Hydrochloric Acid → 5-(2-Bromophenyl)-1H-tetrazole

Participants

Reaction Conditions

Reaction Steps

Into a mixture of 5.0 g (27.5 mmol) of 2-bromobenzonitrile, 30 g of ethanol, 1.10 g (15 mmol) of diethylamine and 1.76 g (55 mmol) of anhydrous hydrazine was bubbled 0.58 g (17 mmol) of hydrogen sulfide gas at room temperature, followed by stirring at 60° C. for 22 hours. The resulting reaction mixture was concentrated, dried and dissolved in 110 g of N,N-dimethylformamide and 50.3 g (138 mmol) of 10% hydrochloric acid added thereto, followed by cooling to 5° C. Then, 19.0 g (55 mmol) of 20% sodium nitrite was added dropwise thereto, followed by stirring at 0-5° C. for 2 hours. The resulting reaction mixture was filtered to remove undissolved matters. The filtrate was analyzed by liquid chromatography with an internal standard, and it was found that 4.88 g (21.7 mmol, 79% yield) of 5-(2-bromophenyl)tetrazole was contained.

Provenance & Evidence