反应详情

Reaction of oxalyl chloride (75 λL, 0.86 mmol) and benzoic acid 4 (212 mg, 0.57 mmol) with subsequent coupling to (1-methyl-1H-imidazol-2-yl)methylamine (70 mg, 0.63 mmol) gave benzamide 14 (185 mg, 70%) as a white powder: mp (EtOAc) 190-192° C.; 1H NMR δ 9.05 (t, J=5.5Hz, 1 H, CONH), 8.00 (dd, J=8.6, 1.8Hz, 2 H, H-2, H-6), 7.87 (dd, J=8.6, 1.8Hz, 2H, H-3, H-5), 7.67 (d, J=8.3Hz, 2 H, H-2′, H-6′), 7.42 (d, J=8.3Hz, 2 H, H-3′, H-5′), 7.08 (d, J=1.1Hz, 1 H, H-5″), 6.80 (d, J=1.1Hz, 1 H, H-4″), 4.62 (s, 2 H, CH2SO2), 4.54 (d, J=5.5 Hz, 2 H, CH2N), 3.66 (s, 3 H, NCH3), 2.40 (s, 3 H, CH3), 2.13 (s, 3 H, CH3); 13C NMR δ 165.2, 158.0, 149.9, 144.5 (2), 135.6, 135.3, 129.6 (2), 128.8, 128.3 (2), 128.2 (2), 126.4, 126.0, 125.3 (2), 121.8, 53.0, 35.5, 32.4, 21.0, 9.6; MS m/z 462.5 (MH+, 100%). Anal. calcd for C24H24N4O4S: C, 62.05; H, 5.21; N, 12.06. Found: C, 61.76; H, 5.09; N, 11.76%.