Pyridine → 2-(1H-Benzimidazol-1-yl)ethane-1-thiol

Participants

Reaction Steps

To a solution of 1-(2-tritylthioethyl)benzimidazole (7.0 g, 16.6 mmol) in a mixture of methanol (50 ml) and chloroform (80 ml), were added pyridine (1.32 ml, 16.3 mmol) and then silver nitrate (2.9 g, 17.1 mmol). The mixture was stirred for 3 hours at room temperature. Precipitates then separated out were collected and washed with methanol and then with ethyl ether to give silver salt of 1-(2-mercaptoethyl)benzimidazole (4.73 g, 99%). The silver salt (4.73 g, 16.6 mmol) was suspended in dichloromethane (250 ml), which was bubbled with hydrogen sulfide at 0° C. for one hour. Precipitates were filtered off, and the filtrate was concentrated to give 1-(2-mercaptoethyl)benzimidazole (2.35 g, 79%) as colorless powder (2.35 g, 79%).

Provenance & Evidence