Sciencemadness Discussion Board - Ester to amide in one step ?


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Sciencemadness Discussion Board » Fundamentals » Beginnings » Ester to amide in one step ?

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ANDLOS

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posted on 22-10-2010 at 03:34

Ester to amide in one step ?

HI to all members,

I try to make amide bond with
ester and amine or amino acid
but the yield of ester is toooooooooooo little
so i search for one sterp conversion
instead of making desterification then acid chloride then amide bond formation,
can any one help me for that item.
thanks alot

Methansaeuretier

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posted on 22-10-2010 at 05:38

Quote: Originally posted by ANDLOS

HI to all members,

I try to make amide bond with
ester and amine or amino acid
but the yield of ester is toooooooooooo little
so i search for one sterp conversion
instead of making desterification then acid chloride then amide bond formation,
can any one help me for that item.
thanks alot

You can direcetly work with the ester and with a BIG excess of the amine without going via the acid chloride.

But reaction time is very long for such reactions, usually exceeding ~50h at room temperature.

What's your substrate?
NH3, Alkylamine or Dialkylamine or another?
With NH3 you may have to use a sealed bomb and heat, because reaction is very slow at room temperature (may take weeks).

[Edited on 22-10-2010 by Methansaeuretier]

Eclectic

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posted on 22-10-2010 at 05:48

Heat with urea?

jon

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posted on 22-10-2010 at 06:37

nope nope heat in a sealed bomb the more nucleophilic the amine the faster it reacts.
also trimethylaluminum forms an active complex with amines that reacts lightning quick and in quantitive yeilds with esters.
but ester is a general, broad term, which way is it oriented to the molecule? is it attached to a secondary or tertiary carbon?
factors like this come into play.
nicodem could clarify this, and all things relative to organic chemistry.