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CAS No. : | 2439-77-2 | MDL No. : | MFCD00017120 |
Formula : | C8H9NO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | MNWSGMTUGXNYHJ-UHFFFAOYSA-N |
M.W : | 151.16 | Pubchem ID : | 75540 |
Synonyms : |
|
Num. heavy atoms : | 11 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.12 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 41.03 |
TPSA : | 52.32 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.61 cm/s |
Log Po/w (iLOGP) : | 1.47 |
Log Po/w (XLOGP3) : | 0.86 |
Log Po/w (WLOGP) : | 0.79 |
Log Po/w (MLOGP) : | 0.91 |
Log Po/w (SILICOS-IT) : | 0.97 |
Consensus Log Po/w : | 1.0 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.59 |
Solubility : | 3.88 mg/ml ; 0.0257 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.54 |
Solubility : | 4.34 mg/ml ; 0.0287 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -2.1 |
Solubility : | 1.21 mg/ml ; 0.008 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.0 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P305+P351+P338-P304+P340-P405-P501 | 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 |
---|---|---|
In 1,2-dichloro-ethane; | (a) 2-Methoxybenzoyl isocyanate 2-Methoxybenzamide (2.27 g, 15.04 mmol) and oxalyl chloride (2.4 g, 18.9 mmol) were heated together in 1,2-dichloroethane (40 ml) for 16 h at reflux. The resulting solution was concentrated under reduced pressure to a residue which was re-evaporated with toluene to give the crude acyl isocyanate as an oil (2.94 g). | |
In dichloromethane;Inert atmosphere; Schlenk technique; Reflux; | General procedure: The appropriate amide 32a-p, benzhydrazide (40a), or p-toluenesulfonylhydrazide (43a) (1.0 mmol, 1.0 equiv) was placed in a SchlenkKjeldahl reaction flask and the flask was evacuated/argon re-filledthree times. Subsequently, anhyd CH2Cl2 (25 mL) was added and themixture was stirred at r.t. for 10 min before dropwise addition of oxalylchloride (3.0 mmol, 3.0 equiv) followed. The reaction mixturewas then stirred at reflux for 2.5-3.0 h before cooling to r.t. and thesolvent was evaporated in vacuo. Subsequently, the appropriate nucleophile32, 34, 36, 38, 40, 42, 43, or 45 (1.1-1.25 mmol, 1.1-1.25equiv) was rapidly added and the flask was evacuated/argon re-filledbefore anhyd toluene (12 mL) was added. The reaction mixture wasthen stirred at reflux for 2.5-3 h before cooling to r.t. and concentrationto about 1/3 of the initial volume on rotavapor. Hexane was addedto the residue and the obtained precipitate (often sonicated) wascollected by filtration under reduced pressure to yield the crudeproduct. When necessary, the isolated material was purified either bycrystallization from MeOH or flash chromatography on silica gel withhexane-EtOAc as the eluent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With lithium hexamethyldisilazane; In diethyl ether; at 0 - 20℃; for 48.0833 - 72.0833h; | At 00C anhydrous ether was introduced to flask under Ar, LiHMDS (94 ml, 93.9 mmol) was then introduced and stirred for 5 mins. 2-methoxy-benzonitrile (5g, 37.6 mmol) was added and the mixture was stirred at room temperature for 2-3 days. Upon completion of the reaction solvent was removed and 200 mL cold 1N HCI was added and stirred. The aqueous layer was extracted with Et2O, then adjust the pH was adjusted by 6N NaOH to 13. Extraction with CH2CI2, dried over Na2SO4 and filtered. Upon concentration the above benzamidine compound was obtained in 91% yield. |
82% | With cobalt(II) chloride hexahydrate; oxygen; ethylenediamine; zinc; In neat (no solvent); at 120℃; under 3800.26 Torr; for 12h;Autoclave; | General procedure: The reaction was carried out in a 100-mL stainless steel autoclave. Phenylcyanide (0.10 g, 1.00 mmol) was added to a mixture of ethylenediamine (0.12 g, 2.00 mmol), CoCl26H2O (0.24 g, 1.00 mmol) and Zn (0.07 g, 1.00 mmol) and the vessel was placed in an autoclave. For some of the reactions that were carried out in solvent, 5 mL of solvent was also added. The autoclave was pressurized to 5.00 atm with O2. The mixture was stirred in a preheated oil bath at 120 C for 12 h. Then, the reaction mixture was cooled to room temperature and the product was purified by column chromatography on silica gel using n-hexane:CH2Cl2 (1:1) to give the benzamide(88 % yield). |
61% | With C12H24O16Ru3*2H2O; In water; at 110℃; for 4h;Schlenk technique; Inert atmosphere; Autoclave;Catalytic behavior; | General procedure: Hydration reactions were carried out in Schlenk tube under N2atmosphere. The reaction mixture was prepared dissolving 5 mg(6.5 lmol) of catalyst 2 in 3 mL of H2O. The mixture was degassedand 1.5 mmol of corresponding acetonitrile substrate was addedwith micropipette to stirred solution. The reaction was allowedfor heating at 110 C using oil bath or microwave-assisted heating.The isomerization reactions of allylic alcohols were conductedSchlenk tube under N2 atmosphere. The reaction mixture wasprepared dissolving 3 mg (3.9 lmol) of catalyst 2 in 2 mL ofappropriate solvent (DMF, EtOH or H2O). The mixture wasdegassed and 1 mmol of corresponding allylic alcohol substratewas added with micropipette to stirred solution. The reactionwas allowed for heating using oil bath.The reaction solutions were analyzed by regular sampling usingGC/FID (Hewlett Packard) equipped with Beta DEX 120(30 m 0.25 mm 0.25 lm) 30 m long column. The degrees ofconversion were calculated on the basis of the ratio of areas ofthe substrate material and the products determined from correspondingchromatograms. The optimization of chromatographicmethods and the calibration procedures for detection of productsas well as substrates were realized by injection of authenticcommercial samples. |
50% | With copper(l) iodide; caesium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In nitromethane; water; at 20 - 100℃; for 2h; | To a nitromethane (0.1 mL) solution of 4-methoxybenzonitrile (1f) (30 mg, 0.225 mmol) were addedH2O (1.0 mL), DBU (69 mg, 0.436 mmol), copper (I) iodide (9 mg, 0.0451 mmol), cesium (I)carbonate (37 mg, 0.113 mmol) at room temperature. The reaction mixture was heated at 100 C for2 h and then poured into water (50 mL). The organic layer was separated and the aqueous layer wasextracted with AcOEt. The combined organic layer was dried over MgSO4. The solvent wasremoved under reduced pressure. The residue was purified by preparative TLC on silica gel elutingwith AcOEt-n-hexane (1:1) to give 2-methoxybenzamide (2f)S5 (17 mg, 50%) as pale yellow powders.mp 123-125 C, |
92%Chromat. | General procedure: 0.6 mmol benzonitrile and 0.6 mmol DMSO were solved in 3 mL EtOH and pumped into inlet A, 50 muL 1 M NaOH (aq) solved in 1 mL EtOH and pumped into inlet B, 30% H2O2 (aq) was solved in 7 mL ethanol and pumped into inlet C (flow rate A: B: C = 1.54 mul/min:0.46 mul/min:0.3 mul/min for a 400s residence time). The whole system was maintained on 25 C. The flow system was equilibrated for 30 min, then the product stream was quenched and collected in a glass vessel with saturated aqueous NaHSO3 in it for 2 h. After being filtered, 5.0 ml of this solution was injected to the HPLC instrument for analysis. The conversion of the reaction was determined by relative area percentage of nitriles and corresponding amides. Conversion = Area (benzamide)/[Area (benzamide) + Area (benzonitrile)]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
64% | With phosphorous (V) sulfide; In tetrahydrofuran; at 20℃; for 1.5h; | Combine <strong>[2439-77-2]2-methoxy benzamide</strong> (10.0 g, 66.2 mmol) with phosporus pentasulfide (10.1 g, 22.7 mmol) and THF (200 mmol) in a sealed vessel and stir for 30 minutes at room temperature. Sonicate the mixture for 1 hour and then allow the mixture to stand at room temperature. Decant the THF solution from the solids and concentrate. Chromatograph the resulting residue over silica gel (MEOH/CH2CL2) to give 2-methoxy- thiobenzamide (7.05 g, 64 %). |
With tetraphosphorus decasulfide; | General procedure: Benzamides 2 (6 mmol) was dissolved in dry THF (20 mL) andthereto was added P2S5 (6 mmol) and heated at 65 C for 3 h, afterwhich the reaction mixture was cooled, poured in NaHCO3 (10%,100 mL), stirred for half an hour, then the resulting solid wasfiltered, dried and recrystallized from ethyl acetate to get compounds3. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With sodium methylate; In 1,4-dioxane; methanol; at 0℃; for 1h;Heating / reflux;Product distribution / selectivity; | Dissolved 2-methoxy-benzamidine (150 mg, 1.0 mmol) in MeOH/dioxane (15 ml/5 ml) and cooled to 0 0C. 25% NaOCH3 in MeOH (0.44ml) was then added and stirred for 15mins. 2-oxo-cyclohexanecarboxylic acid ethyl ester (260 mg, 1.5 mmol) was introduced and the reaction mixture was heated to reflux for 1 h. The reaction was concentrated and the residue was taken up in 10 mL H2O and acetic acid was used to adjust pH to 7-8. Extracted with CH2CI2 (3x 100ml). The combined organic layers were dried over Na2SO4. Purified by flash column chromatography, (70% ethylacetate/hexane) to produce the product 220 mg in 86% yield. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | With hydroxylamine hydrochloride; caesium carbonate; In acetonitrile; at 60 - 65℃; | General procedure: To a stirred solution of acetonitrile (10 mL), aldehyde (1.0 mmol) and bioglycerol-based carbon catalyst (10 wt %) were added and stirred for 10 min. To this NH2OH·HCl (1.0 mmol) followed by Cs2CO3 (1.0 mmol) were added, after which the reaction mixture was heated at 60-65 C until completion of the reaction as indicated by TLC. The reaction mixture was cooled to room temperature and catalyst was filtered, the solvent was removed by rotary evaporator. The crude residue was extracted with ethyl acetate (3 × 10 mL). The combined organic layers were extracted with water, saturated brine solution, and dried over anhydrous Na2SO4. The organic layers were evaporated under reduced pressure and the resulting crude product was purified by column chromatography using ethyl acetate and hexane (2:8) as eluents to give the corresponding substituted benzamide derivative in (71-78%) yield. The identity and purity of the product were confirmed by 1H, 13C NMR, and mass spectra. |
70% | With hydroxylamine; In water; at 110℃; for 12h; | General procedure: Aldehyde (1 mmol), hydroxylamine (1 mmol), polymer supported-Cu (II) catalyst (30 mg-10 mg) and solvent (2 m/L) were added in a 10 mL round bottom flask and the reaction mixture was stirred at 110 C. The progress of the reaction was by TLC. The crude product obtained was purified by column chromatography with ethyl acetate:hexane as 1:5 eluent system. |
70% | With hydroxylamine; In water; at 110℃; for 12h; | General procedure: Aldehyde (1 mmol), hydroxyl amine (1 mmol), polymer supported-Cu (II) catalyst (30 mg-10 mg) and solvent (2 m/L) were added in a 10 mL round bottom flask and the reaction mixture was stirred at110 C. The progress of the reaction was by TLC. The crude product obtained was purified by column chromatography with ethyl acetate:hexane as 1:5 eluent system. |
61% | With hydroxylamine; copper diacetate; In water; at 110℃; for 48h; | General procedure: To a solution of copper(II) acetate (0.04 mmol) in water (1 mL) were added the corresponding aldehyde (3, 2 mmol) and the hydroxylamine (4, 2 mmol). After 2 days stirring at 110 C the mixture was quenched with a saturated solution of ammonium chloride (10 mL), or added ether (2 mL) for the recycling process. The mixture was extracted with AcOEt (3×10 mL) and washed with brine (10 mL), after drying with anhydrous MgSO4, the organic layer was filtered on Celite and the solvents were removed under low pressure (15-18 Torr). The product was purified recrystallization from chloroform/hexane mixtures to give the corresponding product 2. Amides 2a,262b,272c, 272d,172e,282f,292g,272h,172j,302k,172l30 and 2m17 are commercially available and were characterized by comparison of their physical and spectroscopic data with those of pure examples. Yields are included in Table 4 (Fig. 1 for recycling processes). Physical and spectroscopic data, as well as literature data for known compounds, follow. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | With magnesium iodide etherate; In acetonitrile; at 80℃; for 6h; | General procedure: A Schlenk reaction tube was charged with primary aromatic amide (5.0 mmol), 2,5-dimethoxytetrahydrofuran (6.0 mmol), MgI2 etherate (10% mmol), and acetonitrile (10 mL). The reaction mixture was stirred at 80 C for several hours and then concentrated in vacuo. The residue was purified by flash column chromatography on a silica gel to give the desired product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
at 80℃; for 1h; | Example 39: 4-(2-Methoxyphenyl)-N-phenyl-1 ,3,5-triazine-2-amine (P1 ); A mixture of <strong>[2439-77-2]2-methoxybenzamide</strong> (1 .0 eq) and Nu,Nu-dimethylformamide dimethyl acetal (1 .4 eq) was heated at 80C for 1 h. The excess of reagent was removed under reduced pressure. The crude product was dissolved in 1 ,4-dioxane (0.2M) followed by addition of phenylguanidine carbonate (0.43 eq) and potassium tert-butoxide (0.41 eq). The reaction mixture was stirred under reflux and N2 atmosphere for 12 h. After removal of the solvent, the residue was purified by reverse phase RP-HPLC (column: C18), using H20 (0.1 %TFA) and MeOH (0.1 %TFA) as eluents. The desired fractions were lyophilized to yield the title compound P1 (20%) as a white powder. H NMR (400MHz, de-DMSO, 300K) delta 3.87 (s, 3H), 7.08 (t, J = 7.2 Hz, 2H), 7.20 (d, J = 8.3 Hz, 1 H), 7.35 (t, J = 7.8 Hz, 2H), 7.54 (t, J = 7.8 Hz, 1 H), 7.81 (m, 3H), 8.81 (s, 1 H), 10.50 (s, 1 H). MS (ES) C16H14N4O requires: 278, found: 279 (M+H)+. | |
In toluene; at 20 - 100℃; for 12h;Reflux; | General procedure: To a solution of benzamide 1a (1 g, 8.26 mmol) in toluene (10 ml) was added DMF-DMA (5.7 ml, 24.79 mmol) at room temperature and the reaction mixture was stirred at 100 C for 12 h. The progress of the reaction was monitored by TLC (50% EtOAc/petroleum ether). After completion of the reaction, toluene was evaporated to give the crude product. |
Tags: 2439-77-2 synthesis path| 2439-77-2 SDS| 2439-77-2 COA| 2439-77-2 purity| 2439-77-2 application| 2439-77-2 NMR| 2439-77-2 COA| 2439-77-2 structure
[ 262847-54-1 ]
2,3-Dihydrobenzofuran-5-carboxamide
Similarity: 0.88
[ 262847-54-1 ]
2,3-Dihydrobenzofuran-5-carboxamide
Similarity: 0.88
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Health hazards | |
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H316 | Causes mild skin irritation |
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H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
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H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
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 |
Sorry,this product has been discontinued.
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