Month: March 2021

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 321-28-8 as follows. Quality Control of 1-Fluoro-2-methoxybenzene

1-Fluoro-2-methoxybenzene a13 (0.0126 g, 0.10 mmol), acridine photosensitizer (A) (0.0029 g, 0.005 mmol) and L-valine ethyl ester b1 were added sequentially under argon protection. 0.0218 g, 0.15 mmol), 1,2-dichloroethane (DCE) 2.0 mL.The reaction was irradiated for 48 hours under a 6W blue light at room temperature.After completion of the reaction, the solvent was evaporated under reduced pressure and purified by column chromatography, eluting solvent: (V) petroleum ether / (V) ethyl acetate = 20/1.A yellow liquid (30) (0.0188 g, 95%) was obtained.

According to the analysis of related databases, 321-28-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Central China Normal University; Zhou Shaolin; Shi Weimin; (27 pag.)CN110294685; (2019); A;,
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Application of 1484-26-0,Some common heterocyclic compound, 1484-26-0, name is 3-Benzyloxyaniline, molecular formula is C13H13NO, 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.

A mixture of 2,6-dichloropyrimidine (2.00 g, 13.4 mmol), 3-benzyloxoaniline (2.07 g, 13.4 mmol) and triethylamine (2.72 g, 26.8 mmol) in 1-butanol (20 mL) was stirred at 50¡ã C. for 17 h. The reaction mixture was concentrated to remove most of the 1-butanol, the crude product was preadsorbed onto silica gel using chloroform and purified by flash chromatography (95:5 chloroform/methanol) to afford N4-(3-benzyloxyphenyl)-2-chloro-4-pyrimidineamine (1.70 g, 40percent) as colorless oil: 1H NMR (300 MHz, DMSO-d6) delta 10.2 (s, 1H), 8.16 (d, J=6.0 Hz, 1H), 7.48-7.24 (m, 7H), 7.12 (d, J=9.0 Hz, 1H), 6.78 (m, 2H), 5.11 (s, 2H); ESI MS m/z 312 [C17H14ClN3O+H]+.

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

Reference:
Patent; RIGEL PHARMACEUTICALS, INC.; Singh, Rajinder; Argade, Ankush; Payan, Donald; Molineaux, Susan; Holland, Sacha; Clough, Jeffrey; Keim, Holger; Bhamidipati, Somasekhar; Sylvain, Catherine; Li, Hui; Rossi, Alexander; US2015/266828; (2015); A1;,
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Synthetic Route of 54149-17-6, 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. 54149-17-6, name is 1-Bromo-2-(2-methoxyethoxy)ethane, This compound has unique chemical properties. The synthetic route is as follows.

Example 9 Synthesis of 2,7-Dibromo-9,9-bis(3,6-dioxaheptyl)-fluorene Benzyltriethylammonium chloride (3.19 g, 14 mmole, 0.077 eq) and 2,7-dibromofluorene (59 g, 182 mmole, 1 eq) were suspended in 178 mL DMSO. 50% aqeous NaOH (80 mL) was added. 1-Bromo-2-(2-methoxyethoxy)ethane (80 g, 437 mmole, 2.4 eq) was then added in small portions. The reaction was stirred at room temperature for 2 hours before it was stopped and the aqueous layer was extracted with ether. The combined ether layers were washed with water five times and dried over Na2SO4. The organic layer was filtered, evaporated to dryness, and the residual was flash chromatographed on a silica-gel column to give 73 g of the pure compound in a yield of 86%.

The chemical industry reduces the impact on the environment during synthesis 1-Bromo-2-(2-methoxyethoxy)ethane. I believe this compound will play a more active role in future production and life.

Reference:
Patent; 3M Innovative Properties Company; US7094902; (2006); B2;,
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Electric Literature of 1758-46-9, 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. 1758-46-9, name is 2-Phenoxyethylamine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

0.137 g (1 mmol) of phenoxyethylamine, 1.0 mmol of triethylamine, Catalytic amount of 4-dimethylaminopyridine (DMAP), 20 mL of dichloromethane, 1.2 mmol of (R)-2-[4-(6-chloroquinoxalin-2-yloxy)phenoxy]propanoyl chloride was added dropwise under ice bath The dichloromethane solution was dissolved in about 15 minutes and allowed to react at room temperature for 1 hour. After the reaction is completed, the organic layer is washed with water and washed with saturated brine. Dry, desolvent, The crude product was subjected to column chromatography [V petroleum ether: V ethyl acetate = 7:1 to 5:1] to afford white (R)-2-N-(2-phenoxyethyl)-2-[4-(6 -chloroquinoxaline-2-yloxy)phenoxy]propanamide, mp 150-153 C, yield 78.3%,

The synthetic route of 2-Phenoxyethylamine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Anhui Agricultural University; Tian Shengni; Yang Zihui; Ye Aihua; Huang Shixia; Li Junhong; Tian Qi; (8 pag.)CN108689921; (2018); A;,
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Adding a certain compound to certain chemical reactions, such as: 1758-46-9, name is 2-Phenoxyethylamine, 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 1758-46-9, Application In Synthesis of 2-Phenoxyethylamine

General procedure: To a solution of 2-phenoxy-ethylamine (5 eq.) or 2-(2-methoxyphenoxy-)ethylamine (5 eq.) in 2-methoxyethanol(25 mL per mmol of amine) the appropriate aliphatic chloride33-39 (1 eq.) and KI (cat.) was added. The mixturewas refluxed for18-48 h and concentrated. The residue was suspended in CHCl3and washed with 1M NaOH, brine, dried over anhydrous Na2SO4and concentrated. The crude was purified by flash chromatographyto give the titled compound.4.1.2.1 2-(2,2-Diphenyl-1,3-dioxolan-4-yl)-N-(2-phenoxyethyl)ethan-1-amine (17) Pale yellow liquid (74% yield). TLC (cicloexane/EtOAc 3:7): Rf?=?0.38. 1H NMR (600?MHz, Chloroform-d) delta 1.71-1.76 (m, 1H), 1.83-1.89 (m, 1H), 1.98 (bs, 1H), 2.73-2.77 (m, 1H), 2.80-2.84 (m, 1H), 2.92 (t, J?=?5.1?Hz, 2H), 3.63 (t, J?=?7.5?Hz, 1H), 3.97 (t, J?=?5.1, 2H), 4.05 (t, J?=?7.2?Hz, 1H), 4.16-4.20 (m, 1H), 6.77-6.94 (m, 3H), 7.13-7.28 (m, 8H), 7.36-7.49 (m, 4H). 13C NMR (151?MHz, CDCl3) delta 33.65, 46.64, 48.85, 67.06, 70.02, 75.60, 114.54, 120.89, 126.20, 127.96, 128.05, 128.16, 129.48, 142.64, 158.78. MS (ESI): m/z [M + H]+: 389.2.

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

Reference:
Article; Franchini, Silvia; Sorbi, Claudia; Linciano, Pasquale; Carnevale, Gianluca; Tait, Annalisa; Ronsisvalle, Simone; Buccioni, Michela; Del Bello, Fabio; Cilia, Antonio; Pirona, Lorenza; Denora, Nunzio; Iacobazzi, Rosa Maria; Brasili, Livio; European Journal of Medicinal Chemistry; vol. 176; (2019); p. 310 – 325;,
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Synthetic Route of 17715-69-4,Some common heterocyclic compound, 17715-69-4, name is 1-Bromo-2,4-dimethoxybenzene, molecular formula is C8H9BrO2, 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 suspension of Pd2(dba)3 (6.9mg, 0.0075mmol), tBu3PHBF4 (8.7mg, 0.03mmol), KOH (42mg, 0.75mmol), aryl bromide 4 (0.36mmol) and tetralone 3 (0.3mmol) in a mixture of dioxane/water (4:1, v/v, 3mL) was degassed and heated under Ar and microwave irradiation (80W of initial power, 100¡ãC, 40min, infrared probe). Then, the mixture was allowed to cool to rt, diluted in AcOEt, washed with saturated NH4Cl solution, dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The crude material was purified by silica gel chromatography. Dioxane quality is extremely important for the success of the reaction. Characterization of alpha-aryl-alpha-tetralones is given in Ref.[26].

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Bromo-2,4-dimethoxybenzene, its application will become more common.

Reference:
Article; Fernandes, Talita de A.; Costa, Paulo R. R.; Manvar, Dinesh; Basu, Amartya; Kaushik-Basu, Neerja; Domingos, Jorge L. O.; Nichols, Daniel Brian; European Journal of Medicinal Chemistry; vol. 112; (2016); p. 33 – 38;,
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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. 126-38-5, name is 1-Bromo-2,2-dimethoxypropane, A new synthetic method of this compound is introduced below., HPLC of Formula: C5H11BrO2

a sealed flask, 3,6-dichloro-4-methylpyridazine (27 g, 161 mmol) was suspended in aqueous ammonia (25%, 300 mL). The reaction mixture was heated at 110 C. for 48 hours (turned into solution after 1 hour). After cooling to room temperature, the reaction was poured into CH2Cl2, and the organic phase was separated, dried over Na2SO4, and concentrated under vacuum, to give 22.4 g of 6-chloro-4-methyl-pyridazin-3-amine and 6-chloro-5-methyl-pyridazin-3-amine as a mixture of regioisomers which were used directly in the next step.The mixture of regioisomers 6-chloro-4-methyl-pyridazin-3-amine and 6-chloro-5-methyl-pyridazin-3-amine (22.4 g) was suspended in 2-propanol (300 mL). 1-bromo-2,2-dimethoxypropane (36.0 g, 26.6 mL, 193 mmol, 1.2 eq.) and PPTS (2.96 g, 11.6 mmol, 0.0725 eq.) were added, and the resulting solution was heated at 105 C. overnight. The solvent was removed in vacuo and the residue was taken up in CH2Cl2 and washed with NaHCO3. The organic phases were dried over Na2SO4, concentrated in vacuo and the crude light brown solid was chromatographed (EtOAc/Heptane 1/2-1/1) to give separately 6.1 g of 6-chloro-2,8-dimethyl-imidazo[1,2-b]pyridazine MS m/z 182.1 [M+H]+(21%) as a white solid and 5.9 g of 6-chloro-2,7-dimethyl-imidazo[1,2-b]pyridazine MS m/z 182.1 [M+H] (20%) as a white solid.

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; Hoffmann-La Roche Inc.; PTC Therapeutics, Inc.; Ratni, Hasane; Green, Luke; Weetall, Maria L.; Naryshkin, Nikolai A.; (33 pag.)US2019/315773; (2019); 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. 6738-23-4, name is 2,4-Dimethylanisole, A new synthetic method of this compound is introduced below., Formula: C9H12O

Step A: Preparation of 2-chloro-N-[2-methoxy-3,5-dimethylphenyl]methyl acetamide To a solution of 2.72 g. (0.02 mole) of 2,4-dimethylanisole in 20 ml. of acetic acid and 2 ml. of sulfuric acid was added (2.47 g., 0.02 mole) 2-chloro-N-(hydroxymethyl)acetamide at <20 C. over a 10 minute period with stirring. After standing at room temperature about 20 hours the mixture was poured with stirring into 250 ml. of ice-water. After 1 hour the precipitate was collected, washed with water and dried at 60 C. and recrystallized 3 times from methanol:water (3:2), once from ethanol:water (3:2) and twice from ethanol:water (1:1) to give 0.34 g. of 2-chloro-N-[2-methoxy-3,5-dimethylphenyl]methyl acetamide, m.p. 124-124.5 C. 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; Merck & Co., Inc.; US4070464; (1978); A;,
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Some common heterocyclic compound, 7252-83-7, name is 2-Bromo-1,1-dimethoxyethane, molecular formula is C4H9BrO2, 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. Quality Control of 2-Bromo-1,1-dimethoxyethane

[000321] A mixture of 4-chlorophenol (10 g, 78 mmol), 2-bromo-l,l- dimethoxyethane(13.1 g, 78 mmol), K2C03 (14 g, 101 mmol), KI (100 mg) in DMF (50 mL) was stirred at reflux for 3 h. The mixture was cooled to rt and filtered. The filtrate was added water (200 mL), extracted with ethyl acetate (100 mL x 2), washed with water (100 mL x 3), brine (100 mL x 1), dried over Na2S04, concentrated, and purified by column chromatography on silica gel (ethyl acetate in petroleum ether, 10% v/v) to yield Compound 11A (15 g, yield 89 %) as a colorless liquid. 1H-NMR (CDC13, 400 MHz) major characteristic peaks: delta (ppm) 3.45 (s, 6H), 3.96 (d, J= 5.2 Hz, 2H), 4.70 (t, J= 5.6 Hz, 1H), 6.85 (d, J= 8.8 Hz, 2H), 7.21 (d, J= 8.8 Hz, 2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 7252-83-7, its application will become more common.

Reference:
Patent; BIOMARIN PHARMACEUTICAL INC.; WANG, Bing; CHU, Daniel; BRIDGES, Alexander, James; WO2015/42397; (2015); A1;,
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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. 14869-41-1, name is 2-(2-Chloroethoxy)acetic acid belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 2-(2-Chloroethoxy)acetic acid

1.39 g (10.0 mmol) 2-(2-chloro-ethoxy)-acetic acid are heated to 60¡ã C. for 1 h with 1 drop of DMF in 8.0 ml of thionyl chloride and then evaporated down completely i. vac. The residue is added in 5 ml THF to a mixture of 1.18 g (10.0 mmol) 4-amino-benzonitrile and 4.5 ml (32.5 mmol) TEA in 20 ml THF at 0¡ã C. and rinsed with 5 ml THF. Then the mixture is stirred for 16 h at ambient temperature. After evaporation i. vac. the residue is combined with ethyl acetate, washed with 2N hydrochloric acid and sat. sodium hydrogen carbonate solution and dried on sodium sulphate. After evaporation i. vac. the residue is purified by chromatography on silica gel (eluant gradient: petroleum ether/ethyl acetate=6:1–>3:1). Yield: 1.82 g (76percent) Rf value: 0.43 (silica gel, petroleum ether/ethyl acetate 1:1) C11H11ClN2O2 (238.67) Mass spectrum: (M-H)-=237/239 (chlorine isotopes); (c) 2-(2-chloro-ethoxy)-acetic acid-chloride13.86 g (100 mmol) 2-(2-chloro-ethoxy)-acetic acid are combined with 15 ml (207 mmol) thionyl chloride at ambient temperature and 3 drops of DMF are added. The mixture is stirred for 16 h at 60¡ã C. Then it is evaporated down i. vac., the residue is distilled i. vac. and the overflow is collected at 75-78¡ã C.Yield: 12.90 g (82percent)C4H6Cl2O2 (157.00)Mass spectrum: (M+H)+=157/159/161 (chlorine isotopes)

The synthetic route of 14869-41-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Dahmann, Georg; Gerlach, Kai; Pfau, Roland; Priepke, Henning; Wienen, Wolfgang; Schuler-Metz, Annette; Nar, Herbert; US2008/51578; (2008); A1;,
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