Sintesis Tiga Hidrazona dari 5-Bromoisatin dan 5,7-Dibromoisatin

Khumaidah, Laili (2015) Sintesis Tiga Hidrazona dari 5-Bromoisatin dan 5,7-Dibromoisatin. Undergraduate thesis, Institut Teknologi Sepuluh Nopember.

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Abstract

Infeksi yang disebabkan oleh bakteri merupakan salah satu penyebab kematian tertinggi. Hal ini antara lain disebabkan bakteri mampu beradaptasi sehingga menjadi antimicrobial resistant. Hidrazona dapat dikembangkan sebagai lead compound kelompok antibakteri baru. Penelitian yang telah dilakukan berhasil mensintesis tiga hidrazona: 2-tiofenakarbonilhidrazon-5- bromoisatin, 2-tiofenakarbonilhidrazon-5,7-dibromoisatin, dan 2- tiofena-karbonilhidrazon-3-(N-metil)-5,7-dibromoisatin. 2- Tiofena-karbonilhidrazon-5-bromoisatin diperoleh dengan rendemen 90% dari reaksi 5-bromoisatin dan asam 2- tiofenakarboksilat hidrazida dalam pelarut etanol dengan katalis asam sulfat pekat. Brominasi isatin diperoleh 5,7-dibromoisatin dengan rendemen 73%, yang kemudian dimetilasi sehingga dihasilkan 5,7-dibromo-N-metilisatin dengan rendemen 95%. Reaksi asam 2-tiofenakarboksilat hidrazida masing-masing dengan 5,7-dibromoisatin dan 5,7-dibromo-N-metilisatin diperoleh 2-tiofenakarbonil-hidrazon-5,7-dibromoisatin dengan rendemen 91% dan 2-tiofenakarbonilhidrazon-3-(N-metil)-5,7- dibromoisatin dengan rendemen 41%. ============================================================================================ Infections caused by bacteria are one of the leading causes of death. This is due to the bacteria are able to adapt and become antimicrobial resistant. Hydrazone can be developed as the lead compound of a new antibacterial group. Research has been done successfully synthesized three hydrazones: 2- thiophenecarbonylhydrazone-5-bromoisatin, 2- thiophenecarbonylhydrazone-5,7-dibromoisatin, and 2- thiophenecarbonylhydrazone-3- (N-methyl) -5,7-dibromoisatin. 2- Thiophenecarbonylhydrazone-5-bromoisatin obtained 90% yield from the reaction of 5-bromoisatin and 2-tiophenecarboxylic acid hydrazide in ethanol with sulfuric acid as catalyst. Bromination of isatin obtained 5,7-dibromoisatin in 73% yield, which is then methylated to produce 5,7-dibromo-N-methylisatin in 95% yield. The reaction of 2-thiophenecarboxylic acid hydrazide with each 5,7-dibromoisatin and 5,7-dibromo-N-methylisatin obtained 2- thiophenecarbonylhydrazone-5,7-dibromoisatin in 91% yield and 2- thiophenecarbonylhydrazone-3-(N-methyl)-5,7-dibromoisatin in 41% yield.

Item Type: Thesis (Undergraduate)
Additional Information: RSKi 541.39 Khu s
Uncontrolled Keywords: 5-bromoisatin, 5,7-dibromoisatin, hidrazona, hydrazone
Subjects: Q Science > QD Chemistry
Q Science > QD Chemistry > QD251.2 Chemistry, Organic. Biochemistry
Divisions: Faculty of Mathematics and Science > Chemistry > (S1) Undergraduate Theses
Depositing User: Eny Widiastuti -
Date Deposited: 27 Apr 2018 04:28
Last Modified: 27 Apr 2018 04:28
URI: http://repository.its.ac.id/id/eprint/51813

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