Sintesis 1,3-Dimetil-5,5-Difenilimidazolidin-2,4-Dion Dan 3-Metil-5,5-Difenilimidazolidin-2,4-Dion

Nisa, Ridha Agustina Kholifatun (2022) Sintesis 1,3-Dimetil-5,5-Difenilimidazolidin-2,4-Dion Dan 3-Metil-5,5-Difenilimidazolidin-2,4-Dion. Other thesis, Institut Teknologi Sepuluh Nopember.

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Abstract

Imidazola 1 merupakan senyawa cincin planar dengan tiga atom karbon dan dua atom nitrogen pada posisi pertama dan ketiga. Imidazola 1 dan berbagai turunannya menunjukkan aktivitas biologis yang beragam diantaranya adalah antiepilepsi, inhibitor β-laktamase dan karboksipeptidase, antikanker, antiinflamasi, antibakteri, antijamur, antivirus, antituberkular, antidiabetes, dan antimalaria. 5,5-Difenilimidazolidin-2,4-dion 10 dengan kerangka imidazola 1 merupakan kelompok senyawa yang telah digunakan dalam penanganan epilepsi dan kejang. Modifikasi struktur selanjutnya dapat dilakukan melalui alkilasi, arilasi, dan halogenasi pada posisi N1, N3, dan C5. Keberadaan gugus metil dalam suatu struktur senyawa dilaporkan dapat meningkatkan aktivitas biologi. Penelitian yang dilakukan bertujuan untuk mendapatkan 1,3-dimetil-5,5-difenilimidazolidin-2,4-dion 19 dan 3-metil-5,5-difenilimidazolidin-2,4-dion 21 melalui modifikasi 5,5 difenilimidazolidin-2,4-dion 10 dengan penambahan gugus metil. Penelitian dilakukan melalui sintesis 2-hidroksi-1,2-di(fenil)etanona 24, 1,2-difeniletan-1,2-dion 23, dan 5,5-difenilimidazolidin-2,4-dion 10 yang dilanjutkan dengan reaksi metilasi. Penelitian yang dilakukan telah berhasil mendapatkan 2-hidroksi-1,2-di(fenil)etanona 24 dengan rendemen 60% melalui reaksi kondensasi benzoin benzaldehida 25 dengan kalium sianida. 1,2-Difeniletan-1,2-dion 23 dengan rendemen 79% telah diperoleh melalui oksidasi 2-hidroksi-1,2-di(fenil)etanona 24 dengan HNO3 pekat. Selanjutnya, 5,5-difenilimidazolidin-2,4-dion 10 dengan rendemen 23% diperoleh melalui siklisasi 1,2-difeniletan-1,2-dion 23 dengan kalium hidroksida dan urea 22. Akhirnya, 1,3-dimetil-5,5-difenilimidazolidin-2,4-dion 19 dengan rendemen 26% dan 3-metil-5,5-difenilimidazolidin-2,4-dion 21 dengan rendemen 21% telah berhasil diperoleh melalui metilasi 5,5-difenilimidazolidin-2,4-dion 10 dengan tert-BuOK dan iodo metana 20.
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Imidazole 1 is a planar ring compound with three carbon atoms and two nitrogen atoms in the first and third positions. Imidazole 1 and its various derivatives show diverse biological activities including antiepileptic, β-lactamase and carboxypeptidase inhibitors, anticancer, anti-inflammatory, antibacterial, antifungal, antiviral, antitubercular, antidiabetic, and antimalarial activities. 5,5-Diphenylimidazolidine-2,4-dione 10 with imidazole structure 1 is a group of compounds that have been used in the treatment of epilepsy and seizures. Subsequent structural modifications can be carried out through alkylation, arylation, and halogenation at the N1, N3, and C5 positions. The presence of a methyl group in a compound structure was reported can increase the biological activity. The purpose of the research was to obtain 1,3-dimethyl-5,5-diphenylimidazolidine-2,4-dione 19 and 3-methyl-5,5-diphenylimidazolidine-2,4-dione 21 through modification of 5,5-diphenylimidazolidine-2,4-dione 10 with the addition of a methyl group. The research was conducted through the synthesis of 2-hydroxy-1,2-di(phenyl)ethanone 24, 1,2-diphenylethane-1,2-dione 23, and 5,5-diphenylimidazolidine-2,4-dione 10 followed by a methylation reaction. This research has succeeded in obtaining 2-hydroxy-1,2-di(phenyl)ethanone 24 with a yield of 60% through the benzoin condensation reaction of benzaldehyde 25 with potassium cyanide. 1,2-Diphenylethane-1,2-dione 23 with a yield of 79% was obtained by oxidation of 2-hydroxy-1,2-di(phenyl)ethanone 24 with concentrated HNO3. Furthermore, 5,5-diphenylimidazolidine-2,4-dione 10 with a yield of 23% was obtained by cyclization of 1,2-diphenylethanol-1,2-dione 23 with potassium hydroxide and urea 22. Finally, 1,3-dimethyl-5, 5-diphenylimidazolidin-2,4-dione 19 with a yield of 26% and 3-methyl-5,5-diphenylmidazolidine-2,4-dione 21 with a yield of 21% have been successfully obtained by methylation of 5,5-diphenylimidazolidine-2,4- dion 10 with tert-BuOK and iodo methane 20.

Item Type:	Thesis (Other)
Additional Information:	RSKi 541.39 Nis s-1 2022
Uncontrolled Keywords:	imidazola, 5,5-difenilimidazolidin-2,4-dion, metilasi. imidazole, 5,5-diphenylimidazolidine-2,4-dione, methylation.
Subjects:	Q Science > QD Chemistry > QD75.2 Chemistry, Analytic
Divisions:	Faculty of Science and Data Analytics (SCIENTICS) > Chemistry > 47201-(S1) Undergraduate Thesis
Depositing User:	Mr. Marsudiyana -
Date Deposited:	07 May 2026 08:42
Last Modified:	08 May 2026 01:30
URI:	http://repository.its.ac.id/id/eprint/132982

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