Dichloromethane → HCID 18645972, compound

Participants

Reaction Steps

To a solution of this tetrazole (391 mg) in 10 ml of methanol, 0.1 ml of concentrated HCl and 473 mg of SnCl2.2H2O were added. The reaction mixture was heated at reflux under nitrogen for 16 hours and then poured into a solution of CH2Cl2 (45 ml) and 1N NaOH solution (64 ml). The mixture was stirred for 20 minutes and the layers then separated. The aqueous phase was further extracted with CH2Cl2. The combined organic extracts were backed washed with saturated sodium chloride solution and dried with anhydrous magnesium sulfate. The solution was concentrated and the crude residue (309 mg) was purified by preparative TLC on silica gel (90:10:1 CH2Cl2 :MeOH:NH4OH) to afford pure product which was converted to its hydrochloride salt with ethanolic HCl. The salt was isolated by dilution with ether and filtration, 240 mg; mp 264° C.; [α]D 25°=-8.45 (c= 1.0, MeOH); Analysis: Calculated for C19H24N4O2.2HCl: C, 55.21; H, 6.34; N, 13.56. Found: C, 54.82; H, 6.60; N, 13.08.

Provenance & Evidence