Triethylamine → N-benzenesulfonyl-3-(biphenyl-4-ylmethylamino)-4-butyrylaminobenzamide

Participants

Reaction Steps

Triethylamine (0.060 g) and butyryl chloride (0.084 g) are added to an N,N-dimethylformamide (2 ml) solution of N-benzenesulfonyl-4-amino-3-(biphenyl-4-ylmethylamino)benzamide (0.300 g). The solution is stirred for 1.5 hours at room temperature. The reaction solution is purified of itself using silica gel column chromatography Chloroform and N-benzenesulfonyl-3-(biphenyl-4-ylmethylamino)-4-butyrylaminobenzamide (0.250 g) is obtained. Methanol (5 ml) and 35% hydrochloric acid (0.50 g) are added to this and the solution is stirred for three hours at 60° C. The reaction is halted by adding 20% potassium bicarbonate. Extraction is performed with ethyl acetate and water. An organic layer is concentrated and the formed material is dissolved in a small amount of chloroform. By adding ether, crystallization is performed. The crystals are separated through filtration, dried and thus, 6-benzenesulfonyl-carbamoyl-1-(biphenyl-4-ylmethyl)-2-n-propylbenzimidazole Potassium Salt (0.157 g) is obtained. 1H-NMR (DMSO-d6, δ): 0.95 (3H, t, J=7.4 Hz), 1.77 (2H, q, J=7.5 Hz), 2.82 (2H, t, J=7.5 Hz), 5.55 (2H, s), 7.11 (2H, d, J=8.2 Hz), 7.32-7.38 (4H, m), 7.43 (2H, t, J=7.5 Hz), 7.47 (1H, d, J=8.4 Hz), 7.58-7.64 (4H, m), 7.79-7.83 (3H, m), 7.96 (1H, s).

Provenance & Evidence