Question
How can benzotriazole be synthesised starting from ortho-phenylenediamine? Give the mechanism of the reaction.
Answer :
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Benzotriazole can be synthesised from ortho-phenylenediamine through a diazotization–cyclisation reaction involving nitrous acid. In this method, ortho-phenylenediamine is treated with sodium nitrite and a mineral acid such as hydrochloric acid at low temperature, typically between 0–5 °C, to generate nitrous acid in situ. One of the amino groups of ortho-phenylenediamine undergoes diazotization to form an o-aminobenzenediazonium salt. In the first step of the mechanism, nitrous acid reacts with the primary amino group to form a nitrosamine intermediate, which is protonated
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