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Synlett 2016; 27(19): 2699-2704
DOI: 10.1055/s-0036-1588298
DOI: 10.1055/s-0036-1588298
letter
One-Pot Synthesis of Sulfonamides from Sodium Sulfinates and Amines via Sulfonyl Bromides
Weitere Informationen
Publikationsverlauf
Received: 25. Juni 2016
Accepted after revision: 31. Juli 2016
Publikationsdatum:
22. August 2016 (online)
Abstract
a new and convenient procedure has been developed for the preparation of sulfonamides from sodium sulfinates and amines with (n-C4H9)4NBr as bromine source and m-chloroperbenzoic acid as oxidant. This S–N bond formation reaction proceeds efficiently via sulfonyl bromides under neutral conditions to afford the corresponding sulfonamides in good yields at room temperature.
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- 10 A Typical Procedure for the Preparation of Sulfonamides In mixed solvent THF–MeOH (30:1, 2.0 mL), sodium sulfinates 1 (0.45 mmol), amines 2 (0.30 mmol), (n-Bu)4NBr (0.36 mmol), and m-CPBA (0.3 mmol) were added successively. The suspension mixture was vigorously stirred at r.t. for 12 h. Upon completion, the reaction was quenched by addition of sat. aq Na2S2O3 (2 mL), sat. aq Na2CO3 (8 mL), and H2O (5 mL), respectively. The mixture was extracted with CH2Cl2 (3 × 5 mL) and the combined organic phase was dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The residue was then purified on a silica gel plate (PE–EtOAc = 3:1) to furnish products 3. N-Benzylbenzenesulfonamide (3a) White solid; mp 82–83 °C (lit.12 85–87 °C). IR (KBr): 3329, 1326, 1162, 1093, 1061, 750, 687 cm–1. 1H NMR (500 MHz, CDCl3): δ = 7.86 (d, J = 7.2 Hz, 2 H), 7.59–7.54 (m, 1 H), 7.50–7.45 (m, J = 7.7 Hz, 2 H), 7.27–7.21 (m, 3 H), 7.20–7.16 (m, 2 H), 5.43 (t, J = 6.1 Hz, 1 H), 4.12 (d, J = 6.3 Hz, 2 H). 13C NMR (125 MHz, CDCl3): δ = 139.8, 136.2, 132.5, 129.0, 128.5, 127.7, 127.6, 126.9, 47.0. ESI-MS: m/z (%) = 265 (100) [M + NH4]+. N-(4-Methoxybenzyl)benzenesulfonamide (3b) White solid; mp 71–72 °C (lit.13 72–75°C). IR (KBr): 3281, 1513, 1321, 1254, 1158, 1091, 1031, 858, 730, 685, 590 cm–1. 1H NMR (500 MHz, CDCl3): δ = 7.85–7.81 (m, 2 H), 7.57–7.52 (m, 1 H), 7.47 (t, J = 7.7 Hz, 2 H), 7.08 (d, J = 8.6 Hz, 2 H), 6.75 (d, J = 8.7 Hz, 2 H), 5.38 (t, J = 6.1 Hz, 1 H), 4.04 (d, J = 6.1 Hz, 2 H), 3.73 (s, 3 H). 13C NMR (125 MHz, CDCl3): δ = 159.0, 139.8, 132.4, 129.1, 128.9, 128.2, 126.9, 113.8, 55.1, 46.5. ESI-MS: m/z (%) = 295 (100) [M + NH4]+. 4-(Phenylsulfonyl)morpholine (3f) White solid; mp 107–108 °C (lit.14 117–119 °C). IR (KBr): 2979, 2862, 1450, 1347, 1261, 1168, 1109, 943, 746, 693, 579, 532 cm–1. 1H NMR (500 MHz, CDCl3): δ = 7.78–7.73 (m, 2 H), 7.66–7.60 (m, 1 H), 7.58–7.53 (m, 2 H), 3.73 (t, J = 4.8 Hz, 4 H), 3.00 (t, J = 4.7 Hz, 4 H). 13C NMR (125 MHz, CDCl3): δ = 135.1, 133.0, 129.1, 127.8, 66.0, 45.9. ESI-MS: m/z (%) = 228 (100) [M + H]+. N-(4-Chlorobenzyl)-4-methylbenzenesulfonamide (3k) White solid; mp 92–93 °C (lit.15 88 °C). IR (KBr): 3234, 1641, 1492, 1319, 1157, 1091, 816, 549 cm–1. 1H NMR (500 MHz, CDCl3): δ = 7.71 (d, J = 8.3 Hz, 2 H), 7.28 (d, J = 8.0 Hz, 3 H), 7.21 (d, J = 8.5 Hz, 2 H), 7.12 (d, J = 8.5 Hz, 2 H), 5.27 (t, J = 6.3 Hz, 1 H), 4.07 (d, J = 6.4 Hz, 2 H), 2.44 (s, 3 H). 13C NMR (125 MHz, CDCl3): δ = 143.6, 136.8, 135.0, 133.6, 129.8, 129.2, 128.7, 127.1, 46.5, 21.5. ESI-MS: m/z (%) = 313 (73) [M + NH4]+.
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