A simple procedure for synthesis of HIDA (2,6-dimethylphenylcarbamoylmethyl iminodiacetic acid) is described. It was obtained in better yield by reaction of 2,6-dimethylphenylcarbamoylmethyl chloride with iminodiacetic acid in carbon tetrachloride. The HIDA (A) was identified by IR and tH NMR spectroscopy. Two types of crystals were detected in the crystal final product. Since they could be separated, the crystals: A and B were investigated by X-ray analysis. Crystal and molecular structures were solved by direct methods and refined by full-matrix least-squares technique to R = 0.047 and R = 0.056, respectively. In the structure of A, the N2 atom is protonated and the molecule exists as a zwitterion. The crystal structure of compound A is stabilized by strong hydrogen bonds, which are reflected in higher close-packing coefficient, density, and melting point, compared to compound B. Compound B is a monomethyl ester of HIDA, which is present as an impurity in the final recrystallized product.
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