Sintesis Dihidropirimidinon Dalam Pelarut Air Pada Suhu Ruang Menggunakan Katalis Iodin

Khusnayaini, Intan Ali (2025) Sintesis Dihidropirimidinon Dalam Pelarut Air Pada Suhu Ruang Menggunakan Katalis Iodin. Other thesis, Institut Teknologi Sepuluh Nopember.

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Abstract

Dihidropirimidinon (DHPM) merupakan senyawa heterosiklik dengan kerangka pirimidin yang tersusun oleh empat karbon dan dua nitrogen serta mengandung satu gugus karbonil. DHPM dapat diperoleh melalui reaksi Biginelli yang melibatkan aldehida, senyawa β–keto ester, dan urea dalam pelarut etanol dengan penambahan katalis asam kuat. Namun demikian, reaksi Biginelli tidak ramah lingkungan dan dilakukan dengan pemanasan atau refluks. Pengembangan sintesis DHPM dengan katalis yang berbeda maupun kondisi reaksi yang lain juga masih menunjukkan banyak kekurangan. Studi literatur mengungkap iodin telah digunakan sebagai katalis dalam sintesis senyawa organik termasuk DHPM dengan iradiasi gelombang mikro atau pemanasan refluks dan dalam berbagai pelarut atau bebas pelarut. Penelitian ini bertujuan untuk melakukan sintesis DHPM 4a-e pada suhu ruang menggunakan iodin sebagai katalis dan dalam pelarut air. Sintesis DHPM 4a-e dilakukan melalui reaksi aldehida 1a-e, urea 2, dan etil asetoasetat 3 dengan pengadukan pada suhu ruang menggunakan katalis iodin dalam pelarut air. Reaksi antara benzaldehida 1a, urea 2, dan etil asetoasetat 3 menggunakan 5 mol% iodin dalam air pada suhu ruang selama 48 jam menghasilkan etil 4-fenil-6-metil-2-okso-1,2,3,4-tetrahidropirimidin-5-karboksilat 4a dengan yield 87,5%. Selanjutnya, reaksi aldehida 1b-e dengan urea 2 dan etil asetoasetat 3 pada kondisi yang sama masing-masing memberikan senyawa etil 4-(4-nitrofenil)-6-metil-2-okso-1,2,3,4-tetrahidropirimidin-5-karboksilat 4b, etil 4-(p-tolil)-6-metil-2-okso-1,2,3,4-tetrahidropirimidin-5-karboksilat 4c, etil 4-(4-klorofenil)-6-metil-2-okso-1,2,3,4-tetrahidropirimidin-5-karboksilat 4d, dan etil 4-(3-hidroksifenil)-6-metil-2-okso-1,2,3,4-tetrahidropirimidin-5-karboksilat 4e dengan yield berturut-turut 38,35, 69,37, 64,50, dan 20,16%. Spektrometer FTIR dan NMR serta analisis massa digunakan untuk identifikasi struktur senyawa 4a-e.
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Dihydropyrimidinone (DHPM) is a heterocyclic compound with a pyrimidine skeleton composed of four carbons and two nitrogens and contains one carbonyl group. DHPM can be obtained through the Biginelli reaction involving aldehydes, β-keto ester compounds, and urea in ethanol solvent with the addition of a strong acid catalyst. However, the Biginelli reaction is not environmentally friendly and is carried out by heating or reflux. The development of DHPM synthesis with different catalysts and other reaction conditions also shows many shortcomings. Literature studies reveal that iodine has been used as a catalyst in the synthesis of organic compounds including DHPM by microwave irradiation or reflux heating and in various solvents or solvent-free. This study aims to synthesize DHPM 4a-e at room temperature using iodine as catalyst and in water solvent. The synthesis of DHPM 4a-e was carried out through the reaction of aldehyde 1a-e, urea 2, and ethyl acetoacetate 3 with stirring at room temperature using iodine catalyst in aqueous solvent. The reaction between benzaldehyde 1a, urea 2, and ethyl acetoacetate 3 using 5 mol% iodine in water at room temperature for 48 hours gave ethyl 4-phenyl-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate 4a with 87.5% yield. Furthermore, reaction of aldehydes 1b-e with urea 2 and ethyl acetoacetate 3 under the same conditions gave ethyl 4-(4-nitrophenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidin-5-carboxylate 4b, ethyl 4-(p-tolyl)-6-methyl-2-oxo-1,2,3, 4-tetrahydropyrimidin-5-carboxylate 4c, ethyl 4-(4-chlorophenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidin-5-carboxylate 4d, and ethyl 4-(3-hydroxyphenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidin-5-carboxylate 4e with yields of 38.35, 69.37, 64.50, and 20.16%, respectively. FTIR and NMR spectrometers and mass analysis were used for structural identification of compounds 4a-e.

Item Type:	Thesis (Other)
Uncontrolled Keywords:	Dihidropirimidinon, Iodin, Air, Suhu ruang Dihydropyrimidinone, Iodine, Water, Room temperature
Subjects:	Q Science > QD Chemistry > QD251.2 Chemistry, Organic. Biochemistry Q Science > QD Chemistry > QD471 Chemical compounds - Structure and formulas Q Science > QD Chemistry > QD481 Chemical structure.
Divisions:	Faculty of Science and Data Analytics (SCIENTICS) > Chemistry > 47201-(S1) Undergraduate Thesis
Depositing User:	Intan Ali Khusnayaini
Date Deposited:	05 Aug 2025 11:34
Last Modified:	05 Aug 2025 11:34
URI:	http://repository.its.ac.id/id/eprint/127521

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