March 29, 2024, 10:52:44 AM
Forum Rules: Read This Before Posting


Topic: Acylation of primary amine by 5-chlorothiophene-2-carbonyl chloride?  (Read 2914 times)

0 Members and 1 Guest are viewing this topic.

Offline amirkat

  • New Member
  • **
  • Posts: 3
  • Mole Snacks: +0/-0
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  :)

Offline Nobby

  • Full Member
  • ****
  • Posts: 167
  • Mole Snacks: +12/-16
  • Gender: Male
  • Vena lausa moris pax drux bis totis
Re: Acylation of primary amine by 5-chlorothiophene-2-carbonyl chloride?
« Reply #1 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+

Offline amirkat

  • New Member
  • **
  • Posts: 3
  • Mole Snacks: +0/-0
Re: Acylation of primary amine by 5-chlorothiophene-2-carbonyl chloride?
« Reply #2 on: March 27, 2011, 08:51:56 AM »
Thanks. That has helped loads :)

Sponsored Links