Month: August 2021

Related Products of 13726-14-2,Some common heterocyclic compound, 13726-14-2, name is 4-Chloro-3-methoxyaniline, molecular formula is C7H8ClNO, 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.

Step 3: Preparation of N-(4-Chloro-3-methoxyphenyl)-l-(4-methoxybenzyl)-lH- yrazolof 4, 3-b]pyridin-3-amine (Exp- 1 -g4)[0088] Into a vessel containing 1.5 mL dioxane was placed 63 mg of the crude Exp-1- g3 prepared in Step 2 (0.2 mmol). To the vessel was added 39 mg of 4-chloro-3- methoxy-phenylamine (0.25 mmol), 18 mg Pd2dba3 (0.02 mmol), 23 mg Xantphos (0.04 mmol) and 130 mg Cs2C03 (0.4 mmol). The reaction mixture thus provided was refluxed under a nitrogen atmosphere for 4 hours, then filtered and concentrated under reduced pressure. The residue was subjected to Prep-TLC (PE:EtOAc = 2: 1) to obtain Exp-l-g4 (52 mg, 66 %).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Chloro-3-methoxyaniline, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP; ADDEX PHARMA S.A.; LIVERTON, Nigel; JONES, Philip; BOLEA, Christelle; CELANIRE, Sylvain; TANG, Lam; BOUDOU, Cedric; LEI, Zhiyu; LIU, Fuqing; LUO, Yunfu; DONG, Jingchao; SOLL, Richard; WO2013/60029; (2013); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 30273-47-3,Some common heterocyclic compound, 30273-47-3, name is 4-Bromo-5-chloro-2-methylaniline, molecular formula is C7H7BrClN, 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 95 Preparation of 4-bromo-2,3-dichloro-6-methylaniline This material was prepared from 4-bromo-5-chloro-2-methylaniline by chlorination with N-chlorosuccinimide. The product was isolated as a solid, m.p. 66-68 C. The product was characterized by IR and 1 H NMR spectroscopy and combustion analysis.

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-methylaniline, its application will become more common.

Reference:
Patent; The Dow Chemical Company; US4818273; (1989); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 210532-25-5, 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 210532-25-5 as follows.

To a mixture of 3-({3-[(tetrahydro-pyran-4-yl)-(2,2,2-trifluoro-acetyl)-amino]-pyridine- 4-carbonyl}-amino)-5,6-dihydro-4H-pyrrolo[3,4-c]pyrazole-l-carboxylic acid ethyl ester hydrochloride (0.75 mmol), dry dichloromethane (50 mL) and triethylamine (0.84 mL, 6 mmol) was added 3,5-difluorobenzenesulfonyl chloride (478 mg, 2.25 mmol). The mixture was stirred at room temperature for 4 hours then methanol (10 mL) and triethylamine (5 mL) were added. The mixture was then heated to 600C and the stirring continued for 2 hours. The solvents were evaporated and the crude residue purified by flash chromatography on silica gel, affording the title compound as pale yellow solid (100 mg). IH-NMR (400 MHz), delta (ppm, DMSOtZ6): 12.59, 12.35 (2s, IH), 11.04, 11.02 (2s, IH), 8.87, 8.82 (2s, IH), 7.93, 7.86 (2m, IH), 7.71-7.52 (m, 4H), 7.28 (d, IH), 4.61, 4.52 (2s, 2H), 3.86 (m, 2H), 3.81 (m, IH), 3.50 (m, 2H), 1.98 (m, 2H), 1.68, 1.64 (2s, 6H), 1.44 (m, 2H), mixture of tautomers

According to the analysis of related databases, 210532-25-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NERVIANO MEDICAL SCIENCES S.r.l.; WO2007/68637; (2007); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 13726-14-2, 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. 13726-14-2 name is 4-Chloro-3-methoxyaniline, 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.

A solution of 4-chloro-3-methoxy-aniline (7.00 g, 44.4 mmol) dissolved in dichloromethane (100 mL) at 5 C was treated portions with NBS (8.14 g, 45.7 mmol) over 1 hour, then warmed to 20 C and stirred at 20 C for 2 hours. On completion, a 5% aqueous Na2SO3 solution (100 mL) was added and the mixture was stirred for 10 minutes. The layers were separated and the organic layer was washed with water and saturated brine, dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The getting residue was purified by column chromatography (petroleum ether: ethyl acetate = 3:1) to give the title compound (9.00 g, 85% yield) as a dark brown solid.1H NMR (400MHz, CD3Cl) delta = 7.37 (s, 1H), 6.35 (s, 1H), 4.13 (br. s., 2H), 3.83 (s, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Chloro-3-methoxyaniline, and friends who are interested can also refer to it.

Reference:
Patent; RAZE THERAPEUTICS, INC.; MAINOLFI, Nello; (215 pag.)WO2018/106636; (2018); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 4535-90-4,Some common heterocyclic compound, 4535-90-4, name is 2-Chloro-N-methylethanamine hydrochloride, molecular formula is C3H9Cl2N, 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.

A9. (3RS,3aRS)-8-Fluoro-3-phenyl-3a,4-dihydro-3H-chromeno[4,3-c]pyrazole-2-carboxylic acid (2-chloro-ethyl)-methyl-amide; To an ice cold solution of 636 mg (1.92 mmol) (3RS,3aRS)-8-Fluoro-3-phenyl-3a,4-dihydro-3H-chromeno[4,3-c]pyrazole-2-carbonyl chloride (compound A7) in 40 ml dichloromethane are added 389 mg (3.85 mmol) triethyl amine and after 30 min a solution of 250 mg (1.92 mmol) 2-methylaminoethylchloride hydrochloride in 7 ml methanol. The mixture is stirred for 1 h at room temperature. Additional dichloromethane and a diluted aqueous solution of hydrochloric acid are added. The organic layer is dried with magnesium sulfate. The solvents are removed at reduced pressure. The crude product is purified by column chromatography (silica gel, light petroleum/ethyl acetate 2:1). 515 mg of the title compound are obtained as a yellowish solid. (m/z (MH+)=388.1).

The synthetic route of 4535-90-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Vennemann, Matthias; Baer, Thomas; Maier, Thomas; Lindenmaier, Andreas; Braunger, Juergen; Boehm, Markus; Zimmermann, Astrid; Gekeler, Volker; US2010/104659; (2010); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 367-22-6, 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. 367-22-6, name is 4-Chloro-3-fluoroaniline, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: The intermediate 4-ethoxy-1,3-benzenedisulfo chloride(1.2 g, 3.7 mmol) was dropwise added to a solution of 2,4-difluoro aniline (1.0 g, 7.5 mmol) with dichloromethane (15 mL) as solvent at room temperature under magneticstirring. After 10 min, triethylamine (0.5 mL) as acidbindingagent was dropwise added to the reaction mixture.The mixture was stirred under reflux at 35 C for about8 h. After the reaction completed as monitored by TLC, thesolvent was removed under reduced pressure. Under thecondition of ice bath, the mixture was dissolved in cold 5%NaOH aqueous solution to obtain filtrate. The solid wasobtained by adjusting the pH of filtrate with hydrochloricacid (VHCl: Vwater = 1:1) in the condition of ice salt bath.After filtrating and drying, crude product was prepared. Thecrude product was purified by recrystallization from ethanolwith excellent yield (Scheme 1).

The chemical industry reduces the impact on the environment during synthesis 4-Chloro-3-fluoroaniline. I believe this compound will play a more active role in future production and life.

Reference:
Article; Chen, Xin; Liu, Xiujie; Qiu, kai; Xu, Xiang; Li, Caiwen; Wang, Yan; Medicinal Chemistry Research; vol. 28; 9; (2019); p. 1388 – 1401;,
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. 932-96-7, name is 4-Chloro-N-methylaniline belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Safety of 4-Chloro-N-methylaniline

General procedure: Under an argon atmosphere, a 3 mL vial was charged with 6b (5mol%), KOtBu (5 mol%) and CPME (2 mL). Substrate 8 (0.28 mmol,1 equiv.) and PhSiH3(3 equiv.) were added and the vial was sealed with a septum cap. The septum cap was pierced with a syringe needle and placed into a six-slot steal autoclave. The autoclave was sealed, purged twice with CO2 and heated at 100C (oil bath) under CO2 atmosphere (1 bar) for 20 h. After this time the reaction mixture was allowed to cool and the gas was carefully released. The reaction mixture was analyzed by gas chromatography (GC).

The synthetic route of 932-96-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Santoro, Orlando; Nahra, Fady; Cordes, David B.; Slawin, Alexandra M.Z.; Nolan, Steven P.; Cazin, Catherine S.J.; Journal of Molecular Catalysis A: Chemical; vol. 423; (2016); p. 85 – 91;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 108-70-3, These common heterocyclic compound, 108-70-3, name is 1,3,5-Trichlorobenzene, 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.

In a reaction tube was added bis-bis [(1,2,3) -1-phenyl-2-propene] dipalladium(0.005 mmol) and 2-di-tert-butylphosphino-2?,4?,6?-triisopropylbiphenyl(0.02 mmol)Join 1mL1,4-dioxane solvent for 20-60 minutes can be stirred, Raw material 1,3,5-trichlorobenzene (0.5mmol), sodium tert-butoxide (2.25mmol), ammonium sulfate (0.75mmol) placed in a sealed tube, evacuated with nitrogen gas protection, and then has been coordinated The catalyst, then add 0.4mol / L ammonia 1,4-dioxane solution 2mL, finally adding 3mL solvent, sealing the sealed tube, heated to 100 C and stirred for 24h, after completion of the reaction by GCMS detection of raw materials have been completed. The reaction was terminated by adding 5mL of water diluted with tert-butyl methyl ether 5mL extracted three times, then add hydrochloric acid to adjust pH 11, extracted with tert-butyl methyl ether 5mL, The product gave the product 3,5-dichloroaniline (75 mg, 93%).

Statistics shows that 1,3,5-Trichlorobenzene is playing an increasingly important role. we look forward to future research findings about 108-70-3.

Reference:
Patent; East China Normal University; Xiao Yuanjing; Zhou Xiaofan; Hu Anjing; Cheng Huayu; Li Yongfeng; Zhao Qiuhua; Zhang Junliang; (9 pag.)CN106748801; (2017); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 2106-02-7, name is 2-Chloro-4-fluoroaniline, 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 2106-02-7, Application In Synthesis of 2-Chloro-4-fluoroaniline

DISSOLVE 1- (3, 5-BIS-TRIFLUOROMETHYL-BENZYL)-5-PHENYL-1H- [1, 2,3] triazole-4- carboxylic acid (398 mg, 0.96 mmol) in 1, 2-dichloromethane (2 mL) and DMF (2 drops) and add oxalyl chloride (0.083 mL, 0.96 mmol). After 1 h, concentrate the mixture under reduced pressure and dissolve the residue in pyridine (3 mL). Add 2-chloro-4- fluoroaniline (0.12 mL, 0.96 mmol) and DMAP (5 mg) and heat the mixture for 1 h at 100 C. Then cool the mixture to RT and concentrate under reduced pressure. Dissolve the residue in 20% IPROH/CHCL3 and wash with sat. aqueous NAHC03 and brine. Dry the organic layer over NA2SO4, filter and concentrate. Purify the residue by radial chromatography (MEOH/CHC13 gradient) to provide 93 mg (36%) of the title compound as a white foam. MS (ES) 543.0 (M+L) + ; RF= 0. 85 (2% MEOH/CHC13).

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, 2-Chloro-4-fluoroaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ELI LILLY AND COMPANY; WO2005/821; (2005); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 108-37-2, These common heterocyclic compound, 108-37-2, name is 1-Bromo-3-chlorobenzene, 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.

A 1.6 molar solution of butyllithium in hexanes (4.5 mL, 2.8 mmol) was placed in a three-neck flask equipped with a STIRRER, addition funnel, low-temperature thermometer and nitrogen inlet tube at 0 C. A solution of diisopropyl amine (1.13 mL, 8.1 mmol) in anhydrous tetrahydrofuran was added dropwise. The resulting solution was stirred at 0 C for ten minutes, then cooled to-78 C. Upon cooling, a solution of L-BROMO-3- chlorobenzene (1.4 g, 7.3 mmol) in anhydrous tetrahydrofuran was added dropwise. The reaction was allowed to stir at-78 C for one hour. Anhydrous dimethylformamide (636 GEL) was added. The solution was allowed to slowly warm to room temperature, followed by the addition of acetic acid (50 mL) and water (50 mL). The aqueous mixture was extracted with ether twice and the ether layers were separated. The combined ether layers were successively washed with aqueous hydrochloric acid and brine. The separated organic layer was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The resulting residue was purified by flash column chromatography on silica gel, eluting with 9: 1 hexanes: ethyl acetate to yield 2-chloro-6-bromobenzaldehyde as an off white solid (850 mg, 53 % yield). NMR (300 MHz, CDC13): 10.4 (s, 1H), 7.6 (m, 1H), 7.45 (m, 1H), 7.3 ppm (m, 1H).

The synthetic route of 108-37-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; RIGEL PHARMACEUTICALS, INC.; WO2004/99164; (2004); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics