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CAS No. : | 17200-29-2 | MDL No. : | MFCD00216939 |
Formula : | C7H4ClNO | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | VWMQXAYLHOSRKA-UHFFFAOYSA-N |
M.W : | 153.57 | Pubchem ID : | 28398 |
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 : | 39.02 |
TPSA : | 26.03 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) : | -5.66 cm/s |
Log Po/w (iLOGP) : | 1.96 |
Log Po/w (XLOGP3) : | 2.22 |
Log Po/w (WLOGP) : | 2.48 |
Log Po/w (MLOGP) : | 1.58 |
Log Po/w (SILICOS-IT) : | 2.58 |
Consensus Log Po/w : | 2.17 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.86 |
Solubility : | 0.214 mg/ml ; 0.00139 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.4 |
Solubility : | 0.609 mg/ml ; 0.00397 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.51 |
Solubility : | 0.047 mg/ml ; 0.000306 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.05 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-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 |
---|---|---|
96% | With tungstate sulfuric acid In neat (no solvent) at 80 - 90℃; for 0.0666667 h; | General procedure: To a mixture of orthoester (1.1 mmol) and o-aminophenol or o-aminothiophenol (1 mmol) was added TSA (1 molpercent). The mixture was stirred at 80–90 °C for the appropriate time according to Table 4. After the completion of the reaction (as indicated by TLC), the mixture was diluted with chloroform (10 mL) and the catalyst was separated by filtration. Further purification was achieved by column chromatography |
83% | for 4 h; Reflux | General procedure: A mixture of 2-aminophenol derivative (5 mmol) and triethyl orthoformate (15 mL) was heated at reflux for 4 h. After cooling to room temperature, remained triethyl orthoformate was removed under reduced pressure and the residue was purified by column chromatography on silica gel. |
77% | at 150℃; for 8 h; Inert atmosphere | General procedure: A solution of substituted 2-aminophenol (20 mmol) in triethyl orthoformate (30 mL) was heated to 150°C for 8 h under argon. The mixture was cooled to room temperature and the triethyl orthoformate was removed by distillation under reduced pressure. The resulting residue was purified by silica gel column chromatography to afford substituted benzoxazole. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With sodium sulfate In tetrahydrofuran at 55 - 60℃; Inert atmosphere | 2-amino-4-chloro phenol (50 g, 0.349 moles), Trimethyl orthoformate (111 g, 1.048 moles), sodium sulphate (9.93 g, 0.069 moles) and THF (500 mL) were charged in round bottom flask at room temperature (RT) under inert atmosphere. Reaction mass was heated to 55° C. to 60° C. The progress of the reaction was monitored by TLC. After completion of the reaction, reaction mixture was cooled to room temperature and quenched with water (50 ml). Reaction mass was cooled to RT, diluted with water (250 ml) and extracted with ethyl acetate (2*250 ml). The combined organic extracts were dried over sodium sulphate, filtered and concentrated under reduced pressure. The obtained crude material was purified by column chromatography using silica gel (60-120 mesh) eluted with 20percent EtOAc-hexane to give 5-Chloro-1,3-benzoxazole (Formula XI, 50 g, yield 95percent, HPLC purity of 99.46percent) as a yellow color solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | Stage #1: With 3-benzyl-1-(1-((2,6-diisopropylphenyl)imino)ethyl)-1H-imidazol-3-ium chloride; potassium <i>tert</i>-butylate In N,N-dimethyl-formamide at 80℃; for 18 h; Inert atmosphere Stage #2: at 65℃; for 1 h; Inert atmosphere |
In the reaction flask, Under argon, a catalyst (9.9 mg, 0.025 mmol, 5 molpercent), potassium tert-butoxide (0.0672 g, 0.6 mmol) DMF (3.0 ml), 5-chlorobenzoxazole (76.79 mg, 0.5 mmol) was added to the carbon dioxide gas, and the reaction was stirred at 80 ° C for 18 hours under normal pressure. Cooled to 65 ° C, methyl iodide (93 μl, 1.5 mmol) was added, The reaction was stirred at 65 ° C for 1 hour. Cooled to room temperature, the reaction was terminated with deionized water, The reaction product was extracted with ethyl acetate and purified by column chromatography (Using a mixed solvent of ethyl acetate / petroleum ether in a volume ratio of 1:10 as a developing solvent) The yield was 82percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73.7% | With 1.3-propanedithiol; potassium hydroxide In dimethyl sulfoxide at 130℃; for 12 h; Inert atmosphere; Sealed tube | 153.57 mg (1 mmol) of 5-chlorobenzoxazole, 216 μL (2.0 mmol) of 1,3-propanedithiol, 280.55 mg (5.0 mmol) of potassium hydroxide and 3 mL of DMSO were placed in a reaction equipped with a magnetic stir bar. The tube was sealed with argon, heated and stirred, and reacted in an oil bath at 130 ° C for 24 hours. After the reaction is completed, the reaction solution is transferred to a separating funnel with water washing, an appropriate amount of dilute hydrochloric acid is added, the aqueous phase is adjusted to pH 1-3, and the organic phase is extracted with ethyl acetate, and the upper organic phase is transferred with anhydrous magnesium sulfate. The mixture was dried under reduced pressure and purified by column chromatography to yield 113.2mg of product as a red-brown solid, yield 73.7percent. |
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