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Thursday, November 24, 2011

11/24/11 - Carboxylic Acid into Amide

   I figured I would continue with the carbonyl chemistry, and more specifically the carboxylic acid chemistry because it can be applied to perform so many reactions.  This is, again, a simple reaction of converting a carboxylic acid into an amide, where all that is needed is the amine (primary or secondary) or NH3 in the presence of the carboxylic acid.

RCO2H + R'R"NH  \overrightarrow{\leftarrow}  RC(O)NR'R" + H2O

Edit:  The addition of coupling agents in this reaction are requires, such as HATU with triethylamine and DMSO, or with T3P, triethylamine and DMF.
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3 comments:

  1. davieeDecember 14, 2011 at 1:04 PM

    Hi there,

    Just as a correction - the reaction you show here wouldn't work - all that would happen is that the carboxylic acid would protonate the amide. You can use coupling agents such as T3P or HATU to overcome this by activating the acid, or you can use carboxylic acid derivatives such as acid chlorides. If you have the book "Organic Chemistry" by Clayden et al. then it has some examples of this/why you can't do the reaction above.

    Anyway, I enjoyed reading some of your blog posts, interesting to browse through as I too procrastinate!

    David

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  2. UnknownDecember 14, 2011 at 2:01 PM

    Thank you so much David, I'm glad someone is browsing through to make corrections. I'll be sure to make the corrections as soon as I get home!

    ReplyDelete
  3. UnknownJanuary 6, 2013 at 10:23 PM

    I enjoyed by reading this blog and also get more knowledge about the chemical reaction..

    ReplyDelete

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