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CAS No. : | 6609-57-0 | MDL No. : | MFCD00001789 |
Formula : | C9H9NO | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | DXTLCLWOCYLDHL-UHFFFAOYSA-N |
M.W : | 147.17 | Pubchem ID : | 576922 |
Synonyms : |
|
Num. heavy atoms : | 11 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.22 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 42.46 |
TPSA : | 33.02 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) : | -5.54 cm/s |
Log Po/w (iLOGP) : | 2.1 |
Log Po/w (XLOGP3) : | 2.34 |
Log Po/w (WLOGP) : | 1.96 |
Log Po/w (MLOGP) : | 1.44 |
Log Po/w (SILICOS-IT) : | 2.13 |
Consensus Log Po/w : | 1.99 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.5 |
Solubility : | 0.467 mg/ml ; 0.00317 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.67 |
Solubility : | 0.313 mg/ml ; 0.00212 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -2.99 |
Solubility : | 0.149 mg/ml ; 0.00101 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.37 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302+H312+H332-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 |
---|---|---|
98% | With [2,2]bipyridinyl; water; palladium diacetate In 1,4-dioxane at 90℃; for 24 h; Schlenk technique; Sealed tube | General procedure: To an oven dried Schlenk carousel tube containing the appropriate nitrile (1 mmol) was added palladium acetate (11 mg, 5 molpercent), 2,2'-bipyridine (7.8 mg, 5 molpercent), dioxane (0.6 mL) and water (1.4 mL). The tube was then sealed and the reaction mixture heated at 70 °C (unless otherwise stated) for 24 hours. After being allowed to cool to room temperature, the reaction mixture was diluted with methanol (5 mL) and the solvent removed in vacuo on a rotary evaporator whilst azeotroping with toluene. Where the reaction had gone to quantitative conversion or the starting nitrile was volatile, the crude reaction mixture was passed through a short plug of silica to remove the catalyst (eluting with DCM/MeOH, 95:5). Otherwise, the primary amide products were purified by column chromatography (eluting with DCM/MeOH, 95:5, unless otherwise stated). |
19.7 g | With potassium <i>tert</i>-butylate In toluene at 60℃; Inert atmosphere | Under nitrogen protection,200 mL of ethanol, cuprous iodide (3.8 g, 0.02 mol) and potassium hydroxide (16.8 g, 0.3 mol) were mixed uniformly,O-chlorobenzonitrile (27.5 g, 0.2 mol) was added,And then heated to 80 insulation reaction,TLC or liquid phase monitoring reaction,After completion of the reaction, ethanol was recovered,Down to room temperature,Add 100 mL of water and 150 ml of toluene to wash with water,And then toluene recovery,The intermediate of o-ethoxybenzene was purified by distillation under reduced pressure (23.5 g (154 ° C / 20 Torr).20.6 g (0.14 mol) of o-ethoxybenzonitrile was dissolved in 150 mL of toluene, potassium tert-butoxide (47.1 g,0.42 mol), heated to 60 ° C to carry out the reaction, TLC or liquid phase monitoring reaction, the reaction is completed by adding 150mL of water for washing,The organic phase recovered the solvent and the residue was recrystallized from ethanol and dried to give 19.7 g of 2-ethoxybenzamide as a white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | Stage #1: With sodium hydroxide In water; toluene at 70℃; for 1 h; Stage #2: at 60 - 70℃; for 2 h; |
To a 250 mL three-necked flask, 5.95 g (0.05 mol) of o-cyanophenol, 20 mL of 10percent aqueous NaOH solution and 80 mL of toluene were separately added, and the mixture was heated to 70 ° C, and the reaction was kept at this temperature for 1 h. After 1 h, the temperature was lowered to 60 ° C, and 9.24 g of diethyl sulfate was slowly added dropwise.After the dropwise addition, the temperature was raised to 70 ° C and the reaction was continued for 2 h. The disappearance of o-cyanophenol was detected by TLC, and the mixture was cooled to separate liquid. The toluene layer was evaporated to give a pale yellow oily liquid, 2-ethoxybenzonitrile, 6.98 g, yield 95percent. |
93% | Stage #1: With sodium hydroxide In water; toluene at 68℃; for 1 h; Stage #2: at 68 - 75℃; for 3 h; |
11.9 g (0.1 mol) of salicylic acid nitrile, 100 mL of toluene, and 48 g of 10percent aqueous NaOH solution were sequentially added to a 250 mL four-necked flask under stirring.The temperature was raised to 68 ° C in a water bath, and the mixture was kept for 1 hour, and then 9.2 g (0.06 mol) of diethyl sulfate was added dropwise, and after the completion of the dropwise addition, the temperature was raised to 75 ° C, and the reaction was kept for 1 hour.The temperature was lowered to 68 ° C, and 9.2 g (0.06 mol) of diethyl sulfate was added dropwise. After the completion of the dropwise addition, the temperature was raised to 75 ° C, and the reaction was kept for 2 hours. The TLC tracking was carried out until the salicylonitrile was completely reflected.Cooling, liquid separation, collecting the organic layer, drying with anhydrous sodium sulfate, and then evaporating the toluene solvent,A yellowish oily liquid was obtained in an amount of 13.7 g, a yield of 93percent, and a gas-mass spectrometric analysis content of 97percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With thionyl chloride In 5,5-dimethyl-1,3-cyclohexadiene | 4.2 2-Ethoxybenzamidine hydrochloride 6 2-Ethoxybenzonitrile was prepared from 2-ethoxybenzamide 5 according to the method reported by Nowakowski 23 in 89percent yield (lit. 23 yield 92percent); Rf (hexane/EtOAc 9:1) 0.45; νmax (crystal): 2231 cm-1 (C≡N). 1H NMR (CDCl3, δ ppm): 7.57-7.51 (m, 2H, 4-H and 5-H of C6H4), 7.01 (d, J 7.3 Hz, 1H, 6-H of C6H4), 6.97 (d, J 8.8 Hz, 1H, 3-H of C6H4), 4.17 (q, J 7 Hz, 2H, OCH2), 1.49 (t, J 7.1 Hz, 3H, CH3). Ethyl 2-ethoxybenzimidate hydrochloride was synthesized by passing dry HCl(gas) through the solution of 2-ethoxybenzonitrile in anhydrous ethyl alcohol. This compound was obtained as a white solid (46percent); mp 49-54 °C; Rf (hexane/EtOAc 7:3) 0.36. 1H NMR (CDCl3, δ ppm): 13.01 (br s, 1H, NH), 10.14 (br s, 1H, NH), 8.04 (dd, J 1.7 and 8 Hz, 1H, 6-H of C6H4), 7.74-7.70 (m, 1H, 4-H of C6H4), 7.18-7.14 (m, 2H, 3-H and 5-H of C6H4), 5.04 (q, J 7 Hz, 2H, NCOCH2), 4.39 (q, J 7 Hz, 2H, OCOCH2), 1.63 (t, J 7.1 Hz, 3H, NCOCH2CH3), 1.57 (t, J 6.8 Hz, 3H, OCOCH2CH3). |
90% | Stage #1: With Bromotrichloromethane; triphenylphosphine In dichloromethane for 0.416667 h; Reflux Stage #2: With triethylamine In dichloromethane for 12 h; Reflux |
General procedure: BrCCl3 (900 mg, 4.6 mmol) was added to PPh3 (1.22 g, 4.6 mmol) in dry CH2Cl2 (12 mL) and the resulting mixture was stirred at room temperature for 20 min, during which time the solution turned from yellow to red-brownish in colour.Thereafter, 3‑chlorobenzamide (1i, 500 mg, 3.2 mmol) was added. Thereaction mixture was heated under reflux for 25 min. Then, dry Et3N (465 mg, 4.6 mmol) was added dropwise with a syringe over 1 min.The reaction mixture was heated under reflux for 12 h. Thereafter,it was cooled to room temperature and added to cold water (50 mL).The mixture was extracted with dichloromethane (2 × 30 mL) and chloroform (30 mL). The combined organic phases were dried over anhydrous MgSO4, concentrated under reduced pressure and subjected to column chromatography on silica gel (CH2Cl2/hexane 4 : 1) to give 3‑chlorobenzonitrile (2i, 320 mg, 72percent) as a colourless solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
23.5 g | With copper(l) iodide; potassium hydroxide In ethanol at 80℃; Inert atmosphere | Under nitrogen protection,200 mL of ethanol, cuprous iodide (3.8 g, 0.02 mol) and potassium hydroxide (16.8 g, 0.3 mol) were mixed uniformly,O-chlorobenzonitrile (27.5 g, 0.2 mol) was added,And then heated to 80 insulation reaction,TLC or liquid phase monitoring reaction,After completion of the reaction, ethanol was recovered,Down to room temperature,Add 100 mL of water and 150 ml of toluene to wash with water,And then toluene recovery,The intermediate of o-ethoxybenzene was purified by distillation under reduced pressure (23.5 g (154 ° C / 20 Torr). 20.6 g (0.14 mol) of o-ethoxybenzonitrile was dissolved in 150 mL of toluene, potassium tert-butoxide (47.1 g,0.42 mol), heated to 60 ° C to carry out the reaction, TLC or liquid phase monitoring reaction, the reaction is completed by adding 150mL of water for washing,The organic phase recovered the solvent and the residue was recrystallized from ethanol and dried to give 19.7 g of 2-ethoxybenzamide as a white solid. |
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