1H-1,2,4-Triazole, 1-methyl- → HCID 68842365, compound

Participants

Reaction Conditions

Reaction Steps

Butyllithium (2.5 M in hexane, 9.2 ml, 23.0 mmole) was added to a reaction vessel under an argon atmosphere and cooled to −78° C. 1-methyl-1,2,4-triazole (1.30 ml, 23 mmole) was dissolved in absolute tetrahydrofuran (60.0 ml) and added dropwise at −78° C. while cooling with ice. The reaction mixture was then stirred for 10 minutes at this temperature. 8-methylamino-1,4-dioxa-spiro[4.5]decane-8-carbonitrile (2.12 g, 10.8 mmole) in absolute tetrahydrofuran (15 ml) in a cooling bath maintained at −78° C. was then quickly added dropwise to the formed solution. After the addition the reaction solution was stirred for 1 hour in the cooling bath and was then slowly heated to 0° C. The reaction mixture was stirred overnight at room temperature. The mixture was then hydrolysed at 0° C. with water (10 ml), the aqueous phase was extracted with chloroform (3×50 ml), and the organic phase was washed with water (50 ml) and saturated NaCl solution (50 ml), dried over Na2SO4 and concentrated by evaporation in vacuo. The product was purified by means of flash chromatography with chloroform/methanol (15:1).

Provenance & Evidence