Month: June 2021

Application of 39226-96-5,Some common heterocyclic compound, 39226-96-5, name is (2-Chloro-3-(trifluoromethyl)phenyl)methanamine, molecular formula is C8H7ClF3N, 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: Compound 2a (438mg, 2.5mmol) and 2-chloro-3-(trifluoromethyl)benzylamine (419mg, 2.0mmol) were mixed with EDAC (480mg, 2.5mmol) and 1-hydrobenzotrizole (HOBt, 338mg, 2.5mmol) in dry dichloromethane (60mL). The reaction mixture was stirred for overnight at RT. Then the resultant mixture was washed with 2N HCl (50mL) and saturated aqueous NaHCO3 (40mL). The organic layer was dried over Na2SO4 and concentrated. The residue was purified by column chromatography on silica gel with eluent (2:98 MeOH/CH2Cl2) to afford a white solid product 3a (210mg, 28%)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route (2-Chloro-3-(trifluoromethyl)phenyl)methanamine, its application will become more common.

Reference:
Article; Gao, Mingzhang; Wang, Min; Glick-Wilson, Barbara E.; Meyer, Jill A.; Peters, Jonathan S.; Territo, Paul R.; Green, Mark A.; Hutchins, Gary D.; Zarrinmayeh, Hamideh; Zheng, Qi-Huang; Bioorganic and Medicinal Chemistry Letters; vol. 28; 9; (2018); p. 1603 – 1609;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 873-38-1, A common heterocyclic compound, 873-38-1, name is 2-Bromo-4-chloroaniline, molecular formula is C6H5BrClN, 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 2-iodoanilines (1.0 mmol), THF (3 mL), and t-BuOK (3 mmol) was stirred in a 10-mL sealed Schlenk tube for 5 min, and then dimethylthiocarbamoyl chloride (1.2 mmol) and CuBr (10 mol %) were added. The reaction mixture was heated at 60 C until completion as indicated by TLC. Then the mixture was cooled down to room temperature and quenched with sat. NH4Cl solution (5 mL). The aqueous phase was extracted with EtOAc (3 x10 mL). The combined organic phases were dried (Na2SO4), and the solvent was removed under reduced pressure. The obtained crude product was purified by flash column chromatography.

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:
Article; Chang, Cai-Zhu; Xu, Wan; Zeng, Meng-Tian; Liu, Min; Liu, Xing; Zhu, Hui; Dong, Zhi-Bing; Synthetic Communications; vol. 47; 13; (2017); p. 1262 – 1267;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 821-10-3, 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 821-10-3 as follows.

General procedure: K2CO3 (3a, 210 mg, 1.5 mmol) was added to a solution of b-ketoesters 5a-c (0.5 mmol) in acetone (10 mL) at 25 C. The reaction mixture was stirred at 25 C for 10 min. 1,4-Dichloro-2-butyne (2, 68 mg, 0.55 mmol) was added to the reaction mixture at reflux. The reaction mixture was stirred at 56 C for 8 h. The reaction mixture was cooled to 25 C and the solvent was concentrated. The residue was diluted with water (10 mL) and the mixture was extracted with CH2Cl2 (320 mL). The combined organic layers were washed with brine, dried, filtered and evaporated to afford crude product. Purification on silica gel (hexanes/EtOAc20/1e10/1) afforded 6a-c.

According to the analysis of related databases, 821-10-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Chan, Chieh-Kai; Lu, Yi-Ju; Chang, Meng-Yang; Tetrahedron; vol. 71; 51; (2015); p. 9544 – 9549;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 81927-55-1, These common heterocyclic compound, 81927-55-1, name is Benzyl 2,2,2-trichloroacetimidate, 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.

To a solution of scheme 5-8 compound S1 (24 g, 0.136 mol) and benzyl 2,2,2-trichloroacetimidate (51.3 g, 0.204 mol) in cychexane/dichloromethane (600 mL/120 mL) at room temperature was added trifluoromethanesulfonic anhydride (cat.1.2 mL) dropwise. The reaction mixture was stirred at room temperature overnight and filtered. The filtrate was washed with sat. NaHCO3 and brine, dried over anhydrous Na2SO4, filtered and concentrated. The residue was purified by column chromatography on silica gel (eluted with petroleum ether: ethyl acetate =10: 1) to afford the title compound (35 g, 93.3% yield) as a yellow oil.

Statistics shows that Benzyl 2,2,2-trichloroacetimidate is playing an increasingly important role. we look forward to future research findings about 81927-55-1.

Reference:
Patent; ACHILLION PHARMACEUTICALS, INC.; WILES, Jason, Allan; PHADKE, Avinash, S.; DESHPANDE, Milind; AGARWAL, Atul; CHEN, Dawei; GADHACHANDA, Venkat, Rao; HASHIMOTO, Akihiro; PAIS, Godwin; WANG, Qiuping; WANG, Xiangzhu; GREENLEE, William; (508 pag.)WO2017/35409; (2017); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 7464-11-1,Some common heterocyclic compound, 7464-11-1, name is 5,7-Dichloro-2-methylthiazolo[5,4-d]pyrimidine, molecular formula is C6H3Cl2N3S, 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 50-mL round-bottom flask, was charged with a solution of intermediate 41.2 (111 mg, 0.49 mmol, 1.00 equiv) in CH3CN(10 mL), K3P04 (322 mg, 1.52 mmol, 3.07 equiv), and compound 23.1 (125 mg, 0.57 mmol, 1.15 equiv). The reaction was stirred overnight at 85 C in an oil bath. Solids were filtered out and solution was concentrated under vacuum. The crude product obtained was purified using flash column chromatography to yield 180 mg (89%) of intermediate 41.3 as a yellow solid.

The synthetic route of 7464-11-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NIMBUS IRIS, INC.; ROMERO, Donna L.; MASSE, Craig E.; ROBINSON, Shaughnessy; GREENWOOD, Jeremy Robert; HARRIMAN, Geraldine; WO2015/48281; (2015); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 56961-77-4, 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. 56961-77-4, name is 1-Bromo-2,3-dichlorobenzene belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

[Intermediate 5-1] 10 g of 30.2 mmol was dissolved in 100 mL of xylene, followed by the addition of 8.7 g of NatBuO, stirring at 180 C., and then 3.41 g of 1-bromo-2,3-dichlorobenzene and 0.37 g Give it in sequential order. After 12 h, the reaction was quenched with NH4Cl, extracted with EA, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure.This was columned with EA: Hx to obtain 7.2 g (Yield 62%) of [Intermediate 17-1].

The synthetic route of 1-Bromo-2,3-dichlorobenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LG Chem, Ltd.; Gu Gi-dong; Yoon Jeong-min; Kim Gong-gyeom; Huh Nan-seul-a; Lee Gi-gon; Keum Su-jeong; (52 pag.)KR2018/112721; (2018); A;,
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. 102-49-8, name is 3,4-Dichlorobenzylamine, A new synthetic method of this compound is introduced below., category: chlorides-buliding-blocks

General procedure: General procedure: 120 mg of parent compound (i.e. 0.657 mmol of 4 or 0.729 mmol of 6) was dissolved in approx. 20 mL of THF and 1.5 molar equivalents of anhydrous K2CO3 were suspended inthe reaction mixture. 1.2 molar equivalents of respective substituted benzylamine were dilutedseparately in approx. 3 mL of THF and added to the reaction mixture in a dropwise manner (approx 5-min period). The mixture was stirred for 20 – 30 min at RT and the progress was monitored by TLC(Silica 60 F254, hexane : ethyl-acetate from 1:1 to 3:1, according to the expected lipophilicity of theproduct). The reaction mixture was adsorbed to silica. The product was purified by flashchromatography (silica, hexane / ethyl-acetate 0-30 percent gradient elution) and recrystalized fromEtOH / H20 if needed.

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:
Article; Zitko, Jan; Paterova, Pavla; Kubicek, Vladimir; Mandikova, Jana; Trejtnar, Frantisek; Kunes, Jiri; Dolezal, Martin; Bioorganic and Medicinal Chemistry Letters; vol. 23; 2; (2013); p. 476 – 479;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 468075-00-5, 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. 468075-00-5, name is 2-Bromo-1-chloro-4-(trifluoromethoxy)benzene, This compound has unique chemical properties. The synthetic route is as follows.

A suspension of ethyl 2-(3-(2-chloro-5-(trifluoromethoxy)phenyl)-8-methyl-3-azaspiro[5.5]undecan-9-yl)acetate (140 mg, 0.553 mmol), cesium carbonate (540 mg, 1.66 mmol), 2-bromo-1-chloro-4-(trifluoromethoxy)benzene (0.175 ml, 1.105 mmol) and (RuPhos)palladium(II) phenethylamine chloride (40.3 mg, 0.055 mmol) in 1,4-dioxane (3 ml) in amicrowave reaction vial was bubbled with nitrogen. The vial was sealed and the mixture was stirred overnight in an oil bath kept at 100C. The mixture was diluted with aq. NH4Cl solution and extracted 3 times with ethyl acetate. The combined organic layer was washed with brine, dried over MgSO4, filtered and evaporated to dryness. The crude product was purified by chromatography eluting with 0-10%-20% ethyl acetate-hex to give ethyl 2-(3 -(2-chloro-5-(trifluoromethoxy)phenyl)-8-methyl-3-azaspiro[5.5]undecan-9-yl)acetate. LCMS m/z 448.13 [M+H]+.

The chemical industry reduces the impact on the environment during synthesis 2-Bromo-1-chloro-4-(trifluoromethoxy)benzene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; MERCK SHARP & DOHME CORP.; CHELLIAH, Mariappan; CHU, Hong Dong; COX, Jason, M.; DEBENHAM, John, S; EAGEN, Keith; LAN, Ping; LONDON, Clare; PLOTKIN, Michael, A.; SHAH, Unmesh; SINZ, Christopher Joseph; SUN, Zhongxiang; VACCARO, Henry, M.; VENKATRAMAN, Skikanth; WO2014/59232; (2014); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 33863-76-2,Some common heterocyclic compound, 33863-76-2, name is 1-Bromo-3-chloro-5-fluorobenzene, molecular formula is C6H3BrClF, 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.

Reference 7; Synthesis of 2-(3-bromo-5-chlorophenyl)propanoic acid Step 1A heavy- wall flask was charged with sodium hydride (9.5 g, 239 mmol) (60% oil dispersion) in NMP (75 ml) under a positive nitrogen flow. Ethyl 2-cyanoacetate (27 g, 239 mmol) was added in a dropwise manner. The reaction mixture was stirred until no more bubbling was observed. l-Bromo-3-chloro-5-fluorobenzene (10.00 g, 48 mmol) was added to the reaction mixture. The flask was capped and the reaction mixture was heated to 115 0C. After 15 hours, the reaction mixture was cooled down and diluted with water. The pH of the reaction mixture was adjusted to 3 with 2N HCl and extracted with ether. The organics were combined and washed with an aqueous saturated solution of sodium bicarbonate, then with water and then brine. The organic layer was then dried with sodium sulfate and purified by column chromatography on silica gel using a gradient of 5 to 40 % EtOAc in hexanes to give ethyl 2-(3-bromo-5-chlorophenyl)-2-cyanoacetate (10.00 g, 69% yield) as a white semi solid.

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-3-chloro-5-fluorobenzene, its application will become more common.

Reference:
Patent; AMGEN INC.; WO2009/75874; (2009); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 14752-66-0, 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. 14752-66-0 name is Sodium 4-chlorobenzenesulfinate, 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.

0.3 mmol of 1H-indol-2-yldiphenylmethanol (the compound corresponding to the number (1), 0.0897 g) was weighed. 0.9 mmol of sodium 4-chlorobenzenesulfinate (the corresponding compound of No. (16), 0.1787 g) and 0.6 mmol of silver nitrate (0.1019 g) in a 20 mL schlenk reaction tube. Add 2 mL of absolute ethanol as a solvent, protect with argon gas, and stir the reaction at 80 C for 12 hours; After the reaction is completed, column chromatography separation (column chromatography separation conditions: The stationary phase was 200-300 mesh silica gel, the mobile phase was ethyl acetate (A) and petroleum ether (B), and the mobile phase change procedure (A:B) was 1:5) to obtain 0.1440 g of the reaction product. According to the characterization data, the obtained reaction product is pure 3-(4-chlorobenzenesulfonyl)-2-((4-(4-chlorobenzenesulfonyl)phenyl)(phenyl)methyl)-1H-indole (purity > 95) %); Calculated for product yield, the result was 76%.

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

Reference:
Patent; Soochow University (Suzhou); Xu Xiaoping; Ji Shunjun; Zhou Yu; (11 pag.)CN108276324; (2018); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics