afford 4-ethynylbenzenesulfonamides 4h – k.
4-Ethynyl-N-methyl-N-phenylbenzenesulfonamide (4k)
White solid. M. p. 126.0 – 127.0 ◦C. – IR (KBr): ν = 3271,
1600, 1552, 1509, 1485, 1171 cm−1. – 1H NMR (500 MHz,
CDCl3): δ = 3.11 (3H, s), 3.19 (1H, s), 7.00 – 7.02 (2H,
m), 7.19 – 7.25 (3H, m), 7.42 (2H, d, J = 9.0 Hz), 7.48
(2H, d, J = 9.0 Hz). – 13C NMR (125 MHz, CDCl3): δ =
38.18, 80.72, 81.99, 126.62, 126.82, 127.51, 127.74, 128.96,
132.30, 136.57, 141.23. – Anal. for C15H13NO2S: calcd.
C 66.40, H 4.83; found C 66.38, H 4.79.
Acknowledgements
This work was supported by the Natural Science Founda-
tion of Shanghai, China (No. 06ZR14085) and by the Sci-
entific Research Foundation for the Returned Overseas Chi-
nese Scholars, State Education Ministry. We would like to
thank the Center for Instrumental Analysis, Tongji Univer-
sity, China.
4-Ethynyl-N-phenylbenzenesulfonamide (4h)
White solid. M. p. 147.1 – 147.6 ◦C. – IR (KBr): ν =
3247, 1590, 1567, 1490, 1471, 1161 cm−1. – 1H NMR
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Unauthenticated
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