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CAS No. : | 2382-96-9 | MDL No. : | MFCD00005769 |
Formula : | C7H5NOS | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | FLFWJIBUZQARMD-UHFFFAOYSA-N |
M.W : | 151.19 | Pubchem ID : | 712377 |
Synonyms : |
|
Num. heavy atoms : | 10 |
Num. arom. heavy atoms : | 9 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 41.26 |
TPSA : | 64.83 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.55 cm/s |
Log Po/w (iLOGP) : | 1.96 |
Log Po/w (XLOGP3) : | 2.36 |
Log Po/w (WLOGP) : | 2.12 |
Log Po/w (MLOGP) : | 1.25 |
Log Po/w (SILICOS-IT) : | 2.22 |
Consensus Log Po/w : | 1.98 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.93 |
Solubility : | 0.178 mg/ml ; 0.00117 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.36 |
Solubility : | 0.0658 mg/ml ; 0.000435 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.01 |
Solubility : | 0.149 mg/ml ; 0.000984 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.01 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
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 |
---|---|---|
69.7% | Reflux | To a suspension of 1 (10 mmol, 1.51 g) in SOCl2 (50 mL) was added few drops of DMF, and the mixture heated at reflux for 5 h. After the solvent was evaporated, the crude product was purified by silica gel column chromatography (petroleum ether/EtOAc, 10:1). Colorless oil, yield 69.7percent. |
46% | With bis(trichloromethyl) carbonate In cyclohexane; toluene at 50 - 105℃; for 1.33333 h; | Specifically include:Solid phosgene (BTC) is selected as the chlorinating agent.2 mmol of 2-mercaptobenzoxazole prepared in the step 1 was added to the flask.Add 10 mL of toluene or cyclohexane as solvent to the flask.4 mmol of solid triphosgene was added to the flask.Warm up to 50 ° C under magnetic stirring, keep warm for 10 min, and then slowly heat up.Each temperature is raised at 10 ° C for 10 min, when the temperature is raised to 105 ° C, the temperature is kept for 1 h; TCL point plate analysis,Properly extend the reaction time,After separation by column chromatography, 0.142 g of 2-chlorobenzoxazole was obtained.The product was slightly yellowish liquid with a yield of 46percent. |
1.65 g | With phosphorus pentachloride In toluene for 2 h; Reflux | General procedure: The substituted 2-aminophenol (1eq.) in water and 95percent ethanol was added potassium carbonate (1eq.) and CS2 (1eq.).The mixture was heated under reflux for 3 hours. After cooling, the solution was neutralized with 15 mL of acetic acid in 30 mL water. The precipitate was collected to give 2-thiolbenzoxazoles. Then, the substituted 2-thiolbenzoxazoles (1eq.) dissolved in toluene, PCl5 (1.5eq) was added dropwise. The mixture was heated to reflux for 2 hours. After the solvent was evaporated, the crude product was purified by silica gel column chromatography using PE-EA as an eluent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With phosphorus pentachloride; trichlorophosphate In dichloromethane at 20℃; for 12 h; Inert atmosphere | To a suspension of 1.5 g (10 mmol) of product 3 in 8.6 mL (90 mmol) of POCl3at room temperature was added 2.5 g (12 mmol) of PCl5 along with 7 mL of CH2Cl2.The reaction mixture turned into a solution after the addition. After 12h of stirring at3room temperature, the reaction mixture was concentrated to remove excess POCl3,and the residue was treated with saturated aqueous NaHCO3 solution until pH 8 wasreached. The aqueous phase was extracted with CH2Cl2, and the combined CH2Cl2extracts were washed with brine, dried over MgSO4, and then concentrated to give 1.1g of crude product 4. Short-column chromatography on silica gel with petroleumether/ethyl acetate (200: 3) provided 864 mg (60percent yields) of product 4 as thecolorless oil. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With potassium carbonate In ethyl acetate at 20 - 40℃; for 24 h; | Example 1: Preparation of a benzoxazole sulfonamide compound A benzoxazole sulfonamide represented by compound c-6 in the below provided Scheme C, can be prepared as follows. The intermediate c-2 was prepared by adding 2-MERCAPTOBENZOXAZOLE (C-1 which is equal to compound of formula (1) above) (1200 g; 7.94 mol) to 8500 ml ethylacetate in a 20 L flask. Then 1420 g (10.29 mol) potassium carbonate was added at rt. iodomethane (1243 g; 8.76 mol) was added dropwise to this reaction mixture maintaining the internal temperature below 40°C. This mixture was stirred for 24 hours while the internal temperature decreased to 20°C. The reaction mixture was then treated with 4000 ml water and 138 G NH40H at rt for about 20 minutes. The organic layer was separated and filtered. The aqueous phase was extracted with 1200 ml ethylacetate. The organic layers were collected and washed with 1500 ml water. The organic phase was evaporated under reduced pressure until a final volume of about 2000ML. Magnesium sulphate was added and the mixture was filtered. The filtrate was evaporated under reduced pressure yielding 1288 g of the intermediate c-2 (98 percent yield /HPLC purity 99.6 percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With potassium hydroxide In ethanol; water at 80℃; for 3 h; | Add 15 mL of ethanol, 3 mL of water, 10 mmol of o-aminophenol,10 mmol of carbon disulfide, 10 mmol of potassium hydroxide.The reaction temperature was 80 ° C of a solvent, and the mixture was heated under reflux for 3 hours.Add a small amount of zeolite and filter it hot.The filtrate was warmed to 70 ° C and poured into a beaker containing 10 ml of warm water.The temperature of warm water is 60-70 ° C, after adding 1.5-2 mL of acetic acid,Place the beaker in ice water and cool the precipitate.White transparent needle crystals,After filtration and drying, 1.23 g of 2-mercaptobenzoxazole was obtained in a yield of 81percent. |
77% | With potassium hydroxide In ethanol for 10 h; Reflux | In a 100ml round bottom one neck flask was chargedwith 2.20g (20 mmol) of o-aminophenol and 40 ml ofabsolute ethanol was added and the contents were stirred for15 minutes. In the meanwhile, 2.0g (29 mmol) of potassiumhydroxide pellets was powdered and transferred into the flask followed by 15 ml of carbon disulfide. The mixturewas refluxed for 8- 10 hours when a grayish yellow coloredprecipitate appeared. The contents were cooled to roomtemperature and the solvent was rotary evaporated to yield asolid product. This product was carefully transferred into abeaker and 75 ml of water was added when a clear solutionresulted. The clear solution was acidified by adding aceticacid when a precipitate appeared. The precipitate was filteredand then washed with 3x50 ml of water and dried in vacuumover night. A light yellowish powder was obtained: yield2.3g, (yield 77percent). |
54.2% | With potassium hydroxide In ethanol at 50℃; for 4 h; | To a solution of o-amino phenol (10 mmol, 1.09 g) and KOH (10 mmol, 0.56 g) in ethanol (50 mL) was added CS2 (40 mmol, 3.05 g). The mixture was stirred at 50 °C for 4 h and monitored by TLC. After completion of reaction, the solvent was removed under reduced pressure. The residue was poured into ice cold water and 10percent HCl was added to adjust pH = 6-7. The precipitated was filtered, washed with water, dried and purified by silica gel column chromatography (petroleum ether/EtOAc, 8:1). White solid, yield 54.2percent, mp 191-192 °C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92.6% | With 1.3-propanedithiol; potassium hydroxide In dimethyl sulfoxide at 130℃; for 12 h; Inert atmosphere; Sealed tube | Benzoxazole 119.12 mg (1.0 mmol) and 1,3-propanedithiol 325 μL (3.0 mmol), potassium hydroxide 280.55 mg (5.0 mmol), 3 mL DMSO, placed in a reaction tube equipped with a magnetic stir bar The mixture was sealed with argon, heated and stirred, and reacted in an oil bath at 130 ° C for 12 hours. After the reaction is completed, the reaction solution is transferred to a separating funnel with water washing, an appropriate amount of dilute sulfuric acid is added, the pH of the aqueous phase is adjusted to 1-3, and the organic phase is extracted with ethyl acetate, and the upper organic phase is transferred with anhydrous magnesium sulfate. dry.The mixture was decanted under reduced pressure and subjected to column chromatography to give a brown solid product (140 mg).The yield was 92.6percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | Stage #1: With potassium carbonate In N,N-dimethyl-formamide for 0.0833333 h; Stage #2: at 120℃; for 12 h; |
General procedure: 2-Aminophenol (1.0 mmol), K2CO3 (3.0 mmol) was dissolved in DMF (3 mL) in a dried tube, equipped with a magnetic stirring bar and a septum. The mixture was stirred for 5 minutes, and then TMTD (0.6 mmol) was added. The reaction mixture was then heated at 120 °C and checked by TLC until the starting material was finished (around 12 hours). The reaction was cooled down to room temperature, and then quenched with sat. NH4Cl solution and extracted with ethyl acetate, dried over anhydrous Na2SO4 and evaporated under vacuum. The residue was purified by flash column chromatography to afford the desired product. |
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