Sintesis Dihidropirimidinon dalam Pelarut Toluena pada suhu Ruang dengan Penambahan Iodin

Agustin, Lela (2025) Sintesis Dihidropirimidinon dalam Pelarut Toluena pada suhu Ruang dengan Penambahan Iodin. Other thesis, Institut Teknologi Sepuluh Nopember.

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Abstract

Dihidropirimidinon, senyawa heterosiklik berkerangka pirimidina, dapat diperoleh melalui reaksi Biginelli yang melibatkan kondensasi aldehida, senyawa β–keto ester, dan urea. Namun, reaksi Biginelli memiliki kekurangan seperti penggunaan katalis asam kuat yang beracun terhadap lingkungan dan pemakaian suhu tinggi dalam reaksi. Berbagai katalis dan pelarut berbeda maupun reaksi tanpa pelarut telah digunakan, tetapi pengembangan ini masih memiliki kelemahan. Sementara itu, iodin diketahui merupakan asam Lewis ringan yang telah digunakan sebagai katalis dalam sintesis organik. Penelitian ini bertujuan untuk melakukan sintesis senyawa dihidropirimidinon 6, 25-28 dalam pelarut toluena dengan pengadukan pada suhu ruang dan dengan penambahan iodin sebagai katalis. Sintesis dihidropirimidinon 6, 25-28 dilakukan melalui reaksi Biginelli antara benzaldehida 18, 4-hidroksibenzaldehida 19, 4-metoksibenzaldehida 20, 4-nitrobenzaldehida 21, dan 4-metilbenzaldehida 22 dengan urea 23 dan etil asetoasetat 24. Senyawa dihidropirimidinon 6 diperoleh melalui pengadukan benzaldehida 18, urea 23, dan etil asetoasetat 24 dalam toluena pada suhu ruang selama 24 jam dengan yield 91,79%. Senyawa etil 4-(4-hidroksifenil)-6-metil-2-okso-1,2,3,4-tetrahidropirimidin-5-karboksilat 25, etil 4-(4-metoksifenil)-6-metil-2-okso-1,2,3,4-tetrahidropirimidin-5-karboksilat 26, etil 6-metil-4-(4-nitrofenil)-2-okso-1,2,3,4-tetrahidropirimidin-5-karbosilat 27, etil 6-metil-2-okso-4-(p-tolil)-1,2,3,4-tetrahidropirimidin-5-karboksilat 28 selanjutnya masing-masing diperoleh dengan yield 96,34, 61,29, 39,67, dan 91,21%. Spektrometer FTIR, NMR, dan analisis massa digunakan untuk menetapkan struktur senyawa dihidropirimidinon 6, 25-28 hasil sintesis.===============================================================================================================
Dihydropyrimidinones, heterocyclic compounds with a pyrimidine skeleton, can be obtained through the Biginelli reaction involving the condensation of aldehydes, β-keto esters, and urea. However, the Biginelli reaction has drawbacks such as the use of strong acid catalysts that are toxic to the environment and the use of high temperatures in the reaction. Various catalysts and different solvents as well as solvent-free reactions have been used, but these developments still have drawbacks. Meanwhile, iodine is known to be a mild Lewis acid that has been used as a catalyst in organic synthesis. This study aims to synthesis dihydropyrimidinone compounds 6, 25-28 in toluene solvent with stirring at room temperature and with the addition of iodine as a catalyst. The synthesis of dihydropyrimidinone 6, 25-28 was carried out through the Biginelli reaction between benzaldehyde 18, 4-hydroxybenzaldehyde 19, 4-methoxybenzaldehyde 20, 4-nitrobenzaldehyde 21, and 4-methylbenzaldehyde 22 with urea 23 and ethyl acetoacetate 24. The dihydropyrimidinone compound 6 was obtained by stirring benzaldehyde 18, urea 23, and ethyl acetoacetate 24 in toluene at room temperature for 24 hours with a yield of 91,79%. The compounds ethyl 4-(4-hydroxyphenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate 25, ethyl 4-(4-methoxyphenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate 26, ethyl 6-methyl-4-(4-nitrophenyl)-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate 27, ethyl 6-methyl-2-oxo-4-(p-tolyl)-1,2,3,4-tetrahydropyrimidine-5-carboxylate 28 were then obtained with yields of 96,34, 61,29, 39,67, and 91,21%, respectively. FTIR spectrometer, NMR, and mass analysis were used to determine the structure of the synthesized dihydropyrimidinone compound 6, 25-28.

Item Type:	Thesis (Other)
Uncontrolled Keywords:	Dihidropirimidinon, Iodin, Toluena, Suhu ruang, Spektroskopi. Dihydropyrimidinone, Iodine, Toluene, Room temperature, Spectroscopy
Subjects:	Q Science Q Science > QD Chemistry Q Science > QD Chemistry > QD251.2 Chemistry, Organic. Biochemistry Q Science > QD Chemistry > QD471 Chemical compounds - Structure and formulas
Divisions:	Faculty of Science and Data Analytics (SCIENTICS) > Chemistry > 47201-(S1) Undergraduate Thesis
Depositing User:	Lela Agustin
Date Deposited:	04 Aug 2025 08:21
Last Modified:	04 Aug 2025 08:21
URI:	http://repository.its.ac.id/id/eprint/126102

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