[endophytic]

Hello chemists !

I'm planning to couple aniline to a carboxylic acid (with DCC in DMF) Is the addition of a triazole such as HOBt necessary ?
Since I use a planar amine I have no problems of racemization to fear ... Is there another role of the triazole compound here ?

Thnks  for your insights ...

E.

[Dean]

Unnecessary.
DCC/DMAP; Recommend: EDCI

[endophytic]

Thanks Dean !

Why do you recommend EDCI in this case ?
Using EDCI, would the DMAP catalyst also be necessary ?

Is DMF an appropriate solvent for this reaction or could it be another solvent ?
Thanks again 

[Dean]

In the reaction, DCC will lead to a byproduct DCU. That will be not easy to remove DCU. EDCI and its derivatives can be removed by extraction with water.
DCM, DMF, THF... you can use any solvents in which the aniline and carboxylic acid are dissolved, except alcohol. 

[surferkemie]

I'm just following this, coz I'm also doing similar reactions...why NOT an alcohol?

Thanks for the *delete me*

[Doc Oc]

The purpose of the peptide coupling agent is to activate the carboxylic acid towards nucleophilic acyl substitution (think of it being similar to an acid chloride).  As you know (or should know), alcohols can react with acid chlorides to form esters.  This is what you'll get if you use an alcohol solvent.