Methyl iodide → HCID 19612501, compound

Participants

Reaction Steps

5-(3-pyridyl)-tetrazole (11) (J. M. McManus and R. M. Herbst, J. Am. Chem. Soc., 24 (1959) 1462-64) (10 g, 0.068 mol), sodium hydroxide (2.73 g, 0.068 mol), and methyl iodide (14.5 g, 0.1 mol) in ethanol (100 ml) was stirred at 40° C. overnight. The mixture was filtered and the filtrate was evaporated. The residue was dissolved in dichloromethane (100 ml), and the solution was washed three times with water (100 ml). The organic phase was dried over magnesium sulphate and evaporated yielding 3.21 g (0.020 mol, 30%) of 12 with M.P. 108°-110° C. According to the 1H NMR spectrum the product contained less than 10% of the 1-isomer.

Provenance & Evidence