Month: July 2021

Related Products of 1435-48-9, These common heterocyclic compound, 1435-48-9, name is 2,4-Dichloro-1-fluorobenzene, 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.

Alternate preparation: To a solution of 2,4-dichloro-1-fluorobenzene (100 g, 0.606 mol) in THF (1.4 L) under nitrogen at -78 C, was added a 2.5 M solution of n-BuLi in hexanes (267 mL, 0.666 mol) dropwise over a period of 30 min, maintaining the temperature between -70 to -78 C. After 1.5 h stirring at -78 C, methyl formate (72.6 mL, 1.21 mol) was added slowly, and the reaction mixture was stirred overnight, warming up to rt. The reaction was quenched with sat. aqueous NH4CI (200 mL) and the organic layer was separated. The organic solvents were removed by distillation at atmosphere pressure and the crude material which contained a small amount of THF was crystallized from hexanes to give the title compound.

Statistics shows that 2,4-Dichloro-1-fluorobenzene is playing an increasingly important role. we look forward to future research findings about 1435-48-9.

Reference:
Patent; OSI PHARMACEUTICALS, LLC; JIN, Meizhong; MULVIHILL, Mark, J.; STEINIG, Arno, G.; WANG, Jing; WO2012/158658; (2012); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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. 823-57-4, name is 2-Bromo-5-chloroaniline belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. COA of Formula: C6H5BrClN

2,4,6-Tripropyl-1,3,5,2,4,6-trioxatriphosphorinane 2,4,6-trioxide (50 wtpercentsolution in ethyl acetate, 8.1 mL, 13.6 mmol) was added slowly to a stirred solution of2-15 bromo-5-chloroaniline (1.5 g, 7.27 mmol), thiane-4-carboxylic acid (1.0 g, 6.84 mmol)and pyridine (2.7 mL, 33.4 mmol) in ethyl acetate (14 mL) at ooc under nitrogen. Thereaction mixture was allowed to warm slowly to 20°C and stirred for 64 h. The resultantsuspension was diluted with ethyl acetate (20 mL) and quenched with water (30 mL).The solids were collected by filtration, washing sequentially with ethyl acetate (2 x 2020 mL), water (20 mL) and diethyl ether (2 x 20 mL). The solids were dried at 50°C invacuo for 16 h, to afford the title compound (2.08 g, 86percent) as a pink powder. DH (500MHz, DMSO-d6) 9.51 (br s, 1H), 7.71-7.65 (m, 2H), 7.21 (dd, J8.6, 2.6 Hz, 1H), 2.71-2.62 (m, 4H), 2.57 (tt, J 11.5, 3.1 Hz, 1H), 2.19-2.08 (m, 2H), 1.78-1.63 (m, 2H). HPLCMS(method 5): MH+ m/z 334, RT 1.90 minutes.

The synthetic route of 823-57-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UCB BIOPHARMA SPRL; BRACE, Gareth Neil; CHAPPELL, Rose Elizabeth; DEBOVES, Herve Jean Claude; FOLEY, Anne Marie; FOULKES, Gregory; JONES, Elizabeth Pearl; LECOMTE, Fabien Claude; QUINCEY, Joanna Rachel; SCHULZE, Monika-Sarah Elisabeth Dorothea; SELBY, Matthew Duncan; SMALLEY, Adam Peter; TAYLOR, Richard David; TOWNSEND, Robert James; ZHU, Zhaoning; (278 pag.)WO2018/229079; (2018); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 116369-24-5,Some common heterocyclic compound, 116369-24-5, name is 4-Bromo-5-chloro-2-fluoroaniline, molecular formula is C6H4BrClFN, 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.

Add 4-bromo-5-chloro-2-fluoroaniline (0.5 g, 2.24 mmol) to 1,4-dioxane (8.0 mL) and water (4.0 mL), and then add 1-isopropyl-5 in this order. -(4,4,5,5-tetramethyl-1,3,2-dioxorane-2-yl) pyridine-2 (1H) -one (0.65 g, 2.46 mmol),Potassium carbonate (0.94g, 6.72mmol) and Pd (dppf) Cl2 (0.1g, 0.12mmol),After replacing with nitrogen three times, the reaction was carried out at 80 C for 10 hours.After the reaction is completed, cool to room temperature, pour the reaction solution into water, extract with ethyl acetate, combine the organic phases, dry, filter, and concentrate. The residue is purified by silica gel column chromatography (eluent: ethyl acetate / petroleum ether). = 3/1),The title compound (0.4 g, yield: 64%) was obtained in this step.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Bromo-5-chloro-2-fluoroaniline, its application will become more common.

Reference:
Patent; Sichuan Kelun Botai Bio-pharmaceutical Co., Ltd.; Liu Jinming; Cai Jiaqiang; He Ting; Wang Lichun; Wang Jingyi; (27 pag.)CN110240593; (2019); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 102-49-8, These common heterocyclic compound, 102-49-8, name is 3,4-Dichlorobenzylamine, 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: EDC hydrochloride (1.2 mmol) and HOBt (1.0 mmol) were added at 0 °C to each parallel vial containing a solution of the appropriate acid 44-53 (1 mmol) in dichloromethane, and either cyclohexylamine or 2,3-dichlorobenzylamine (1.5 mmol) was added at the same temperature. After warming up to room temperature, the vials were placed in the Buechi Syncore reactor. Stirring was maintained at 300 rpm overnight and then morpholinomethylpolystyrene (3 equiv/mol) was added. The solutions were kept at room temperature for 1 h, then polymer bound p-toluenesulfonic acid (3 equiv/mol) was added to each vial, and the reaction mixtures were stirred at room temperature for an additional 24 h. The mixtures were filtered and the solutions were evaporated to dryness to give carboxamides 6-25. Solid products were purified by crystallization from ethanol or aqueous ethanol. Oil products were purified by silica gel column chromatography column (dichloromethane as eluent).

The synthetic route of 102-49-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Piscitelli, Francesco; Ligresti, Alessia; La Regina, Giuseppe; Gatti, Valerio; Brizzi, Antonella; Pasquini, Serena; Allar, Marco; Carai, Mauro Antonio Maria; Novellino, Ettore; Colombo, Giancarlo; Di Marzo, Vincenzo; Corelli, Federico; Silvestri, Romano; European Journal of Medicinal Chemistry; vol. 46; 11; (2011); p. 5641 – 5653;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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. 1005-56-7, name is O-Phenyl carbonochloridothioate, A new synthetic method of this compound is introduced below., COA of Formula: C7H5ClOS

In a 30 ml eggplant type flask,Methyl alpha-L-fucopyranoside178.2 mg (1.0 mmol),Dioctyldichlorotin41.6 mg (0.10 mmol),Tetrabutylammonium iodide110.7 mg (0.30 mmol),Tetrahydrofuran10 ml was added,Followed by stirring.To this mixed solutionPhenyl chlorothionoformate0.175 ml (1.3 mmol) was added,Then,1,2,2,6,6-pentamethylpiperidine0.271 ml (1.5 mmol) was added,The reaction was carried out at 20 C. for 6 hours.After completion of the reaction,To the reaction solution was added saturated aqueous solution of ammonium chloride20 ml was added,The extraction operation was carried out three times with 20 ml of ethyl acetate.The organic phase (ethyl acetate phase) was washed with 20 ml of water,After washing with 20 ml of an aqueous sodium chloride solution,It was dried over anhydrous magnesium sulfate,After filtration,The solvent (ethyl acetate) was distilled off under reduced pressure.The residueBy silica gel chromatographyAs a result of purification (developing solvent n-hexane: ethyl acetate = 5: 1)Methyl 3-O-phenoxythiocarbonyl-alpha-L-fucopyranosideWas obtained at 283.8 mg (yield 90%).Since the alpha-L-fucopyranoside in which the hydroxyl group other than the 3-position was monophenoxythiocarbonylated could not be obtained, the selectivity of methyl 3-O-phenoxythiocarbonyl-alpha-L-D-fucopyranoside was 100%.

The synthetic route of 1005-56-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NAGASAKI UNIVERSITY; TOKUYAMA CORPORATION; ONOMURA, OSAMU; MURAMATSU, WATARU; IWASAKI, FUMIAKI; (32 pag.)JP5669643; (2015); B2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 6529-53-9, 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 6529-53-9 as follows.

Step D: Preparation of 6-chloro-2-[2-(4-chlorophenyl)ethoxy]-9-(2,3,5-tri-O-acetyl-beta-D-ribofuranosyl)purine To a solution of crude 6-chloro-2-hydroxy-9-(2,3,5-tri-O-acetyl-beta-D-ribofuranosyl)-purine (44.0 g, ca 100 mmoles), dissolved in glass distilled dimethylformamide (2 Liters), is added 2-(4-chlorophenyl)ethyl bromide (43.6 g, 200 mmoles), followed by cesium carbonate (100 g, 307 mmoles). The mixture is stirred at room temperature for 24 hours, evaporated to dryness (TBath<50 C.), and the residue partitioned between dichloromethane (1 liter) and water (1 liter). The organic phase is dried (Na2SO4), filtered, and evaporated. The residue is washed with. hexanes (2*500 mL) to remove excess 2-(4-chlorophenyl)ethyl bromide, then dissolved in dichloromethane (250 mL), adsorbed onto silica gel (100 g), and chromatographed over silica gel (1000 g) using a gradient of ethyl acetate (30%?50%) in hexanes. Fractions containing product are collected and evaporated to dryness to afford the desired intermediate as a yellow foam. Typical yield: 40-70% for Steps C and D combined. 1H-NMR (DMSO-d6): delta8.06 (s, 1H, H-8), 7.25 (s, 4H, Ar), 6.10 (d, 1H, H-1', J=4.8 Hz), 5.90 (dd, 1H, H-2', J=5.3, 5.0 Hz), 5.62 (dd, 1H, H-3', J=5.3, 5.2 Hz), 4.63-4.56 (m, 2H, OCH2-C), 4.43-4.37 (m, 2H, H-4' & H-5'alpha), 4.29 (dd, 1H, H-5'beta, J=12.0, 4.1 Hz), 3.11 (t, 2H, O-C-CH2-, J=6.9 Hz), 2.10 (s, 3H, COCH3), 2.06 (s, 3H, COCH3), 2.05 (s, 3H, COCH3). ; Step D: Preparation of 6-chloro-2-[2-(4-chlorophenyl)ethoxy]-9-(2,3,5-tri-O-acetyl-[beta]-D-ribofuranosyl)purineEMI8.0[0062] To a mixture of 6-chloro-2-hydroxy-9-(2,3,5-tri-O-acetyl-[beta]-D-ribofuranosyl)purine (Example 2, Step C) and 2-(4-chlorophenyl)ethyl bromide (300.1 g, 1.36 mol) in dimethylformamide (7,280 mL), cesium carbonate (665 g, 2.04 mol) was added. The reaction was allowed to stir under inert atmosphere for 32 hours. The reaction was concentrated under reduced pressure and partitioned between dichloromethane and water. The organic layer was dried over magnesium sulfate, filtered, and evaporated under reduced pressure. The crude product was purified by column chromatography eluting with ethyl acetate/heptanes to yield a yellow solid of 6-chloro-2-[2-(4-chlorophenyl)ethoxy]-9-(2,3,5-tri-O-acetyl-[beta]-D-ribofuranosyl)purine Typical Yield: 64% According to the analysis of related databases, 6529-53-9, the application of this compound in the production field has become more and more popular. Reference:
Patent; Moorman, Allan R.; US2003/199686; (2003); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 202197-26-0, A common heterocyclic compound, 202197-26-0, name is 3-Chloro-4-((3-fluorobenzyl)oxy)aniline, molecular formula is C13H11ClFNO, 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 6 4-[3-chloro-4-(3-fluoro-benzyloxy)-phenylamino]-6-nitro-quinazoline In a flask equipped with a reflux condenser, 6-nitro-4-chloro-quinazoline 1.20g (5.7mmol) and 4-(3-fluorobenzyloxy)-3-chloroaniline 1.37g (5.6mmol) were dissolved into 80mL of isopropanol, and the solution was refluxed for 3h. Then a lot of yellow solid was deposited, which was filtered, dried under vacuum, and identified as the title compound. Yield: 67%. 1H-NMR (400MHz, CDCl3): delta11.30(1H, br), 9.54-9.48(1H, m), 8.45-8.41(1H, m), 8.31-8.25(1H, m), 7.98-7.89(1H, m), 7.50-7.47(1H, m), 7.35-7.26 (1H, m), 7.05-6.96(1H, m), 6.90-6.80(2H, m), 7.74-7.60(2H, m), 4.84(2H, s).

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; SHANGHAI ALLIST PHARMACEUTICAL., INC.; EP1990337; (2008); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 2533-69-9, name is Methyl 2,2,2-trichloroacetimidate, belongs to chlorides-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 2533-69-9, category: chlorides-buliding-blocks

2-amino-4-(2-methoxypyridin-3-yl)phenyIamine 3; To a solution of 4- bromo-o-phenylenediainine 1 (0.935g, 5 mmol), 2-methoxy-3-pyridyl boronic acid 2 and Na2CO3 (1.06Og, lOmmols) in l,4-dioxane/H2O (3:1, 2OmL) flushed with N2 was added Pd(PPh3)4 (0.575g, 0.5mmol) in one portion. Resulting reaction mixture was stirred under N2 atmosphere at 100 0C for 12h. Solvent was evaporated and residue was extracted with ethyl acetate (20 mL). Dried over anhydrous sodiumsulfate. Filtered, and evaporation of solvent gave a crude residue which was used as such in the following reaction. (0.850g).[00532] 5-(2-methoxypyridin-3-yl)-2-(trichIoromethyl)-lH-benzimidazole 4: To a solution of 2-amino-4-(2-methoxypyridin-3-yl)phenylamine 3 obtained from above reaction (0.215g, 1 mmol) in acetic acid (2mL) cooled to 0 0C was added methyl trichloroacetimidate (0.193g, 1.1 mmol) under N2 atmosphere and resulting reaction mixture was stirred at room temperature for 3h. Acetic acid was evaporated to give crude 5-(2-methoxypyridin-3-yl)-2- (trichloromethyl)-lH-benzimidazole which was used as such in the following step (0.3g). Reference: Louvet, P.; Lallement, G.; Pernot-Marino, L; Luu-Duc, C; Blanchet, G. Eur. J.Med.Chem. 1993, 28, 71-75.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; CHEMBRIDGE RESEARCH LABORATORIES, INC.; WO2007/56155; (2007); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 932-96-7, The chemical industry reduces the impact on the environment during synthesis 932-96-7, name is 4-Chloro-N-methylaniline, I believe this compound will play a more active role in future production and life.

General procedure: A definite amount of polymer-supported ruthenium(II)-pheox complex cat. A was evacuated and backfilled with argon. The reaction flask was charged with (0.3 mmol) of amines dissolved in CH2Cl2 (3 mL) by injection through the side arm of the flask and the reaction flask was cooled in ice bath. Ethyldiazoacetate (0.035mL, 0.33 mmol) was slowly inserted and the reaction was stirred for 15 min at room temperature. The reaction product was isolated by centrifugation and the catalyst was separated by washing with acetonitrile and hexane respectively and dried under vacuum to be ready for the next use. The product in the filtrate was concentrated to afford the desired product in a pure form without further purification.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 4-Chloro-N-methylaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Abu-Elfotoh, Abdel-Moneim; Asian Journal of Chemistry; vol. 29; 2; (2017); p. 349 – 352;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 2687-12-9,Some common heterocyclic compound, 2687-12-9, name is Cinnamyl chloride, molecular formula is C9H9Cl, 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 the reaction (R10), the compound (A1-1) was reacted with triethyl phosphite to obtain a compound (B1-1). Specifically, 15.2 g (0.10 mol) of the compound (A1-1) and 25.0 g (0.15 mol) of triethyl phosphite were added to a flask having a capacity of 200 mL. The content of the flask was stirred at 180 C. for 8 hours and then cooled to room temperature. Subsequently, unreacted triethyl phosphite contained in the content of the flask was distilled off under reduced pressure. Thereby, a compound (B1-1) which is a white liquid was obtained. The yield of the compound (B1-1) was 22.9 g, and the yield of the compound (B1-1) from the compound (A1-1) was 90%.

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

Reference:
Patent; Kyocera Document Solutions Co., Ltd.; Okada, Hideki; (38 pag.)JP2018/95596; (2018); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics