Synthesis, Crystal Structure and IR Spectrum Studies of 2-(4-Methyl-2-Phenyl-4,5-Dihydrooxazol-4-ylmethyl)-Isoindole-1,3-Dione: New Perspectives

Khadim Dioukhane; Younas Aouine; Anouar Alami; Hassane Faraj; Abdelilah El Hallaoui

Khadim Dioukhane Doctoral Training �Bioactive Molecules, Health and Biotechnology�, Center of Doctoral Studies �Sciences and Technology�, Faculty of Sciences Dhar El Mahraz, Sidi Mohamed Ben Abdellah University, P.B. 2626, Fez 30000, Morocco and Organic Chemistry Laboratory (LCO), Faculty of Sciences Dhar El Mahraz, Sidi Mohammed Ben Abdellah University, P.B. 2626, Fez 30000, Morocco.
Younas Aouine Organic Chemistry Laboratory (LCO), Faculty of Sciences Dhar El Mahraz, Sidi Mohammed Ben Abdellah University, P.B. 2626, Fez 30000, Morocco and Department of Chemistry, Faculty of Sciences, Ibn Zohr University, P.B. 8106, Cit� Dakhla, Agadir 80060, Morocco.
Anouar Alami Organic Chemistry Laboratory (LCO), Faculty of Sciences Dhar El Mahraz, Sidi Mohammed Ben Abdellah University, P.B. 2626, Fez 30000, Morocco.
Hassane Faraj Organic Chemistry Laboratory (LCO), Faculty of Sciences Dhar El Mahraz, Sidi Mohammed Ben Abdellah University, P.B. 2626, Fez 30000, Morocco.
Abdelilah El Hallaoui Organic Chemistry Laboratory (LCO), Faculty of Sciences Dhar El Mahraz, Sidi Mohammed Ben Abdellah University, P.B. 2626, Fez 30000, Morocco.

Keywords: Oxazolinic precursors, isoindoline-1,3-dione, N-alkylation

Abstract

The organo-amino compound of title 2-(4-methyl-2-phenyl-4,5-dihydro-oxazol-4-ylmethyl)-isoindole-1,3-dione was synthesized by the mixture of (4-methyl-2-phenyl-4,5-dihydrooxazol-4-yl)methyl-4-methylbenzenesulfonate and isoindoline-1,3-dione in N,N-dimethylformamide with a yield of around 65%. The structural study of the compound, C₁₉H₁₆N₂O₃, is realized using single crystal X-Ray diffraction which shows that this compound crystallizes in the monoclinic system (P21/c, Z = 4) with the unit cell parameters: A = 14.3728 (13) b = 9.6829 (10) c = 11.8964 (12) and ? = 107.384 (3). The refinement of the structure by the least-squares method with complete matrix leads to the following reliability factors R/Rw are 0.044/0.130. In the crystal, the molecules are linked together by hydrogen bonds and ?? interactions. The Infrared spectroscopic studies show the bands confirming the presence of the groups C=O, C-O, C-N, -CH₃, -CH₂ and =CH.