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Chemistry Forums for Students => Undergraduate General Chemistry Forum => Topic started by: amirkat on March 26, 2011, 05:49:47 AM

Title: Acylation of primary amine by 5-chlorothiophene-2-carbonyl chloride?
Post by: amirkat on March 26, 2011, 05:49:47 AM

Hey guys, i'm a student at university and i have to write this essay on Rivaroxaban, but i've come to a problem, i can't manage to talk about the synthesis as i do not really know what is going on.

A primary amine si being acylated by 5-chlorothiophene-2-carbonyl chloride,  and i have to show the mechanism but i'm not too sure of how to do this (with the curly arrows and all that). I thought the chlorine from the 5-chlorothiophene-2-carbonyl chloride would protonate one of the Hydrogens of the primary amine and leave as HCl, leaving just NH- and the cation of 5-chlorothiophene-2-carbonyl chloride. Is this correct. Im sorry for not being able to be more useful and not being able to upload a mechanism. But i don't have the programs to do that.

Thanks in advance  :)

Title: Re: Acylation of primary amine by 5-chlorothiophene-2-carbonyl chloride?
Post by: Nobby on March 26, 2011, 08:41:23 AM

The electronpair from the nitrogen of the amin group attacks the carbonyl carbon. The Chlorine will pushed out a Hydrogen also will go out.

R-CO-Cl + H₂N-R^' => R-CO-NH₂⁺-R^' + Cl^-

R-CO-NH₂⁺-R^' => R-CO-NH₂-R^' + H⁺

Title: Re: Acylation of primary amine by 5-chlorothiophene-2-carbonyl chloride?
Post by: amirkat on March 27, 2011, 08:51:56 AM

Thanks. That has helped loads :)