Month: October 2020

36216-80-5,A common heterocyclic compound, 36216-80-5,Benzo[d]isoxazol-3-amine, 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: To a stirred solution of pyridin-2-amine (1.0 g, 10.6 mmol) and pyridine (1.01 mL, 12.7 mmol) in THF (35 mL) was added 2,2,2- trichloroethyl chloroformate (1.76 mL, 12.7 mmol) dropwise at 0 C. The mixture was stirred at 0 C for 1.5 h, poured into water, and extracted with EtOAc. The organic layer was washed with water, dried over anhydrous MgSO4, and concentrated in vacuo. The residue was triturated with Et2O-hexane to give 36 (1.76 g, 62%) as a colorless powder.

The chemical industry reduces the impact on the environment during synthesis, 36216-80-5,Benzo[d]isoxazol-3-amine,I believe this compound will play a more active role in future production and life.

Reference£º
Article; Kono, Mitsunori; Matsumoto, Takahiro; Kawamura, Toru; Nishimura, Atsushi; Kiyota, Yoshihiro; Oki, Hideyuki; Miyazaki, Junichi; Igaki, Shigeru; Behnke, Craig A.; Shimojo, Masato; Kori, Masakuni; Bioorganic and Medicinal Chemistry; vol. 21; 1; (2013); p. 28 – 41;,
Benzisoxazole – Wikipedia
Benzisoxazole – an overview | ScienceDirect Topics

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 16263-54-0,3,6-Dichlorobenzo[d]isoxazole, as follows.16263-54-0

5) Preparation 6-chloro-3-piperazinyl-benzisoxazole 3,6-dichlorobenzisoxazole (5.2g, 27.8 mmol), and anhydrous piperazine (24g, 278 mmol) are placed in an egg type flask and react at 120C for 24 hours. After completion of the reaction, 52 ml of an ice-water mixture is added for quenching the reaction. Further 15 ml of 50% NaOH solution is added to the reaction solution. The reaction solution is stirred for 5 minutes and extracted with dichloromethane (30ml*3). The dichloromethane layer is combined, washed with 20 ml of saturated saline, dried over anhydrous MgSO4, evaporated to dryness, and subjected to a separation on a column of alumina (200-300mesh), eluting with dichloromethane_methanol=100:1, to obtain 4.7g of 6-chloro-3-piperazinyl-benzisoxazole, with a yield of 71%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3,6-Dichlorobenzo[d]isoxazole, and friends who are interested can also refer to it.

Reference£º
Patent; Jiangsu Guohua Investment Co., Ltd; Shanghai Institute of Pharmaceutical Industry; EP2322520; (2011); A1;,
Benzisoxazole – Wikipedia
Benzisoxazole – an overview | ScienceDirect Topics

651780-27-7,A common heterocyclic compound, 651780-27-7,Ethyl 6-bromobenzo[d]isoxazole-3-carboxylate, 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.

10% Palladium on carbon (1.5 g) and triethylamine (7.5 g, 82.4 mmol) were added to a solution of ethyl 6-bromobenzisoxazole-3-carboxylate (20 g, 0.081 mol) in ethanol (300ml) at 0 C. under an atmosphere of nitrogen. The nitrogen atmosphere was removed by evacuation and replaced with hydrogen gas, and the reaction mixture was maintained for 1 hour. The hydrogen atmosphere was removed by evacuation and replaced with nitrogen gas, and the palladium removed by filtration through Celite. The filter cake was washed with ethanol (3¡Á50 mL) and the filtrates were concentrated. The residue was dissolved in dichloromethane (200 mL) and the solution was washed with water (4¡Á50 mL), dried (sodium sulfate) and evaporated to provide 13.0 g of the product as a yellow solid (96%). The ester was saponified using sodium hydroxide to provide the acid. The acid was coupled with the bicyclobase according to procedure A.

The chemical industry reduces the impact on the environment during synthesis, 651780-27-7,Ethyl 6-bromobenzo[d]isoxazole-3-carboxylate,I believe this compound will play a more active role in future production and life.

Reference£º
Patent; Xie, Wenge; Herbert, Brian; Ma, Jianguo; Nguyen, Truc Minh; Schumacher, Richard; Gauss, Carla Maria; Tehim, Ashok; US2005/250808; (2005); A1;,
Benzisoxazole – Wikipedia
Benzisoxazole – an overview | ScienceDirect Topics

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 651780-27-7,Ethyl 6-bromobenzo[d]isoxazole-3-carboxylate, as follows.651780-27-7

20a) Ethyl 6-(4-hydroxyphenyl)-l,2-benzisoxazole-3-carboxylateEthyl 6-bromo-l,2-benzisoxazole-3-carboxylate (0.34 g, 1.26 mmol), (4- hydroxyphenyl)boronic acid (0.21, 1.51 mmol), tetrakis(triphenylphosphine)palladium (0) (0.06 g, 0.05 mmol) and 2 M sodium carbonate (5 mL) in 1 ,2-dimethoxyethane (6 mL) were stirred at 80 0C for 1 hour. The reaction mixture was diluted with water, followed by ethyl acetate. The layers were separated and the ethyl acetate layer was washed with brine, dried over magnesium sulfate, filtered, and concentrated to afford the crude material. The crude material was purified using hexanes: ethyl acetate (0 to 40% ethyl acetate) to afford a mixture of desired product, plus the free acid of the desired product, 6-(4-hydroxyphenyl)-l,2- benzisoxazole-3-carboxylic acid. All the fractions were combined and concentrated. The mixture was then dissolved in ethanol. Thionyl chloride was added, and the reaction mixture was reflux for 8 days. The reaction mixture was cooled to room temperature and concentrated. The concentrated material was diluted with 5% sodium bicarbonate, and extracted with ethyl acetate. The ethyl acetate layer was washed with water followed by brine, dried over magnesium sulfate, filtered, and concentrated. The crude material was purified using hexanes: ethyl acetate (0 to 100% ethyl acetate) to afford 0.044 g (13%) of ethyl 6-(4-hydroxyphenyl)- 1 ,2-benzisoxazole-3- carboxylate. 1H NMR (400 MHz, d6-DMSO): delta 9.76 (s, IH), 8.05 (m, 2H), 7.79 (dd, J = 8, 1 Hz, IH), 7.65 (d, J = 9 Hz, 2H), 6.88 (d, J = 9 Hz, 2H), 4.47 (q, J = 7 Hz, 2H), 1.39 (t, J = 7 Hz, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 651780-27-7, and friends who are interested can also refer to it.

Reference£º
Patent; SMITHKLINE BEECHAM CORPORATION; WO2008/157270; (2008); A1;,
Benzisoxazole – Wikipedia
Benzisoxazole – an overview | ScienceDirect Topics

36216-80-5,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. Benzo[d]isoxazol-3-amine,36216-80-5, This compound has unique chemical properties. The synthetic route is as follows.

EXAMPLE 27 1-(2,6-DICHLOROBENZOYL)-3-(3-BENZISOXAZOLYL)UREA 3-Aminobenzisoxazole (300 grams) and 2,6-dichlorobenzoyl isocyanate (600 grams) in 50 ml. methylene chloride were stirred at room temperature for one hour. The solvent was then evaporated and the precipitate recrystallized from ethanol. The identity of the product was determined by NMR and IR analysis, yield 500 mg., m.p.=212-215 C. Calculated: C, 51.45; H, 2.59; N, 12.00. Found: C, 51.35; H, 2.40; N, 11.84.

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, 36216-80-5.

Reference£º
Patent; Eli Lilly and Company; US4336264; (1982); A;,
Benzisoxazole – Wikipedia
Benzisoxazole – an overview | ScienceDirect Topics

719-64-2,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. 5-Chloro-3-phenylbenzo[c]isoxazole,719-64-2, This compound has unique chemical properties. The synthetic route is as follows.

A, in a reaction vessel equipped with a stirrer, a reflux condenser, 5-chloro-3-phenyl-benzisoxazole 0.26 mol, the mass fraction of 30% 2-bromo-5-fluoronitrobenzene solution 390ml, nickel chloride powder 0.46 mol, control the stirring speed at 190 rpm, raise the solution temperature to 78 C, reflux reaction 120 min; B, adding 90% of 4-chlorophenethylamine solution with a mass fraction of 21% slowly add the ethylene glycol dimethyl ether solution with a mass fraction of 37% adding time to control at 110min, continue to reflux reaction 5h. C, add the mass fraction of 27% sodium bicarbonate solution 200ml, reduce the solution temperature to 16 C, molecular sieve bleaching, filtration, the filtrate was concentrated, again lowering the solution temperature to 5 C, the mass fraction of 70% triethylamine solution washing, calcium oxide dehydrating agent dehydration, to give crystals of 2-amino-5-chlorobenzophenone 55.59 g, yield 92%.

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, 719-64-2.

Reference£º
Patent; Chengdu Qiesite Technology Co., Ltd.; Peng Fei; (9 pag.)CN106083621; (2016); A;,
Benzisoxazole – Wikipedia
Benzisoxazole – an overview | ScienceDirect Topics

651780-27-7 A common heterocyclic compound, 651780-27-7,Ethyl 6-bromobenzo[d]isoxazole-3-carboxylate, 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.

20a) Ethyl 6-(4-hydroxyphenyl)-l,2-benzisoxazole-3-carboxylateEthyl 6-bromo-l,2-benzisoxazole-3-carboxylate (0.34 g, 1.26 mmol), (4- hydroxyphenyl)boronic acid (0.21, 1.51 mmol), tetrakis(triphenylphosphine)palladium (0) (0.06 g, 0.05 mmol) and 2 M sodium carbonate (5 mL) in 1 ,2-dimethoxyethane (6 mL) were stirred at 80 0C for 1 hour. The reaction mixture was diluted with water, followed by ethyl acetate. The layers were separated and the ethyl acetate layer was washed with brine, dried over magnesium sulfate, filtered, and concentrated to afford the crude material. The crude material was purified using hexanes: ethyl acetate (0 to 40% ethyl acetate) to afford a mixture of desired product, plus the free acid of the desired product, 6-(4-hydroxyphenyl)-l,2- benzisoxazole-3-carboxylic acid. All the fractions were combined and concentrated.

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 651780-27-7 reaction routes.

Reference£º
Patent; SMITHKLINE BEECHAM CORPORATION; WO2008/157270; (2008); A1;,
Benzisoxazole – Wikipedia
Benzisoxazole – 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.651780-27-7,A new synthetic method of this compound is introduced below.651780-27-7

To a stirred solution of ethyl 6-bromo-1,2-benzoxazole-3-carboxylate (1.1 g) in THF (10 ml) and EtOH (3 ml), LiBH4 (0.133 g) was added drop wise at 0oC under inert atmosphere. The re- action mixture was stirred at 0oC for 2 h. Reaction was monitored by TLC. After the completion, the reaction mixture was diluted with Water (20 ml), quenched with 5% NaOH solution and ex- tracted with Ethyl acetate (30 ml x 2). The combined organic extracts were dried over Na2SO4, filtered and concentrated under reduced pressure. The crude product was purified by flash chro- matography (eluting in 15-20% ethyl acetate in heptane as a mobile phase) to afford (0.8 g) of the title compound. HPLC/MS (method 1): Rt : 1.587 min; MS: m / z = 229 (M+1).

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, Ethyl 6-bromobenzo[d]isoxazole-3-carboxylate.

Reference£º
Patent; BASF SE; NARINE, Arun; ADISECHAN, Ashokkumar; VYAS, Devendra; DATTA, Gopal Krishna; VALLINAYAGAM, Ramakrishnan; CHAUDHURI, Rupsha; SAMBASIVAN, Sunderraman; (127 pag.)WO2018/177781; (2018); A1;,
Benzisoxazole – Wikipedia
Benzisoxazole – an overview | ScienceDirect Topics

36216-80-5,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. Benzo[d]isoxazol-3-amine,36216-80-5, This compound has unique chemical properties. The synthetic route is as follows.

A solution of 1 ,2-benzisoxazol-3-amine (1.00 g; CASNo. 36216-80-5) and triethylamine (1.09 mL) in acetonitrile (5 mL) was added dropwise to at 0 0C solution of phenyl chloroformate (0.989 mL) in THF (20 mL). The reaction was stirred at 0 0C for 1 h and then allowed to warm to room temp overnight. The reaction was diluted with ethyl acetate and washed with 1 N HCI and brine. The organic layer was dried over sodium sulfate, filtered, and concentrated to give the crude product as a reddish brown solid. The solid was triturated with refluxing diisopropyl ether, cooled to room temp, and filtered to give the final product as a tan solid (1.22 g, 64%). m/z 255 (MH+).

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, 36216-80-5.

Reference£º
Patent; PFIZER INC.; WO2009/127948; (2009); A1;; ; Patent; PFIZER INC.; WO2009/127949; (2009); A1;,
Benzisoxazole – Wikipedia
Benzisoxazole – an overview | ScienceDirect Topics

89976-56-7,The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a downstream synthesis route of the compound 89976-56-7

89976-56-7, A solution of 2,4-dimethoxybenzene-1-sulfonyl chloride (0.0799 g, 0.337 mmol) and 5-methylbenzo[d]isoxazol-3-amine I60 (0.050 g, 0.34 mmol) in pyridine (1 ml.) was irradiated in the microwave at 110 C for 2 hours. The resultant mixture was loaded onto silica gel and the product purified by column chromatography (12 g S1O2 cartridge, 0-45% EtOAc in petroleum benzine 40-60 C) [205] to yield the title compound (55.0 mg, 42% yield) as a white solid. NMR (400 MHz, CDCb) d 7.86 – 7.82 (m,1H), 7.72 (d, J = 8.81Hz, 1H), 7.37 – 7.28 (m, 2H), 6.49 (d, J = 2.26 Hz, 1H), 6.43 (dd, J = 2.29, 8.82 Hz, 1H), 3.96 (s, 3H), 3.80 (s, 3H), 2.47 (s, 3H). LCMS-A: rt 5.66 min, m/z 348.8 [M+H]+, 347.1 [M-H]

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 5-Methylbenzo[d]isoxazol-3-amine.

Reference£º
Patent; CTXT PTY LIMITED; STUPPLE, Paul, Anthony; LAGIAKOS, Helen, Rachel; MORROW, Benjamin, Joseph; FOITZIK, Richard, Charles; HEMLEY, Catherine, Fae; CAMERINO, Michelle, Ang; BOZIKIS, Ylva, Elisabet, Bergman; WALKER, Scott, Raymond; (321 pag.)WO2019/243491; (2019); A1;,
Benzisoxazole – Wikipedia
Benzisoxazole – an overview | ScienceDirect Topics