Open in another window Twenty-eight brand-new substituted = 4. 1254053-43-4 supplier 122.9, 119.0, 117.9, 44.3, 41.9, 21.2. MS (ESI+) present 368.9; C16H18ClN2O4S (M+ + H) needs 369.1. 4-Tolyl 4-[3-(2-Chloroethyl)ureido]benzenesulfonate (6) Technique A in dried out DCM was utilized. The crude item was purified by display chromatography (silica gel, hexanes/ethyl acetate (80:20) to hexanes/ethyl acetate (60:40)). Produce, 33%; colorless essential oil. IR : 3369 (NH), 1539 (C=O) cmC1. 1H NMR (CDCl3): 8.17 (s, 1H, NH), 7.66C7.63 (m, 2H, Ar), 7.53C7.50 (m, 2H, Ar), 7.02 (d, 2H, = 8.4 Hz, Ar), 6.81 (d, 2H, = 8.4 Hz, Ar), 6.13 (brs, 1H, NH), 3.58 (brs, 4H, 2 CH2), 2.25 (s, 3H, CH3). 13C NMR (CDCl3): 155.2, 147.2, 145.2, 137.3, 130.3, 129.9, 127.1, 122.0, 118.0, 44.2, 41.9, 20.9. MS (ESI+) present 368.9; C16H18ClN2O4S (M+ + H) needs 369.1. 4-Methoxyphenyl 4-[3-(2-Chloroethyl)ureido]benzenesulfonate (7) Technique A in THF was utilized. The crude item was purified by display chromatography (silica gel, methylene chloride to methylene chloride/ethyl acetate (80:20)). Produce, 46%; colorless essential oil. IR : 1500 (C=O) cmC1. 1H NMR (CDCl3): 7.92 (s, 1H, NH), 7.64C7.62 (m, 2H, Ar), 7.50C7.48 (m, 2H, Ar), 6.86C6.83 (m, 2H, Ar), 6.75C6.72 (m, 2H, Ar), 5.97 (t, 1H, = 5.2 Hz, NH), 3.72 (s, 3H, CH3), 3.62C3.57 (m, 4H, 2 CH2). 13C NMR (CDCl3): 158.4, 154.9, 145.1, 142.8, 130.0, 127.1, 123.3, 118.0, 114.6, 55.6, 44.3, 42.0. MS 1254053-43-4 supplier (ESI+) found out 385.0; C16H18ClN2O5S (M+ + H) needs 385.1. 4-(Dimethylamino)phenyl 4-[3-(2-Chloroethyl)ureido]benzenesulfonate (8) Technique C in dried out THF under microwave at 60 C for 15 min without cleaning with HCl (1 N) was utilized. The crude item was purified by adobe flash chromatography (silica gel, methylene chloride to methylene chloride/ethyl acetate (95:5)). Produce, 22%; white sticky solid. IR : 3355 (NH), 1569 (C=O) cmC1. 1H NMR (CDCl3): 7.95 (s, 1H, NH), 7.65C7.63 (m, 2H, Ar), 7.51C7.49 (m, 2H, Ar), 6.78C6.76 (m, 2H, Ar), 6.50C6.48 (m, 2H, Ar), 5.98 (t, 1H, = 5.3 Hz, NH), 3.63C3.57 (m, 4H, 2 CH2), 2.87 (s, 6H, 2 CH3). 13C NMR (CDCl3): 154.9, 149.4, 145.1, 139.9, 129.9, 127.4, 122.8, 117.9, 112.5, 44.3, 41.9, 40.5. MS (ESI+) found out 397.9; C17H21ClN3O4S (M+ + H) needs 398.1. 4-(= 7.9 Hz, CH2), 3.65C3.60 (m, 2H, CH2), 3.31 (brs, 1H, OH). 13C NMR (CDCl3/DMSO-found 369.0; C15H14ClN2O5S (MC C H) needs 369.0. 2-Tolyl 3-[3-(2-Chloroethyl)ureido]benzenesulfonate (11) Technique A in dried out DCM was utilized. The crude item was purified by adobe flash chromatography (silica gel, methylene chloride to methylene chloride/ethyl acetate (90:10)). Produce, 57%; sticky solid. IR : 3330 (NH), 1658 (C=O) cmC1. 1H NMR (CDCl3): 8.26 (s, 1H, NH), 7.97 (s, 1H, Ar), 7.68C7.65 (m, 1H, Ar), 7.83C7.30 (m, 2H, Ar), 7.14C7.02 (m, 3H, Ar), 6.93C6.90 (m, 1H, Ar), 6.18 (brs, 1H, NH), 3.57 (s, 4H, 2 CH2), 2.07 (s, 3H, CH3). 13C NMR (CDCl3): 155.7, 148.2, 140.4, 136.3, 131.7, 131.5, 129.9, 127.2, 127.0, 124.6, 122.1, 122.0, 118.0, 44.2, 41.9, 16.3. MS (APSI+) found out 369.1; C16H18ClN2O4S (M+ + H) needs 369.1. 2-Ethylphenyl 3-[3-(2-Chloroethyl)ureido]benzenesulfonate (12) Technique A in dried out DCM was utilized. The crude item was purified by adobe flash chromatography (silica gel, methylene chloride to methylene chloride/ethyl acetate (90:10)). Produce, 53%; colorless essential oil. IR : 3343 (NH), 1658 (C=O) cmC1. 1H NMR (CDCl3): 8.17 (s, 1H, NH), 7.95 (s, 1H, Ar), 7.70C7.68 (m, 1H, Ar), 7.41C7.34 (m, 2H, Ar), 7.19C7.03 (m, 3H, Ar), 6.92C6.90 (m, 1H, Ar), Bmp3 6.08 (brs, 1H, NH), 3.56 (s, 4H, 2 CH2), 2.50 (q, 2H, = 7.5 Hz, CH2), 1.07 (t, 3H, = 7.5 Hz, CH3). 13C NMR (CDCl3): 155.8, 147.7, 140.4, 137.2, 136.4, 130.0, 127.4, 127.0, 124.6, 121.9, 121.9, 118.0, 102.7, 44.1, 41.9, 22.8, 14.1. MS (APSI+) found out 383.1; C17H20ClN2O4S (M+ + H) needs 383.1. 2-Propylphenyl 3-[3-(2-Chloroethyl)ureido]benzenesulfonate (13) Technique A in dried out DCM was utilized. The crude item was purified by adobe flash chromatography (silica gel, methylene chloride to methylene chloride/ethyl acetate (90:10)). Produce, 12%; yellow essential oil. IR : 3300 (NH), 1657 (C=O) cmC1. 1H NMR (CDCl3): 8.42 (s, 1H, NH), 8.08 (s, 1H, Ar) 7.57C7.55 1254053-43-4 supplier (m, 1H, Ar), 7.38C7.32 (m, 2H, Ar), 7.14C7.05 (m, 3H, Ar), 6.93C6.91 (m,.