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* Storage: {[proInfo.prStorage]}
CAS No. : | 43210-67-9 | MDL No. : | MFCD00144301 |
Formula : | C15H13N3O2S | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | HDDSHPAODJUKPD-UHFFFAOYSA-N |
M.W : | 299.35 | Pubchem ID : | 3334 |
Synonyms : |
Methyl 5-(phenylthio)-2-benzimidazolecarbamate
|
Signal Word: | Danger | Class: | 9 |
Precautionary Statements: | P201-P202-P260-P273-P280-P308+P313-P391-P405-P501 | UN#: | 3077 |
Hazard Statements: | H361-H373-H410 | Packing Group: | Ⅲ |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98.8% | With dihydrogen peroxide; sodium sulfite In methanol; water | EXAMPLE 2 186.4 g of fenbendazole are dissolved in 700 ml of methanol, 513 g of 48percent strength hydrobromic acid and 400 ml of water at 60° C., and 65.4 g of a 35percent strength hydrogen peroxide solution are added at a pH of -0.5. The reaction solution is heated at 60° C. for 7 hours, and 10.0 g of sodium sulfite are then added. After cooling to room temperature, the reaction mixture is introduced into 20percent strength sodium hydroxide solution, the product crystallizing out. After drying in vacuo, 194.5 g of oxfendazole remain, corresponding to a yield of 98.8percent, relative to the fenbendazole employed. The purity is 98.7percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
(2) when an R contains one or more R1, R2, or R4 substituents, the total number of substituents on that R is not more than 3; or a physiologically acceptable salt thereof; as well as a second active agent, which is a compound selected from the group consisting of albendazole, fenbendazole, flubendazole, mebendazole, oxfendazole, oxibendazole, thiabendazole, levamisole, morantel, ... |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98.8% | With dihydrogen peroxide; sodium sulfite; In methanol; water; | EXAMPLE 2 186.4 g of fenbendazole are dissolved in 700 ml of methanol, 513 g of 48% strength hydrobromic acid and 400 ml of water at 60 C., and 65.4 g of a 35% strength hydrogen peroxide solution are added at a pH of -0.5. The reaction solution is heated at 60 C. for 7 hours, and 10.0 g of sodium sulfite are then added. After cooling to room temperature, the reaction mixture is introduced into 20% strength sodium hydroxide solution, the product crystallizing out. After drying in vacuo, 194.5 g of oxfendazole remain, corresponding to a yield of 98.8%, relative to the fenbendazole employed. The purity is 98.7%. |
98% | With urea hydrogen peroxide adduct; In formic acid; water; at 25 - 45℃; for 5.5h; | (1) Oxidation: 75 g of formic acid and 30 g (0.1 mol) of fenbendazole were added to a 250 mL four-necked flask, and the temperature was raised with stirring, and the temperature was raised to 45 C., so that the reaction solution was completely dissolved.The temperature was lowered to 35 C, 31.7g (0.101mol) of a 30.0% urea peroxide aqueous solution was added dropwise, and the dropwise addition was completed within 3.5 hours, and the dropwise addition temperature was 25-35 C.After dripping and holding for 2 hours, the reaction was stopped by adding 1.2 g of sodium sulfite.(2) Decolorization and crystallization: add 1.2g of activated carbon to the oxidation reaction solution in the previous step, hold at 45-50 C for 1 hour, and then filter with suction. The filtrate is transferred to a 500ml reaction bottle at 45-50 C within 2-3 hours Add 55g of isopropanol, lower the temperature to 20 C, add 70g of 30% liquid alkali dropwise, adjust pH = 5, after the end of the addition, filter with suction, wash with water to pH = 6-7, and dry at 90 C for 15 hours to obtain white Ofendazole 30.9g, yield 98.0%.The content detected by HPLC was 98.9%, impurity A was 0.23%, and impurity B was 0.94%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; In ethanol; for 5h;UV-irradiation; | General procedure: Individual solutions of PZQ and FBZ containing 4.0 x 10-5 mol/L of eachdrug in EtOH-HCl 0.1 mol/L solution were used in photo-stability studies. Thesolutions were exposed to direct light, indirect light and darkness. The zeroorderspectra of each drug were evaluated every 30 min over 5 hours. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In methanol; water; for 6h;Reflux; | General procedure: Methanolic solution containing one mmol of Co(NO3)2·6H2O (291mg), NiCl2·6H2O (238mg), Ni(CH3COO)2·4H2O (249mg) and Cu(NO3)2·3H2O (242mg) was added to two mmol of FBZ (299mg), (supplied from Sigma chemical company) and then the reaction mixtures were heated to reflux (6h), whereupon the solid complexes precipitated. Single crystals of the studied complexes could not be obtained, since they are amorphous in their nature. The purity of the investigated compounds has been checked by thin-layer chromatography as a secondary determinant of purity. Higher molar conductance values (in DMF) were reported for complexes 1 and 4 compared with the reported values [21] for 1:1 (65-90-1cm2mol-1) and 1:2 (130-170-1cm2mol-1), ML:X ratio, electrolytes in DMF, indicating their electrolytic nature. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In methanol; water; for 6h;Reflux; | General procedure: Methanolic solution containing one mmol of Co(NO3)2·6H2O (291mg), NiCl2·6H2O (238mg), Ni(CH3COO)2·4H2O (249mg) and Cu(NO3)2·3H2O (242mg) was added to two mmol of FBZ (299mg), (supplied from Sigma chemical company) and then the reaction mixtures were heated to reflux (6h), whereupon the solid complexes precipitated. Single crystals of the studied complexes could not be obtained, since they are amorphous in their nature. The purity of the investigated compounds has been checked by thin-layer chromatography as a secondary determinant of purity. Higher molar conductance values (in DMF) were reported for complexes 1 and 4 compared with the reported values [21] for 1:1 (65-90-1cm2mol-1) and 1:2 (130-170-1cm2mol-1), ML:X ratio, electrolytes in DMF, indicating their electrolytic nature. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In methanol; water; for 6h;Reflux; | General procedure: Methanolic solution containing one mmol of Co(NO3)2·6H2O (291mg), NiCl2·6H2O (238mg), Ni(CH3COO)2·4H2O (249mg) and Cu(NO3)2·3H2O (242mg) was added to two mmol of FBZ (299mg), (supplied from Sigma chemical company) and then the reaction mixtures were heated to reflux (6h), whereupon the solid complexes precipitated. Single crystals of the studied complexes could not be obtained, since they are amorphous in their nature. The purity of the investigated compounds has been checked by thin-layer chromatography as a secondary determinant of purity. Higher molar conductance values (in DMF) were reported for complexes 1 and 4 compared with the reported values [21] for 1:1 (65-90-1cm2mol-1) and 1:2 (130-170-1cm2mol-1), ML:X ratio, electrolytes in DMF, indicating their electrolytic nature. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In methanol; water; for 6h;Reflux; | General procedure: Methanolic solution containing one mmol of Co(NO3)2·6H2O (291mg), NiCl2·6H2O (238mg), Ni(CH3COO)2·4H2O (249mg) and Cu(NO3)2·3H2O (242mg) was added to two mmol of FBZ (299mg), (supplied from Sigma chemical company) and then the reaction mixtures were heated to reflux (6h), whereupon the solid complexes precipitated. Single crystals of the studied complexes could not be obtained, since they are amorphous in their nature. The purity of the investigated compounds has been checked by thin-layer chromatography as a secondary determinant of purity. Higher molar conductance values (in DMF) were reported for complexes 1 and 4 compared with the reported values [21] for 1:1 (65-90-1cm2mol-1) and 1:2 (130-170-1cm2mol-1), ML:X ratio, electrolytes in DMF, indicating their electrolytic nature. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine; In N,N-dimethyl-formamide; at 70℃; for 0.0833333h;Microwave irradiation; | The mixture of fenbendazoie (299mg), 3 -hydroxy loxetane (370mg), and triethylamine (0.5mL) in DMF (15mL) was heated in a microwave synthesizer at then 70 C for 5 minutes. The solvent was removed under vacuum. The desired product was isolated by silica gel chromatography (dichloromethane: methanol = 9:1) as a white solid. MS (ES): 342.4 | |
With triethylamine; In N,N-dimethyl-formamide; for 0.25h;Microwave irradiation; | General procedure: To a stirred mixture of each bendazole in base/solvent (100mM) were added 10 equiv of alcohols indicated in Scheme 1. The reaction proceeded at 90, 100, or 110C for 3h to o/n. For compounds 5 and 7, the reaction mixture was exposed to microwave irradiation for 5-15minat 60 or 70C. Workup: Once the reaction was complete, the solvent was removed under reduced pressure, diluted with four times the reaction volume of EtOAc and washed with water and brine. The organic layer was dried with Na2SO4 and concentrated in vacuo, followed by purification performed on automated flash chromatography system with the desired method commented below. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine; In N,N-dimethyl-formamide; at 110℃; | General procedure: To a stirred mixture of each bendazole in base/solvent (100mM) were added 10 equiv of alcohols indicated in Scheme 1. The reaction proceeded at 90, 100, or 110C for 3h to o/n. For compounds 5 and 7, the reaction mixture was exposed to microwave irradiation for 5-15minat 60 or 70C. Workup: Once the reaction was complete, the solvent was removed under reduced pressure, diluted with four times the reaction volume of EtOAc and washed with water and brine. The organic layer was dried with Na2SO4 and concentrated in vacuo, followed by purification performed on automated flash chromatography system with the desired method commented below. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86.8% | With hydrogenchloride; In toluene; at 20 - 55℃; for 2h; | 355.0 g of methyl cyanamidoformate which was cryopreserved in the step 1 was added to a solution of 545.5 g of the intermediate 4 in toluene in the step 5 at room temperature.Raise the temperature to 45-55 C, and add 67.65 g of concentrated hydrochloric acid (36.5%) under stirring. After the addition is completed, stir at 55-60 C for 2 hours.After completion of the reaction, the temperature was lowered to 10-15 C, filtered, and the filter cake was washed with 202.5 g of methanol.The moisture product was dried under hot air at 70 C for 6 hours to obtain 124.5 g of dry product, the purity was 99.7%, and the total yield of the product was 86.8%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: sodium hydroxide / water; propan-1-ol / 5 h / 88 °C / Inert atmosphere 2: hydrogen / toluene / 2 h / 80 °C / 22502.3 Torr / Autoclave 3: acetone / 2.5 h / 40 - 60 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89.99% | In acetone at 40 - 60℃; for 2.5h; | 9-22 Example 16 Preparation of fenbendazole Add 43.26g of 4-phenylthio-o-phenylenediamine prepared in Example 8 and 129.78g of acetone into a 250ml four-necked flask. After the temperature is raised to 40°C, 50.03g of methyl N-(trichloromethyl)carbamate is added dropwise. After 30 minutes, the dripping was completed, then the temperature was raised to 60°C, and the temperature was kept for 2 hours. After the warming, it was filtered. The filter cake was washed with acetone and placed in an oven at 70°C for 2 hours to obtain 55.47g of fenbendazole with a yield of 89.99% and a purity of 97.12. % |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: hydrogen bromide / 24 h / Reflux 2.1: tetrahydrofuran / 0.5 h / 20 °C 2.2: 16 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94 % | With hydrogen at 59.84℃; |
Tags: 43210-67-9 synthesis path| 43210-67-9 SDS| 43210-67-9 COA| 43210-67-9 purity| 43210-67-9 application| 43210-67-9 NMR| 43210-67-9 COA| 43210-67-9 structure
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H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
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H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
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