Sodium hydride → HCID 21906696, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2,5-dichloroisonicotinic acid (1.82 g) in anhydrous N,N-dimethylformamide (10 ml) was added 60% sodium hydride (0.455 g) in small portions. After gas evolution had ceased tert-butyl 2-mercaptoethylcarbamate (1.60 ml) was added. The reaction mixture was then heated at 60° C. under nitrogen for 10 hours. Further amounts of 60% sodium hydride (0.225 g) and tert-butyl 2-mercaptoethylcarbamate (1.60 ml) were then added and heating was continued for 2 hours. The reaction mixture was concentrated and the residue suspended in 2M aqueous hydrochloric acid (25 ml) and extracted into ethyl acetate (3×25 ml). The combined extracts were dried over anhydrous sodium sulphate, filtered and concentrated. The residue was purified by chromatography on silica gel eluting with iso-hexane:ethyl acetate:acetic acid (6:4:0.1) to afford the sub-titled compound (1.0 g) as a colourless powder.

Provenance & Evidence