Ammonia → HCID 15334434, compound

Participants

Reaction Steps

89.7 ml (021 mol) of n-butyllithium in hexane are added at -40° C., with stirring and under a nitrogen atmosphere, to a solution of 22.5 g (0.1 mol) of 4-(1-chlorocyclopropyl)4hydroxy-5-(1,2,4-triazol-1-yl)1-pentine in 350 ml of liquid ammonia. After the end of the addition, stirring is continued initially at from -30° C. to -40° C. for 1 hour, and then a solution of 17.2 g (0.11 mol) of ethyl iodide in 20 ml of absolute tetrahydrofuran is added dropwise. The reaction mixture is subsequently stirred under ammonia reflux. For working up, the ammonia is evaporated off, ethyl acetate and water are added to the residue, and the organic phase is separated off, dried over sodium sulphate and concentrated under reduced pressure. This gives 25 g of a product which consists to the extent of 85.3% of 6-(1-chlorocyclopropyl)-6-hydroxy-7-(1,2,4-triazol-1-yl)-3-heptine. Recrystallization from ethanol gives 6-(1-chlorocyclopropyl)-6-hydroxy-7-(1,2,4triazol-1-yl)3-heptine in the form of a solid of melting point 83°-84° C. ##STR63##

Provenance & Evidence