Synthesis of 3-pentyl-5-(4-chlorobenzylidene)imidazolidine-2,4-dione and 1,3-dipentyl-5-(4-chlorobenzylidene)imidazolidine-2,4-dione | ||||
Egyptian Journal of Chemistry | ||||
Article 11, Volume 65, Issue 12, December 2022, Page 95-99 PDF (848.66 K) | ||||
Document Type: Original Article | ||||
DOI: 10.21608/ejchem.2022.69081.3512 | ||||
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Authors | ||||
muhammad naufal1; Irana Rahmawati Sabana2; Jamaludin Al-Anshori2; Rani Maharani2; Achmad Zainuddin2; Dadan Sumiarsa3; Ace Tatang Hidayat2; Ika Wiani 2 | ||||
1Department of Chemistry, Faculty of Mathematics and Natural Products, Universitas Padjadjaran | ||||
2Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Padjadjaran | ||||
3Department of Chemistry, Faculty of Mathematics and Natural Science, Universitas Padjadjaran, Indonesia | ||||
Abstract | ||||
A novel N3-alkylation of 5-(4-chlorobenzylidene)imidazolidine-2,4-dione with 1-chloropentane in the presence of a base potassium carbonate was carried out in N,N-dimethyl formamide at 70 °C and 100 °C for 24 hours. At 70 oC, two products were obtained as 3-pentyl-5-(4-chlorobenzylidene)imidazolidine-2,4-dione 5 and the unexpected 1,3-dipentyl-5-(4-chlorobenzylidene)imidazolidine-2,4-dione 6 with the respective yields of 11% and 12%. Meanwhile, a two-fold increase of the synthetic yield of 5 (22%) was obtained when the reaction was undertaken at higher temperature (100 °C). Both products were characterized through several spectroscopic methods and reported as novel compounds. | ||||
Keywords | ||||
Hydantoin; Knoevenagel Condensation; Amide Alkylation; Heterocyclic Synthesis | ||||
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