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5-Trifluoromethyl Oxazole

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The methods which substitute fluorine for proton at an aimed position in chemicals has an ability to convert into useful pharmaceuticals or functional materials due to fluorine specific potency, and is often used as one of the improvement means. Whereas compounds possessing 2-phenyl-5-methyl oxazole in a structure are known to quite a few, the papers related to 2-phenyl-5-trifluoromethyl oxazole of which substituted trifluoromethyl group instead of a methyl group as a partial structure are not so many. For instance, it has been reported that the 5-trifluoromethylated oxazole part was constructed by Dakin-West reaction1) with TFAA or was synthesized by an introduction of the leaving group at 5-position of oxazole, following by substituted reaction …show more content…

In addition, methyl ether (**) can be generated as cis- and trans- isomers, but was isolated as a single isomer. This compound was stable against heat at 60 degrees and was not transformed into 5-trifluoromethyl oxazole (**), whereas compound (*) was unstable, turned into easily rearrangement oxazole (**) in the middle of isolation. To confirm this rearrangement of compound (*), when we heated at 60 degrees for 30min, the compound (*) was observed to convert into oxazole (**) …show more content…

If these unstable precursors were isolated as yilde forms, it was assumed that the value of δC of the 13CNMR chemical shift on C2-position of precursors would indicate near a value of benzo nitrile whose δC at nitrile carbon is about 120 ppm. However, δC of C2-position of the precursors were about 151 ppm. Rather, δC of C2- and C5-position of the precursors showed near a value of the chemical shift in comparison with starting materials. Furthermore, characteristic absorption peak of nitrile was not observed in IR spectral, but we viewed absorption one peak of near about 1700 cmm-1 derived from carbonyl

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The yellow solution containing the reactants was slowly poured into the beaker containing the cold water and the acid in order to cause the precipitation of the alcohol, 9-fluorenol and to destroy (hydrolyzed) the unreacted excess sodium borohydride. Subsequently, the white precipitate was vacuum filtered and washed twice with 20.0 ml portions of distilled cold water by pouring the liquid into the Buchner Funnel during filtration. It was necessary to wash the alcohol prior to recrystallization considering that the C-OH bond is easily broken by the formation of a stable and benzylic carbocation that favors the synthesis of difluorenyl ether. Finally, before the purification by recrystallization of the obtained product, the white solid alcohol was allowed to dry over a period of a

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691 Words | 3 Pages

A new oral pharmaceutical drug for type- two diabetes had been approved for clinical use, it was called Compound 17392. Marketing companies instantly wanted to have prescribers adopt and sell the product and researchers wanted to further investigate previous reports of liver toxicity in patients. Now since paying patients to try new pharmaceutical drugs was an issue due to it appearing to interfere with clinical judgement and upholding the duty to do what is best for the patient, a new idea of furthering research for the drug came into play. The idea included recruiting a group of physicians who were in the top ten percent of prescribers for type-two diabetes. Following regulations put in place by researchers, these physicians were to enter eligible patients into the trial for Compound

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Abstract – Methyl trans-cinnamate is an ester that contributes to the aroma of strawberry. It can be synthesized by an acid-catalyzed Fischer esterification of a methanol and trans-cinnamic acid under reflux. The solution was extracted to obtain the organic product, and evaporated residual solvent The yield was 68%, but there is some conflicting data regarding the purity. The melting point, IR, GC-MS indicate a highly pure desired product whereas 1H NMR shows there are unreacted reagents still present.

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Radioactively Labeled Azole Import by M. oryzae Radioactively labeled FLC (3H-FLC), (481 GBa/mmol, 13 Ci/mmol, 1 µCi/µL; 77 µM FLC) was custom synthesized by Amersham Biosciences. The drug concentration used during the import assay was well below the Minimum Inhibitory Concentration (MIC) for the strain (M. oryzae FLC MIC >32 µg/ml). To directly measure azole intracellular accumulation in the fungal cell, we used 3H-FLC in our drug uptake assay designed for M. oryzae.

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(Gale, Howle, & Walker Jr., 1971) IR spectroscopy can be used to characterize certain organometallic compounds by measuring

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Objective: The objective of the experiment is to synthesis cis-Norbornene-5,6-endo-Dicarboxylic anhydride in a Diels-alder reaction. The chemicals used are Maleic anhydride and Cyclopentadiene. In this experiment, the melting point and of cis-Norbornene-5,6-endo-Dicarboxylic anhydride is determine. Also, the percent yield.

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The purpose of this experiment was to learn about the electrophilic aromatic substitution reactions that take place on benzene, and how the presence of substituents in the ring affect the orientation of the incoming electrophile. Using acetanilide, as the starting material, glacial acetic acid, sulfuric acid, and nitric acid were mixed and stirred to produce p-nitroacetanilide. In a 125 mL Erlenmeyer flask, 3.305 g of acetanilide were allowed to mix with 5.0 mL of glacial acetic acid. This mixture was warmed in a hot plate with constantly stirring at a lukewarm temperature so as to avoid excess heating. If this happens, the mixture boils and it would be necessary to start the experiment all over again.

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In our initial experiments, a 19% yield of 3,4-dicarbonyl substituted furan 3a was obtained when α,β-unsaturated carbonyl (1a) and 1,3 diketone (2b) were employed for the reaction (Table 1, entry 1) in a 1:2 molar ratio in the presence of 10mg of CuO-NPs in EtOH at room temperature without any oxidizing agent. When molar ratio of the reactants 1a and 2b were increased to 1:3, an improvement in the yield to 28% was observed (Table 1, entry 2) and molar ratio 1:5 gives the highest yield in the same reaction conditions 38% (Table 1, entry 3). The polar solvent such as DMF, DMSO, H2O, Xylene also gave the desired products but in low yield, while no reactions occurred in acetonitrile, toluene (Table 1, entries 4−9).When we employed a mixture of solvent EtOH: H2O (4:1) slight increase of yield 46% was obtained (Table 1, entry 10), increasing the mixture of solvent ratio to 2:1give the yield 51% (Table 1, entry 11) and solvent ratio 1:1 give the highest yield 60% (Table 1, entry 12).

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629 Words | 3 Pages

In other lab procedures, benzoic acid is sometimes substituted for anisole in the Friedel-Craft acylation. However, the reason benzoic acid

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Ethylene dichloride is a chlorinated organic compound consisting of two singly bonded carbon atoms bonded to one chlorine atom on each carbon and is assigned the CAS registry number 107-06-2scifinder. Ethylene dichloride should not be confused with 1,2-dichloroethylene which contains a double bond between the two carbons. Although a stable compound at room temperature, it does slowly decompose in the presence of oxygen and UV light turning a darker colour, and at temperatures above 340 oC it begins to decomposes forming vinyl chloride & HCL Ullmann’s & http://www.cdc.gov/niosh/npg/npgd0271.html . Table 1 lists the basic physical and chemical properties on ethylene dichloride.

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1,3,4-Oxadiazole (1) is a heterocyclic compound containing an oxygen atom and two nitrogen atoms in a five-membered ring. It is derived from furan by substitution of two methylene groups (=CH) with two pyridine type nitrogens (-N=) [1,2]. There are three known isomers: 1,2,4-oxadiazole (2), 1,2,3-oxadiazole (3) and 1,2,5-oxadiazole (4). However, 1,3,4-oxadiazole and 1,2,4-oxadiazole are better known, and more widely studied by researchers because of their many important chemical and biological properties.

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907 Words | 4 Pages

The goal of this lab was to prepare methyl m-nitrobenzoate using electrophilic aromatic substitution using nitration. The reaction used methyl benzoate with the acid catalyst as sulfuric acid. The mechanism for the nitration using methyl benzoate is presented in Figure 1. Figure 1: Benzene can only undergo substitution reactions that are called electrophilic aromatic substitution reactions. Given that benzene rings are used commonly in the production of many organic compounds, the capability to make substitutions to benzene is critical.

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418 Words | 2 Pages

The purpose of this laboratory experiment was to react methyl benzoate with nitric acid and identify the position of the substituted nitro group in the final product molecule. Methyl benzoate was added to cool concentrated sulfuric acid in order to amplify the directing effect of the nitro group addition, such that without the sulfuric acid the protonation would have happened at the carbon oxygen double bond. The mixing of concentrated nitric acid with concentrated sulfuric acid was to achieve Reaction 1 from Table 1, formation of the nitronium ion. Both of these reactions were kept at temperatures around 0°C, since they are exothermic reaction and presence of heat could lead to production of unnecessary dinitro by-products.

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INTRODUCTION Carbon tetrachloride (CCl4) - an organic industrial solvent used in industry – is a vigorous carcinogenic agent that may create dysfunction of lung, liver, kidney and nervous system (1, 2). After being absorbed from gastrointestinal system, respiratory system and skin CCl4 is metabolized by cytochrome P-450 and exerts its toxic effects via its metabolites trichloromethyl free radical and trichloromethyl peroxyl radical (1-3). These free radicals interacts with fatty acids of lung cell membrane and increase lipid peroxidation and DNA fragmentation. Moreover, they suppress antioxidant enzymes including catalase, superoxide dismutase, glutathione (GSH), oxidized glutathione (GSSG), glutathione reductase and glutathione peroxide (1,2,4).

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5-membered rings containing heteroatom11 One hetero atom11 Figure 1.3: Structure showing the heterocyclic compound having one hetero atom Two hetero atoms Figure 1.4: Structure showing the heterocyclic compound having two hetero atoms 6-membered ring containing heteroatom11 Figure 1.5: Structure showing the six membered heterocyclic compounds Unsaturated and saturated heterocyclic compound12 Figure 1.6: Structure of saturated and unsaturated heterocyclic compounds 1.7 AZOLES Azoles are the class which contain five member ring, having nitrogen heterocyclic ring compound containing at least one other heteroatom (or non-carbon atom) of nitrogen, sulfur or oxygen and are considered to be derived from pyrrole, furan and thiophene by substitution of methane groups (―CH=) by pyridine type nitrogen (―N=) atoms from the different positions. Azole mainly consists of: (i) Oxygen is referred as oxazole (ii) Sulphur is referred as thiazole and (iii) Nitrogen is referred as pyrazole, imidazoles or imidazolines12. 1, 3-Azoles synthesis12 Scheme 1.1: Synthesis of 1, 3-Azoles by Cyclodehydration of α-acylaminocarbonyl compound12 1.8 OXAZOLE

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