I am planning to synthesis some compounds with two amide bonds from acyl chloride and amine in dichloromethane and in presence of TEA. The first amide bond was easily formed and the second one is successful with aniline and phenylenediamine but it doesn't work with the other amines like o-Toluidine , o-anisidine and amino phenol, what's the problem?
I tested different ways and conditions for this reaction like reflux/room temperature, time, solvent and also with coupling agents like CDI and to ensure the quality of amines, I performed a reaction between the mentioned amines and benzoyl chloride and that's OK.
can anyone help me?
Dear Narges Cheshmazar, as you can see from the article cited below, the compound N,N-diacetyl-o-toluidine is known:
Article The ortho-Substituted N,N-Diacetylaniline as a Selective Ace...
However, if your acyl chloride contains a bulky substituent, I assume that steric hindrance with the o-substituents in you aniline precursors might become a factor preventing reaction with a second equivalent of acyl chloride.
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