Methylhydrazine → Cyclopropyl-methyl-[1-methyl-5-(2-methyl-propenyl)-1H-[1,2,4]triazol-3-yl]-amine

Participants

Reaction Steps

To a solution of 3-methylbut-2-enoyl isothiocyanate (500 mg, 3.54 mmol, Eq: 1.00) in Tetrahydrofuran (3.5 ml) was added a solution of N-methylcyclopropanamine (264 mg, 3.72 mmol, Eq: 1.05) in Tetrahydrofuran (3.5 ml). The mixture was stirred for 30 minutes. Sodium carbonate (394 mg, 3.72 mmol, Eq: 1.05) and iodomethane (1.01 g, 443 μl, 7.08 mmol, Eq: 2) was added and stirred overnight at 70° C. The solvent was evaporated. Methylhydrazine (1.63 g, 1.86 ml, 35.4 mmol, Eq: 10) was added and the mixture was stirred for 2 hours at 100° C. MS showed just product peak. The crude material was applied on silica gel and purified by column chromatography using heptane/ethyl acetate (0-40% ethyl acetate) as eluent affording

Provenance & Evidence