Benzoyl chloride → N-benzenesulfonyl-4-benzoylamino-3-(biphenyl-4-ylmethylamino)benzamide

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Reaction Steps

Triethylamine (0.115 g) and benzoyl chloride (0.200 g) are added to an N,N-dimethylformamide (5 ml) solution of N-benzenesulfonyl-4-amino-3-(biphenyl-4-ylmethylamino)benzamide (0.50 g). After stirring the solution for 15 hours at room temperature, a potassium bicarbonate aqueous solution is added to halt the reaction. Under reduced pressure, the solvent is removed. The residue is dissolved in a mixture of water and methanol, and its acidity is adjusted to pH 5˜6 with 10% hydrochloric acid. Precipitated crystals are collected, and dried. Preliminarily purified N-benzenesulfonyl-4-benzoylamino-3-(biphenyl-4-ylmethylamino)benzamide (0.393 g) is obtained, which is added to a mixture solvent of 10% hydrochloric acid (3.3 g), methanol (6 ml), and water (4 ml). Furthermore, 35% hydrochloric acid (0.5 g) is added and the solution is stirred for three hours at 60° C. After 20% potassium bicarbonate solution is added to turn the reaction solution into a basic, its acidity is adjusted to pH 5˜6 with 10% hydrochloric acid. Precipitated crystals are separated through filtration, dried and thus, 6-benzenesulfonylcarbamoyl-1-(biphenyl-4-ylmethyl)-2-phenylbenzimidazole (0.270 g) is obtained.

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