Tag: M.W=100-200

321-28-8, name is 1-Fluoro-2-methoxybenzene, 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. Computed Properties of C7H7FO

(A) 3-fluoro-4-methoxybenzaldehyde. To a solution of o-fluoroanisole, 101 g. (0.80 mole) in 500 ml. dry methylene chloride is added dropwise over 30 minutes a solution of titanium tetrachloride, 182 g. (0.96 mole, 1.2 equiv.) and alpha,alpha-dichloromethylmethyl ether, 110 g. (0.96 mole) in an equal volume of methylene chloride. The temperature is maintained at 10-20 C. with an ice-bath. The mixture is stirred at room temperature for 1 hour longer and then poured over crushed ice-water with stirring. Ether (1l.) is added, and the mixture stirred under nitrogen until solution occurs. The organic layer is extracted with water (3*), sodium bicarbonate solution (3*) and dried (MgSO4). The solvent is evaporated off at 30 to give crude product as an oil. The oil is vacuum distilled through a jacketed Vigreux column when it gives 3-fluoro-4-methoxybenzaldehyde, B.P. 120-121 C., at 10 mm. Hg; Rf 0.6 on a silica-gel G plate with methylene chloride.

The synthetic route of 321-28-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; University of Arizona; FGN, Inc.; US5401774; (1995); A;,
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Reference of 41864-45-3, These common heterocyclic compound, 41864-45-3, name is 4,5-Dimethoxy-2-methylaniline, 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.

The compound 63 (100 mg, 0.33 mmol) was dissolved in propionic acid (1 mL). 4,5-dimethoxy-2-methylaniline (223 mg, 1.33 mmol) was added to the solution. The mixture was stirred at 150C for 30 minutes. The reaction mixture was poured into ice water, and neutralized with the aqueous solution of sodium hydrogen carbonate. The mixture was extracted with ethyl acetate. The organic layer was washed by water and brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The obtained oil was purified by silica-gel column chromatography (hexane-ethyl acetate). The obtained residue was solidified with ethyl acetate-hexane to give the compound 5 (66 mg, yield 47%). 1H-NMR (CDCl3) delta: 1.91 (s, 3H), 2.20 (s, 3H), 3.81 (s, 3H), 3.85 (s, 3H), 5.24 (br s, 2H), 5.38 (s, 1H), 6.26 (s, 1H), 6.70 (s, 1H), 6.50-6.85 (m, 2H), 7.52 (br s, 1H).

Statistics shows that 4,5-Dimethoxy-2-methylaniline is playing an increasingly important role. we look forward to future research findings about 41864-45-3.

Reference:
Patent; Shionogi & Co., Ltd; TANAKA, Satoru; OGAWA, Tomoyuki; KAI, Hiroyuki; OGATA, Yuki; HIRAI, Keiichiro; KUROSE, Noriyuki; FUJII, Yasuhiko; (438 pag.)EP3287443; (2018); A1;,
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Synthetic Route of 74654-07-2, 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. 74654-07-2 name is 2-(2-(2-Methoxyethoxy)ethoxy)ethanamine, 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.

Step a):Under inert atmosphere,5.00 g of 4-bromo-1,8-naphthalic anhydride was added to 100 mL of anhydrous methanol,1.96 g of 3,6,9-trioxa-1-aminodecane was further injected, and the mixture was refluxed for 10 hours.After the reaction was completed, overnight needle-like crystals were precipitated, filtered, washed with cold ethanol three times,The intermediate N-3,6,9-trioxadecyl-4-bromo-1,8-naphthalimide was obtained4.90 g (96% yield).

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

Reference:
Patent; Zhejiang Sci-Tech University; Han Yifeng; Chen Bo; Wei Ting; (13 pag.)CN105542756; (2017); B;,
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Electric Literature of 1758-46-9, 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. 1758-46-9, name is 2-Phenoxyethylamine, This compound has unique chemical properties. The synthetic route is as follows.

A mixture of intermediate compound (prepared ac- cording to teachings in WO99/58530 of which the content is included herein) (0.025 mol) and 2-phenoxyethanamine (0.036 mol) in THF (300 ml) was hydrogenated at 140 °C for 16 hours with Pd/C 10 percent (3 g) as a catalyst in the presence of thiophene solution (3ml). After uptake of H2 (1 equivalent), the catalyst was filtered off and the filtrate was evaporated. The residue was triturated in 2-propanol. The precipitate was filtered off and dried. Yielding: 12.4 g of final compound 7 (94 percent).

The chemical industry reduces the impact on the environment during synthesis 2-Phenoxyethylamine. I believe this compound will play a more active role in future production and life.

Reference:
Patent; JANSSEN PHARMACEUTICA N.V.; WO2006/67139; (2006); A1;,
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Reference of 41789-95-1, A common heterocyclic compound, 41789-95-1, name is 1-(3-Methoxyphenyl)-N-methylmethanamine, molecular formula is C9H13NO, 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.

General procedure: A mixture of Pd(OAc)2 (6.7 mg, 0.030 mmol, 10 mmol%), Cu(OAc)2 (54.45 mg, 0.30 mmol, 1 equiv.), 1a (32.1 mg, 0.30 mmol, 1equiv.), CsF (136.7 mg, 0.90 mmol, 3 equiv.) was dissolved in a solvent of acetonitrile (3 mL) followed by addition of 2a (179 mg,0.60 mmol, 2 equiv.). The reaction mixture was stirred at 120 C for 24 h and progress of the reaction was monitored continuously byTLC with ethyl acetate: hexane eluent system. Upon completion of reaction the mixture was cooled to room temperature, poured into brine, and extracted with EtOAc. The combined extracts were dried over MgSO4 and filtered through pad of Celite eluting with ethylacetate. The filtrate was concentrated under reduced pressure and was purified by column chromatography (EtOAc/hexane) on silicagel to afford the 5,6-dihydrophenanthridine 3a. Compound 1i was synthesized in accordance with reported literature [25]. Characterization data of compounds 3a, 3c, and 3e were found exactly similar as reported in the literature (References of above compounds are mentioned in Supplementary data).

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

Reference:
Article; Asamdi, Manjoorahmed; Chauhan, Prakashsingh M.; Patel, Janki J.; Chikhalia, Kishor H.; Tetrahedron; vol. 75; 25; (2019); p. 3485 – 3494;,
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Some common heterocyclic compound, 22483-09-6, name is 2,2-Dimethoxyethanamine, molecular formula is C4H11NO2, 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. SDS of cas: 22483-09-6

Example 7A (2,2-Dimethoxy-ethyl)-carbamic Acid Benzyl Ester Benzyl chloroformate (Aldrich, 231.3 g, 1.3 mol) was added gradually to a mixture of aminoacetaldehyde dimethyl acetal (Aldrich, 152.0 g, 1.3 mol) in toluene (750 mL) and aqueous NaOH (72.8 g, 1.82 mol; in 375 mL of water) at 10-20 C. After the addition was complete, the mixture was stirred at ambient temperature for 4 h. The layers were separated and the organic layer was washed with brine (2*100 mL) and concentrated under reduced pressure to provide the title compound as an oil (281.5 g, 90% yield). 1H NMR (CDCl4, 300 MHz) delta 3.33 (t, J=6.0 Hz, 2H), 3.39 (s, 6H), 4.37 (t, J=6.0 Hz, 1H), 5.11 (s, 2H), 7.30 (m, 5H); MS (DCl/NH3) m/z 257 (M+NH4)+, 240 (M+H)+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 22483-09-6, its application will become more common.

Reference:
Patent; Basha, Anwer; Bunnelle, William H.; Dart, Michael J.; Gallagher, Megan E.; Ji, Jianguo; Li, Tao; Pace, Jennifer M.; Ryther, Keith B.; Tietje, Karin R.; Mortell, Kathleen H.; Nersesian, Diana L.; Schrimpf, Michael R.; US2005/101602; (2005); A1;,
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Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 31576-51-9, name is 2-(2-Methoxyethoxy)ethanamine, A new synthetic method of this compound is introduced below., Application In Synthesis of 2-(2-Methoxyethoxy)ethanamine

PRODUCTION EXAMPLE 7 2-(2-methoxyethoxy)ethylguanidine 5.96 g (50.0 mmol) of 2-(2-methoxyethoxy)ethylamine and 3.00 g (50.0 mmol) of acetic acid were placed in a 30 ml two neck flask. While heating the flask in a 90 C. oil bath, 3.10 g (73.7 mmol) of cyanamide was added. After 5 hours of the reaction, the product was purified by a silica gel column chromatography (eluent, chloroform/ethanol=2/1 containing 0.5% acetic acid) to obtain 3.15 g of the title compound (wax-like, 14.2 mmol, 28.5% in yield) in the form of acetate. Results of the analysis of this compound are as follows. 1 H-NMR (200 MHz, D2 O, TSP standard): delta 3.8 – 3.6 (m, 6 H), 3.45 – 3.30 (m, 5 H), 1.92 (s, 3 H) 13 C-NMR (50 MHz, D2 O, TSP standard) delta: 183.70, 160.06, 73.72, 72.24, 71.54, 60.77, 43.92, 26.06 IR (KBr, cm-1): 3348, 3104, 3084, 1686, 1650, 1554, 1456, 1406, 1356, 1304, 1246, 1202, 1100, 1018, 920, 846, 800, 760, 648

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; Kao Corporation; US5723133; (1998); A;,
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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. 10541-78-3, name is 2-Methoxy-N-methylaniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 2-Methoxy-N-methylaniline

(a) 5-Methoxy-4-methyl-2H-benzo[e][1 ,2,4]thiadiazin-3(4H)-one 1 ,1 -dioxide (2913) To a vigorously stirred solution of chlorosulfonyl isocyanate (1 .52 mL) in 1 -nitropropane (20 mL) at -40 C, under nitrogen, was slowly added over 10 min a solution of 2-methoxy-N- methylaniline (2.0 g) in 1 -nitropropane (10 mL). The mixture was then allowed to warm to RT and stirred for 60 min. Anhydrous aluminum chloride (2.53 g) was added and the mixture was then allowed to stir at 120 C for 2 h. The hot solution was poured onto ice (~40 g) and, after stirring and complete melting of ice, the resulting precipitate was collected by filtration and rinsed with water (5 mL). The insoluble crude material was suspended in an aqueous solution of NaHC03 (1 .5 g/30 mL) and heated until most of the precipitate was dissolved. The suspension was filtered, and the filtrate was adjusted to pH ~1 with 6 N HCI. The resulting solid was collected by filtration, rinsed with water, and dried to give the titled compound (0.79 g) as a yellowish solid. LCMS m/z 242.9 (M+H); 1H NMR (400 MHz, DMSO-c/e) delta ppm 3.40 (s, 3H), 3.92 (s, 3H), 7.38-7.50 (m, 3H).

The synthetic route of 10541-78-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; ADAMS, Jerry Leroy; ATOR, Laura E.; DUFFY, Kevin J.; GRAYBILL, Todd L.; KIESOW, Terence John; LIAN, Yiqian; MOORE, Michael Lee; RALPH, Jeffrey M.; RIDGERS, Lance Howard; (370 pag.)WO2017/98421; (2017); A1;,
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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. 910251-11-5, name is Potassium trifluoro(methoxymethyl)borate, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C2H5BF3KO

Intermediate 52a 6-chloro-3-(methoxymethyI)-l-trityl-lH-pyrazolo[43-c]pyridine Under Argon, the solution of 6-cUoro-3-iodo-l-trityl-lH-pyrazolot4,3-c]pyridine (52 mg, 0.100 mmol), potassium methoxymethyltrifluoroborate (16.66 mg, 0.110 mmol), palladium(n) acetate (0.671 mg, 2.99 mupiiotaomicron), (2-DICYCLOHEXYLPHOSPfflNO-2′,6′- DIISOPROPYL-l,l’-BIPHENYL)[2-(2-AMINOETHYL)PHENYL)]PALLADIUM(n) (4.36 mg, 5.98 mol) and cesium carbonate (0.024 ml, 0.299 mmol) in 1,4-Dioxane (0.9 ml) and Water (0.1 ml) was allowed to stir at 100 C for 24h. LC-MS showed the desired product’s mass. EtOAc was added into the mixture and the organic layer was washed by water and brine. After drying over Na2S04 the organic layer was evaporated under reduced pressure yielding 6- c oro-3-(memoxymethyl)-l-1rityl-lH-pyrazolo[4,3-c]pyridine, 52a. The intermediate was taken to the next reaction without further purification. MS ESI Calc’d for C27H22CIN3O [M+H]+ 440, found 440.

According to the analysis of related databases, 910251-11-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP & DOHME CORP.; LIM, Jongwon; KELLEY, Elizabeth Helen; METHOT, Joey, L.; ZHOU, Hua; PETROCCHI, Alessia; MANSOOR, Umar Faruk; FISCHER, Christian; O’BOYLE, Brendan, M.; GUERIN, David Joseph; BIENSTOCK, Corey, E.; BOYCE, Christopher, W.; DANIELS, Matthew, H.; FALCONE, Danielle; FERGUSON, Ronald, D., II; FEVRIER, Salem; HUANG, Xianhai; LIPFORD, Kathryn Ann; SLOMAN, David, L.; WILSON, Kevin; ZHOU, Wei; WITTER, David; MALETIC, Milana, M.; SILIPHAIVANH, Phieng; WO2013/63214; (2013); A1;,
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These common heterocyclic compound, 41406-00-2, name is 3-Isopropoxyaniline, 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. Formula: C9H13NO

EXAMPLE A; 3-(3-Isopropoxy-phenyl)-2-thioxo-2,3-dhydr-1H-quinazolin-4-one To a solution of 3-isopropoxy aniline (6.0 g, 40 mmol) in 150 ml of CHCl3 was added dropwise thiophos-gene (2.81 ml, 44 mmol) at 0 C. After the addition of thiophosgene, triethylamine (7.0 ml, 48 mmol) was added slowly and the reaction mixture was stirred for 2 hours at room temperature. It was then concentrated and diluted with 200 ml of ethyl acetate. The triethylamine hydrochloride salt was filtered off and the filtrate was concentrated to yield crude 3-isopropoxyphenyl isothiocyanate.The crude 3-isopropoxyphenyl isothiocyanate was dissolved in 150 ml of acetic acid, and anthranilic acid (6.04 g, 44 mmol) was added. The resulting reaction mixture was refluxed for 16 hours and then cooled to room temperature. The white solid was separated which was filtered to yield 9.0 g of the title compound (72.1%) mp 288-290 C.

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

Reference:
Patent; Warner-Lambert Company; US6897213; (2005); B1;,
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