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CAS No. : | 7505-81-9 | MDL No. : | MFCD00025469 |
Formula : | C8H10N2O | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | KTDNXQLRLSPQOK-UHFFFAOYSA-N |
M.W : | 150.18 | Pubchem ID : | 101222 |
Synonyms : |
|
Num. heavy atoms : | 11 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.12 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 1.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 43.84 |
TPSA : | 55.12 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) : | -6.31 cm/s |
Log Po/w (iLOGP) : | 1.15 |
Log Po/w (XLOGP3) : | 1.27 |
Log Po/w (WLOGP) : | 0.64 |
Log Po/w (MLOGP) : | 0.91 |
Log Po/w (SILICOS-IT) : | 0.65 |
Consensus Log Po/w : | 0.92 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.84 |
Solubility : | 2.16 mg/ml ; 0.0144 mol/l |
Class : | Very soluble |
Log S (Ali) : | -2.03 |
Solubility : | 1.41 mg/ml ; 0.00941 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -2.41 |
Solubility : | 0.588 mg/ml ; 0.00392 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: | P233-P260-P261-P264-P271-P280-P302+P352-P304-P304+P340-P305+P351+P338-P312-P321-P332+P313-P337+P313-P340-P362-P403-P403+P233-P405-P501 | 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 |
---|---|---|
With phosphorus pentoxide; xylene |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
5.27 g | In acetone; at 100℃; for 4h;Sealed tube; | Ethyl chloroformate (20 mL, 209 mmol) was added to 2-(methylamino)benzamide (10 g, 67 mmol). The vial was sealed and heated to 100 00 for 4h. The ethyl chloroformate was removed under vacuum and the residue loaded onto Biotage 50 g KP-Sil column (2 batches) and eluted with 20 - 100% EtOAc in cyclohexane followed by 0 - 20% MeOH in DCM. 1- methylquinazoline-2,4(1H,3H)-dione (5.27 g) was obtained as a white solid. LCMS (Method T2) Rt = 0.83 mins, mlz 177.06 [M+H]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With ethanol at 100℃; im geschlossenen Rohr und Zerlegen des gebildeten Hydrojodid durch Ammoniak; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride In ethanol for 36h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride In ethanol for 36h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With acetic acid for 3h; Ambient temperature; | |
With acetic acid In ethanol for 12h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | Stage #1: isatoic anhydride; methyl iodide With potassium hydroxide In N,N-dimethyl-formamide at 20℃; Stage #2: With ammonia In water; N,N-dimethyl-formamide at 50℃; for 0.5h; | Synthesis of Naryl-methyl anthranilamide Isatoic anhydride (1.63 g, 10 mmol), KOH (0.67 g, 12 mmol) and DMF (25 mL) were added to a Schlenk tube andthen CH3I (1.3 mL, 20 mmol) was added dropwise. The mixture wasstirred at room temperature overnight. The solution was diluted with ethylacetate, washed with diluted hydrochloric acid, saturated NaHCO3,brine, and dried over anhydrous Na2SO4. The organic phasewas concentrated in vacuo and the crude solid was then purified by crystalizationfrom ethyl acetate. The obtained intermediate (885mg, 5 mmol), 25% ammonia water(10 mL) and DMF (20 mL) were added to a Schlenk tube, heated at 50 oC for 30min. The solution was then cooled to room temperature, diluted with ethylacetate, washed with saturated NH4Cl solution. The organic layer wasdried over anhydrous Na2SO4, concentrated and thenpurified by crystalization to afford the desired substrate 623 mg, and theyield was 83%. white solid. 1H NMR(DMSO, 500 MHz) δ 8.00 (d, J = 5.5Hz, 1H), 7.79 (s, br, 1H), 7.59 (dd, J= 8.0, 1.5 Hz, 1H), 7.29 (t, J = 7.5Hz, 1H), 7.12 (s, br, 1H), 6.62 (d, J= 8.5 Hz, 1H), 6.52 (t, J = 7.5 Hz,1H), 2.78 (d, J = 5.0 Hz, 3H). 13CNMR (DMSO, 125 MHz) δ 172.1, 151.2, 133.1, 129.4, 114.3, 114.2, 111.0, 29.7. |
(i) NaH, DMF, (ii) aq. NH3; Multistep reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In toluene |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With lithium aluminium tetrahydride In 1,4-dioxane Heating; | |
68.5% | Stage #1: 2-methylaminobenzamide With lithium aluminium tetrahydride In 1,4-dioxane at 100℃; for 96h; Inert atmosphere; Stage #2: With sodium hydroxide In 1,4-dioxane; water for 1h; Inert atmosphere; | |
(i) LiAlH4, dioxane, (ii) aq. NaOH; Multistep reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With ammonium hydroxide In acetonitrile at 20℃; | |
97% | With ammonium hydroxide In [D3]acetonitrile at 20℃; | |
87.3% | With ammonium hydroxide for 1.5h; Reflux; |
80% | With ammonium hydroxide Heating; | |
59.6% | With ammonia In ethanol; water at 20 - 100℃; for 0.166667h; Inert atmosphere; | |
59.6% | With ammonium hydroxide In ethanol at 100℃; for 0.25h; | 2-(Methylamino)benzamide 27b A flask (100 mL) was charged with N-methylisatanhydride 6.18 g (34.9 mmol), EtOH (10 mL), the mixturestirred for 10 min, aq. NH3 (30 mL, 26%) was added while stirringand the flask immersed in hot oil bath (100°C) while stirring for 5 min. The mixturewas then cooled to r.t., volatile components were removed (rotary avaporator).The solid residue (5.68 g)was crystallised from EtOH, then from aqueous EtOH and finally from EtOH. Thewhite crystals were dried over P2O5 (132 Pa, 4 h) toobtain 3.125 g(59.6%) of pure amide 27b. Mp158-159°C(Ref. [18] 158-161°C). 1H NMR (300 MHz, CDCl3):d 7.76 (1H, bs),7.38 (dd, 1H, J 1.1 and 7.7), 7.35 (ddd,1H, J 1.7, 7.2 and 8.8), 6.69 (dd, 1H, J 1.1 and 8.8), 6.58 (dt, 1H, J 1.1 and 7.4), 5.83 (bs, 2H), 2.87 (s, 3H) ppm.13CNMR (75 MHz, CDCl3): due to low sample concentration, only thefollowing signals were identified: d 133.7 (CH), 128.3 (CH), 114.4 (CH), 111.4(CH), 29.5 (CH3). C8H10N2O (151.18)calcd. C 63.98, H 6.71, N 18.65; foundC 64.09, H 6.53, N 18.57. |
54% | With ammonium hydroxide In ethanol Heating; | |
With ammonium hydroxide In ethanol | ||
With acetic acid; D,L-valine for 4h; Heating; | ||
With ammonia | ||
With ammonia In water; N,N-dimethyl-formamide at 50℃; for 0.5h; Schlenk technique; | ||
With ammonium hydroxide In water |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | In toluene for 1h; Inert atmosphere; Reflux; | |
In toluene | ||
In xylene |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50% | at 140℃; for 6h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
39% | at 120℃; for 5h; | |
24% | With sulfuric acid; acetic acid for 0.5h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | With acetic acid for 3h; Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | In chloroform for 22h; Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With acetic acid for 3h; Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
66% | With acetic acid for 3h; Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
27% | With triethyl phosphite In water; N,N-dimethyl-formamide overnight; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | at 150℃; for 0.25h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61% | at 160℃; for 0.25h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
66% | at 120 - 150℃; for 0.25h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | at 150℃; for 0.25h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97.7% | Stage #1: cyclopentanone With toluene-4-sulfonic acid In methanol for 0.166667h; Reflux; Stage #2: 2-methylaminobenzamide In methanol for 2h; Reflux; | |
74% | at 150℃; for 0.25h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | With aluminum oxide; 2,3-dicyano-5,6-dichloro-p-benzoquinone for 0.15h; microwave irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With aluminum oxide; 2,3-dicyano-5,6-dichloro-p-benzoquinone for 0.15h; microwave irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | With aluminum oxide; 2,3-dicyano-5,6-dichloro-p-benzoquinone for 0.15h; microwave irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69% | With diphosphorus pentasulfide for 1.5h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | With 4-methyl-morpholine In tetrahydrofuran at 40℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With sodium-exchanged Y-zeolite at 90℃; for 22h; | |
With NaY faujasite at 90℃; for 9h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With sulfuric acid; acetic acid for 0.5h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: sodium methoxide / methanol / 25 °C | ||
Multi-step reaction with 2 steps 1: pyridine 2: aq. KOH / 25 °C / ionic strength 1 M (KCl), also at pH 9.5 and 50 deg C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: tetrahydrofuran / Heating 3: 75 percent / TiCl3, Zn / 1,2-dimethoxy-ethane / 4 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: tetrahydrofuran / Heating 3: 88 percent / TiCl3, Zn / 1,2-dimethoxy-ethane / 67 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: POCl3 / pyridine 2: 2.) 10 percent HCl / 1.) Et2O, a.) 0 deg C to r.t., b.) r.t., 5 h, 2.) 0 deg C, 3 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: POCl3 / pyridine 2: 2) 10 percent HCl / 1.) THF/hexane, a.) 0 deg C to r.t., b.) r.t., 5 h, 2.) 0 deg C, 3 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: POCl3 / pyridine 2: toluene / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: POCl3 / pyridine 2: 2.) 10 percent HCl / 1.) Et2O, a.) 0 deg C to r.t., b.) r.t., 5 h, 2.) 0 deg C, 3 h 3: toluene / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: POCl3 / pyridine 2: 2) 10 percent HCl / 1.) THF/hexane, a.) 0 deg C to r.t., b.) r.t., 5 h, 2.) 0 deg C, 3 h 3: toluene / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: POCl3 / pyridine 2: toluene / Heating 3: 2.) K2CO3 / 1.) THF, r.t., 1 h, 2.) 15 min 4: 93 percent / LDA / hexane; tetrahydrofuran / a) -78 deg C, 0.5 h, b) to -30 deg C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: POCl3 / pyridine 2: toluene / Heating 3: 2.) K2CO3 / 1.) THF, r.t., 1 h, 2.) 15 min |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: POCl3 / pyridine 2: 2.) 10 percent HCl / 1.) Et2O, a.) 0 deg C to r.t., b.) r.t., 5 h, 2.) 0 deg C, 3 h 3: toluene / Heating 4: 2.) K2CO3 / 1.) THF, r.t., 1 h, 2.) 15 min 5: 90 percent / LDA / hexane; tetrahydrofuran / a) -78 deg C, 0.5 h, b) to -30 deg C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: POCl3 / pyridine 2: 2.) 10 percent HCl / 1.) Et2O, a.) 0 deg C to r.t., b.) r.t., 5 h, 2.) 0 deg C, 3 h 3: toluene / Heating 4: 2.) K2CO3 / 1.) THF, r.t., 1 h, 2.) 15 min |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: POCl3 / pyridine 2: 2) 10 percent HCl / 1.) THF/hexane, a.) 0 deg C to r.t., b.) r.t., 5 h, 2.) 0 deg C, 3 h 3: toluene / Heating 4: 2.) K2CO3 / 1.) THF, r.t., 1 h, 2.) 15 min 5: 87 percent / LDA / hexane; tetrahydrofuran / a) -78 deg C, 0.5 h, b) to -30 deg C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: POCl3 / pyridine 2: 2) 10 percent HCl / 1.) THF/hexane, a.) 0 deg C to r.t., b.) r.t., 5 h, 2.) 0 deg C, 3 h 3: toluene / Heating 4: 2.) K2CO3 / 1.) THF, r.t., 1 h, 2.) 15 min |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 50 percent / p-TsOH / 6 h / 140 °C 2: 55 percent / pyridine, acetic anhydride / 4 h / 100 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 91 percent / CHCl3 / 22 h / Ambient temperature 2: 91.2 percent / KOH / ethanol; H2O / 1.5 h / Ambient temperature 3: 93.5 percent / CHCl3 / 3 h / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 91 percent / CHCl3 / 22 h / Ambient temperature 2: 98.5 percent / conc. NH3 / 1.5 h / Ambient temperature 3: 50.9 percent / pyrophosphoryl chloride / 3 h / 40 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 91 percent / CHCl3 / 22 h / Ambient temperature 2: 91.2 percent / KOH / ethanol; H2O / 1.5 h / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 91 percent / CHCl3 / 22 h / Ambient temperature 2: 98.5 percent / conc. NH3 / 1.5 h / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 91 percent / CHCl3 / 22 h / Ambient temperature 2: 60.9 percent / KOH, NH2OH*HCl / ethanol / 5 h / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: 91 percent / CHCl3 / 22 h / Ambient temperature 2: 98.5 percent / conc. NH3 / 1.5 h / Ambient temperature 3: 50.9 percent / pyrophosphoryl chloride / 3 h / 40 °C 4: 41.4 percent / triethylamine / dimethylformamide / 2 h / 60 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: 91 percent / CHCl3 / 22 h / Ambient temperature 2: 98.5 percent / conc. NH3 / 1.5 h / Ambient temperature 3: 50.9 percent / pyrophosphoryl chloride / 3 h / 40 °C 4: 46.7 percent / triethylamine / dimethylformamide / 22.5 h / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: 91 percent / CHCl3 / 22 h / Ambient temperature 2: 98.5 percent / conc. NH3 / 1.5 h / Ambient temperature 3: 50.9 percent / pyrophosphoryl chloride / 3 h / 40 °C 4: 67.3 percent / NaN3 / dimethylformamide / 0.5 h / 80 °C 5: dimethylformamide; H2O / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: 91 percent / CHCl3 / 22 h / Ambient temperature 2: 98.5 percent / conc. NH3 / 1.5 h / Ambient temperature 3: 50.9 percent / pyrophosphoryl chloride / 3 h / 40 °C 4: 67.3 percent / NaN3 / dimethylformamide / 0.5 h / 80 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: 91 percent / CHCl3 / 22 h / Ambient temperature 2: 98.5 percent / conc. NH3 / 1.5 h / Ambient temperature 3: 50.9 percent / pyrophosphoryl chloride / 3 h / 40 °C 4: 70.8 percent / NaH / tetrahydrofuran / 1 h / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: 91 percent / CHCl3 / 22 h / Ambient temperature 2: 98.5 percent / conc. NH3 / 1.5 h / Ambient temperature 3: 50.9 percent / pyrophosphoryl chloride / 3 h / 40 °C 4: 63.4 percent / ammonia / dimethylformamide / 1 h | ||
Multi-step reaction with 3 steps 1: 91 percent / CHCl3 / 22 h / Ambient temperature 2: 60.9 percent / KOH, NH2OH*HCl / ethanol / 5 h / Ambient temperature 3: 62.6 percent / naphtalene / 3 h / 190 - 200 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: 91 percent / CHCl3 / 22 h / Ambient temperature 2: 98.5 percent / conc. NH3 / 1.5 h / Ambient temperature 3: 50.9 percent / pyrophosphoryl chloride / 3 h / 40 °C 4: 61.4 percent / H2O / 3 h / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
(2-Carbamoyl-phenyl)-methyl-carbamic Acid 4-(5-trifluoromethyl-pyridin-2-yloxy)-phenyl Ester (2-Carbamoyl-phenyl)-methyl-carbamic Acid 4-(5-trifluoromethyl-pyridin-2-yloxy)-phenyl Ester The title product was prepared from 2-(methylamino)benzamide and 4-(5-trifluoromethylpyridin-2-yloxy)-phenyl chloroformate, preparative HPLC (method C) (57%, light yellow oil). HPLC-MS m/z=454.2 (M+Na), Rt: 3.66 min. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1 N-[[[2-(Aminocarbonyl)phenyl]methylamino]thioxomethyl]benzamide EXAMPLE 1 N-[[[2-(Aminocarbonyl)phenyl]methylamino]thioxomethyl]benzamide To a stirred mixture of 3.0 g. of 2-methylaminobenzamide in 150 ml of ether was added dropwise, a solution of 3.26 g of benzoyl isothiocyanate in 50 ml of ether over 15 minutes. The mixture was stirred overnight, then the solid was collected, giving 5.2 g of the desired product as cream-colored crystals, mp 147°-150° C. | ||
1 N-(1,4-Dihydro-1-methyl-4-oxo-2-quinazolinyl)benzamide EXAMPLE 1 N-(1,4-Dihydro-1-methyl-4-oxo-2-quinazolinyl)benzamide To a stirred mixture of 12.0 g of 2-methylaminobenzamide in 300 ml of ether was added dropwise, a solution of 11.8 ml of benzoyl isothiocyanate in 100 ml of ether over 15 minutes. The mixture was stirred overnight, then the solid was collected, giving 22.4 g of N-[[[2-(aminocarbonyl)phenyl]methylamino]thioxomethyl]benzamide. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium acetate In ethanol; water | XV Preparation of 2-(2-[4-phenyl-1-piperazinyl]ethylamino)-N-methylbenzamide. (763-423) EXAMPLE XV Preparation of 2-(2-[4-phenyl-1-piperazinyl]ethylamino)-N-methylbenzamide. (763-423) N-Methylanthranilamide (14 g), 28 g 1-(2-chloroethyl)-4-phenylpiperazine hydrochloride, 17.5 g sodium acetate and 100 ml water were refluxed 24 hrs, 100 ml water and 100 ml conc NH4 OH added and the solid filtered and dissolved in 125 ml hot 60% ethanol. After stirring for 4 days, the solid was filtered to give 15 g, m.98-100. The solid was dissolved in 800 ml dry ether and acidified with dry HCl gas dissolved in ether. The solid as filtered and dried to give the HCl salt. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69% | With platinum(II) bromde In methanol at 80℃; for 30h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
59% | With 1H-imidazole In tetrahydrofuran at 20℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With 1H-imidazole In tetrahydrofuran at 20℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: toluene / 1 h / Inert atmosphere; Reflux 2: carbonyl bis(hydrido)tris(triphenylphosphine)ruthenium(II); norbornene / toluene / 20 h / 135 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With palladium diacetate; sodium 3-(diphenylphosphanyl)benzenesulfonate In water at 120℃; for 48h; sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: copper diacetate; palladium diacetate; potassium iodide / acetonitrile / 60 °C / 760.05 Torr 2: ammonium hydroxide / [D3]acetonitrile / 20 °C | ||
Multi-step reaction with 3 steps 1: palladium diacetate; potassium iodide / acetonitrile / 5 h / 20 °C / 760.05 Torr 2: carbon monoxide; copper diacetate; potassium iodide / acetonitrile / 60 °C / 760.05 Torr 3: ammonium hydroxide / [D3]acetonitrile / 20 °C | ||
Multi-step reaction with 4 steps 1: palladium diacetate; potassium iodide / acetonitrile / 5 h / 20 °C / 760.05 Torr 2: dichloromethane / 12 h / 20 °C / Inert atmosphere 3: carbon monoxide; copper diacetate; potassium iodide / acetonitrile / 60 °C / 760.05 Torr 4: ammonium hydroxide / [D3]acetonitrile / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: carbon monoxide; copper diacetate; potassium iodide / acetonitrile / 60 °C / 760.05 Torr 2: ammonium hydroxide / [D3]acetonitrile / 20 °C | ||
Multi-step reaction with 3 steps 1: dichloromethane / 12 h / 20 °C / Inert atmosphere 2: carbon monoxide; copper diacetate; potassium iodide / acetonitrile / 60 °C / 760.05 Torr 3: ammonium hydroxide / [D3]acetonitrile / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90.2% | In 1,4-dioxane at 100℃; for 1.33333h; Inert atmosphere; diastereoselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: lithium aluminium tetrahydride / 1,4-dioxane / 96 h / 100 °C / Inert atmosphere 1.2: 1 h / Inert atmosphere 2.1: diethyl ether / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: lithium aluminium tetrahydride / 1,4-dioxane / 96 h / 100 °C / Inert atmosphere 1.2: 1 h / Inert atmosphere 2.1: diethyl ether / Inert atmosphere 3.1: 1,4-dioxane / 35 h / 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
15% | Stage #1: N-Methylanthranilic acid In dichloromethane; N,N-dimethyl-formamide for 4.5h; Inert atmosphere; Reflux; Cooling with ice; Stage #2: With ammonia In dichloromethane; water; N,N-dimethyl-formamide at 20℃; for 6h; Inert atmosphere; | |
Multi-step reaction with 2 steps 1: tetrahydrofuran / 3 h / 20 °C / Inert atmosphere 2: ammonium hydroxide / water; dichloromethane / 1 h / 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With dmap In chloroform at 70℃; for 1h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | With copper(l) iodide; caesium carbonate; N,N`-dimethylethylenediamine In 1,4-dioxane for 30h; Inert atmosphere; Reflux; | General methods for the tandem reaction of 2-aminobenzamide with vinyl halide General procedure: To a solution of 2-aminobenzamide 1a-e (1.0 mmol), CuI (19.0 mg, 10 mol% or 38.1 mg, 20 mol%) and Cs2CO3 (977.5 mg, 3 mmol) in dioxane (2 mL) were added DMEDA (23.2 mg, 20 mol% or 46.5 mg, 40 mol%) and vinyl halide 2a-e (2 eq. or 3 eq.) under nitrogen atmosphere. The reaction mixture was heated to reflux (bath temperature: 110 °C). Upon completion of the reaction, EtOAc (20 mL) and activated carbon (50.0 mg) were added, and the slurry was filtrated. The organic layer was washed with water and concentrated. Then, the residue was purified by column chromatography with EtOAc and hexane to afford the title compound 3a-j. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | With copper(l) iodide; caesium carbonate; N,N`-dimethylethylenediamine In 1,4-dioxane for 24h; Inert atmosphere; Reflux; | General methods for the tandem reaction of 2-aminobenzamide with vinyl halide General procedure: To a solution of 2-aminobenzamide 1a-e (1.0 mmol), CuI (19.0 mg, 10 mol% or 38.1 mg, 20 mol%) and Cs2CO3 (977.5 mg, 3 mmol) in dioxane (2 mL) were added DMEDA (23.2 mg, 20 mol% or 46.5 mg, 40 mol%) and vinyl halide 2a-e (2 eq. or 3 eq.) under nitrogen atmosphere. The reaction mixture was heated to reflux (bath temperature: 110 °C). Upon completion of the reaction, EtOAc (20 mL) and activated carbon (50.0 mg) were added, and the slurry was filtrated. The organic layer was washed with water and concentrated. Then, the residue was purified by column chromatography with EtOAc and hexane to afford the title compound 3a-j. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
7% | Stage #1: ferrocene boronic acid; 2-methylaminobenzamide With 1H-imidazole; iron(III) chloride In water; dimethyl sulfoxide; toluene at 20℃; for 0.25h; Stage #2: In water; dimethyl sulfoxide; toluene for 1h; Dean-Stark; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
47% | With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate; potassium carbonate In toluene at 110℃; for 24h; Sealed tube; Inert atmosphere; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
42% | With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate; potassium carbonate In toluene at 110℃; for 24h; Sealed tube; Inert atmosphere; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
40% | With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate; potassium carbonate In toluene at 110℃; for 24h; Sealed tube; Inert atmosphere; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
44% | With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate; potassium carbonate In toluene at 110℃; for 24h; Sealed tube; Inert atmosphere; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84.6% | Stage #1: 2-methylaminobenzamide; C25H28ClNO4 In tetrahydrofuran at 20 - 25℃; for 0.5h; Stage #2: With triethylamine In tetrahydrofuran at 20 - 25℃; for 1h; | 50.1 Step 1 A 50 mL round bottom flask was loaded with 4a (900 mg, 2.036 mmol), Compound 50.1 (150 mg, 1 mmol) and 10 mL of tetrahydrofuran. The mixture was stirred at room temperature for 30 minutes, added with 10 drops of triethylamine, and stirred for 1 hour at room temperature. The reaction was monitored by LC-MS until completion. The reaction solution was washed with 1 M hydrochloric acid solution, extracted with EA, after which the organic layer was dried, concentrated and purified by combiflash (0-70% EA/n-hexane) to give Compound 50-1 (570 mg, 84.6%) as a white solid. MS m/z (ESI): 556.0 [M+H]+ |
Tags: 7505-81-9 synthesis path| 7505-81-9 SDS| 7505-81-9 COA| 7505-81-9 purity| 7505-81-9 application| 7505-81-9 NMR| 7505-81-9 COA| 7505-81-9 structure
[ 1226805-88-4 ]
5-Amino-2-(dimethylamino)benzamide
Similarity: 0.95
[ 1226805-88-4 ]
5-Amino-2-(dimethylamino)benzamide
Similarity: 0.95
[ 1226805-88-4 ]
5-Amino-2-(dimethylamino)benzamide
Similarity: 0.95
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Code | Phrase |
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P220 | Keep/Store away from clothing/combustible materials. |
P221 | Take any precaution to avoid mixing with combustibles |
P222 | Do not allow contact with air. |
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P265 | Wash skin thouroughly after handling. |
P270 | Do not eat, drink or smoke when using this product. |
P271 | Use only outdoors or in a well-ventilated area. |
P272 | Contaminated work clothing should not be allowed out of the workplace. |
P273 | Avoid release to the environment. |
P280 | Wear protective gloves/protective clothing/eye protection/face protection. |
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P282 | Wear cold insulating gloves/face shield/eye protection. |
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Code | Phrase |
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P304 | IF INHALED: |
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P306 | IF ON CLOTHING: |
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P321 | |
P322 | |
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P371 | In case of major fire and large quantities: |
P372 | Explosion risk in case of fire. |
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P376 | Stop leak if safe to do so. Oxidising gases (section 2.4) 1 |
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P378 | |
P380 | Evacuate area. |
P381 | Eliminate all ignition sources if safe to do so. |
P390 | Absorb spillage to prevent material damage. |
P391 | Collect spillage. Hazardous to the aquatic environment |
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P301 + P312 | IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell. |
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P302 + P334 | IF ON SKIN: Immerse in cool water/wrap in wet bandages. |
P302 + P350 | IF ON SKIN: Gently wash with plenty of soap and water. |
P303 + P361 + P353 | IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower. |
P304 + P312 | IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell. |
P304 + P340 | IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing. |
P304 + P341 | IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P305 + P351 + P338 | IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. |
P306 + P360 | IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes. |
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P332 + P313 | IF SKIN irritation occurs: Get medical advice/attention. |
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P335 + P334 | Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages. |
P337 + P313 | IF eye irritation persists: Get medical advice/attention. |
P342 + P311 | IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician. |
P370 + P376 | In case of fire: Stop leak if safe to Do so. |
P370 + P378 | In case of fire: |
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P370 + P380 + P375 | In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion. |
P371 + P380 + P375 | In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion. |
Storage | |
Code | Phrase |
P401 | |
P402 | Store in a dry place. |
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P405 | Store locked up. |
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P420 | Store away from other materials. |
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Disposal | |
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Physical hazards | |
Code | Phrase |
H200 | Unstable explosive |
H201 | Explosive; mass explosion hazard |
H202 | Explosive; severe projection hazard |
H203 | Explosive; fire, blast or projection hazard |
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H220 | Extremely flammable gas |
H221 | Flammable gas |
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H223 | Flammable aerosol |
H224 | Extremely flammable liquid and vapour |
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H228 | Flammable solid |
H229 | Pressurized container: may burst if heated |
H230 | May react explosively even in the absence of air |
H231 | May react explosively even in the absence of air at elevated pressure and/or temperature |
H240 | Heating may cause an explosion |
H241 | Heating may cause a fire or explosion |
H242 | Heating may cause a fire |
H250 | Catches fire spontaneously if exposed to air |
H251 | Self-heating; may catch fire |
H252 | Self-heating in large quantities; may catch fire |
H260 | In contact with water releases flammable gases which may ignite spontaneously |
H261 | In contact with water releases flammable gas |
H270 | May cause or intensify fire; oxidizer |
H271 | May cause fire or explosion; strong oxidizer |
H272 | May intensify fire; oxidizer |
H280 | Contains gas under pressure; may explode if heated |
H281 | Contains refrigerated gas; may cause cryogenic burns or injury |
H290 | May be corrosive to metals |
Health hazards | |
Code | Phrase |
H300 | Fatal if swallowed |
H301 | Toxic if swallowed |
H302 | Harmful if swallowed |
H303 | May be harmful if swallowed |
H304 | May be fatal if swallowed and enters airways |
H305 | May be harmful if swallowed and enters airways |
H310 | Fatal in contact with skin |
H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
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 |
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