ChemInform Abstract: SYNTHESE UND STRUKTUR VON N‐PHENYL‐BENZAMIDINEN

Reinvestigating the synthesis of N-arylbenzamidines from benzonitriles and anilines in the presence of AlCl3

“…100 C for 6 h gave the title compound 3h (622.5 mg, 85%) as colourless needles, mp 137 C (lit., 30 139 C) (cyclohexane/EtOH, 95:05); R f (t-BuOMe) 0.86; l max (DCM)/nm 231 (log 3 4.91), 246 (5.03), 280 inf (4.70); n max / cm À1 3470w and 3345w (NH 2 ), 3071 (Ar CH), 1612s, 1568s, 1481w, 1470w, 1447w, 1396w, 1375m, 1298w, 1238m, 1177w, 1101w, 1076w, 1063w, 1001m, 858m, 777m, 717m, 704s; 3.09 mmol) and 3,4-dichloroaniline (500 mg, 3.09 mmol) heated at ca. 100 C for 6 h gave the title compound 3i (746 mg, 91%) as colourless plates, mp 108e109 C (lit., 6b 110e111 C) (cyclohexane/ EtOH, 95:05); R f (t-BuOMe) 0.79; l max (DCM)/nm 231 (log 3 4.46), 246 (4.43), 285 (4.13); n max /cm À1 3449w and 3326w (NH 2 ), 1614s, 1568s, 1470m, 1458m, 1387m, 1371m, 1227w, 1128m, 1024m, 930w, 897m, 3495m, 3453w and 3395m (NH 2 ), 3277w, 1632s, 1576m, 1574m, 1547m, 1495w, 1468m, 1450m, 1387s, 1375m, 1321m, 1261w, 1252m, 1223w, 1157w, 1119m, 1020w, 889s, 852m, 835m, 771m, 750s, 717w; 6,148.3,147.7,133.0,131.6 (CH) (17), 208 (2), 192 (3), 163 (28), 161 (49), 119 (100), 92 (29), 75 (5), 65 (22).…”