Thionyl Chloride → 7-(1-Chloroethyl)-1,2,4-triazolo[1,5-a]pyrimidine

Participants

Reaction Steps

A solution of 1-(1,2,4-triazolo[1,5-a]pyrimidin-7-yl)ethanol (1 g, prepared in an similiar manner to that described above) in dichloromethane (30 ml) was added dropwise over 30 minutes to a solution of thionyl chloride (0.5 ml) in dichloromethane (50 ml), heated under reflux, and the heating was continued for a further 2 hours. Further thionyl chloride (0.5 ml) was added and the heating continued overnight. The dichloromethane was removed by distillation and the residue dissolved in further dichloromethane (50 ml). The solution was washed with a mixture of water (20 ml) with 1M sodium bicarbonate (3 ml), and the aqueous washings were extracted with dichloromethane (20 ml). The dichloromethane solutions were combined, washed with brine (40 ml), dried over magnesium sulphate and the solvent was evaporated to give, as a light brown solid, 7-(1-chloroethyl)-1,2,4-triazolo[1,5-a]pyrimidine. Yield 1.00 g.

Provenance & Evidence