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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
Synonyms: Potassium carbonate
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Beteck, Richard M ; Legoabe, Lesetja J ; Dube, Phelelisiwe S ; Jordaan, Audrey ; Warner, Digby F ;
Abstract: Diphenyl ether and quinoline based compounds have been reported to show antibacterial activity. Against Mycobacterium tuberculosis, drug targets inhibited by diphenyl ether compounds are reportedly different from those perturbed by quinoline based antitubercular hits/drugs. Herein, we conceptualized and synthesized novel molecules incorporating quinoline and diphenyl ether moieties. The antitubercular property of the synthesized compounds were measured in vitro using Tween 80 and Tyloxapol supplemented growth media. Compounds in this study generally showed sub micromolar antitubercular activity in tween 80/ albumin supplemented growth medium, and moderate to poor activity in tyloxapol/casitone supplemented growth medium. Compound 4e, havin a trimethylenediamine moiety and low melting point of 68°C, emerged as the hit compound, possessing MIC90 value of 0.2 µM. 4e is non-cytotoxic when tested against normal human cell line, exhibiting CC50 value > 20 µM.
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Keywords: Quinoline ; Diphenyl ether ; Tuberculosis ; Cytotoxicity ; Antitubercular
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Gendron, David ; Labrecque, Josée ;
Abstract: This report discusses the synthesis of a biosourced divanillin derivative obtained by Knoevenagel condensation. The compound was fully characterized by proton (1H), carbon (13C), heteronuclear single quantum coherence (HSQC), homonuclear correlation spectroscopy (COSY), and heteronuclear multiple bond correlation (HMBC) NMR, as well as high-resolution mass spectroscopy (HRMS). We also investigated the optical properties through UV-visible spectroscopy and Fourier-transform infrared (FTIR) spectroscopy. At last, the thermal properties of this divanillin derivative were evaluated by thermogravimetric analysis (TGA) as well as differential scanning calorimetry (DSC).
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Keywords: vanillin ; biosourced ; Knoevenagel condensation ; dyes ; organic pigments
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MR Imaging Reveals Dynamic Aggregation of Multivalent Glycoconjugates in Aqueous Solution
Tang, Jian-Hong ; Luo, Minrui ; Tsao, Wilhelmina ; Waters, Emily Alexandria ; Parigi, Giacomo ; Luchinat, Claudio , et al.
Abstract: Glycoconjugates forming from the conjugation of carbohydrates to other biomolecules, such as proteins, lipids, or other carbohydrates, are essential components of mammalian cells and are involved in numerous biological processes. Due to the capability of sugars to form multiple hydrogen bonds, many synthetic glycoconjugates are desirable biocompatible platforms for imaging, diagnostics, drugs, and supramolecular self-assemblies. Herein, we present a multimeric galactose functionalized paramagnetic gadolinium (Gd(III)) chelate that displays spontaneous dynamic aggregation in aqueous conditions. The dynamic aggregation of the Gd(III) complex was shown by the concentration-dependent magnetic resonance (MR) relaxation measurements, nuclear magnetic resonance dispersion (NMRD) analysis, and dynamic light scattering (DLS). Notably, these data showed a nonlinear relationship between magnetic resonance relaxation rate and concentrations (0.03−1.35 mM), and a large DLS hydrodynamic radius was observed in the high-concentration solutions. MR phantom images were acquired to visualize real-time dynamic aggregation behaviors in aqueous solutions. The in situ visualization of the dynamic self-assembling process of multivalent glycoconjugates has rarely been reported.
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Qing Yun Li ; Leigh Anna Hunt ; Kalpani Hirunika Wijesinghe ; Christine Curiac ; Ashley Williams ; Amala Dass , et al.
Abstract: Strong photoinduced oxidants are important to organic synthesis and solar energy conversion, to chemical fuels or electric. For these applications, visible light absorption is important to solar energy conversion and long-lived excited states are needed to drive catalysis. With respect to these desirable qualities, a series of five 5,6-dicyano[2,1,3]benzothiadiazole (DCBT) dyes are examined as organic chromophores that can serve as strong photooxidants in catalytic systems. The series utilizes a DCBT core with aryl groups on the periphery with varying electron donation strengths relative to the core. The dyes are studied via both steady-state and transient absorption and emission studies. Additionally, computational analysis, voltammetry, crystallography, and absorption spectroelectrochemistry are also used to better understand the behavior of these dyes. Ultimately, a strong photooxidant is arrived at with an exceptionally long excited state lifetime for an organic chromophore of 16 µs. The long-lived excited state photosensitizer is well-suited for use in catalysis, and visible light driven photosensitized water oxidation is demonstrated using a water-soluble photosensitizer.
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Purchased from AmBeed: 54512-79-7 ; 5798-75-4 ; 328-70-1 ; 586-76-5 ; 22385-77-9 ; 3109-63-5 ; 23783-42-8 ; 3375-31-3 ; 1122-58-3 ; 479094-62-7 ; 75-98-9 ; 51364-51-3 ; 538-75-0 ; 584-08-7 ; 1122-91-4 ; 123-30-8 ; 108-88-3 ; 109-77-3 ; 64-19-7 ; 603-35-0
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Highly selective catalytic transfer hydrodeuteration of cyclic alkenes
Hintzsche, Samuel J. ; Vang, Zoua Pa ; Rivera Torres, Emanuel ; Podoski, Mykaela ; Clark, Joseph R. ;
Abstract: Selective deuterium installation into small molecules is becoming increasingly desirable not only for the elucidation of mechanistic pathways and studying biological processes but also because of deuterium's ability to favorably adjust the pharmacokinetic parameters of bioactive molecules. Fused bicyclic moieties, especially those containing heteroatoms, are prevalent in drug discovery and pharmaceuticals. Herein, we report a copper-catalyzed transfer hydrodeuteration of cyclic and heterocyclic alkenes, which enables the synthesis of chromans, quinolinones, and tetrahydronaphthalenes that are precisely deuterated at the benzylic position. We also demonstrate the ability to place one deuterium atom at the homobenzylic site of these scaffolds with high regioselectivity by swapping transfer reagents for their isotopic analogs. Furthermore, examples of chemoselective transfer hydrogenation and transfer deuteration are disclosed, allowing for the simultaneous incorporation of two vicinal hydrogen or deuterium atoms into a double bond.
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Keywords: copper ; deuteration ; hydrodeuteration ; hydrogenation ; transition metal catalysis
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Purchased from AmBeed: 6836-19-7 ; 14243-64-2 ; 19315-93-6 ; 1810-66-8 ; 584-08-7 ; 189114-61-2 ; 447-53-0
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CAS No. : | 584-08-7 |
Formula : | K2CO3 |
M.W : | 138.21 |
SMILES Code : | [O-]C([O-])=O.[K+].[K+] |
Synonyms : |
Potassium carbonate
|
MDL No. : | MFCD00011382 |
InChI Key : | BWHMMNNQKKPAPP-UHFFFAOYSA-L |
Pubchem ID : | 11430 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H315-H319 |
Precautionary Statements: | P264-P270-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330-P501 |
* 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 |
---|---|---|
78% | With sodium cyanoborohydride; benzaldehyde; acetic acid In tetrahydrofuran; methanol | 3. 4-Benzyl-2-hydroxymethylpiperazine To a cooled (0° C.) and stirred solution of Intermediate 1 (22 g, 57 mmol), acetic acid (9.7 mL, 171 mmol) and sodium cyanoborohydride (7.16 g, 114 mmol) in methanol (440 mL) was added benzaldehyde (5.8 mL, 57 mmol). The cooling bath was removed and the mixture stirred at room temperature for 3 h. Saturated K2 CO3 solution (200 mL) was added and the mixture stirred for 15 min. The solvents were evaporated and the residue partitioned between CH2 Cl2 (2*400 mL) and water (500 mL). The combined organic layers were dried (Na2 SO4) and evaporated. The residue was chromatographed on silica gel, eluding with CH2 Cl2: MeOH (95:5) to afford an inseparable mixture of 4-benzylpiperazine-2-carboxylic acid methyl ester and the corresponding ethyl ester (5.33 g, 40percent), in a 7:1 ratio respectively. To a solution of the esters (5.33 g, 22.8 mmol) in THF (200 mL) was added LiAl H4 (22.8 mL of a 1.0M solution in ether) dropwise at -10° C. Stirring was continued at -10° C. for 2.5 h. After this time saturated Na2 SO4 solution (30 mL) was added and the cooling bath removed. Stirring was continued at room temperature for 10 min then the mixture was filtered and the filtrate evaporated. The residue was chromatographed on silica gel, eluding with CH2 Cl2:MeOH:NH3 (90:8:1-->60:8:1) to afford the title compound (3.7 g, 78percent) as a colourless oil. 1 H NMR (360 MHz, CDCl3) δ 1.89-1.95 (1H, m), 2.08-2.30 (3H, m), 2.68-2.71 (2H, m), 2.86-3.04 (3H, m), 3.45-3.60 (4H, m), 7.13-7.32 (5H, m). MS (ES+) 207 (M+1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In dichloromethane; acetonitrile; | PART A -- Preparation of methyl 3-fluoro-4-[2-(2-ethoxyethoxy)-ethoxy]-benzoate. Into a 500-ml, round-bottom flask equipped with a magnetic stirrer, heating mantle and condenser were placed 5.7 g (33.5 mmol) <strong>[403-01-0]methyl 3-fluoro-4-hydroxybenzoate</strong>, 8.5 g (43.2 mmol) 1-bromo-2-(2-ethoxyethoxy)-ethane, 23.2 g of powdered anhydrous potassium carbonate and 350 ml acetonitrile. After stirring the reaction mixture under reflux for four hours, TLC analysis showed that none of the phenolic starting material remained. Three hundred ml of the acetonitrile was then distilled off and 300 ml dichloromethane was added. The reaction mixture was filtered through Celite and the solids were washed thoroughly with dichloromethane. Evaporation of the filtrate yielded product in the form of a yellow oil. Purification by flash chromatography on silica gel with 4percent ethyl ether in dichloromethane, followed by low temperature recrystallization from pentane, yielded 0.55 g of white crystals, 89percent, m.p. 33-36.5°C. The structure was confirmed by infrared, nuclear magnetic resonance and mass spectral analyses. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
EXAMPLE II Synthesis of 4,4'-Bis-[9-(3,6-diphenylcarbazolyl)]-1-1,1'-biphenyl In a 50 milliliter round bottom flask there were added 4,4'-diiodo-1,1'-biphenyl (2.1 grams), 3,6-diphenyl carbazole (3.3 grams), potassium carbonate powder (1.4 grams), copper sulfate pentahydrate (0.06 grams), and 5 milliliters of tridecane. The resulting mixture was heated to 230° C. and stirred at this temperature under argon for 24 hours. After cooling to room temperature (~23° C.), the solids content resulting was ground into slurry, which slurry was then transferred to a filtration funnel, washed with hexane to remove the tridecane, followed by washing with 3 percent hydrochloric acid and water. The solid resulting was then dissolved in hot toluene. The insoluble residue was filtered hot. After cooling to room temperature, the product was crystallized from the solution to yield 2.3 grams of 4,4'-bis-[9-(3,6-diphenylcarbazolyl)]-1,1'-biphenyl as a yellowish powder. This compound had a melting point of 294° C. Its chemical structure was confirmed by proton analysis. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With copper; In 5,5-dimethyl-1,3-cyclohexadiene; ethyl acetate; | Step 2 5-(5-chloro-2-oxo-2H-pyridin-1-yl)-pyrazine-2-carboxylic acid methyl ester <strong>[4214-79-3]5-Chloro-2-pyridinol</strong> (1.43 g, 11.05 mmol), the bromide from step 1 (2.39 g, 11.05 mmol), copper (0.021 g, 0.33 mmol) and K2 CO3 (1.68 g, 12.15 mmol) were heated at 120° C. for 3 hrs. Xylene (2 ml) was added and heating was continued at 1 reflux for 2 hrs. The reaction mixture was cooled, diluted with EtOAc and water and the pH was adjusted to 9 with NH4 Cl. The aqueous layer was extracted with EtOAc (2*) and the combined organic extracts were washed with brine, dried (Na2 SO4) and evaporated in vacuo. The residue was chromatographed (silica gel, EtOAc: hexanes 20:80 to EtOAc: CH2 Cl2 10:90 gradient elution) to afford the title compound as a solid. 1 H NMR (400 MHz, CDCl3) delta 9.60 (d, J=1.3 Hz, 1H), 9.23 (d, J=1.3 Hz,1H), 8.13 (d, J=2.9 Hz,1H), 7.38(dd, J=9.8 and 2.9 Hz, 1H), 6.66(d, J=9.7 Hz, 1H) and 4.07 (s, 3H) ppm. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With copper; | Step 1 5-Chloro-5'-methyl-[1,2']bipyridinyl-2-one <strong>[4214-79-3]5-Chloro-2-pyridinol</strong> (2.26 g, 17.4 mmol), 2-bromo-5-methylpyridine (3.00 g, 17.4 mmol), copper (0.022 g, 0.35 mmol) and K2 CO3 (2.66 g, 19.2 mmol) were heated at 180° C. for 16 hrs. The brown reaction mixture was cooled, diluted with EtOAc and washed with saturated NaHCO3. The aqueous layer was extracted with EtOAc (2*) and the combined organic extracts were washed with brine, dried (Na2 SO4) and evaporated in vacuo. The residue was chromatographed (silica gel, EtOAc: CH2 Cl2 20:80 to 50:50 gradient elution) to afford the title compound as a white solid. 1 H NMR (400 MHz, CDCl3) delta 8.37 (s, 1H), 7.96(d, J=3.0 Hz, 1H), 7.83 (d, J=8.4 Hz, 1H), 7.65(dd, J=2.4 and 8.2 Hz, 1H), 7.32(dd, J=2.9 and 9.7 Hz, 1H), 6.61(d, J=9.7 Hz, 1H) and 2.39(s,3H)ppm. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With copper; | Step 1 5-Chloro-1-(4-hydroxymethyl-phenyl)-1H-pyridin-2-one <strong>[4214-79-3]5-Chloro-2-pyridinol</strong> (0.61 g, 4.7 mmol), 4-iodobenzyl-alcohol (1.00 g, 4.27 mmol), Copper (0.27 g, 4.27 mmol) and K2 CO3 (0.65 g, 4.70 mmol) were heated at 180° C. for 16 hrs. The brown reaction mixture was cooled, diluted with EtOAc and washed with saturated NaHCO3. The aqueous layer was extracted with EtOAc (2*) and the combined organic extracts were washed with brine, dried (Na2 SO4) and evaporated in vacuo. The residue was chromatographed (silica gel, EtOAc as eluent) to afford the title compound as a white solid. 1 H NMR (400 MHz, CD3 OD) delta 7.74 (d, J=2.7 Hz, 1H), 7.59 (dd, J=3.0 and 9.6 Hz, 1H), 7.51 (d, J=8.6 Hz, 2H), 7.37 (d, J=8.4 Hz, 2H), 6.61 (d, J=9.4 Hz, 1H) and 4.67(s,1H) ppm. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
56% | In diethyl ether; acetone; | 3-Chloro-4-methoxybenzaldehyde A mixture of 3-chloro-4-hydroxybenzaldehyde (25 g, 160 mmol), iodomethane (27.25 g, 192 mmol), K2 CO3 (granular, anhydrous) (110.6 g, 800 mmol), and acetone (300 mL) was refluxed for 3 hours. The reaction mixture was then cooled to room temperature. Diethyl ether (500 mL) was added and the mixture was filtered through paper to remove the inorganic solids. the filtrate was evaporated under reduced pressure, dissolved in diethyl ether (800 mL), and washed with 0.1 N NaOH (3*100 mL). The organic layer was dried (Na2 SO4) and evaporated under vacuum to yield 24 g, 92percent yield of crude product. This material was further purified by chromatography on silica gel (50 mm*30 cm) (elution with hexane-EtOAc, 5:1) to give 15.02 g, 56percent yield of a white solid: TLC (hexane-EtOAc, 5:1) Rf =0.24; GC Rt =4.75 min; MS (EI) m/z 170(M+), 172(M+2). |
56% | In diethyl ether; acetone; | 3-Chloro-4-methoxybenzaldehyde A mixture of 3-chloro-4-hydroxybenzaldehyde (25 g, 160 mmol), iodomethane (27.25 g, 192 mmol), K2 CO3 (granular, anhydrous) (110.6 g, 800 mmol), and acetone (300 mL) was refluxed for 3 hours. The reaction mixture was then cooled to room temperature. Diethyl ether (500 mL) was added and the mixture was filtered through paper to remove the inorganic solids. the filtrate was evaporated under reduced pressure, dissolved in diethyl ether (800 mL), and washed with 0.1N NaOH (3*100 mL). The organic layer was dried (Na2 SO4) and evaporated under vacuum to yield 24 g, 92percent yield of crude product. This material was further purified by chromatography on silica gel (50 mm*30 cm) (elution with hexane-EtOAc, 5:1) to give 15.02 g, 56percent yield of a white solid: TLC (hexane-EtOAc, 5:1) Rf =0.24; GC Rt =4.75 min; MS (EI) m/z 170(M+), 172(M+2). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In sodium hydroxide; hexane; ethyl acetate; acetone; | PREPARATION 1 5-Benzyloxy-2-hydroxyacetophenone To 2,5-dihydroxyacetophenone (30 g, 0.197 mol) dissolved in 600 ml acetone was added benzyl bromide (24.64 ml, 1.05 equiv) and K2 CO3 (68.0 g, 0.492 mol). The mixture was heated at reflux under N2 for 2 days, then cooled to room temperature, filtered and stripped of solvent in vacuo. The residue was taken up in 500 ml ethyl acetate, washed 3* with ice cold IN NaOH, 2* with H2 O and 2* with brine, dried (Na2 SO4), stripped to solids, and chromatographed on silica gel using 9:1 hexane:ethyl acetate as eluant to yield 35 g of purified title product. A portion was recrystallized as needles from hexane; mp 68-70 C.; Anal. C 74.37, H 5.69, calcd. C 74.36, H 5.82, 1 H-NMR (300 MHz, CDCl3) delta (ppm) 2.6 (s, 3H), 5.05 (s, 2 H), 6.9 (d, 1H), 7.1-7.45 (m, 7H), 11.85 (s, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | In benzene; | EXAMPLE 5 5,5-Dideutero-<strong>[5650-52-2]4,5-dihydro-6H-cyclopenta[b]thiophen-6-one</strong> To a solution of <strong>[5650-52-2]4,5-dihydro-6H-cyclopenta[b]thiophen-6-one</strong> (10.4 g, 75 mmol) in dry benzene (100 mL) was added solid K2 CO3. The mixture was heated to reflux under nitrogen, CD3 OD (10 g) was carefully added, and heating at reflux was continued for 1 hour. After fitting a distillation head to the reaction flask, methanol was removed by heating until the temperature of the distillate reached 77 C. Another portion of CD3 OD was then added, the reflux condenser was refitted and heating at reflux was resumed for 0.5 hour. This process was repeated two more times. After the final removal of methanol, the dark purple mixture was diluted with CH2 Cl2, treated with activated charcoal and filtered through diatomaceous earth [Celite (trademark)]. The resulting clear solution was concentrated in vacuo to leave a light yellow solid (10.5 g, 100%). 1 H NMR: delta 7.87 (d, J=4.5 Hz, 1 H), 7.02 (d, J=4.5 Hz, 1 H), 3.02 (s, 2 H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In propan-1-ol; | Preparation of N-(2-Pyrimidinyl)ethylenediamine a)N-Boc-N'-(2-Pyrimidinyl)ethylenediamine N-(Boc)ethylenediamine (0.80 g, 5.0 mmol) (Syn. Commun. 1990, 20, 255-264) was dissolved in 1-propanol (12 mL) and treated with K2 CO3 (1.2 g, 9.0 mmol), followed by 2-chloropyrimidine (0.91 g, 8.0 mmol), and the mixture was heated to reflux for 24 h. The reaction mixture was poured into H2 O (30 mL) and extracted with EtOAc (3*30 mL). The combined organic fractions were dried (MgSO4) and concentrated to give the title compound as a yellow solid (1.6 g): MS (ES) m/e 238.9 [M+H]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With ammonia; sodium formate; In diethyl ether; water; | EXAMPLE 1 4,6-Dimethoxypyrimidine 5.0 g of dimethyl-1,3-propanediimidate dihydrochloride was added by vigorous stirring to a mixture of 25 ml of CH2 Cl2 and 25 ml of aqueous K2 CO3 solution (300 g of K2 CO3 /1 solution). After 5 minutes the organic phase was separated and the aqueous phase was extracted with 10 ml of Ch2 Cl2. The combined organic phases were dried on Na2 SO4 and filtered. A freshly prepared mixture of 2.5 g of formyl acetate [produced from acetyl choloride and sodium formate according to Muramatsu et al., Bull. Chem. Soc., Japan, 38, (1965), p. 244] in 2 ml of diethyl ether was added at 0 C. to the above solution of the diimidate and stirred for two hours at this temperature. A small amount of ammonia gas was introduced (or ethereal ammonia solution was added) so that the reaction mixture showed an approximately neutral reaction with moistened pH paper. After another hour of stirring at 0 C., 10 ml of water was added. The organic phase was separated, dried on Na2 SO4 and gently concentrated by evaporation. After distillation in a bulb tube furnace (product fraction: 110 C./16 mbar) the product was obtained as a colorless oil, which gradually solidified when allowed to stand. The yield of the product was: 2.4 g, which was 66.3 percent relative to the dihydrochloride used with a product content of 96 percent (GC). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
189.49 g (96%) | With sodium hydroxide; In chloroform; water; acetonitrile; | Step 2 Synthesis of 2-chloro-3,4-dimethoxybenzaldehyde 184 g (0.986 mol) of 2-chloro-3-hydroxy-4-methoxybenzaldehyde was dissolved in 2 l of CH3 CN. 204 g (1.476 mol) of K2 CO3 and 298 g (2.096 mol) of CH3 I were added to the solution, which was heated under reflux for 4 hours. After cooling, the crystals were separated by filtration and the mother liquor was concentrated under reduced pressure. 800 ml of water and 600 ml of CHCl3 were added to the residue to conduct extraction. The CHCl3 layer was washed with 500 ml of 10percent NaOH and a saturated Nacl aqueous solution. It was dehydrated over MgSO4 and concentrated to dryness under reduced pressure to obtain 189.49 g (96percent) of 2-chloro-3,4-dimethoxybenzaldehyde. mp 70°~72° C. NMR (90 MHz, CDCl3) delta:3.88 (3H, s), 3.96 (3H, s), 6.92 (1H, d), 7.72 (1H, d), 10.28 (1H, s) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
53% | Ki; In methanol; acetonitrile; | EXAMPLE 58 4-[(2-benzoxazolyl)methyl]-N-(2,6-dimethylphenyl)-1-piperazineacetamide Maleate (1:2.75) 1.45 g of the intermediate piperazineacetamide of Example 15 in acetonitrile (30 ml); 3 g K2 CO3; a catalytic amount of KI and leq (0.95 g, 4.53 mMol) of <strong>[73101-74-3]bromomethylbenzoxazole</strong> was stirred 24 hrs, filtered, and the solvents evaporated. The residue was dissolved in MeOH, made acidic with maleaic acid and allowed to crystalize. Filtration gave 1.67 g product 53% yield; mp 163-165 C.; 1 H-NMR (300 MHz DMSO-d6) delta 9.81 (s, 1H), 7.74 (m, 2H) 7.41 (m, 2H), 7.07 (m, 3H), 4.09 (s, 2H), 4.02 (s, 2H), 3.28 (s, 4H), 2.90 (s, 4H), 2.13 (s, 6H); 13 C NMR (75 MHz DMSO-d6) delta 166.96(0), 162.41(0), 150.30(0), 140.49(0), 135.05(0), 133.80(0), 133.36(+), 127.85(+), 127.00(+), 125.40(+), 124.59(+), 119.76(+), 110.89(+), 56.64(-), 53.17(-), 51.80(-), 48.95(-), 18.07(+); IR (KBr) 3392, 1696, 1620, 1574, 1518, 1468, 1454, 1428, 1356, 1218, 1082, 990, 868; MS (DCI) m/e 379; Analysis calc'd for C22 H26 N4 O2.2.75C4 H4 O4: C, 56.81 H, 5.35 N, 8.03; found: C, 56.52 H, 5.34 N, 8.39. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
42% | In water; N,N-dimethyl-formamide; | 2. Intermediate 2: 4-(4-tert-Butyloxycarbonyl)piperazin-1-yl Butanal Dimethyl Acetal A mixture of <strong>[29882-07-3]4-chlorobutanal dimethyl acetal</strong> (J. Chem. Soc., Perkin Trans. 1, 1981, 251-255; 4.1 g, 26.9 mmol), K2 CO3 (4.08 g, 29.6 mmol) and tert-butyl-1-piperazinecarboxylate (5.00 g, 26.9 mmol), in anhydrous DMF (100 ml) was heated at 100° C. for 24 h. The mixture was cooled to room temperature, water (75 ml) added and extracted with ethyl acetate (5*100 ml). The combined extracts were washed with water (*3), dried (Na2 SO4) and evaporated. The crude product was chromatographed on silica gel eluding with ethyl acetate to give the title-product (3.41 g, 42percent). delta (250 MHz, CDCl3) 1.46 (9H, s, OC(Me)3); 1.50-1.68 (4H, m, 2 of CH2); 2.32-2.42 (6H, m, 3 of CH2); 3.30 (6H, s, (OMe)2); 3.40-3.48 (4H, m, 2 of CH2); 4.38 (1H, t, J=6 Hz, CH). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydroxide; In water; N,N-dimethyl-formamide; | (a) 3-Isopropoxybenzaldehyde 50 g of 3-hydroxybenzaldehyde are dissolved, under nitrogen, in 250 ml of DMF. 60 g of K2 CO3 and then 60 ml of 2-iodopropane are added and the reaction mixture is heated for 18 hours at 50 C. and poured into 2.5 liters of water. Extraction is carried out with ethyl ether and the ether phase is washed with a dilute solution of NaOH, dried over MgSO4 and concentrated under vacuum to give 53.5 g of an oil. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | In water; | EXAMPLE 7 Preparation of N-methoxy-N-methylchloroacetamide (3b). To a cold (0° C.), stirred solution of K2 CO3 (62.4 g, 450 mmol) in H2 O (250 mL) was added, successively, N,O-dimethylhydroxylamine hydrochloride (20 g, 205 mmol) and organic solvent (250 mL, toluene or MTBE). The resulting two phase mixture was cooled to -5° C. and chloroacetyl chloride (19.6 ml, 246 mmol) was added over 5 min (solution temperature maintained below 0° C.). The vigorously stirred mixture was allowed to warm to 15° C. over 30 min, the layers were separated, and the aqueous layer was extracted with organic solvent (3*100 mL, toluene or MTBE). The combined organic extracts were concentrated (MTBE used as solvent) to give the amide 3b (26.8 g, 95percent) as a white solid. Alternatively, the combined organic extracts (toluene used as solvent) were concentrated to 250 mL to effect azeotropic drying (water content 100 mug/mL) and the solution of 3b was used directly in reactions with organometallic reagents. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In ethanol; | STR99 N-Indan-2-ylglycine t-Butyl Ester (721) To a suspension of <strong>[2338-18-3]2-aminoindane hydrochloride</strong> (5.0g, 29.5 mmol) and powdered K2 CO3 (8.3 g, 60.0 mmol) in absolute EtOH (30 mL) was added tert-butyl bromoacetate (4.4 mL, 29.5 mmol). After stirring for 10 min at rt the reaction was heated to 45 C. and stirred for 2 hr. The reaction was cooled to rt, diluted with EtOAc, filtered and concentrated. Chromatography of the residue on silica gel (elution with 20% EtOAc:hexane) provided 4.7g of compound 721 as a white crystalline solid. STR100 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
39% | Example 48 5-CHLORO-6-METHYL-2-PYRAZINECARBOXYLIC ACID A mixture of <strong>[77168-85-5]methyl 5-chloro-6-methyl-2-pyrazine carboxylate</strong> (0.16 g, 0.86 mmol), K2 CO3 (0.31 g, 2.18 mmol) and H2 O was stirred for 2 h at room temperature. The reaction was filtered and acidified (20percent HCl), and the resulting solid collected to provide the title compound (0.057 g, 39percent yield); m.p. 116°-117° C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In N,N-dimethyl-formamide; | (a) To a mixture of ethyl 2-hydroxybenzoate (2.4 ml, 16.38 mmol), K2 CO3 (4.98 g), and DMF (30 ml) was added <strong>[57616-74-7]N-<strong>[57616-74-7](3-chloropropyl)morpholine hydrochloride</strong></strong> (3.93 g). The mixture was stirred at room temperature for 30 minutes, then was warmed on a steam bath overnight. The reaction mixture was cooled, filtered and stripped to afford a liquid which was partitioned between EtOAc (350 ml) and water. The organic layer was separated, washed with water (2*200 ml), dried over MgSO4 and stripped to afford ethyl 2-[3-(4-morpholinyl)propoxy]benzoate. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
10.2 g (96%) | In ethyl acetate; acetone; | Step 1 Preparation of 4-bromo-2-chloroanisole Under nitrogen, 7.3 mL (77 mmol) of dimethylsulfate was added to a stirred suspension of 10 g (48 mmol) of 4-bromo-2-chlorophenol and 5.4 g (38 mmol) of powered K2 CO3 in 75 mL of fresh acetone. After 2 hours at reflux, the reaction was cooled to ambient temperature, filtered, and concentrated in vacuo. The residue was dissolved in ethyl acetate; the resulting solution was washed with water and dried over MgSO4. Concentration in vacuo gave 10.2 g (96%) of 4-bromo-2-chloroanisole as a colorless solid: mp 68.5-70.5 C.; NHR (CDCl3) delta 3.88 (s, 3H), 6.80 (d, J=9 Hz, 1H), 7.33 (dd, J=2, 9 Hz, 1H), 7.50 (d, J=2 Hz, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
101 g (92%) | With potassium hydroxide; In methanol; water; butanone; | (B) 3,4-DIBENZYLOXYBENZOIC ACID To 60 g (0.33 mole) of ethyl 3,4-dihydroxybenzoate in 50 ml of methyl ethyl ketone was added 105.5 g (0.76 mole) of K2 CO3 and 168.8 g (0.76 mole) of benzyl bromide. The mixture was refluxed for 16 hours and filtered. Evaporation of the filtration gave an oil. This oil was mixed with 40 g of KOH, 350 ml of water and 350 ml of methanol and refluxed for 2.5 hours. The methanol was evaporated and the reaction mixture was acidified with concentrated HCl. The precipitate was filtered to give 101 g (92percent) of the desired product; m.p. 184°-185° C. The NMR and IR spectra were consistent with the assigned structure. |
101 g (92%) | With potassium hydroxide; In methanol; water; butanone; | 3,4-Dibenzyloxybenzoic Acid To 60 g (0.33 mole) of ethyl 3,4-dihydroxybenzoate in 50 ml of methyl ethyl ketone was added 105.5 g (0.76 mole) of K2 CO3 and 168.8 g (0.76 mole) of benzyl bromide. The mixture was refluxed for 16 hours and filtered. Evaporation of the filtration gave an oil. This oil was mixed with 40 g of KOH, 350 ml of water and 350 ml of methanol and refluxed for 2.5 hours. The methanol was evaporated and the reaction mixture was acidified with concentrated HCl. The precipitate was filtered to give 101 g (92percent) of the desired product; m.p. 184°-5° C. The NMR and IR spectra were consistent with the assigned structure. |
101 g (92%) | With potassium hydroxide; In methanol; water; butanone; | (b) 3,4-Dibenzyloxybenzoic Acid To 60 g (0.33 mole) of ethyl 3,4-dihydroxybenzoate in 50 ml of methyl ethyl ketone was added 105.5 g (0.76 mole) of K2 CO3 and 168.8 g (0.76 mole) of benzyl bromide. The mixture was refluxed for 16 hours and filtered. Evaporation of the filtration gave an oil. This oil was mixed with 40 g of KOH, 350 ml of water and 350 ml of methanol and refluxed for 2.5 hours. The methanol was evaporated and the reaction mixture was acidified with concentrated HCl. The precipitate was filtered to give 101 g (92percent) of the desired product; m.p. 184°-185° C. The NMR and IR spectra were consistent with the assigned structure. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | In ethanol; Petroleum ether; | EXAMPLE 3a 1-(phenylmethyl)-2-methyl-3-(phenylmethoxy) 4-pyridone 73 g of the product of Example 2 were dissolved in 4 liters of ethanol (dry). 25 g K2 CO3 powderized and 70 g benzylbromide were added. After refluxing for 4 hours and filtration, the solvent was distilled off and the residue extracted with 4 liters of hot petroleum ether in 3 parts. After cooling to room temperature and filtration the petroleum ether filtrate was concentrated to 2 liters and cooled to -10° C. 31 g of white crystals of the title compound of Example 3 were obtained. The formed title compound 3A was insoluble in petroleum ether at room temperature white crystals. 70percent of total yield. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
16.5 g (94%) | In N-methyl-acetamide; | EXAMPLE 12 Methyl(6,11-dihydro-11-oxodibenz[b,e]oxepin-2-yl)acetoxyacetate A mixture of 15 g (0.052 m) of 6,11-dihydro-11-oxodibenz[b,e]oxepin-2-acetic acid in 100 ml of dimethylformamide and 3.87 g (0.028 m) of K2 CO3 was warmed to an internal temperature of 50° C. in an atmosphere of nitrogen for 1.5 hours. To this mixture, 9.41 g (0.062 m) of methyl bromoacetate was added dropwise and the mixture was held at 50° C. overnight. The reaction mixture was poured into water and extracted with ether. The ether extract was washed with 5percent NaHCO3 and water, dried over Na2 SO4, filtered and evaporated to give 16.5 g (94percent) of an oil of methyl(6,11-dihydro-11-oxodibenz[b,e]oxepin-2-yl)acetoxyacetate. ANALYSIS: Calculated for C19 H16 O6: 67.05percentC; 4.74percentH; Found: 66.88percentC; 4.74percentH |
16.5 g (94%) | In N-methyl-acetamide; | EXAMPLE 12 Methyl-(6,11-dihydro-11-oxodibenz[b,e]oxepin-2-yl)acetoxyacetate A mixture of 15 g (0.052 m) of 6,11-dihydro-11-oxodibenz[b,e]oxepin-2-acetic acid in 100 ml of dimethylformamide and 3.87 g (0.028 m) of K2 CO3 was warmed to an internal temperature of 50° C. in an atmosphere of nitrogen for 1.5 hours. To this mixture, 9.41 g (0.062 m) of methyl bromoacetate was added dropwise and the mixture kept at 50° C. overnight. The reaction mixture was poured into water and extracted with ether. The ether extract was washed with 5percent NaHCO3 and water, dried over Na2 SO4, filtered and evaporated to give 16.5 g (94percent) of an oil of methyl-(6,11-dihydro-11-oxodibenz[b,e]oxepin-2-yl)acetoxyacetate. ANALYSIS: Calculated for C19 H16 O6: 67.05percentC. 4.74percentH. Found: 66.88percentC, 4.74percentH. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydroxide; In dichloromethane; acetonitrile; | EXAMPLE 9 (Method e) 17 g of N-(2-((2-hydroxy-3-(4-hydroxyphenoxy)propyl)amino)ethyl)-4-morpholinecarboxamide and 6 g of 2-methoxyethyl mesylate and 6.9 g of K2 CO3 was refluxed in acetonitril for 20 h. The resulting mixture was filtered and evaporated. The residue was dissolved in methylene chloride and extracted with water containing 1 g of NaOH, then with water and then dried over Na2 SO4, filtered and evaporated. The residue was crystallized from ethyl acetate yielding N-(2-((2-hydroxy-3-(4-(2-methoxyethoxy)phenoxy)propyl)amino)ethyl)-4-morpholinecarboxamide. Melting point 69 C. (base). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With CuI; In acetone; | EXAMPLE 18 2-Methyl-4-(2,4-dibenzyloxyphenyl)-2-Buten-1-ol A mixture of 7.5 g (0.039 mol) of <strong>[14381-51-2]1-bromo-2,3-dihydroxybenzene</strong>, 11.2 g (0.082 mol) of K2 CO3, and 14 g (0.082 mol) of benzyl bromide in 70 ml of acetone was stirred at room temperature overnight, or until all starting material disappeared as indicated by TLC. The reaction mixture was poured into water and the aqueous solution was extracted with ether. The organic layer was separated, dried over MgSO4 and concentrated to give 14.5 g product as white solid. This compound, 1-bromo-2,4-dibenzyloxybenzene, as formed in accordance with the above procedure is conveniently summarized by the following reaction: STR9 A solution of 5.5 g (0.015 mol) of 1-bromo-2,4-dibenzyloxybenzene and 3.7 g (0.025 mol) of CH3 I in 20 ml of ether was added dropwise to 950 mg of Mg turning. The reaction mixture was refluxed for 2 hours and then cooled to -10° C. One gram of CuI was added, and stirring was continued at -10° C. for 30 min. A solution of 3.5 g (01042 mol) of 3-methyl-3,4-epoxy-1-butene in 10 ml of ether was then added dropwise to the reaction mixture, and stirring continued for another hour at -10° C. The reaction was quenced by satd. NH4 Cl solution. The organic layer was separated, dried over MgSO4 and concentrated. Purification of the crude product by dry column chromatography gave 1.6 g of product (a mixture of cis/trans isomer 8:2) as white solid; m.p. 83°-85° C. The product, 2-methyl-4-(2,4-dibenzyloxyphenyl)-2-buten-1-ol, formed from 1-homo-2,4-dibenzyloxybenzene, is conveniently depicted by the following reaction: STR10 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
45% | In sulfolane; | EXAMPLE 5 To a 1 liter 3-necked flask equipped with a simple distillation head, thermometer, stirrer and heater was charged 72 g (0.47 mole) of dried CsF, 2.5 g of K2 CO3 and 400 ml of sulfolane. Ca. 20 ml of the solvent was distilled in vacuo to dry the ystem, and 50 (0.16 mole) of <strong>[75806-85-8]2,3,5-tribromopyridine</strong> was added. The mixture was heated to 180-190 C. for 7 hr. Vacuum distillation yielded a mixture which, by glpc analysis, showed the presence of a 45% of yield of 2,3-difluoro-5-bromopyridine, and small amounts of 2-fluoro-5-bromopyridine and 2,3,5-trifluoropyridine. Analysis of the residual material in the sulfolane showed the presence of 3,5-dibromo-2-fluoropyridine. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With ethanethiol; In hexane; ethyl acetate; isopropyl alcohol; | EXAMPLE 6 Preparation of 2-chloro-5-ethylthio-4-pyridinecarbonitrile and 5-chloro-2-ethylthio-4-pyridinecarbonitrile A solution of 2.77 g of ethanethiol in 30 ml of 2-propanol was added to a mixture containing 7.7 g of <strong>[102645-35-2]2,5-dichloro-4-pyridinecarbonitrile</strong> and 3.08 g of K2 CO3 in 60 ml of 2-propanol at 0 C. The reaction mixture was allowed to warm to room temperature and then stirred for 4 days, after which it was poured onto 200 g of ice, stirred and extracted with CH2 Cl2. Thin layer chromatography (using 10 percent ethyl acetate in hexane) disclosed the presence of three components. The CH2 Cl2 solution was dried and concentrated to 25 ml and then diluted with 12.5 ml of hexane to give a crystalline material which was separated by filtration and identified as 2-chloro-5-ethylthio-4-pyridinecarbonitrile. The filtrate was concentrated and separated on a Water's Prep LC 500 instrument eluted with 2 percent ethyl acetate in hexane. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine; In water; benzene; | EXAMPLE II 3-BENZYL-5-[2-(4-CHLOROPHENYL)3-METHYL BUTOXYMETHYL]1,2,4-OXADIAZOLE This example teaches the synthesis of a representative compound of reaction step 2 using the intermediate prepared in Example I. First, 2.1 grams (0.01 mole) of the intermediate of Example I, 2.3 grams (0.011 mole) of 2-(4-chlorophenyl)3-methyl butyric acid, 1.0 grams (0.01 mole) of triethylamine, and 100 milliliters of methylethylketone were combined and heated under reflux for 2 hours. The mixture was then cooled and poured into 200 milliliters of benzene. The benzene mixture was then washed in turn with 100 milliliters of H2 O, 100 milliliters of 5% K2 CO3 solution, and 100 milliliters of H2 O. The benzene phase was then dried with MgSO4 and evaporated in vacuo to yield 3.0 grams (78% of theory) of the desired product. nD30 1.5210. The following is a table of certain selected compounds that are preparable according to the procedure described hereto. Compound numbers are assigned to each compound and are used throughout the remainder of the specification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In water; N,N-dimethyl-formamide; | 4-(1-Azetidinyl)butanal dimethylacetal A mixture of azetidine (2.0 g, 35.0 mmol), 4-chlorobutanal dimethylacetal (5.88 g, 39.0 mmol) and K2 CO3 (5.38 g, 39.0 mmol), in anhydrous DMF (100ml), was stirred at room temperature for 72 h. Water (50 ml) was added and the mixture extracted with EtOAc (3*150 ml). The combined extracts were washed with H2 O (3*50ml), dried (Na2 SO4) and evaporated. The crude product was purified by distillation (1.2 g). delta (360 MHz, CDCl3) 1.35-1.42 (2H, m, CH2), 1.57-1.64 (2H, m, CH2), 2.00-2.40 (2H, m, CH2), 2.36 (2H, t, J=9.0 Hz, CH2), 3.15 (4H, m, t, J=7.0 Hz, 2 of CH2), 3.33 (6H, s, 2 of OMe), 4.35 (1H, t, J=5.7 Hz, CH). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | Example 11 Enhanced preparation of 4-(3-trifluoromethylphenoxy)-2-(4-trifluoromethylphenyl)-pyrimidine Water (20 mmoles) is added to a solution of 1,1,1,3-tetrachloro-3-ethoxypropane (10 mmoles) in dimethoxyethane (25 ml). The reaction mixture is stirred for 2 h under reflux. The resulting mixture is slowly added to a mixture consisting of a <strong>[38980-96-0]4-<strong>[38980-96-0]trifluoromethylbenzamidine hydrochloride</strong></strong> (10 mmoles), 3-trifluoromethylphenol (11 mmoles), potassium carbonate (60 mmoles) and dimethoxyethane (50 ml), which is stirred under reflux. When the addition of 3,3-dichloroacrolein solution is completed additional <strong>[38980-96-0]4-<strong>[38980-96-0]trifluoromethylbenzamidine hydrochloride</strong></strong> (1 mmoles) is added. The reaction mixture is stirred for 2 hours under reflux and subsequently cooled down to ambient temperature, filtered through silica, and the organic phase is concentrated in vacuo. The residue is purified by chromatography on SiO2 (petrol ethers / diisopropylether: 6 / 1) to yield 3,07 g (80 %) of the product having a melting point of 66-67 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In methanol; water;Product distribution / selectivity; | Example 4: Preparation of <strong>[4773-96-0]mangiferin</strong> monopotassiumMangiferin 42.2(0. lmol) is suspended in the mixture of water 200ml and methanol 1800ml in reactor, mixing round adequately. Potassium carbonate 6.9g(0.05mol) is dissolved in water ,the concentration is 0.2%( w/v ) . The solution of potassium carbonate is added slowly into the <strong>[4773-96-0]mangiferin</strong> suspended solution while mixing round until the solution is clear, then the reaction solution is filtrated, appropriate quantity ethanol- chloroform (4:1 v/v) is added into the reaction solution, mixing round adequately . A lot of deposition is come into being, the reaction solution is filtrated to get the depositon, the solid substance is heated up no excess <n="12"/>60 C to dry. The yellow substance is <strong>[4773-96-0]mangiferin</strong> monopotassium. Its weight is 3 Ig, the productivity is 73.4%. The purity of <strong>[4773-96-0]mangiferin</strong> monopotassium is 98.6% detected by HPLC. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
43% | With sodium iodide; In N,N-dimethyl-formamide; at 60℃; for 24h; | A mixture of <strong>[387350-92-7]5-(methylsulfonyl)-2,3-dihydro-1H-indole</strong> (1, 150 mg, 0.760 mmol), tert-butyl 4-{2-[(methylsulfonyl)oxy]ethyl}piperidine-1-carboxylate (468 mg, 1.52 mmol), potassium carbonate (210 mg, 1.52 mmol), and sodium iodide (114 mg, 0.765 mmol) in DMF (10 mL) was stirred at 60 C for 24 h. The reaction was quenched with water and extracted with AcOEt. The organic layer was washed with brine, dried over MgSO4, and concentrated under reduced pressure. Purification by silica gel column chromatography (hexane/AcOEt = 100/0 to 50/50) gave the title compound as a white solid (146 mg, 43%). MS (ESI/APCI) m/z 353 [M-Boc+2H]+. 1H NMR (300 MHz, CDCl3) δ 1.10-1.26 (2H, m), 1.39-1.78 (14H, m), 2.61-2.78 (2H, m), 3.03 (3H, s), 3.20 (2H, t, J = 8.5 Hz), 4.01-4.18 (4H, m), 4.25-4.38 (2H, m), 7.71 (1H, s), 7.74-7.82 (1H, m), 7.98 (1H, br s). 13C NMR (100.6 MHz, CDCl3) δ 27.0, 28.5, 32.0, 33.2, 35.4, 43.7, 44.8, 48.1, 63.8, 79.4, 114.6, 123.9, 128.2, 134.1, 153.1, 154.8. Mp 126-129 C. Anal. Calcd for C22H32N2O6S: C, 58.39; H, 7.13; N, 6.19. Found: C, 58.38; H, 7.02; N, 6.10. |
Tags: 584-08-7 synthesis path| 584-08-7 SDS| 584-08-7 COA| 584-08-7 purity| 584-08-7 application| 584-08-7 NMR| 584-08-7 COA| 584-08-7 structure
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H201 | Explosive; mass explosion hazard |
H202 | Explosive; severe projection hazard |
H203 | Explosive; fire, blast or projection hazard |
H204 | Fire or projection hazard |
H205 | May mass explode in fire |
H220 | Extremely flammable gas |
H221 | Flammable gas |
H222 | Extremely flammable aerosol |
H223 | Flammable aerosol |
H224 | Extremely flammable liquid and vapour |
H225 | Highly flammable liquid and vapour |
H226 | Flammable liquid and vapour |
H227 | Combustible liquid |
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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