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Synthesis Synthesis Lab Report

Decent Essays

Abstract: Synthesis of new compounds 2-(bis((1H-benzo[d]imidazol-2- yl)methylthio)methyl)-1H-benzo[d]imidazole (6a) and 2-((((1H-benzo[d]imidazol-2-yl)(((5- hydroxy-1H-benzo[d]imidazol-2-yl)methyl)sulfanyl)methyl)sulfanyl)methyl)-3H- benzo[d]imidazol-5-ol (6b) were carried out under two different reaction conditions, namely the conventional method and microwave irradiation conditions. The compounds (3a,b), (5a,b) and (6a,b) were synthesized by using microwave methods which showed decrease in the reaction time and increasing in the yield as shown in Table (1). The structures of the synthesized compounds were confirmed by IR; NMR and elemental analysis. The antimicrobial activityof the synthesized benzimidazolemethanethiol derivatives …show more content…

HCl)33, respectively, with 2-mercaptoacetic acid (2) in the presence of 6M hydrochloric acid under reflux for 4 hours in 70% yield. 1H-NMR spectrum of 3a , as an example, showed a singlet at 1.7 for SH, singlet at 3.8 for methylene group and benzimidazole protons at 7.4 and 7.6 ppm. Compounds 3a and 3b were heated with 2,2-dichloroacetic acid (4) and potassium carbonate in absolute ethanol under reflux for 3 hours to give 2,2-bis(((1H-benzo[d]imidazol-2-yl)methyl)thio)acetic acid (5a) in 69% yield and 2,2`-bis(((5-hydroxy-1H-benzo[d]imidazolyl)methyl)thio)acetic acid (5b) in 66% yield, respectively. Compounds 5a,b gave compatible spectroscopic data (Experimental). Condensation of o-phenylenediamine (1) with each of 5a,b in the present of 6N hydrochloric acid give 2,2`-((((1H-benzo[d]imidazol-2-yl)methylene)bis(sulfane-diyl))bis-(methylene))bis-(1H-benzo[d]imidazole(6a) in 66% yield, and2,2`-((((1H-benzo[d]imi-dazol-2-yl)bis(sulfane-diyl)bis(methylene))-bis(1H-benzo-d]imidazol-5-ol) (6b) in 61% yield; Scheme (1). 1H-NMR of 6a showed a singlet signal at 4.2 ppm for two methylene group, a singlet at 5.1 ppm for CH, 7.4 and 7.7 ppm for aromatic protons. Its 13C-NMR spectrum showed signal at 36.3 ppm for two methylene groups, 68.8 ppm for methine. 1H-NMR spectrum of (5b) showed a singlet at 4.3 ppm as four protons for two methylene groups; singlet at 5.3 ppm as one proton for methine group, and 6 aromatic protons at 7.2, 7.4 and 7.6

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