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LETTER
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(20) Typical Experimental Procedure for the Synthesis of
N-Benzyl-2-(propargylamino)benzenesulfonamide (2c):
2-Iodobenzenesulfonamide (300 mg, 1 mmol), K2CO3 (138
mg, 1 mmol) and anhyd DMF (10 mL) were introduced into
a dry Schlenk flask under argon. The mixture was cooled to
0 °C and degassed under agitation (10 min). Then amine (1.1
mmol) and CuI (19 mg, 0.1 mmol) were introduced
successively under argon flux. The mixture was brought to
r.t. and left under stirring for 12 h. The reaction mixture was
diluted with Et2O, washed with aq NH4Cl and H2O, dried
over MgSO4, filtered and concentrated under vacuum. The
residue was purified by chromatography on silica gel
(petroleum ether–Et2O, 50:50) or by crystallization
(petroleum ether–CH2Cl2, 80:20); yield: 79%; white solid;
mp 64–66 °C. IR (KBr): 1599, 2114, 2963, 3252, 3389 cm–1.
1H NMR (200 MHz, CDCl3): d = 7.79 (dd, J = 7.9, 1.3 Hz, 1
H), 7.47 (td, J = 7.9, 1.3 Hz, 1 H), 7.13–7.26 (m, 5 H), 6.79–
6.91 (m, 2 H), 6.06 (t, J = 5.4 Hz, 1 H), 5.25 (t, J = 6.2 Hz, 1
H), 3.94–4.06 (m, 4 H), 2.24 (t, J = 2.4 Hz, 1 H). 13C NMR
(50 MHz, CDCl3): d = 144.2, 139.4, 135.7, 134.0, 129.8,
128.2 (2 × C), 127.4 (2 × C), 121.4, 116.9, 112.6, 79.5, 71.4,
46.8, 32.4. MS (EI): m/z = 300 [M] (8), 130 (51), 129 (59),
108, 106 (100), 102 (22), 91 (63). Anal. Calcd for
C16H16N2O2S: C, 63.98; H, 5.37; N, 9.33. Found: C, 63.83;
H, 5.41; N, 9.35.
Synlett 2011, No. 17, 2509–2512 © Thieme Stuttgart · New York