# Mechanism for reaction of NOCl (Tilden reagent) with primary amines

According to my textbook, the reaction between $$\ce{NOCl}$$ and $$\ce{CH3CH2-NH2}$$ is as follows:

$$\ce{CH3CH2-NH2 + NOCl -> CH3CH2Cl + N2 + H2O}$$

But how exactly does the reaction proceed?

The first step (what I think) could be that $$\ce{NOCl}$$ dissociates into $$\ce{NO+}$$ and $$\ce{Cl-}$$ ions and then the $$\ce{Cl-}$$ ion attacks the amine group and replaces it by $$\mathrm{S_N2}$$ mechanism.

But according to this site, a diazonium product is produced. Even though a diazo product is formed, how does it produce an alkyl halide according to my textbook?

• Umm, judging from your idea for this mechanism, perhaps you should brush up on basics rather then get into details of less known reactions... – Mithoron Nov 26 '19 at 23:48
• If you know how to form a diazonium salt with NOCl (or HONO/HCl) then you are an SN2 reaction away from the answer. – user55119 Nov 27 '19 at 16:30
• Please cite the textbook (as in 'according to my textbook'), or leave out that statement if it is not relevant. Always cite the sources you are using. – Martin - マーチン Nov 28 '19 at 16:17