Hydrogen Sulfide → 3-[2-(Dimethylamino)ethyl]-1H-indole-5-carbothioamide

Participants

Reaction Steps

A solution of 3-[2-(dimethylamino)ethyl]-1H-indole-5-carbonitrile (13.0 g) and triethylamine (50 ml) in dimethylformamide (300 ml) was stirred for 2 h whilst gaseous hydrogen sulphide was bubbled through it. More triethylamine (10 ml) was added and the solution was stirred at room temperature for 2 days, then evaporated in vacuo to give an oil (15 g) which was partitioned between ethyl acetate (500 ml) and water (3×250 ml). The organic layer was dried (MgSO4) pre-absorbed onto silica and purified by flash chromatography (A). The appropriate fractions were combined, concentrated in vacuo and triturated with ether (250 ml) to give the title compound (12.0 g) as a solid, m.p. 155°.

Provenance & Evidence