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

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.

1. temperatureheated
2. temperatureunder reflux
3. waitthe heating continued overnight
4. customThe dichloromethane was removed by distillation
5. dissolutionthe residue dissolved in further dichloromethane (50 ml)
6. washThe solution was washed with a mixture of water (20 ml) with 1M sodium bicarbonate (3 ml)
7. extractionthe aqueous washings were extracted with dichloromethane (20 ml)
8. washwashed with brine (40 ml)
9. dry with materialdried over magnesium sulphate
10. customthe solvent was evaporated

ORD record

ord-81c542545d044ac789978c67b22a365c

Source dataset

uspto-grants-1998_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05753665