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CAS No. : | 28059-64-5 | MDL No. : | MFCD00007750 |
Formula : | C13H13N | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | DWOBGCPUQNFAFB-UHFFFAOYSA-N |
M.W : | 183.25 | Pubchem ID : | 119805 |
Synonyms : |
|
Num. heavy atoms : | 14 |
Num. arom. heavy atoms : | 12 |
Fraction Csp3 : | 0.08 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 0.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 60.3 |
TPSA : | 26.02 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | Yes |
CYP2C9 inhibitor : | Yes |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.39 cm/s |
Log Po/w (iLOGP) : | 2.06 |
Log Po/w (XLOGP3) : | 2.86 |
Log Po/w (WLOGP) : | 2.87 |
Log Po/w (MLOGP) : | 3.34 |
Log Po/w (SILICOS-IT) : | 3.18 |
Consensus Log Po/w : | 2.86 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 2.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.28 |
Solubility : | 0.0961 mg/ml ; 0.000525 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.07 |
Solubility : | 0.158 mg/ml ; 0.00086 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -4.96 |
Solubility : | 0.00201 mg/ml ; 0.000011 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.36 |
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 |
---|---|---|
0.16 g (87%) | palladium; In methanol; | Example 4 Synthesis of 2-Benzyl-phenylamine 11 Under hydrogen atmosphere: 10% palladium on carbon (20 mg, 50% wet) was added to a solution of 2-benzyl-nitrobenzene 10 (0.22 g, 1 mmol) in MeOH (15 mL). Full conversion was reached after 1 h, as indicated by TLC. The mixture was filtered and the solvent was removed in vacuo to afford 0.16 g (87%) of the product. 1H NMR (400 MHz, CDCl3): delta=7.4 (m, 6H), delta=6.768 (td, J=7.6, 1.2 Hz, 1H), delta=6.678 (d, J=8 Hz), delta=3.908 (s, 2H), delta=3.5 (bs, 2H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With pyridine; In toluene; at 0 - 20℃; for 1.5h;Inert atmosphere; | A samples of commercially available <strong>[28059-64-5]2-benzylaniline</strong> (1841 mg, 10.05 mmol) in toluene (10 mL) at 0 C under Ar was treated with chloroacetyl chloride (0.82 mL, 10.25 mmol) and pyridine (0.98 mL, 12.11 mmol). Reaction mixture was stirred at 0 C for 30 min and at rt for 1 h, and the reaction was quenched with water (5 mL). Resulting mixture was stirred for 20 min, diluted with EtOAc (200 mL), washed with aqueous 1N HCl (3 x 30 mL) and saturated aqueous NaCl, dried over anhydrous MgSO4 and concentrated under reduced pressure to provide compound 12 as a gray solid (2205 mg, 85%): 1H NMR (CDCl3, 400 MHz) delta 7.99 (br s, 1H), 7.84 (d, J = 8.0 Hz, 1H), 7.34-7.11 (m, 8H), 4.06 (s, 2H), 4.00 (s, 2H); CAS Registry: 21535-43-3. |
85% | With pyridine; In toluene; at 0 - 20℃; for 1.5h;Inert atmosphere; | Under argon atmosphere, commercially available 2-benzyl aniline (1841 mg, 10.05 mmol) in toluene (10 mL) at 0 C was treated with chloroacetyl chloride (0.82 mL, 10.25 mmol) and pyridine (0.98 mL, 12.11 mmol). The reaction mixture was stirred at 0 C. for 30 minutes and at room temperature for 1 hour, and the reaction was terminated by adding water (5 mL). The resulting mixture was stirred for 20 min, diluted with ethyl acetate (200 mL), washed with 1 N hydrochloric acid 3 * 30 mL) and saturated aqueous sodium chloride solution, dried (MgSO4),Concentrated under reduced pressure to give N- (2-benzylphenyl) -2-chloroacetamide as a gray solid (2205 mg, 85%): |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99.5% | With potassium hydroxide; In water; at 50℃; for 4h; | 5.8 g of 2-aminobenzophenone, 25 ml of distilled water, and 16 g of nickel-aluminum alloy were added to a four-necked flask equipped with a stirrer, a thermometer, a reflux condenser and a separating funnel at room temperature. After confirming that the temperature of the mixed solution in the reaction vessel has reached 50 , 10 ml of a 14% aqueous potassium hydroxide solution is slowly added dropwise over 1 hour while maintaining the temperature at 50 . After the dropwise addition is completed, the mixture is stirred for 3 hours while maintaining the same temperature. After the starting material is disappeared by liquid chromatography, it is confirmed that 95% or more of 2-benzyl aniline as a target substance is formed, and the reaction is terminated. The reaction solution is slowly cooled to room temperature and filtered using a celite filter aid. After filtration, the residue is washed with 10 ml of purified water. After filtration, 20 ml of dichloromethane is added to the aqueous layer, and the mixture is stirred at room temperature for 10 minutes. Separate the layers using a separatory funnel.After the organic layer the dichloro methane takes a lower brine 10 minutes stirring at room temperature to 20 ml, washed and delamination through the funnel, and the organic layer which was stirred for 10 minutes at room temperature added and the dichloromethane layer to take over anhydrous sodium sulfate, the drying agent 3 g The residue cake was washed with 5 ml of dichloromethane, filtered, and concentrated under reduced pressure in vacuo to give 4.47 g (yield 99.5%) of the desired product as an oil. |
With triethylsilane; boron trifluoride diethyl etherate; In dichloromethane; ethyl acetate; at 5℃; for 10h; | A method for the synthesis of epinastine hydrochloride comprises the steps of mixing 2-amino-benzophenone with ethyl acetate, cooling to 5 C, adding triethylsilane, boron trifluoride diethyl ether, and refluxing for 10 hours , And the organic layer was extracted by water extraction, washed with water, saturated aqueous sodium hydrogencarbonate solution and saturated aqueous sodium chloride solution, and dried to obtain a solution of substance A, wherein 2-amino-benzophenone, triethylsilane, boron trifluoride diethyl ether Of the weight ratio of 10:18:21; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 4% 2: 89% | With aluminium trichloride In dichloromethane Ambient temperature; | |
1: 89% 2: 4% | With aluminium trichloride In dichloromethane Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In dichloromethane |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With copper diacetate In isopropyl alcohol at 85℃; for 23h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | In acetonitrile; at 90℃; for 2h;Inert atmosphere; | An apparatus (a reaction flask, a three-way stopcock, a rotor, a septum, and a Dimroth condenser) was set up, the inside of the apparatus was dried with a heat gun, and then the apparatus was purged with argon. 2-l3enzylaniline (1.77 g, 9.66 mmol), acetonitrile, and hexyl isocyanate (1.40 mE, 9.66 mmol) were placed in this order in the reaction flask while cooling with ice, and the mixture was stirred at 90 C. for 2 hours. After the completion of the reaction was confirmed by TEC, the precipitated solid was collected by filtration. The product was purified by reprecipitation with acetone/hexane to obtain a target product as a white solid (yield: 91%, amount: 2.74 g). 1H NMR (400 MHz, DMSO-d5) oe=7.73 (2H, t, J=8.5 Hz), 7.27 (2H, t, J=7.6 Hz), 7.18 (3H, m), 7.11 (1H, m), 7.00 (1H, d, J=7.8 Hz), 6.90 (1H, t, J=7.6 Hz), 6.45 (1H, J=5.6 Hz), 3.91 (2H, s), 3.05 (2H, t, J=6.5 Hz),1.40-1.28 (8H, m), 0.87 (3H, t, J=6.6 Hz). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 79 percent / pyridine / benzene 2: 86 percent / POCl3 / acetonitrile / 1.5 h / Heating | ||
Multi-step reaction with 2 steps 1: pyridine / toluene / 1.5 h / 0 - 20 °C / Inert atmosphere 2: trichlorophosphate / 2 h / 120 °C / Inert atmosphere | ||
Multi-step reaction with 2 steps 1: pyridine / toluene / 1.5 h / 0 - 20 °C / Inert atmosphere 2: trichlorophosphate / 2 h / 120 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 82 percent / 2 h / Heating 2: 70 percent / polyphosphoric acid; POCl3 / 12 h / 120 °C 3: 91 percent / H2 / 10 percent Pd/C / methanol / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94.6% | 37.5 g of 2-amino-5-chlorobenzophenone, 15.8 ml of triethylamine and 188 ml of dimethylformamide were added into a 500 ml autoclave (by Hastelloy Inc.) equipped with an agitator and a thermometer, and 1.88 g of 10% palladium carbon (M type) (wet type, water: 55 5 wt%) by Kawaken Fine Chemical Inc. was then added. Air in the autoclave was replaced by nitrogen and then by hydrogen. After that, the reaction was performed at a hydrogen pressure of 3.0 MPa, a reaction temperature of 30 through 35 C and an agitation speed of 1000 through 1100 rpm. About three hours later, the hydrogen absorption speed was reduced, and heating was applied until about 45 C was reached. About five hours later, when there was almost no hydrogen absorption, cooling was carried out to reduce the temperature to the room temperature. The contents were then transferred into a 500 ml flask. The catalyst was removed by filtering with a pressure filter, and the catalyst was washed with 19 ml of dimethylformamide. Then, 200 ml of toluene, 19.4 g of 25% sodium hydroxide aqueous solution and 50 ml of water were added to the filtrate and were agitated. After that, it was transferred into a separate solution funnel, and the water layer was removed. The organic layer was washed three times with 50 ml of water. The extracted solution was concentrated under a reduced pressure and 29.7 g of brown oil was obtained. The brown oil was subjected to distillation under a reduced pressure (0.6 KPa and 170C) to get 28.0 g of 2-benzylaniline.???Yield rate: 94.6%???HPLC purity: 98.8% The spectra according to the mass spectrometry and nuclear magnetic resonance spectroscopy were the same as that of the 2-benzylaniline obtained in EXAMPLE 1. | |
93.9% | 37.5 g of 2-amino-5-chlorobenzophenone, 15.8 ml of triethylamine and 188 ml of tetrahydrofuran were added into a 500 ml autoclave (by Hastelloy Inc.) equipped with an agitator and a thermometer, and 1.88 g of 10% palladium carbon (M type) (wet type, water: 55 5 wt%) by Kawaken Fine Chemical Inc. was then added. Air in the autoclave was replaced by nitrogen and then by hydrogen. After that, the reaction was performed at a hydrogen pressure of 3.0 MPa, a reaction temperature of 30 through 35C and an agitation speed of 1000 through 1100 rpm. About two hours later, the hydrogen absorption speed was reduced, and heating was aaplied until about 45C was reached. About one hour later, when there was almost no hydrogen absorption, cooling was carried out to reduce the temperature to the room temperature. The contents were then transferred into a 500 ml flask. The catalyst was removed by filtering with a pressure filter, and the catalyst was washed with 19 ml of tetrahydrofuran. Then, 200 ml of toluene, 19.4 g of 25% sodium hydroxide aqueous solution and 50 ml of water were added to the filtrate and were agitated. After that, it was transferred into a separate solution funnel, and the water layer was removed. The organic layer was washed three times with 50 ml of water. The extracted solution was concentrated under a reduced pressure and 29.5 g of brown oil was obtained. The brown oil was subjected to distillation under a reduced pressure (0.6 KPa and 170C) to get 27.8 g of 2-benzylaniline.???Yield rate: 93.9%???HPLC purity: 98.8% The spectra according to the mass spectrometry and nuclear magnetic resonance spectroscopy were the same as that of the 2-benzylaniline obtained in EXAMPLE 1. | |
92.9% | 37.5 g of 2-amino-5-chlorobenzophenone, 15.8 ml of triethylamine and 188 ml of N-methylpyrrolidone were added into a 500 ml autoclave (by Hastelloy Inc.) equipped with an agitator and a thermometer, and 1.88 g of 10% palladium carbon (M type) (wet type, water: 55 5 wt%) by Kawaken Fine Chemical Inc. was then added. Air in the autoclave was replaced by nitrogen and then by hydrogen. After that, the reaction was performed at a hydrogen pressure of 3.0 MPa, a reaction temperature of 30 through 35C and an agitation speed of 1000 through 1100 rpm. About three hours later, the hydrogen absorption speed was reduced, and heating was applied until about 45 C was reached. About two hours later, when there was almost no hydrogen absorption, cooling was carried out to reduce the temperature to the room temperature. The contents were then transferred into a 500 ml flask. The catalyst was removed by filtering with a pressure filter, and the catalyst was washed with 19 ml of N-methylpyrrolidone. Then, 200 ml of toluene, 19.4 g of 25% sodium hydroxide aqueous solution and 50 ml of water were added to the filtrate and were agitated. After that, it was transferred into a separate solution funnel, and the water layer was removed. The organic layer was washed three times with 50 ml of water. The extracted solution was concentrated under a reduced pressure and 32.1 g of brown oil was obtained. The brown oil was subjected to distillation under a reduced pressure (0.6 KPa and 170 C) to get 27.5 g of 2-benzylaniline.???Yield rate: 92.9%???HPLC purity: 98.5% The spectra according to the mass spectrometry and nuclear magnetic resonance spectroscopy were the same as that of the 2-benzylaniline obtained in EXAMPLE 1. |
91.2% | 37.5 g of 2-amino-5-chlorobenzophenone, 15.8 ml of triethylamine and 188 ml of dimethylformamide were added into a 500 ml autoclave (by Hastelloy Inc.) equipped with an agitator and a thermometer, and 0.38 g of palladium black by Kawaken Fine Chemical Inc. was then added. Air in the autoclave was replaced by nitrogen and then by hydrogen. After that, the reaction was performed at a hydrogen pressure of 3.0 MPa, a reaction temperature of 30 through 35C and an agitation speed of 1000 through 1100 rpm. Since there was almost no hydrogen absorption about three hours later, cooling was carried out to reduce the temperature to the room temperature. The contents were then transferred into a 500 ml flask. The catalyst was removed by filtering with a pressure filter, and the catalyst was washed with 19 ml of dimethylformamide. Then, 200 ml of toluene, 19.4 g of 25% sodium hydroxide aqueous solution and 50 ml of water were added to the filtrate and were agitated. After that, it was transferred into a separate solution funnel, and the water layer was removed. The organic layer was washed three times with 50 ml of water. The extracted solution was concentrated under a reduced pressure and 30.3 g of brown oil was obtained. The brown oil was subjected to distillation under a reduced pressure (0.6 KPa and 170C) to get 27.0 g of 2-benzylaniline.???Yield rate: 91.2%???HPLC purity: 98.9% The spectra according to the mass spectrometry and nuclear magnetic resonance spectroscopy were the same as that of the 2-benzylaniline obtained in EXAMPLE 1. | |
91.2% | 37.5 g of 2-amino-5-chlorobenzophenone, 20.3 g of taurine and 188 ml of dimethylformamide were added into a 500 ml autoclave (by Hastelloy Inc.) equipped with an agitator and a thermometer, and 5.63 g of 10% palladium carbon (M type) (wet type, water: 55 5 wt%) by Kawaken Fine Chemical Inc. was then added. Air in the autoclave was replaced by nitrogen and then by hydrogen. After that, the reaction was performed at a hydrogen pressure of 3.0 MPa, a reaction temperature of 30 through 35 C and an agitation speed of 1000 through 1100 rpm. About two hours later, the hydrogen absorption speed was reduced, and heating was applied until about 50 C was reached. About another hour later, when there was almost no hydrogen absorption, cooling was carried out to reduce the temperature to the room temperature. The contents were then transferred into a 500 ml flask. The catalyst was removed by filtering with a pressure filter, and the catalyst was washed with 19 ml of dimethylformamide. Then, 200 ml of toluene, 38.8 g of 25% sodium hydroxide aqueous solution and 75 ml of water were added to the filtrate and were agitated. After that, it was transferred into a separate solution funnel, and the water layer was removed. The organic layer was washed three times with 50 ml of water. The extracted solution was concentrated under a reduced pressure and 30.7 g of brown oil was obtained. The brown oil was subjected to distillation under a reduced presure (0.6 KPa and 170C) to get 27.1 g of 2-benzylaniline.???Yield rate: 91.2%???HPLC purity: 98.7% The spectra according to the mass spectrometry and nuclear magnetic resonance spectroscopy were the same as that of the 2-benzylaniline obtained in EXAMPLE 1. | |
90.1% | 37.5 g of 2-amino-5-chlorobenzophenone and 188 ml of dimethylformamide were added into a 500 ml autoclave (by Hastelloy Inc.) equipped with an agitator and a thermometer, and 5.63 g of 10% palladium carbon (M type) (wet type, water: 55 5 wt%) by Kawaken Fine Chemical Inc. was then added. Air in the autoclave was replaced by nitrogen and then by hydrogen. After that, the reaction was performed at a hydrogen pressure of 3.0 MPa, a reaction temperature of 30 through 35 C and an agitation speed of 1000 through 1100 rpm. About one hour later, the hydrogen absorption speed was reduced, and heating was applied until about 60 C was reached. Further about one hour later, when there was almost no hydrogen absorption, cooling was carried out to reduce the temperature to the room temperature. The contents were then transferred into a 500 ml flask. The catalyst was removed by filtering with a pressure filter, and the catalyst was washed with 19 ml of dimethylformamide. Then, 200 ml of toluene, 38.8 g of 25% sodium hydroxide aqueous solution and 50 ml of water were added to the filtrate and were agitated. After that, it was transferred into a separate solution funnel, and the water layer was removed. The organic layer was washed three times with 50 ml of water. The extracted solution was concentrated under a reduced pressure and 30.1 gram of brown oil was obtained. The brown oil was subjected to distillation under a reduced pressure(0.6 KPa and 170C) to get 26.7 g of 2-benzylaniline.???Yield rate: 90.1%???HPLC purity: 98.7%???MS m/z = 183 (molecule ion peak)???1H-NMR (CDCl3) ?3.4 - 3.6 (broad, 2H, -NH2), 3.9 (s, 2H, -CH2-), 6.7 - 7.3 (m, 9H, aromatics) | |
85.1% | 25.0 g of 2-amino-5-chlorobenzophenone, 8.2 g of potassium carbonate, 150 ml of dimethylformamide and 50 ml of water were added into a 500 ml autoclave (by Hastelloy Inc.) equipped with an agitator and a thermometer, and 3.75 g of 10% palladium carbon (M type) (wet type, water: 55 5 wt%) by Kawaken Fine Chemical Inc. was then added. Air in the autoclave was replaced by nitrogen and then by hydrogen. After that, the reaction was performed at a hydrogen pressure of 3.0 MPa, a reaction temperature of 30 through 35 C and an agitation speed of 1000 through 1100 rpm. About twelve hours later, when there was almost no hydrogen absorption, cooling was carried out to reduce the temperature to the room temperature. The contents were then transferred into a 500 ml flask. The catalyst was removed by filtering with a pressure filter, and the catalyst was washed with 12 ml of dimethylformamide. Then, 130 ml of toluene, was added to the filtrate and was agitated. After that, it was transferred into a separate solution funnel, and the water layer was removed. The organic layer was washed three times with 30 ml of water. The extracted solution was concentrated under a reduced pressure and 21.0 g of brown oil was obtained. The brown oil was subjected to distillation under a reduced pressure (0.6 KPa and 170C) to get 16.8 g of 2-benzylaniline.???Yield rate: 85.1%???HPLC purity: 98.4% The spectra according to the mass spectrometry and nuclear magnetic resonance spectroscopy were the same as that of the 2-benzylaniline obtained in EXAMPLE 1. | |
81.4% | 37.5 g of 2-amino-5-chlorobenzophenone, 12.3 g of potassium carbonate, 113 ml of dimethylformamide and 75 ml of water were added into a 500 ml autoclave (by Hastelloy Inc.) equipped with an agitator and a thermometer, and 5.63 g of 10% palladium carbon (M type) (wet type, water: 55 5 wt%) by Kawaken Fine Chemical Inc. was then added. Air in the autoclave was replaced by nitrogen and then by hydrogen. After that, the reaction was performed at a hydrogen pressure of 3.0 MPa, a reaction temperature of 30 through 35C and an agitation speed of 1000 through 1100 rpm. About seven hours later, it was confirmed that the hydrogen absorption speed was reduced, and 14 ml of acetic acid was added to continue reaction for five hours. Since there was almost no hydrogen absorption, cooling was carried out to reduce the temperature to the room temperature. The contents were then transferred into a 500 ml flask. The catalyst was removed by filtering with a pressure filter, and the catalyst was washed with 19 ml of dimethylformamide. Then, 200 ml of toluene, 38.8 g of 25% sodium hydroxide aqueous solution and 50 ml of water were added to the filtrate and were agitated. After that, it was transferred into a separate solution funnel, and the water layer was removed. The organic layer was washed three times with 50 ml of water. The extracted solution was concentrated under a reduced pressure and 28.7 g of brown oil was obtained. The brown oil was subjected to distillation under a reduced pressure (0.6 KPa and 170C) to get 24.1 g of 2-benzylaniline.???Yield rate: 81.4%???HPLC purity: 98.5% The spectra according to the mass spectrometry and nuclear magnetic resonance spectroscopy were the same as that of the 2-benzylaniline obtained in EXAMPLE 1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
p-toluenesulfonic acid monohydrate; In toluene; | Preparation 5 (+-) trans 1-(2-Benzylanilino)-2-ethoxycarbonylaminoindane A solution of (+-) cis-2-ethoxy-3a,8b-dihydro-4H-indeno[2,1-d]oxazole (2.0 g, 0.01 mol) in dry toluene (15 ml) was treated with <strong>[28059-64-5]2-benzylaniline</strong> (1.83 g, 0.01 mol) and a catalytic amount of p-toluenesulfonic acid monohydrate (50 mg), and the mixture was heated at 60 C. for 1.5 h. The reaction was diluted with diethyl ether, and washed with water followed by brine. The organic phase was dried over Na2 SO4 and concentrated in vacuo to give the title compound as a brown foam (3.37 g) which was used in the next stage without purification. 1 H Nmr (CDCl3) delta:1.20 (3H, t, J=7Hz), 2.71 (1H, dd, J=16Hz and J=6Hz), 3.13 (1H, dd, J=16Hz and J=7Hz), 3.82 (2H, s), 3.93 (1H, br s), 4.00-4.28 (3H, m), 4.65 (1H, br s), 4.83 (1H, br s), 6.76 (1H, t, J=8Hz), 6.90-7.32 (12H, m). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93.4% | With potassium hydroxide; In 2-methoxy-ethanol; at 60℃; | To a 500L three-necked bottle, 50 g of 2-aminobenzophenone, 250 ml of ethylene glycol monomethyl ether, and 80% of hydrazine hydrate 68 ml were heated to reflux, and the reflux liquid was dried by adding anhydrous sodium sulfate and rapidly dropped into the reaction solution.The progress of the reaction was monitored by HPLC, and the remaining 0.4% of the 2-aminobenzophenone raw material was cooled down to 60 C., 27.5 g of potassium hydroxide was added, and the temperature was raised to reflux.The progress of the reaction was monitored by HPLC, and the remaining compound was 0.3%.The solvent was distilled off under reduced pressure, 250 ml of water was added, and the mixture was stirred at 50 C. for 30 minutes. The aqueous layer was separated, and the oil was evaporated under reduced pressure to give 43.4 g of an off white solid.That is, high-purity o-benzylaniline, yield 93.4%, purity 99.9%, the largest single impurity 0.04%. |
With potassium hydroxide; In diethylene glycol; | Preparation 15 2-benzylaniline In the manner given in Preparation 11, 2-aminobenzophenone hydrazone is refluxed with potassium hydroxide in diethylene glycol to give 2-benzylaniline. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | In methanol; at 20℃; for 92h;Heating / reflux; | Aminodiphenylmethane (16.2ml, 93.9mmol) was added dropwise to a solution of 2- chloromethyl-2-methyloxirane (1Og, 94mmol), in methanol (40ml) and the reaction stirred at r.t. for 72 hours followed by reflux for 20 hours. The reaction was cooled to r.t., evaporated in vacuo and suspended in acetone (50ml). The solid material was collected by filtration to afford the title compound as a white solid. Yield 20.4g, (75%): HPLC retention time, 3.56min (Solvent: CH3CN/H2O/0.05% NH3, 5-95% gradient H2O-6min. Column: Xterra 50 x 4.60 Ld., Cl 8 reverse phase. Flow rate: 1.5mL/min.). Mass spectrum (ES+) m/z 254 (M + H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | With acetic acid; at 80℃; for 2h; | Example 1 l-(2-Benzylphenyl)-lH-pyrro.e (compound 3 of scheme 1)A mixture of <strong>[28059-64-5]2-benzylaniline</strong> (2, 0.30 g, 1.64 mmol) in glacial acetic acid (15 mL) with 2,5-dimethoxytetrahydrofuran (0.26 mL, 1.96 mmol) was heated at 80 C for 2 h. The solvent was then removed under reduced pressure and the residue was partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over sodium sulfate, and concentrated under reduced pressure. Purification of the residue by flash chromatography with n-hexane-ethyl acetate (8:2) as the eluent gave compound 3 as an orange oil (0.32 g, yield 84%). 1H-NMR (CDCl3): 3.93 (s, 2H), 6.35 (t, J= 1.8, 2H), 6.79(t, J= 1.9, 2H), 7.07 (m, 2H), 7.22-7.35 (m, 7H>. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
33% | at 150℃; for 0.25h;Microwave irradiation; Neat (no solvent); | General procedure: A mixture of 2-chloroquinoline 17 (200 mg, 1.22 mmol) and aniline (455 mg, 4.89 mmol) was heated 15 min at 150 C using microwave synthesizer. The resulting reaction mixture was dissolved in ethyl acetate (50 ml) and washed with saturated Na2CO3 (2× 50 ml) and H2O (2× 50 ml). The organic phase was dried (Na2SO4) and evaporated to leave a clear oil. This oil was purified by flash chromatography (silica gel) eluting with dichloromethane to give 12a as a light brown solid (133 mg, 49%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
59% | With pyridine; In tetrahydrofuran; at 20℃; | General procedure: N,N'-di(2-fluorophenyl)-4-methoxyl-isophthalamide(1a): Equipped a stirrer in a three-necked flask (100 ml), to a mixture of 2-fluoroaniline (1.11 g, 10.0 mmol),anhydrous tetrahydrofuran (15 ml) and dry pyridine (1 ml), dropwise added 4-methoxyl-isophthaloyl dichloride (1.17 g, 5.0 mmol) which had been dissolved in dry tetrahydrofuran (10 ml). After the mixture reaction at room temperature for 8 h under continuous stirring, the excess tetrahydrofuran was distilled off in vacuum. The residue was recrystallized by acetone. Its melting point is 204-206 C, and yield is 67%. The other compounds 1b-1j, 2a-2k, 3a-3l and 4a-4h were prepared in the same manner. |
59% | General procedure: A round-bottomed flask (100 ml) equipped with a magneticstirrers was charged with 2-ethylaniline (10.0 mmol, 1.2 g)in anhydrous tetrahydrofuran (15 ml). The fresh 4-methoxyisophthaloyl dichloride 5 (5.0 mmol, 1.2 g) in drytetrahydrofuran (15 ml) was added drop-wise to the abovesolution at room temperature. Ten hours after the additionof compound 5, dry triethylamine (1 ml) was added dropwiseto the reaction mixture. The resultant mixture reactionwas stirred for 24 h at room temperature. After the reactioncompleted as monitored by thin layer chromatography(TLC). The solvent was removed under reduced pressure toobtain the crude product. The crude product was furtherpurified by recrystallization from anhydrous ethanol to yieldthe desired product 1d as white solid. Yield: 55.00% |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With acetic acid; In water; for 9h;Reflux; | 2-Benzylaniline (1.00 g, 5.45 mmol) was added to a round bottom flask with acrylic acid(0.374 mL, 5.45 mmol) and 20 % acetic acid (4 mL). The reaction mixture was stirred at refluxfor 9 h. The mixture was made basic with 1 M NaOH and washed with ether (10 mL) to removeany remaining starting material. The aqueous layer was acidified to pH 7 with 10 % by volumeHCl solution. The product was extracted with ether (3 × 40 mL). The combined organic layers S40were washed with brine, dried over Na2SO4, and concentrated under reduced pressure. Crudebrown oil 3-((2-benzylphenyl)-amino)propanoic acid (0.930 g) was taken on to the cyclizationwithout further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | In neat (no solvent); for 0.333333h;Reflux; | For the synthesis of the novel ligand L3, ethanol (40mL), <strong>[28059-64-5]2-benzylaniline</strong> (1.95g, 10.1mmol) and 2-quinolinecarboxaldehyde (1.60g, 10.1mmol) were combined and refluxed for 20min. Ethanol was removed and L3 was isolated as viscous yellow oil in 85% yield (2.81g). 1H NMR (200MHz, CDCl3, TMS) deltaH (ppm): 4.24 (2H, s, CH2), 7.03-7.36 (9H, m, H-Ar), 7.57 (1H, t, 3JHH=8.0Hz, H-Ar), 7.74 (1H, t, 3JHH=7.5Hz, H-Ar), 7.84 (1H, d, 3JHH=7.8Hz, H-Ar), 8.14-8.23 (2H, m, H-Ar), 8.35 (1H, d, 3JHH=8.6Hz, H-Ar), 8.70 (1H, s, CH=N). HRMS (m/z), Calc. for [C23H18N2+H]+: 323.1549. Found: 323.1543 (error 1.91ppm). FTIR (cm-1): nu 1625 (s, imine C=N). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | In neat (no solvent); at 120℃; | General procedure: L2 was synthesized by modifying a literature procedure [16a]. A mixture of 2-quinolinecarboxaldehyde (1.00g, 6.3mmol) and aniline (0.65g, 6.9mmol) was stirred overnight at 120C under solvent-free conditions. The obtained crude product was dissolved in n-pentane and L2 was collected as a yellow crystalline solid after slow evaporation of the solvent. Yield 81% (1.21g). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | With 1-butyl-3-methyl-pyridinium dichloroiodate; at 80℃; for 1h;Inert atmosphere; | 2-Benzylaniline (0.1 g, 0.54mmol) and l-butyl-3-methylpyridinium dichloroiodate (BMPDCI) (0.23 g, 0.65 mmol) were added in 10 ml one necked round bottomed flask in an inert atmosphere. The reaction mixture was heated at 80 C for lhr. After the reaction was completed (TLC), ethyl acetate (10ml) was added followed by addition of water (10ml). The entire reaction mixture was extracted with ethyl acetate (3x10ml). The combined ethyl acetate layer was washed with water, brine and dried over anhydrous sodium sulphate. Solvent was evaporated under vacuum, the residue purified by silica gel chromatography to afford the pure 2-benzyl-4-iodoaniline in 0.128 g, (76% yield). 1H NMR (CDC13 delta/ppm): 7.04-7.26 (m, 7H), 6.31-6.35 (d, 1H, 7=8.71 Hz), 3.72 (s, 2H, CH2), 3.36 (broad singlet, 2H, NH2). 13C NMR (CDCI3): 37.62, 79.95, 117.98, 126.56, 127.67, 128.32, 128.71, 136.22, 138.34, 138.98, 144.22. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; at 120℃; for 0.5h;Microwave irradiation; | General procedure: To a microwave vial containing a solution of Boc-L-glutamic acid tert-butyl ester (0.165 mmol, 1.0 equiv) and HATU (0.165 mmol, 1.0 equiv) in DMF (1.65 mL) was added the amine followed by DIPEA (57.5 muL, 2.0 equiv). The vial was sealed and heated under microwave irradiation for 30 min at 120 C. Upon completion, the reaction was partitioned between water and CH2Cl2, extracted 3× with CH2Cl2, dried over anhydrous Na2SO4, and concentrated under vacuum. Compounds were purified via reverse phase chromatography (5-95% acetonitrile/water) to afford the N-Boc-glutamylanilide-tert-butyl esters. The compounds were transferred to vials followed by the addition of 2.0 mL of 4.0 M HCl in dioxane. The reaction stirred at 40 C for 4 h. The reactions were concentrated under vacuum to afford the title compounds which were used without further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With triethylamine; In chloroform; at 5 - 24℃; for 1h; | General procedure: To a stirred solution of 3 (10.00 g, 54.57 mmol) and triethylamine (15.21 mL, 109.10mmol) in 200 mL CHCl3 at 5-10 C a solution of phthalylglycyl chloride 4 (14.64 g, 65,48 mmol) in CHCl3 (50 mL) was added dropwise over 30 min. During the chlorideaddition the product precipitated. The mixture was stirred additionally at 24 oC for 30min and then chloroform (1.50 L) was added to completely dissolve the product. Theorganic phase was washed with water (300 mL), 5% sodium carbonate solution (300mL) and water (300 mL) and dried over MgSO4. The solution was concentrated invacuo to 1/3 of the initial volume and after cooling to 10 C the precipitated productwas filtered off to give 17.60 g (87%) of product 5 as pale beige solid; mp = 234-235C. IR (KBr): 3269, 3063, 3026, 1772, 1732, 1666, 1587, 1541, 1413, 1257, 1211,952, 715 cm-1; 1H NMR (500 MHz, CDCl3): delta 3.99 (s, 2 H), 4.30 (s, 2 H), 7.05-7.18(m, 7 H, Ar), 7.22-7.30 (m, 2H, Ar), 7.75-7.77 (m, 2 H, Ar), 7.85-7.87 (m, 2 H, Ar); 13C NMR (125 MHz, CDCl3): delta 38.3, 41.6, 123.8, 124.1, 125.8, 126.7, 127.7, 128.1,128.9, 128.9, 131.0, 131.4, 131.9, 134.3, 135.1, 138.7, 164.2, 167.6; HRMS (ESI):m/z calcd for C23H18N2O3Na [M+Na]+: 393.1215; found: 393.1223. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89.2% | With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; at 180℃; for 24h; | A. Added in the reaction bottle 10mmol ferulic acid, 30 ml dry THF, 15mmolEDCI, 15mmolHOBT, 10mmol substituted aniline, stirring the mixture at room temperature for reaction 24h; after the reaction, reducing pressure and evaporating the solvent, the residue is added in 50 ml methylene chloride, with saturated sodium carbonate aqueous solution and washing with saturated sodium chloride aqueous solution, an organic layer after drying by anhydrous sodium sulfate filtering, reducing pressure and evaporating the solvent, the residue is chromatographically purified (eluent: dichloromethane: methanol =30:1v/v), corresponding Ferulicacid benzoyl amines compound, to yield 87.8% |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
A method for the synthesis of epinastine hydrochloride comprises the steps of mixing the benzyl-protected substance B with ethyl acetate, adjusting the temperature to 35 C, adding 4,5-dicyanoimidazole, stirring for 1 hour, Add the material A ethyl acetate solution, stir for 2h, add water, the mass fraction of 7wt% aqueous solution of sodium carbonate, saturated sodium chloride aqueous solution of each extraction time, each extract were taken organic layer, and then concentrated under reduced pressure, drying To obtain the substance C, wherein the molar ratio of the substance A to the substance B is 1: 1, the weight ratio of the substance B to the 4,5-dicyanoimidazole is 1: 1.2; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
A method for the synthesis of epinastine hydrochloride comprises the steps of mixing benzyloxycarbonyl protected substance B with methylene chloride, adjusting the temperature to 20 C, adding N, N-carbonyl-diimidazole, stirring for 0.6 h, And then dropping the 1,2-dichloroethane solution of substance A, stirring for 10 hours, then adding water, the mass fraction of 4wt% aqueous solution of sodium hydroxide, saturated sodium chloride aqueous solution of each washing once, each extraction were organic Layer, and then concentrated under reduced pressure to dry the material C, wherein the molar ratio of substance A to material B is 1: 1.18, the weight ratio of substance B to N, N-carbonyl-diimidazole is 1: 1.13; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
The methoxycarbonyl group tablet held by officials during imperial audience armor protection material B and ethyl acetate mixing, regulating the temperature to 30 C, adding dicyclohexyl carbodiimide, stirring 0.8 h, drip and adds the material A solution, thermal insulation stirring 4 h, orderly adding water, the mass fraction is 6 wt % sodium carbonate aqueous solution, saturated sodium chloride aqueous solution of a [...], each [...] are the organic layer, then concentrated under reduced pressure, and dried to obtain the material C, wherein material A and material B molar ratio of 1: 1.12, material B with dicyclohexyl carbodiimide in the weight ratio of 1: 1.17; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: 4,5-dicyano-1H-imidazole / ethyl acetate / 1 h / 35 °C 1.2: 2 h 2.1: polyphosphoric acid / dichloromethane / 0.5 h / 160 °C 3.1: palladium-carbon / methanol / 1 h / 80 °C 4.1: hydrogenchloride / water | ||
Multi-step reaction with 4 steps 1.1: dicyclohexyl-carbodiimide / dichloromethane / 0.5 h / 15 °C 1.2: 12 h 2.1: polyphosphoric acid / dichloromethane / 2 h / 120 °C 3.1: hydrogenchloride / ethyl acetate; water / 4 h / 20 °C 4.1: hydrogenchloride / water | ||
Multi-step reaction with 4 steps 1.1: dicyclohexyl-carbodiimide / dichloromethane / 0.5 h / 15 °C 1.2: 12 h 2.1: polyphosphoric acid / dichloromethane / 1.5 h / 130 °C 3.1: palladium-carbon / 3 h / 40 °C 4.1: hydrogenchloride / water |
Multi-step reaction with 5 steps 1.1: 4,5-dicyano-1H-imidazole / ethyl acetate / 1 h / 35 °C 1.2: 2 h 2.1: polyphosphoric acid / dichloromethane / 0.5 h / 160 °C 3.1: palladium-carbon / methanol / 1 h / 80 °C 4.1: ethyl acetate; methanol / 6 h / 10 - 20 °C 5.1: hydrogenchloride / water; methanol / 10 h / -10 - 20 °C | ||
Multi-step reaction with 5 steps 1.1: dicyclohexyl-carbodiimide / dichloromethane / 0.5 h / 15 °C 1.2: 12 h 2.1: polyphosphoric acid / dichloromethane / 2 h / 120 °C 3.1: hydrogenchloride / ethyl acetate; water / 4 h / 20 °C 4.1: ethyl acetate; methanol / 6 h / 10 - 20 °C 5.1: hydrogenchloride / water; methanol / 10 h / -10 - 20 °C | ||
Multi-step reaction with 5 steps 1.1: dicyclohexyl-carbodiimide / dichloromethane / 0.5 h / 15 °C 1.2: 12 h 2.1: polyphosphoric acid / dichloromethane / 1.5 h / 130 °C 3.1: palladium-carbon / 3 h / 40 °C 4.1: ethyl acetate; methanol / 6 h / 10 - 20 °C 5.1: hydrogenchloride / water; methanol / 10 h / -10 - 20 °C | ||
Multi-step reaction with 4 steps 1: pyridine / toluene / 1.5 h / 0 - 20 °C / Inert atmosphere 2: trichlorophosphate / 2 h / 120 °C / Inert atmosphere 3: sodium t-butanolate / acetonitrile / 20 h / Reflux; Inert atmosphere 4: hydrogenchloride; 10% Pd/C; hydrogen / ethanol; water / 24 h | ||
Multi-step reaction with 4 steps 1: pyridine / toluene / 1.5 h / 0 - 20 °C / Inert atmosphere 2: trichlorophosphate / 2 h / 120 °C 3: sodium t-butanolate / acetonitrile / 0.5 h / 120 °C / Microwave irradiation 4: hydrogenchloride; 10% Pd/C; hydrogen / ethanol; water / 24 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: 4,5-dicyano-1H-imidazole / ethyl acetate / 1 h / 35 °C 1.2: 2 h 2.1: polyphosphoric acid / dichloromethane / 0.5 h / 160 °C 3.1: 5%-palladium/activated carbon / methanol / 1 h / 80 °C 4.1: ethyl acetate; methanol / 6 h / 10 - 20 °C | ||
Multi-step reaction with 4 steps 1.1: dicyclohexyl-carbodiimide / dichloromethane / 0.5 h / 15 °C 1.2: 12 h 2.1: polyphosphoric acid / dichloromethane / 2 h / 120 °C 3.1: hydrogenchloride / ethyl acetate; water / 4 h / 20 °C 4.1: ethyl acetate; methanol / 6 h / 10 - 20 °C | ||
Multi-step reaction with 4 steps 1.1: dicyclohexyl-carbodiimide / dichloromethane / 0.5 h / 15 °C 1.2: 12 h 2.1: polyphosphoric acid / dichloromethane / 1.5 h / 130 °C 3.1: 5%-palladium/activated carbon / 3 h / 40 °C 4.1: ethyl acetate; methanol / 6 h / 10 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
A method for the synthesis of epinastine hydrochloride comprises the steps of: mixing the tert-butoxycarbonyl-protected substance B with methylene chloride to adjust the temperature to 15 C, adding dicyclohexylcarbodiimide, stirring for 0.5 h, And then dropping material A methylene chloride solution, stirring for 12h, followed by adding water, the mass fraction of 3wt% potassium carbonate aqueous solution, saturated sodium chloride aqueous solution of each wash once, each extract the organic layer, and then concentrated under reduced pressure, Drying the material C, wherein the molar ratio of substance A to material B is 1: 1.2, the weight ratio of substance B to dicyclohexylcarbodiimide is 1: 1; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50% | With Hbeta zeolite; In toluene; at 120℃; for 24h;Sealed tube; Green chemistry; | General procedure: Hbeta zeolite (100mg) was added to the well stirred solutionof aromatic ketone (2mmol), aniline (2mmol) and toluene(1mL) in a 15mL sealed tube and the reaction mixturewas allowed to stir at 120C. After 24h, the reaction mixturewas cooled to room temperature and diluted with ethylacetate (10mL). The catalyst was separated by simple fltrationand the exclusion of solvent in vacuo yielded the crudewhich was further purified by column chromatography usingsilica gel (100-200 mesh) to afford pure products. All theproducts were identified on the basis of 1H and 13C NMRspectral data. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99.5% | With potassium hydroxide; In water; at 50℃; for 4h; | 5.8 g of 2'-amino-3-chlorobenzophenone, 25 ml of distilled water and 16 g of Raney nickel-aluminum alloy were added to a four-necked reaction flask equipped with a stirrer, a thermometer, a reflux condenser and a separating funnel at room temperature. After confirming that the temperature of the mixture in the reaction vessel has reached 50 C, 10 ml of a 14% potassium hydroxide aqueous solution is slowly added dropwise over 1 hour at 50 C. After the dropwise addition is completed, the mixture is stirred for 3 hours while maintaining the same temperature. After the starting material is disappeared by liquid chromatography, it is confirmed that 95% or more of 2-benzylaniline as a target substance is formed, and the reaction is terminated. The reaction mixture is slowly cooled to room temperature and filtered using a celite filter cake. After filtration, the residue is washed with 10 ml of purified water. After filtration, 20 ml of dichloromethane is added to the filtrate aqueous layer, the mixture is stirred at room temperature for 10 minutes, and the layer is separated using a separatory funnel. The organic layer was washed with 20 ml of saturated aqueous sodium chloride solution for 10 minutes at room temperature for 10 minutes. The organic layer was washed with a separating funnel and the dichloromethane layer was separated. The organic layer was washed with 3 g of anhydrous sodium sulfate and stirred at room temperature for 10 minutes Filter. The residue cake was washed with 5 ml of dichloromethane, filtered, and concentrated under reduced pressure in vacuo to obtain 4.47 g (yield: 99.5%) of 2-benzyl aniline as a target oil. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | In acetonitrile; at 90℃; for 2.5h;Inert atmosphere; | An apparatus (a reaction flask, a three-way stopcock, a rotor, a septum, and a Dimroth condenser) was set up, the inside of the apparatus was dried with a heat gun, and then the apparatus was purged with argon. 2-l3enzylaniline (0.93 g, 5.07 mmol), acetonitrile, and dodecyl isocyanate (1.2 mE, 5.07 mmol) were placed in this order in the reaction flask, and the mixture was stirred at 90 C. for 2.5 hours. Afier the completion of the reaction was confirmed by TEC, the precipitated solid was collected by filtration, and reprecipitated with chloroform/hexane to obtain a target product as a white solid (yield: 72%, 1.43 g). 1H-NMR (600 MHz, CDC13) oe=7.42 (1H, d, J=7.6 Hz), 7.28 (4H, m), 7.21 (2H, t, J=6.9 Hz), 7.14 (2H, d, J=6.9 Hz), 5.75 (1H, s), 4.32 (1H, t, J=5.8 Hz), 3.99 (2H, s), 3.08 (2H, t, J=6.6 Hz), 1.41-1.28 (20H, t, J=19.9 Hz), 0.88 (3H,t, J=6.9 Hz). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | In acetonitrile; at 90℃; for 2h;Inert atmosphere; | An apparatus (a reaction flask, a three-way stopcock, a rotor, and a septum) was set up, the inside of the apparatus was dried with a heat gun, and then the apparatus was purged with argon. 2-l3enzylaniline (0.87 g, 4.73 mmol), acetonitrile, and tetradecyl isocyanate (1.3 mE, 4.73 mmol) were placed in this order in the reaction flask, and the mixture was stirred at 90 C. for 2 hours. After the completion of the reaction was confirmed by TEC, the resulting solid was collected by filtration, and thermally recrystallized from chloroform to obtain a target product as a white solid (yield: 73%, 1.47 g). ?H-NMR (600 MHz, DMSO-d5) oe=7.73 (2H, d, J=9.6 Hz), 7.27 (2H, t, J=7.6 Hz), 7.17 (3H, t, J=6.9 Hz), 7.10 (1H, t, J=7.6 Hz), 6.99 (1H, d, J=6.2 Hz), 6.90 (1H, t, J=7.9 Hz), 6.46 (1H, t, J=5.5 Hz), 3.91 (2H, s), 3.05 (2H, t, J=6.4 Hz), 1.39-1.25 (24H, m), 0.85 (3H, t, J=6.9 Hz). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | In acetonitrile; at 90℃; for 2.5h;Inert atmosphere; | An apparatus (a Schlenk tube, a rotor, and a septum) was set up, the inside of the apparatus was dried with a heat gun, and then the apparatus was purged with argon. Acetonitrile, <strong>[28059-64-5]2-benzylaniline</strong> (125 mg, 0.68 mmol), and pentadecyl isocyanate (0.2 mE, 0.68 mmol) were placed in this order in the Schlenk tube, and the mixture was stirred at 90 C. for 2.5 hours. Afier the completion of the reaction was confirmed by TEC, the resulting solid was collected by filtration, and washed with acetonitrile to obtain a target product as a white solid (yield: 87%, 258 g). ?H-NMR (600 MHz, DMSO-d5) oe: 7.74 (1H, d,J=8.2 Hz), 7.71 (1H, s), 7.27 (2H, t, J=7.9 Hz), 7.18 (3H, t,J=7.2 Hz), 7.11 (1H, t, J=6.9 Hz), 6.99 (1H, d, J=6.2 Hz),6.90 (1H, t, J=7.9 Hz), 6.45 (1H, t, J=5.5 Hz), 3.91 (2H, s),3.05 (2H, t, J=6.6 Hz), 1.39-1.25 (26H, m), 0.85 (3H, t,J=6.9 Hz). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
51% | In acetonitrile; at 90℃; for 4h;Inert atmosphere; | An apparatus (a reaction flask, a three-way stopcock, a rotor, a septum, and a Dimroth condenser) was set up, the inside of the apparatus was dried with a heat gun, and then the apparatus was purged with argon. 2-l3enzylaniline (0.81 g, 4.44 mmol), acetonitrile, and hexadecyl isocyanate (1.4 mE, 4.44 mmol) were placed in this order in the reaction flask, and the mixture was stirred at 90 C. for 4 hours. After the completion of the reaction was confirmed by TEC, the precipitated solid was collected by filtration, and reprecipitated with chloroformlhexane to obtain a target product as a white solid (yield: 51%, 1.02 g). 1H-NMR (600 MHz, DMSO-d5) oe=7.73 (2H, d,J=10.3 Hz), 7.27 (2H, t, J=7.9 Hz), 7.17 (3H, t, J=7.6 Hz),7.10 (1H, t, J=7.6 Hz), 6.99 (1H, d, J=6.2 Hz), 6.90 (1H, t,J=6.9 Hz), 6.45 (1H, t, J=5.5 Hz), 3.91 (2H, s), 3.05 (2H, t,J=6.4 Hz), 1.39-1.25 (28H, m), 0.85 (3H, t, J=7.2 Hz). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | In acetonitrile; at 90℃; for 13h;Inert atmosphere; | An apparatus (a reaction flask, a three-way stopcock, a rotor, a septum, and a Dimroth condenser) was set up, the inside of the apparatus was dried with a heat gun, and then the apparatus was purged with argon. 2-l3enzylaniline (1.08 g, 5.90 mmol), acetonitrile, and ethyl isocyanate (0.47 mE, 5.90 mmol) were placed in this order in the reaction flask, and the mixture was stirred at 90 C. for 13 hours. Afier the completion of the reaction was confirmed by TEC, the precipitated solid was collected by filtration. The product was purified by reprecipitation with acetone/hexane to obtain a target product as a white solid (yield: 60%, amount:0.89 g). ?H NMR (400 MHz, DMSO-d5) &7.75 (1H, d, J=8.3 Hz), 7.69 (1H, s), 7.28 (2H, t, J=7.3 Hz), 7.17 (3H, m), 7.13-7.09 (1H, m), 6.99 (1H, dd, J=7.3, 1.5 Hz), 6.91 (1H, td, J=7.3, 1.5 Hz), 6.42 (1H, s), 3.91 (2H, s), 3.08 (2H, t, J=7.0 Hz), 1.04 (3H, t, J=7.1 Hz). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | In acetonitrile; at 90℃; for 3h;Inert atmosphere; | An apparatus (a reaction flask, a three-way stopcock, a rotor, a septum, and a Dimroth condenser) was set up, the inside of the apparatus was dried with a heat gun, and then the apparatus was purged with argon. 2-l3enzylaniline (2.05 g, 11.2 mmol), acetonitrile, and propyl isocyanate (1.05 mE, 11.2 mmol) were placed in this order in the reaction flask while cooling with ice, and the mixture was stirred at 90 C. for 3 hours. Afier the completion of the reaction was confirmed by TEC, the precipitated solid was collected by filtration. The product was purified by reprecipitation with acetone/hexane to obtain a target product as a white solid (yield: 80%, amount: 2.41 g). ?H NMR (400 MHz, DMSO-d5) oe=7.74 (2H, t,J=9.5 Hz), 7.28 (2H, t, J=7.8 Hz), 7.18 (3H, m), 7.11 (1H,t, J=7.8 Hz), 6.99 (1H, d, J=7.8 Hz), 6.90 (1H, t, J=7.6 Hz),6.47 (1H, s), 3.91 (2H, s), 3.02 (2H, t, J=6.3 Hz), 1.42 (2H,tq, J=6.5, 7.6 Hz), 0.87 (3H, t, J=7.6 Hz). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | In acetonitrile; at 90℃; for 13h;Inert atmosphere; | An apparatus (a reaction flask, a three-way stop-cock, a rotor, a septum, and a Dimroth condenser) was setup, the inside of the apparatus was dried with a heat gun, and then the apparatus was purged with argon. 2-l3enzylaniline (0.97 g, 5.31 mmol), acetonitrile, and n-butyl isocyanate (0.6 mE, 5.31 mmol) were placed in this order in the reaction flask, and the mixture was stirred at 90 C. for 13 hours. After the completion of the reaction was confirmed by TEC, the precipitated solid was collected by filtration. The productwas purified by reprecipitation with acetone/hexane toobtain a target product as a white solid (yield: 86%, amount:1.29 g). 1H NMR (400 MHz, DMSO-d5) oe=7.75 (1H, d,J=8.3 Hz), 7.70 (1H, s), 7.27 (2H, t, J=7.3 Hz), 7.18 (3H, dd,J=7.8, 6.3 Hz), 7.11 (1H, t, J=8.5 Hz), 6.99 (1H, d, J=5.9Hz), 6.90 (1H, m), 6.43 (1H, s), 3.91 (2H, s), 3.06 (2H, t,J=6.3 Hz), 1.34 (4H, m), 0.89 (3H, t, J=7.3 Hz). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
54% | In acetonitrile; at 90℃; for 48h;Inert atmosphere; | An apparatus (a reaction flask, a three-way stopcock, a rotor, a septum, and a Dimroth condenser) was set up, the inside of the apparatus was dried with a heat gun, and then the apparatus was purged with argon. 2-l3enzylaniline (1.85 g, 10.1 mmol), acetonitrile, and pentyl isocyanate (1.30 mE, 10.1 mmol) were placed in this order in the reaction flask while cooling with ice, and the mixture was stirred at 90 C. for 2 days. After the completion of the reaction was confirmed by TEC, the precipitated solid was collected by filtration. The product was purified by reprecipitation with acetone/hexane to obtain a target product as a white solid (yield: 54%, amount: 1.61 g). ?H NMR (400 MHz, DMSO-d5) oe=7.74 (1H, d,J=8.3 Hz), 7.70 (1H, s), 7.27 (2H, dd, J=8.3, 2.1 Hz), 7.18(3H, m), 7.11 (1H, t, J=6.8 Hz), 7.00 (1H, d, J=7.3 Hz), 6.90(1H, t, J=7.3 Hz), 6.44 (1H, t, J=5.6 Hz), 3.91 (2H, s), 3.05(2H, t, J=6.3 Hz), 1.41-1.25 (6H, m), 0.87 (3H, t, J=7.1 Hz). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | In acetonitrile; at 90℃; for 3h;Inert atmosphere; | An apparatus (a reaction flask, a three-way stopcock, a rotor, a septum, and a Dimroth condenser) was set up, the inside of the apparatus was dried with a heat gun, and then the apparatus was purged with argon. 2-l3enzylaniline (1.77 g, 9.66 mmol), acetonitrile, and hexyl isocyanate (1.40 mE, 9.66 mmol) were placed in this order in the reaction flask while cooling with ice, and the mixture was stirred at 90 C. for 2 hours. After the completion of the reaction was confirmed by TEC, the precipitated solid was collected by filtration. The product was purified by reprecipitation with acetone/hexane to obtain a target product as a white solid (yield: 91%, amount: 2.74 g). 1H NMR (400 MHz, DMSO-d5) oe=7.73 (2H, t, J=8.5 Hz), 7.27 (2H, t, J=7.6 Hz), 7.18 (3H, m), 7.11 (1H, m), 7.00 (1H, d, J=7.8 Hz), 6.90 (1H, t, J=7.6 Hz), 6.45 (1H, J=5.6 Hz), 3.91 (2H, s), 3.05 (2H, t, J=6.5 Hz),1.40-1.28 (8H, m), 0.87 (3H, t, J=6.6 Hz). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67% | In acetonitrile; at 90℃; for 2.5h;Inert atmosphere; | An apparatus (a reaction flask, a three-way stopcock, a rotor, a septum, and a Dimroth condenser) was set up, the inside of the apparatus was dried with a heat gun, and then the apparatus was purged with argon. 2-l3enzylaniline (1.8 g, 9.80 mmol), acetonitrile, and octyl isocyanate (1.7 mE, 9.80 mmol) were placed in this order in the reaction flask, and the mixture was stirred at 90 C. for 2.5 hours. Afier the completion of the reaction was confirmed by TEC, the precipitated solid was collected by filtration, and washed with acetonitrile to obtain a target product as a white solid (yield: 67%, 2.23 g). ?H-NMR (600 MHz, CDC13) 6 =7.41 (2H, d, J=7.6 Hz), 7.28 (2H, m), 7.21 (2H, m), 7.14 (2H, d, J=7.6 Hz), 5.74 (1H, s), 4.32 (1H, t, J=5.2 Hz), 3.99 (2H, s), 3.08 (2H, t, J=6.6 Hz), 1.41-1.36 (2H, m), 1.30-1.24 (1OH, m), 0.88 (3H, t, J=7.2 Hz) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | In tetrahydrofuran; at 20℃; for 36h;Inert atmosphere; | An apparatus (a reaction flask, a three-way stopcock, a rotor, and a septum) was set up, the inside of the apparatus was dried with a heat gun, and then the apparatus was purged with argon. 2-l3enzylaniline (1.2 g, 6.48 mmol), tetrahydroffiran (THF), and cyclohexyl isocyanate (0.8 mE, 6.48 mmol) were placed in this order in the reaction flask, and the mixture was stirred at room temperature for 1.5 days. After the completion of the reaction was confirmed by TLC, the solvent was distilled under reduced pressure, and the resulting solid was washed with THF to obtain a target product as a white solid (yield: 65%, 1.30 g).10241] ?H-NMR (600 MHz, CDC13) oe=7.43 (1H, d, J=7.6 Hz), 7.30 (3H, m), 7.26 (1H, s), 7.23-7.19 (2H, m), 7.15 (2H, d, J=7.6 Hz), 5.73 (1H, s), 4.25 (1H, s), 4.00 (2H, s), 3.52 (1H, s), 1.86 (2H, dd, J=12.7, 3.1 Hz), 1.66-1.63 (2H, m), 1.60 (1H, dd, J=7.9, 3.8 Hz), 1.36-1.28 (2H, m), 1.10 (1H, m), 1.01 (2H, m). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | In acetonitrile; at 90℃; for 2h;Inert atmosphere; | An apparatus (a reaction flask, a three-way stopcock, a rotor, a septum, and a Dimroth condenser) was set up, the inside of the apparatus was dried with a heat gun, and then the apparatus was purged with argon. 2-Benzylaniline (1.08 g, 5.90 mmol), acetonitrile, and 2-ethylhexyl isocyanate (1.1 mE, 5.90 mmol) were placed in this order in the reaction flask while cooling with ice, and the mixture was stirred at 90 C. for 2 hours. After the completion of the reaction was confirmed by TLC, the precipitated solid was collected by filtration. The product was purified by washing with acetonitrile to obtain a target product as a white solid (yield: 56%, 1.12 g). 1H NMR (400 MHz, DMSO-d5) oe=7.75 (2H, d, J=7.8 Hz), 7.27 (2H, t, J=7.3 Hz), 7.23-7.15 (3H, m), 7.11 (1H, t, J=7.6 Hz), 7.00 (1H, d, J=7.8 Hz), 6.90 (1H, t, J=7.3 Hz), 6.42 (1H, t, J=5.6 Hz), 3.91 (2H, s), 3.03 (2H, m), 1.40-1.16 (9H, m), 0.89-0.83 (6H, m). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
55% | In toluene; at 110℃; for 72h;Inert atmosphere; | In an argon atmosphere, 2-aminodiphenylmethane(500 mg, 1.80 mmol) was dissolved in toluene (100 mE),octadecyl isocyanate (0.62 mE, 1.80 mmol) was addedthereto, and the mixture was stirred at 110 C. for 3 days.Afier the completion of the reaction was confirmed by TEC,the solvent was concentrated, and the product precipitated asa solid was collected by filtration. The product was purified by washing with acetoneto obtain a monourea compound of formula 7 as a whitesolid (amount: 498 mg, yield: 55%).?H NMR (600 MHz, DMSO-d5) oe 0.85 (t, J6.9Hz, 3H), 1.23 (m, 30H), 1.40 (m, 2H), 3.05 (dt, J5.6, 6.9Hz, 2H), 3.91 (s, 2H), 6.42 (t, J5.5 Hz 1H), 6.90 (dd, J7.6,7.6 Hz, 1H), 6.99 (d, J6.9 Hz, 1H), 7.11 (dd, J6.9, 6.9 Hz,1H), 7.15-7.18 (m, 3H), 7.27 (dd, J7.6, 7.6 Hz, 2H), 7.69(s, 1H), 7.73 (d, J7.6 Hz, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91.6% | With sodium hypochlorite; In water; at 60℃; for 7h; | (3) Into a 2000 mL bottle with a thermometer, put the front batch of o-amidodiphenylmethane, 500 mL of water, 900 g of 12% sodium hypochlorite, heat up to 60 C, and keep the reaction at 60 ± 5 C for 7 h. Into a 2000 mL separatory funnel, the bottom oil was separated, and distillation under reduced pressure was carried out to collect a fraction of 214-216 C / 14 mmHg to obtain 167.6 g of a product, and the purity of the ortho-aminodiphenylmethane in the product was 99.4%.The total yield of the ortho-aminodiphenylmethane product obtained in this example was 91.6% based on o-cyanobenzyl chloride. |
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