Hydrochloric Acid → 1-(3-Chlorophenyl)-1,2-dihydro-5H-tetrazol-5-one

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Reaction Conditions

Reaction Steps

DMF (5.0 ml) was cooled to 0° C. and stirred as 0.48 gram (0.0074 mole) of sodium azide was added. To this mixture was added 50 milligrams of aluminum chloride. The mixture was heated to 70° C. for 15 minutes, then the known compound 3-chlorophenylisocyanate was added neet in one portion. The mixture was heated at 75° C. for 3 hours and then cooled and poured into 100 ml of water containing 0.5 gram of sodium nitrite and 50 grams ice. To this was slowly added sufficient 10% hydrogen chloride to cause a change in KI/starch test paper. The resulting solid was filtered and dried. The filtrate was dissolved in ethyl acetate, washed with water and concentrated to a residue. The crude residue was purified with column chromatography on silica gel using 95:5 dichloromethane-methanol as an eluant yielding 0.38 gram of 1-(3-chlorophenyl)-tetrazolin-5-one.

Provenance & Evidence