Hydrochloric Acid → HCID 178478026, compound

Participants

Reaction Conditions

Reaction Steps

Into a mixture of 4.13 g (30 mmol) of 2-chlorobenzonitrile, 30 g of ethanol, 1.10 g (15 mmol) of diethylamine and 1.92 g (60 mmol) of anhydrous hydrazine was bubbled 0.62 g (18.2 mmol) of hydrogen sulfide gas at room temperature, followed by stirring at 60° C. for 9.5 hours. The resulting reaction mixture was concentrated, dried and dissolved in 120 g of N,N-dimethylformamide and 54.7 g (150 mmol) of 10% hydrochloric acid added thereto, followed by cooling to 5° C. Then 20.7 g (60 mmol) of 20% sodium nitrite was added dropwise thereto, followed by stirring at 0-5° C. for 3 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 3.76 g (20.8 mmol, 69% yield) of 5-(2-chlorophenyl)tetrazole was contained.

Provenance & Evidence