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
4 Conclusions Undoped LaGaO3, Bi3+ doped-LaGaO3, Eu3+doped-LaGaO3, Bi3+ and Eu3+ co-doped LaGaO3 (LaGaO3:Bi3+, Eu3+) nanophosphors were successfully synthesized by polyol method. PXRD confirmed the pure orthorhombic phase of LaGaO3:Bi3+, Eu3+ nanophosphors heated at 1000oC. Field Emission Scanning electron microscopy (FE-SEM) micrographs showed that LaGaO3:Bi3+, Eu3+ nanophosphors were composed of agglomerated and quasi spherical shaped particles with sizes ranging from 20 nm to 30 nm with an average crystallite size of 50 nm and the results were in good agreement with the values obtained by Debye Scherer’s formula. The elemental composition of the synthesized nanophosphors was confirmed by EDAX. From UV-Vis studies, it is found that the absorption of undoped LaGaO3 nanophosphor is less compared with Bi3+, Eu3+ co-doped LaGaO3 nanophosphors and the optical band gap decreases in LaGaO3: Bi3+, Eu3+
2-methylmercapto-4,5-dihydroimidazole hydroiodide was synthesized imidazolidine-2-thione by reaction with methyl iodide and this compound was used as the starting material. 2-alkylamino-imidazolines was obtained from the nucleophilic substitution reaction with 2-methylmercapto-4,5-dihydroimidazol hidroiyodür and different aliphatic amine such as, diamine, triamine and tetramine. The syntheses of the salts of these compounds were prepared from the reaction of the 2-alkylaminoimidazolines and various organic acids such as, succinic acid, picric acid, fumaric acid and phthalic
The purpose if this experiment is to prepare 5-cis- and 5-trans-3-(4-methylphenyl)-2-propenoic acid ethyl ester using formation of a stabilize ylide and p-tolualdehyde in a methanol solvent. The stabilize ylide is formed by a reaction of phosphonium salt, triphenylphosphonium bromide, and aqueous sodium hydroxide. The products made under reflux are separated using liquid-liquid extraction, and purified using rotary evaporator. The product was analyze using H-nuclear magnetic spectroscopy to determine the desired prepare 5-cis- and 5-trans-3-(4-methylphenyl)-2-propenoic acid ethyl ester formed with hexane by products. The percent yield was 72%.
1H NMR spectra was recorded in the indicated solvent on Bruker AMX 400 MHz spectrometer with TMS as internal standard. The mass spectra of the compounds were recorded on Agilent 1100 ESI-Mass (Turbo Spray) using positive mode ionization method. Elemental analyses were carried out with a Perkin-Elmer model 2400 series II apparatus. The results of elemental analyses (C,H,N) were within ± 0.4 % of the calculated values. Infrared spectra were recorded in KBr on Perkin-Elmer AC-1 spectrophotometer.
. Ecologically safe methods for the synthesis of five-membered and six-membered cyclic carbonates by the reaction of transesterification of dialkyl carbonates with dihydric alcohols will be developed.
The synthesis required that the starting materials contain an aniline and aldehyde in order to produce an imine, which is a primary amine. Using p-chlorobenzaldehyde and p-bromoaniline along with the addition of dichloromethane and, in some cases, a water trapping reagent, the group was able to synthesize 4-bromo-N-[4-(chlorophenyl)methylene]-benzenamine. Three different reactions using the same reactants but different water trapping agents were employed in order to determine which trapping agent, either molecular sieves or sodium sulfate, would remove the most water and leave the purest product. Upon completion of TLC, melting point analysis, as well as IR spectrum, and 1H NMR analysis, it was determined that the reaction using the molecular sieves produced the purest substance. Furthermore, it was hypothesized that the molecular sieves would produce the greatest percent yield of pure product since it is the only water trapping agent that can also separate out non-water
The formation of 10 is assumed to proceed via an initial Michael addition of the endocyclic NH in 5 to the double bond in 8 to yield the non-isolable intermediate 9 followed by intramolecular cyclization and aromatization by loss of hydrogen to afford 10, (Scheme IV). Similar to its behavior towards α-substituted cinnamonitrile, compound 5 was reacted with 2-(bis(methylthio)methylene)malononitrile (12) in ethanol containing a catalytic amount of piperidine as catalyst to produce pyrazolo[1,5-a]pyrimidine derivative 14 on the basis of analytical and spectral measurements. The infrared spectrum of compounds 14 indicated the presence of exhibited strong stretching frequencies in the region of 3452, 3398, 3336 and 2191 cm-1 attributable to the amino, imino and nitrile groups, in addition to the presence of a strong absorption band at 1631 cm-1 due to a carbonyl group. The mass spectrum of compound 14 revealed a molecular ion peak at m/z = 575 (28.29%), and the base peak was found in the spectrum at m/z = 115.The formation of 14 is assumed to proceed through an initial Michael addition of the endocyclic NH in 5 to the double bond in 12 to yield the non-isolable intermediate 13 followed by intramolecular cyclization and aromatization (Scheme
Choline acetate (Entry 15, Table 4) To 2.02 g (12.25 mmol) of commercial choline bicarbonate (Entry 14), 0.80 g (13.48 mmol) of acetic acid were added and then the mixture was kept under constant stirring at 25 °C for 4 h. A colorless liquid was obtained (90 %): 1H NMR (300 MHz, D2O), 1.77 (s, 3H), 3.02 (s, 9H), 3.34 (t, 2H, J= 5.1 Hz), 3.843-3.920 (m, 2H) ppm; 13C NMR (75 MHz, D2O), δ(ppm): 22.80, 53.92 (3C), 55.66, 67.48, 180.46 ppm. IR (cm-1): 3161, 3027, 2967, 2856, 1568, 1480, 1388, 1331, 1267, 1088, 1007, 953, 866, 643, 580. Compounds at entries 16 and 17 were obtained under similar conditions, using butyric or hexanoic acid instead of acetic acid. The purity of all the synthesized ILs seems to be higher than 90 %, considering that the 1H NMR and 13C NMR spectra do not show signals from the starting materials or other
The experimental values of the aqueous phase reaction rate constant kOH (M-1 s-1) for 958 organic compounds were obtained from the compilation of NDRL Radiation Chemistry Data Center (https://www3.nd.edu/~ndrlrcdc/ Compilations/Hydroxyl/OH.htm) and Borhani et al. (2016).These data sets comprised the second-order kinetic rate constant values for the reaction of •OH with structurally heterogeneous compounds of a number of chemical classes, such as the acrylamides, acrylates, aldehydes, aliphatic amines, aliphatic amines-acid, aromatic amines, aromatic amines-acid, aldehydes-acid, allylic/vinyl nitriles, anilines, benzyl alcohols, benzyl amines, benzotriazoles, benzyl halides, diketones, dinitrobenzenes, epoxides, esters, esters-acid, hydrazines, haloacetamides, imidazoles , imidazoles-acid, imides, imides-acid, neutral organics, neutral organics-acid, phenols,
At this point, only the anisole was eliminated. The 1H NMR, RM-03-NMRC1, eliminated more options. The spectra showed that there were protons on a ring, multiplet at 7.32 ppm, and two other types of protons. One type of proton was a quartet at 2.74 ppm and the other was a triplet at 1.33 ppm. This data, if interpreted correctly means that the compound consist of an ethyl group and a ring. Other peaks shown on the spectrum RM-02-NMRC1 were two peaks for 1,2-dimethoxyethane, and one for acetone. This means that with fraction was slightly contaminated, as well as the NMR tube was not completely dry. At this point it was determined that the identity of the compound in fraction C was ethylbenzene. This identity was confirmed with the 13C NMR. The RM-03-NMR2C2 spectrum shows that six types of carbons were present. Two of the six types of carbons were sp3 hybridized and found in the 0-75 ppm region. The two peaks were found at 29.1 ppm and 16.0 ppm. In the region between 50-80 ppm, a peak for CDCl3 was shown, as well as, two small peaks from 1,2-dimethoxyethane. In the region of 100-150 ppm, a cluster for the carbons on the ring was found at 127.8 ppm and125.8 ppm, while an sp2 hybridized peak was observed at 144.4
In the view of the aforementioned remarked values of inhibition efficiency of this class of organic inhibitors, this paper aims to study the concerned function of the first utilized Schiff bases 3a-k towards mild steel in 0.5 M H2SO4 solution. N-aryl- (Sb_a-g), N-heteryl- (Sb_h-j)-, and the Schiff base Sb_k have been obtained condensation of N-aminophthalimide (S) with the corresponding aromatic aldehydes 2a-e, heterylaldehydes 2f-j and isatine 2k, respectively. This study takes into account the beneficial role that could be played by the p-electrons of the heterocyclic aldehyde or ketone N- and O- atoms present in the heterocyclic aldehyde and ketone moieties. The name of products and symbols were listed in Table 2. The melting point, yield, time of reaction and IR spectra of products were listed in Table 3. Spectral study has been used to characterize the structure of the novel synthesized Schiff bases (Sb_f-k) which to our knowledge have not been previously reported as shown in Table 4. The structure of the Schiff bases Sb_a-e was confirmed by identity of melting point and spectral data in the literature 25-27. The infrared spectra all the products Sb_a-k revealed that no coupling bonds in the 3 Mm region that refers to the absence of the amino –NH2 functionality of compound S instead a sharp absorption band appears on the region of 1604-1688 cm-1. Characteristic to the imino –c=N- group, indicating that compound
All the chemicals used in the synthesis were of analytical grade purity and were purchased from Sigma-Aldrich (India). Rivastigmine was obtained as a gift sample from Sun Pharmaceutical Industries Ltd (Silvassa, India). Melting point of the synthesized analogues was determined by using Stuart melting point apparatus and were uncorrected. Equimolar (0.01mol) quantity of NaCNO in 25ml of warm water was added with continuous stirring, the reaction mixture was allowed to stand for 4 h and the product was obtained by filtration, washed with water, dried in an oven below melting point and recrystallized from ethanol to afford key intermediate-1 .The precipitate was obtained by filtration, washed with water, dried in an oven below melting point and recrystallized from ethanol to afford key intermediate-2 .Equal moles of intermediate-2 (0.456g, 0.003mol) in 5ml of ethanol mixed with equal moles of the different aldehyde or ketone was refluxed for 2hrs and glacial acetic acid was added to adjust the pH of the reaction between 5-6. The solid obtained after cooling was filtred, dried and crystallized from 95% ethanol to afford compounds .Ellman’s spectrophotometric analysis [16] was used to determine IC50 values. This method is based on the reaction between synthetic substrate acetylthiocholine iodide (ATChI) and 5,5-dithio-bis-(2-nitrobenzoicacid) (DTNB) to produce a yellow colour (5-mercapto-2-nitrobenzoicacid) which was detected by Colorimeter. Determination of IC50 values was performed by recording the rate of increase in the absorbance at 412 nm for 5 min.
The signals at CH2CH2COOH didn’t split from water and resonated at 3.3 ppm. The T (-OH) and L (-OH) groups resonated at 9.15 and 9.21 ppm, respectively. Degree of modification was calculated to be correspondingly 40%, 60% and 80% and it was evaluated from the 1H NMR signals at 3.7-3.6 owing to the methylene groups in the ethoxysilane and 1.62-1.51 related to the methyl groups in the ethoxysilane).
1-Vinylimidazole (VIm), 1-idobutane (IB), 2-aminoethanethiol (AET), acetylacetate, N,N'-dicyclohexylcarbodiimide (DCC), N-hydroxysuccinimide (NHS), posstasium carbonate (K2CO3), and azobisisobutyronitrile (AIBN) were purchased from Sigma-Aldrich (Milwaukee, WI, USA). 4,4′-Bis(4-hydroxylphenyl) valeic acid (HPV), 4,4′-difluorobenzophenone (DBP), chloroform, sodium hydroxide (NaOH), dimethylacetamide (DMAc), dimethyl sulfoxide (DMSO), toluene, hydrochloric acid (HCl), tetrahydrofuran (THF), iso-propanol (IPA), and dimethylformamide (DMF) were purchased from TCI company (Tokyo, Japan).
Imidazoline and its derivatives are important sort of inhibitors which could effectively inhibit corrosion of carbon steel against CO2 and H2S [6, 7]. Recently C.D Contreras [8] was reported the structural and vibrational analyses of 2-(2-benzofuranyl)-2-imidazoline.