Sintesis Asam 2-(4-((5-Merkapto-1,3,4-Oksadiazol-2-Il)Metoksi)Benzilidena)Hidrazina-1-Karboditioat

Nurhasan, Moch (2023) Sintesis Asam 2-(4-((5-Merkapto-1,3,4-Oksadiazol-2-Il)Metoksi)Benzilidena)Hidrazina-1-Karboditioat. Other thesis, Institut Teknologi Sepuluh Nopember.

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Abstract

Senyawa 4-hidroksibenzaldehida 1 merupakan golongan senyawa fenolat yang dijumpai pada beberapa spesies tumbuhan terutama dari genus vanilla memiliki beberapa aktivitas biologis. 4-Hidroksibenzaldehida 1 dapat mengalami reaksi substitusi pada gugus hidroksil dan reaksi adisi pada gugus aldehida menghasilkan berbagai senyawa turunan yang memiliki aktivitas biologis lebih baik dari senyawa induknya. Sementara itu, isomer oksadiazola berupa 1,3,4-oksadiazola 10 juga dapat bereaksi dengan berbagai pereaksi menghasilkan senyawa turunan yang bervariasi dengan aktivitas biologis yang beragam. Penelitian yang dilakukan bertujuan untuk mendapatkan turunan 4-hidroksibenzaldehida dengan substituen 1,3,4-oksadiazola 10 dan substituen asam karboditioat berupa asam 2-(4-((5-merkapto-1,3,4-oksadiazol-2-il)metoksi)benzilidena)hidrazina-1-karboditioat 16 melalui reaksi substitusi, adisi, dan siklokondensasi. Reaksi dengan bahan awal 4-hidroksibenzaldehida 1 menghasilkan etil 2-(4-formilfenoksi)asetat 20 dan 2-(4-(hidrazinilidenametil)fenoksi)asetohidrazida 18 yang dilanjutkan dengan pembentukan senyawa 16. Senyawa etil 2-(4-formilfenoksi)asetat 20 telah berhasil didapatkan dengan rendemen 69,98% melalui reaksi substitusi nukleofilik antara 4-hidroksibenzaldehida 1 dan etil kloroasetat 21. Senyawa 2-(4-(hidrazinilidenametil)fenoksi)asetohidrazida 18 dengan rendemen 92,34% selanjutnya diperoleh melalui reaksi adisi nukleofilik antara etil 2-(4-formilfenoksi)asetat 20 dan hidrazin hidrat 19. Akhirnya, asam 2-(4-((5-merkapto-1,3,4-oksadiazol-2-il)metoksi)benzilidena)hidrazina-1-karboditioat 16 dengan rendemen 72,98% telah berhasil diperoleh melalui reaksi siklokondensasi antara 2-(4-(hidrazinilidenametil)fenoksi)asetohidrazida 18 dan karbon disulfida 17 dengan penambahan KOH.
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4-Hydroxybenzaldehyde 1 compound is a group of phenolic compounds found in several plant species, especially from the genus vanilla, which has several biological activities. 4-Hydroxybenzaldehide 1 can undergo substitution reactions on hydroxyl groups and addition reactions on aldehyde groups to produce various derivative compounds that have better biological activity than the parent compound. Meanwhile, the oxadiazole isomer in the form of 1,3,4-oxadiazole 10 can also react with various reagents to produce various derivative compounds with diverse biological activities. The aim of the research was to obtain a 4-hydroxybenzaldehyde derivative with 1,3,4-oxadiazole 10 substituent and carbodithioic acid substituent in the form of 2-(4-((5-mercapto-1,3,4-oxadiazol-2-yl)methoxy)benzylidene)hydrazine- 1-carbodithioic acid 16 through substitution, addition, and cyclocondensation reactions. The reaction with the starting material 4-hydroxybenzaldehyde 1 produces ethyl 2-(4-formylphenoxy)acetate 20 and 2-(4-(hidrazineylidenemethyl)phenoxy)acetohydrazide 18 which is followed by the formation of 16 compound. Ethyl 2-(4-formylphenoxy)acetate 20 has been successfully obtained with a yield of 69.98% through a nucleophilic substitution reaction between 4-hydroxybenzaldehyde 1 and ethyl chloroacetate 21. 2-(4-(hydrazineylidenemethyl)phenoxy)acetohydrazide 18 compound with a yield of 92.34% was then obtained through a nucleophilic addition reaction between ethyl 2-(4-formylphenoxy)acetate 20 and hydrazine hydrate 19. Finally, 2-(4-((5-mercapto-1,3,4-oxadiazol-2-yl)methoxy)benzylidene)hydrazine-1-carbodithioic acid 16 with a yield of 72.98% was successfully obtained by a cyclocondensation reaction between 2-(4-(hydrazineylidenemethyl)phenoxy)acetohydrazide 18 and carbon disulfide 17 with the addition of KOH.

Item Type:	Thesis (Other)
Uncontrolled Keywords:	4-hydroxybenzaldehyde, 1,3,4-oxadiazole, carbon disulfide, 4-hidroksibenzaldehida, 1,3,4-oksadiazola, karbon disulfida
Subjects:	Q Science > QD Chemistry > QD251.2 Chemistry, Organic. Biochemistry
Divisions:	Faculty of Science and Data Analytics (SCIENTICS) > Chemistry > 47201-(S1) Undergraduate Thesis
Depositing User:	Moch. Nurhasan
Date Deposited:	08 Aug 2023 03:59
Last Modified:	08 Aug 2023 03:59
URI:	http://repository.its.ac.id/id/eprint/103998

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