Sintesis 5,5-Difenilimidazolidin-2,4-Dion Termetilasi.

Putra, Aji Purnama (2022) Sintesis 5,5-Difenilimidazolidin-2,4-Dion Termetilasi. Other thesis, Institut Teknologi Sepuluh Nopember.

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Abstract

Senyawa 1,3-Diazola 1 adalah senyawa heterosiklik dengan tiga atom karbon, dua atom nitrogen, empat atom hidrogen, dan dua ikatan rangkap yang dapat ditemui dalam senyawa bahan alam maupun obat-obatan. Imidazolidin-2,4-dion 10, senyawa berkerangka 1,3-diazola 1 dengan inti urea, menunjukkan aktivitas biologis diantaranya sebagai antikonvulsan dan antibakteri. 5,5′-Difenilimidazolidin-2,4-dion 11 selanjutnya banyak dikembangkan melalui modifikasi dengan substituen alkil, aril, dan halogen pada posisi N1, N3, dan C5. Penelitian sebelumnya melaporkan bahwa alkilasi dapat menghasilkan senyawa-senyawa dengan aktivitas yang menjanjikan. Gugus metil dalam struktur senyawa juga diketahui dapat mengingkatkan aktivitas biologis. Penelitian yang dilakukan bertujuan untuk mendapatkan 3-metil-5,5-difenilimidazolidin-2,4-dion 26 melalui modifikasi 5,5′-difenilimidazolidin-2,4-dion 11 dengan gugus metil. Penelitian dilakukan dengan sintesis 2-hidroksi-1,2-di(fenil)etanona 30, 1,2-difeniletan-1,2-dion 29, dan 5,5-difenilimidazolidin-2,4-dion 11 yang dilanjutkan dengan reaksi metilasi. Penelitian telah berhasil mendapatkan 2-hidroksi-1,2-di(fenil)etanona 30 dengan rendemen 60% dari reaksi antara benzaldehida 31 dengan kalium sianida, 1,2-difeniletan-1,2-diona 29 dengan rendemen 79% dari oksidasi 2-hidroksi-1,2-di(fenil)etanona 30 dengan asam nitrat pekat, 5,5-difenilimidazolidin-2,4-dion 11 dengan rendemen 37% dari reaksi 1,2-difeniletan-1,2-dion 29 dengan larutan kalium hidroksida 70% dan urea 27, dan 3-metil-5,5-difenilimidazolidin-2,4-dion 26 dengan rendemen 89% dari metilasi 5,5-difenilimidazolidin-2,4-dion 11 dengan metil iodida 28.===================================================================================================================================
1,3-Diazole 1 compound is a heterocyclic compound containing three carbon atoms, two nitrogen atoms, four hydrogen atoms, and two double bonds found in natural and medicinal compounds. Imidazolidine-2,4-dione 10, a 1,3-diazole 1 skeletal compound with a urea core, exhibits biological activities including antispasmodic and antibacterial activity. 5,5′-Diphenimidazolidine-2,4-dione 11 was further developed by modification with alkyl, aryl, and halogen substituents at the N1, N3, and C5 positions. Previous studies reported that alkylation can generate compounds with promising activity. It is also known that the methyl group in the link structure increases biological activity. The aim of the research was to obtain 3-methyl-5,5-diphenylmidazolidine-2,4-dione 26 by modifying 5,5'-diphenylmidazolidine-2,4-dione 11 with a methyl group. The research was conducted by synthesizing 2-hydroxy-1,2-di(phenyl)ethanone 30, 1,2-diphenylethane-1,2-dione 29 and 5,5-diphenylimidazolidine-2,4-dione 11, followed of a methylation reaction. Research succeeded in obtaining 2-hydroxy-1,2-di(phenyl)ethanone 30 in 60% yield from the reaction between benzaldehyde 30 and potassium cyanide, 1,2-diphenylethane-1,2-dione 29 in yield obtained 79% from the oxidation of 2-hydroxy-1,2-di(phenyl)ethanone 30 with concentrated nitric acid, 5,5-diphenylmidazolidine-2,4-dione 11 in 37% yield from the reaction of 1, 2-diphenylethanol-1,2-dione 29 with a solution of potassium hydroxide 70% and urea 27, and 3-methyl-5,5-diphenylmidazolidine-2,4-dione 26 in 89% yield from the methylation of 5,5-diphenylmidazolidine-2,4-dione 11 with methyl iodide 28.

Item Type:	Thesis (Other)
Additional Information:	RSKi 541.39 Put s-1 2022
Uncontrolled Keywords:	1,3-diazola, 5,5’-difenilimidazolidin-2,4-dion, Metilasi. 1,3-diazole, 5,5’-diphenylimidazolidine-2,4-dione, Methylation.
Divisions:	Faculty of Science and Data Analytics (SCIENTICS) > Chemistry > 47201-(S1) Undergraduate Thesis
Depositing User:	Mr. Marsudiyana -
Date Deposited:	06 May 2026 04:42
Last Modified:	06 May 2026 04:42
URI:	http://repository.its.ac.id/id/eprint/133011

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