Hello, the reaction is aromatic acid-dependent. There is a substituent? It's just an aromatic ring? Can it be any amide? Regards
1) PCl5, to obtain a chloroanhydride; 2) add it to amine solved in the CH3CN.
Isobutylchloroformate + amine in anhydrous THF
or
Carbonyldiimidazol + amine
It;s condensation reaction ,easily aromatic carboxylic acid possessing substituted donating group in para or ortho with amine using dean stark in acidic medium .
Try a Curtius Rearrangements; it converts COOH to a carbamate, which is just a N-protected amine. It's easier to isolate and purify and can be used in successive reactions. Deprotect with light acid treatment.
Raction with TsCl, NH4Cl supported on silica and Et3N. Reaction is in solid médium and triggered by addition of Et3N. There is a paper by an iranian group about this method.
The paper Teodoro Kaufman is referring to I believe is,
Efficient method for the direct preparation of amides from carboxylic acids using tosyl chloride under solvent-free conditions. Tetrahedron Letters. Volume 46, Issue 40, 3 October 2005, Pages 6879–6882. http://dx.doi.org/10.1016/j.tetlet.2005.08.021
Take aromatic acid in THF then add TEA (2 eq.) followed by addition of methyl chloroformmate 1 eq. under nitrogen atm. at 0 oC. The RM was stirred for 10 min. then add amine compound. to the precipitated mixed unhydride. The rM was stirred at RT for overnight. Then followed DCM workup. The organic layer washed by NaHCO3 sol.
Take aromatic acid , add PCl5 srirr wel then add slowly NH3 with stirring , immediately solid amide separates out. . Carry out reaction in fume hood in a evaporating dish.
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