Tag: M.W=100-200

Adding a certain compound to certain chemical reactions, such as: 111-95-5, name is Bis(2-methoxyethyl)amine, belongs to ethers-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 111-95-5, SDS of cas: 111-95-5

Example 2 8.0 g (60 mmol) of bis(methoxyethyl) amine was added to 100 ml of dehydrated dichlorrmethane in a flask followed by Ar gas replacement. Thereafter, 8.8 g (87 mmol) of triethyl amine was added thereto. Next, the system was cooled down to about -10 C. 6.5 g (72 mmol) of acrylic acid chloride was slowly dropped in the system while keeping the temperature in the system ranged from -10 C. to -5 C. and thereafter stirred for two hours at room temperature. Furthermore, subsequent to removal of precipitants by filtration, the filtrate was washed with saturated sodium hydrogen carbonate aqueous solution and saturated sodium chloride aqueous solution. Next, subsequent to drying by sodium sulfate, the dried resultant was condensed under a reduced pressure to obtain an oily brown material. (0184) Furthermore, by a column chromatography filled with 300 g of Wakogel C300 (manufactured by Wako Pure Chemical Industries, Ltd.) using hexane and ethyl acetate as eluate, the oily brown material was fined to obtain 5.5 g (yield: about 50%) of an oily, pale yellow material represented by the following chemical formula. 1H-NMR (CDCl3): delta3.34 (d, 6H), 3.51 (t, 2H), 3.57 (t, 2H), 3.63 (t, 4H), 5.67 (dd, 1H), 6.34 (dd, 1H), 6.64-6.69 (m, 1H) IR(NaCl): 2982, 2930, 2981, 2829, 1651, 1613, 1447, 1366, 1315, 1270, 1230, 1193, 1157, 1118, 1069, 1015, 981, 962, 824, 795, 529 cm-1

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Bis(2-methoxyethyl)amine, and friends who are interested can also refer to it.

Reference:
Patent; Ricoh Company, Ltd.; Morita, Mitsunobu; Noguchi, Soh; Kimura, Okitoshi; (28 pag.)US9593248; (2017); B2;,
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Adding a certain compound to certain chemical reactions, such as: 7252-83-7, name is 2-Bromo-1,1-dimethoxyethane, belongs to ethers-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 7252-83-7, HPLC of Formula: C4H9BrO2

Acid 101 (all material prepared in the previous step, 10.9 mmol) was dissolved in 150 mL of DMF. Powdered K2CO3 (25 g, 180 mmol) was added to the solution followed by adding of bromoacetaldehyde dimethyl acetal (33.3. mL, 283 mmol). The reaction mixture was stirred overnight at 110 C. DMF solution was removed from the flask (leaving insoluble material in the flask) and evaporated. The residue was mixed with 150 mL of water and combined with the solid left in the flask. The product was extracted with ethyl acetate (4¡Á45 mL), combined extracts were washed with water (4¡Á30 mL), brine (30 mL), dried over sodium sulfate and evaporated in vacuum. The residue was dissolved in chloroform, loaded on silica gel column (packed in 100:3 chloroform-EtOAc mixture). The column was eluted with 100:3 chloroform-EtOAc mixture. Pure fractions containing the product were combined and evaporated to give ester 102 as a clear oil, solidified later to form white solid (4.54 g, 66%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Bromo-1,1-dimethoxyethane, and friends who are interested can also refer to it.

Reference:
Patent; Life Technologies Corporation; CORRY, Schuyler; Downey, William; Filanoski, Brian; Gee, Kyle; Greenfield, Lawrence; Hirsch, James; Johnson, Iain; Rukavishnikov, Aleksey; (129 pag.)US2016/139135; (2016); A1;,
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Electric Literature of 171290-52-1, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 171290-52-1, name is 3,5-Dimethoxyphenylacetylene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: Azide 13 (300 mumol), alkyne (750 mumol), CuSO4 (9.6 mg, 60 mumol) and sodium ascorbate (60.0 mg, 300 mumol) were dissolved in 1:1 t-BuOH/H2O (3 mL). The mixture was stirred for 2 h at rt. After the completion of the reaction, the mixture was filtered and washed with H2O (70 mL) (solid A). The filtrate was extracted with EtOAc (3 * 70 mL). The combined organic extracts were dried over anhyd MgSO4, filtered, and concentrated by rotary evaporation (residue B). The solid A and residue B were combined and purified by column chromatography to afford 8 or 9.

The synthetic route of 3,5-Dimethoxyphenylacetylene has been constantly updated, and we look forward to future research findings.

Reference:
Article; Song, Doohee; Park, Yunjeong; Yoon, Jieun; Aman, Waqar; Hah, Jung-Mi; Ryu, Jae-Sang; Bioorganic and Medicinal Chemistry; vol. 22; 17; (2014); p. 4855 – 4866;,
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Synthetic Route of 22236-10-8, A common heterocyclic compound, 22236-10-8, name is 4-(Difluoromethoxy)aniline, molecular formula is C7H7F2NO, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

To a suspension of p-toluenesulfonic acid monohydrate (9.25 g, 48.6 mmol) in acetonitrile (65 mL)4- (difluoromethyloxy) aniline (2.00 mL, 16.2 mmol) was added at room temperature.To the reaction solution was added dropwise a solution of sodium nitrite (2.24 g, 32.4 mmol) and potassium iodide (6.72 g, 40.5 mmol) in water (11 mL) at 10 C., and the mixture was stirred at room temperature for 3 hours did.Water was added to the reaction solution,And extracted with ethyl acetate.The combined organic layers were successively washed with a saturated aqueous sodium hydrogen carbonate solution and an aqueous sodium thiosulfate solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure.The obtained crude product was purified by column chromatography (hexane) to obtain a pale pink oil (3.98 g, yield: 91%) of 1-difluoromethyloxy-4-iodobenzene.

The synthetic route of 22236-10-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SAGAMI CHEMICAL RESEARCH INSTITUTE; HOKKO CHEMICAL INDUSTRY COMPANY LIMITED; HANDA, MASAMI; MIZUTA, SATOSHI; HIRAI, KENJI; OKAMURA, DAIGO; GUSHIKAWA, TORU; (111 pag.)JP2015/848; (2015); A;,
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Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 592-55-2, name is 1-Bromo-2-ethoxyethane, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 1-Bromo-2-ethoxyethane

1-Boc-piperazine (1.86 g, 10.0 mmol), 2-bromoethyl ethyl ether (1.92 g, 12.5 mmol) and K2CO3 (2.07 g, 15.0 mmol) in CH3CN (25 mL) were stirred at 70 C for 19 h. The mixture was allowed to cool to room temperature. The solids were filtered off and the filtrate was diluted with EtOAc (60 mL). The organic phase was washed with water (6 mL) and brine (6 mL), dried over Na2SO4, and evaporated to yield 2.45 g (95%) of tert-butyl 4-(2- ethoxyethyl)piperazine-1-carboxylate.1H NMR (600 MHz, DMSO-d6) delta ppm 3.46 (t, J=6.0 Hz, 2 H) 3.40 (q, J=7.0 Hz, 2 H) 3.28 (br. s., 4 H) 2.46 (t, J=6.0 Hz, 2 H) 2.34 (t, J=5.2 Hz, 4 H) 1.39 (s, 9 H) 1.09 (t, J=7.0 Hz, 3 H). MS (ESI+) m/z 259 [M+H]+ .

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 592-55-2.

Reference:
Patent; KANCERA AB; MELLSTEDT, Hakan; BYSTROeM, Styrbjoern; VAGBERG, Jan; OLSSON, Elisabeth; (302 pag.)WO2018/11138; (2018); A1;,
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Related Products of 19500-02-8, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 19500-02-8 as follows.

A solution of dimethyl acetylenedicarboxylate (17 g, 0.12 mol) in MeOH (20 mL) was added dropwise over 1 h to a solution of 3-methoxy-2-methylaniline (13.7 g, 0.1 mol) in MeOH (80 mL) stirred at r.t., and the mixture was stirred at r.t. for an additional 4 h. Evaporation of MeOH provided 7a (29.7 g; quantitative yield corresponds to 27.9 g) of yellowish oil (HPLC purity 93.5percent), which was used for the following step without further purification.

According to the analysis of related databases, 19500-02-8, the application of this compound in the production field has become more and more popular.

Reference:
Article; Radl, Stanislav; Rezkova, Hana; Obadalova, Iva; Srbek, Jan; B?icha?, Ji?i; Pekarek, Toma?; Synthesis; vol. 46; 7; (2014); p. 899 – 908;,
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Electric Literature of 134364-69-5,Some common heterocyclic compound, 134364-69-5, name is 2,3-Difluoroanisole, molecular formula is C7H6F2O, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

In a 1 L four-necked flask purged with nitrogen, 102 gOf 1, 2-difluoro-3-methoxybenzene was dissolved in 300 ml of THF and cooled to -78 C. To this was added 326 ml of a 2.4 M solution of butyllithium in hexane over 1 hour. After 1 hour, a solution of 133 g of trimethyl borate dissolved in 130 ml of THF was added dropwise over 1 hour. After 1 hour, the temperature of the system was brought to -30 C., 160 ml of 36% hydrochloric acid was added and the mixture was stirred for 2 hours. To the system, 500 ml of ethyl acetate and 200 ml of water were added and stirred, and the organic layer was separated. The mixture was further extracted with 200 ml of ethyl acetate and combined with the above organic layer, which was washed with 100 ml of saturated brine. After drying the solution with magnesium sulfate, the solvent was distilled off to obtain 133 g of the desired product as a white solid. Yield 100%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2,3-Difluoroanisole, its application will become more common.

Reference:
Patent; DIC CORPORATION; KUSUMOTO, TETSUO; AOKI, YOSHIO; (47 pag.)JP6136589; (2017); B2;,
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7252-83-7, name is 2-Bromo-1,1-dimethoxyethane, belongs to ethers-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Recommanded Product: 7252-83-7

To a solution of o-thiocresol (16. 89g, 136mmo1) in acetone (130ml) is added potassium carbonate (20. 5g, 148mmol) and a solution of bromoacetaldehyde dimethylacetal (19.93g, 123mmol) in acetone (20ml) and the reaction mixture is stirred at ambient temperature overnight. The solids are filtered and washed with diethyl ether. The filtrate is concentrated and dissolved into ethyl acetate, washed successively with water, 0.5 N NaOH, and 2N NaOH. The combined aqueous fractions are extracted with dichloromethane. The combined organic fractions are dried over anhydrous MgS04, filtered and concentrated to afford 1- [ (2, 2-dimethoxyethyl) thio] -2-methyl-benzene as a brown oil (23.4g, 90%) that is used without further purification.’H NMR (CDC13) : 8= 7.33 (1H, brd), 7.19-7. 08 (3H, m), 4.56 (1H, t), 3.38 (6H, s), 3.10 (2H, d), 2.42 (3H, s).

The synthetic route of 7252-83-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ELI LILLY AND COMPANY; WO2005/92885; (2005); A1;,
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Synthetic Route of 41789-95-1, These common heterocyclic compound, 41789-95-1, name is 1-(3-Methoxyphenyl)-N-methylmethanamine, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Example 8; 3-amino-4-(2,4-dichlorophenyl)-N-(3-methoxybenzyl)-N-methylpyrrolidine-1-carboxamide A solution of 1-benzyl-3-(2,4-dichlorophenyl)-4-nitropyrrolidine (1.5 g, 4.3 mmol) in dry CH2Cl2 (5 mL) was cooled to 0 C. and triphosgene (500 mg, 1.7 mmol) in CH2Cl2 was added over the course of 30 minutes. The reaction was quenched with H2O and extracted with CH2Cl2. The organics were then washed with saturated aqueous NaHCO3, dried, filtered and concentrated under reduced pressure. The crude material was divided into 10 portions (0.43 mmol each), and (3-methoxy-benzyl)methyl-amine (45 mg, 0.30 mmol), Et3N (30 mg, 0.30 mmol) and CH2Cl2 (1 mL) were added to a single portion. The solution was stirred for 4 hours and concentrated under reduced pressure. The unpurified material was taken up in 1:1 MeOH/AcOH (2 ml) and zinc dust (200 mg, 3 mmol) was added. After stirring 4 hours, the solution was carefully quenched with saturated aqueous NaHCO3 and extracted with several portions of EtOAc. The organics were combined, concentrated under reduced pressure and purified employing reverse phase chromatography (samples were purified by preparative HPLC on a Waters Symmetry C8 column (25 mm¡Á100 mm, 7 um particle size) using a gradient of 10% to 100% acetonitrile: 0.1% aqueous TFA over 8 minutes (10 minutes run time) at a flow rate of 40 mL/minutes) to provide the title compound. 1H NMR (300 MHz, d6-DMSO) delta ppm 7.60-7.61 (m, 1H), 7.39-7.43 (m, 2H), 7.24-7.27 (m, 1H), 6.82-6.85 (m, 3H), 4.30-4.34 (m, 2H), 3.73-3.84 (m, 4H), 3.47-3.54 (m, 2H), 3.27-3.34 (m, 2H), 3.14-3.18 (m, 1H), 2.67-2.73 (s, 3H). MS (ESI+) m/z 408 (M+H)+

The synthetic route of 41789-95-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Backes, Bradley J.; Hamilton, Gregory L.; Kopecka, Hana A.; Lai, Chunqiu; Longenecker, Kenton L.; Madar, David J.; Pei, Zhonghua; Stewart, Kent D.; Von Geldern, Thomas W.; US2006/264433; (2006); A1;,
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Electric Literature of 60792-79-2, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 60792-79-2 name is 2,2′-Oxybis(ethylamine) dihydrochloride, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

N,N-(2,2′-oxybis(ethane-2.1-divfflbis(2,4,6-trimethylaniline) (Example 1 1) [0088] In a drybox, 2,4,6-trimethylbromobenzene (500.0 muL, 3.27 mmol), 2,2′- oxydiethylamine dihydrochloride (289.3 mg, 1.63 mmol), sodium terf-butoxide (706.5 mg, 7.35 mmol), 4.0 mL of dimethyoxyethane, and 10.0 mM Pd(OAc)2 / CyPF-r-Bu (81.8 muL, 8.18 x 10-4 mmol) were added to a 20 mL scintillation vial equipped with a magnetic stirbar and sealed with a cap containing a PTFE septum. The reaction was placed into a temperature controlled aluminum heating block and stirred at 100 0C for 6 h. After cooling to room temperature, the reaction mixture was partitioned between 100 mL H2O/Et2O (1 :1), the organic phase separated and dried over MgSO4, followed by the removal of all volatiles to afford 505 mg (91.0 %) of the title compound.[0089] 1H NuMR spectra were obtained at 400 MHz and recorded relative to residual protio solvent. 13C NuMR spectra were obtained at 101 MHz and recorded relative to the residual solvent resonance. The spectra recorded are as follows:Eta NuMR (CDC13, 400 MHz, 22 0C): delta 2.24 (s, 6H), 2.28 (s, 12H), 3.15 (t, J= 5.0 Hz, 4H), 3.49 (br s), 3.61 (t, J = 5.0 Hz, 4H), 6.84 (s, 4H). 13C NuMR (CDCI3, 101 MHz, 22 0C): delta 18.2, 20.5, 48.2, 70.4, 129.4, 129.8, 131.3, 143.1.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2,2′-Oxybis(ethylamine) dihydrochloride, and friends who are interested can also refer to it.

Reference:
Patent; UNIVATION TECHNOLOGIES, LLC; JOHNS, Adam, M.; WO2010/53696; (2010); A2;,
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