Acetic Acid → 4-[(1H-Benzimidazol-2-ylmethyl)-amino]-N-(pyrimidin-2-yl)-benzenesulfonamide

Participants

Reaction Steps

628 mg (3.8 mmol) sulfadiazine and 728 mg (3.0 mmol) 2-chloromethylbenzimidazole were dissolved in 10 ml 1 M NaOH. Solution was stirred and refluxed for four hours. Reaction mixture was neutralised with addition of 1 M acetic acid until product precipitated. Crystals were filtered and purified on silica using gradient elution (chloroform to 5% methanol in chloroform) to obtain the title compound as white crystals with 38% yield. 1H NMR (DMSO-d6, 500 MHz): 8.46 (2H, m), 7.70 (2H, m) 7.49 (2H, br, m), 7.14 (1H, t, 5.7 Hz) 7.13 (2H, m), 6.98 (1H, m), 6.72 (2H, m), 4.53 (2H, 5.7 Hz); MS (ESI+): m/z 381 (M+H)+.

Provenance & Evidence