3-Chloroaniline → HCID 14492036, compound

Participants

Reaction Steps

A solution of 3-chloroaniline (5.0 g) in 1.5 M hydrochloric acid (100 ml) was diazotised by the gradual addition of a solution of sodium nitrate (3.0 g) in water (6 ml) at 0° C. Sodium bicarbonate (7.5 g) was then added to the solution and the whole reaction mixture was added rapidly with stirring to a solution of 2-mercaptopyrimidine (4.5 g) in water (3 l). When the addition of the diazonium salt solution was completed, 10 ml of a 15% solution of sodium carbonate was added causing precipitation of a colourless solid. The solid was collected by filtration and allowed to stand overnight during which time it decomposed to an oil which was purified by chromatography (70 g silica, chloroform elution). The title compound was obtained as a red oil (2.5 g, 29%) and identified by its pmr spectrum.

Provenance & Evidence