I wish to synthesize mono amide of carboxylic acid. For this i am trying to partial esterify the diacid followed by reacting the monoacid with amine but i got diester and very small quantity of monoester which was difficult to remove using column.Can anyone suggest me a single step process to synthesize a monoamide of the diacid.
Hi Rakesh, I think you might need to give more detail about your diacid. Firstly is it actually a diacid, such as malonic acid or succinic acid or is it a bis carboxylic acid? Secondly, is it possible to take advantage of differences in the steric and chemical environment of each carboxylic acid group, for example protect just one of the carboxylic acid groups with a bulky alcohol (eg. t-butyl or even fluoren-9-ylmethyl). What type of ester did you already try?
Or else you may need to take a step back and see if you can first synthesize your diacid with one group already protected. For example, if you can start from a cyclic anhydride then you can ring open that with an amine to give a monoamide, though you may get a mixture of regioisomers.
I think selective way to make a monoamide from diacid is through conversion of diacid to corresponding anhydride with subsequent ring opening by ammonia.
I am working with malonic acid and wish to work with symmetic acids. I have come across a paper which states that the use of coupling these symmetric acids with one equivalent of amine in the presence of DCC gives monoamides . Plz help
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