Month: June 2021

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. 14862-52-3, name is 3,5-Dibromochlorobenzene, A new synthetic method of this compound is introduced below., HPLC of Formula: C6H3Br2Cl

1-chloro-3,5-dibromobenzene (5.40 g, 20 mmol) and 3-pyridine boronic acid (5.17 g, 42 mmol) were added to a 100 mL three neck round bottom flask. To this flask, dioxane (80 mL) and aqueous K2CO3 (2 N, 40 mL) were added. The mixture was stirred and degassed with a steam of argon for 30 minutes. Then under argon atmosphere, 200 mg (0.16 mmol) Pd(PPh3)4 was added. The mixture was brought to 100 C. and stirred overnight. The next day, solvent was removed by roto-evaporation and residue was suspended into an equal amount of water (50 mL) and CH2Cl2 (50 mL). The organic layer was separated from aqueous layer and washed with brine (50 mL×3). After drying over Na2SO4, and removal of drying agent, 5.33 g transparent liquid 3,3′-(5-chloro-1,3-phenylene)dipyridine (100%, Compound L) was obtained. 1H NMR (400 MHz, CDCl3) 8.91 (s, 2H), 8.69 (d, 2H), 7.95 (d, 2H), 7.66 (s, 1H), 7.63 (s, 2H), 7.50-7.44 (m, 2H).

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; General Electric Company; US2010/331547; (2010); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 13078-79-0,Some common heterocyclic compound, 13078-79-0, name is 2-(3-Chlorophenyl)ethanamine, molecular formula is C8H10ClN, 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 26 (100mg, 0.27mmol), 4-tolylmethanamine (100mg, 0.08mL, 0.81mmol), BOP reagent (120mg, 0.27mmol), and triethylamine (80mg, 0.11mL, 0.81mmol) in anhydrous DMF (5mL) was stirred at 25C for 12h. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with brine, dried and filtered. Removal of the solvent gave a residue that was purified by column chromatography (silica gel, ethyl acetate:n-hexane=1:2 as eluent) to furnish 4 (70mg, 56%), mp 240-242C (from ethanol).

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

Reference:
Article; Famiglini, Valeria; La Regina, Giuseppe; Coluccia, Antonio; Pelliccia, Sveva; Brancale, Andrea; Maga, Giovanni; Crespan, Emmanuele; Badia, Roger; Clotet, Bonaventura; Este, Jose A.; Cirilli, Roberto; Novellino, Ettore; Silvestri, Romano; European Journal of Medicinal Chemistry; vol. 80; (2014); p. 101 – 111;,
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, Product Details of 2106-02-7

[3452] A solution of 2-chloro-4-fluoroaniline ( 1.000 g, 6.870 mmol), methyl 4-(bromomethyl)-3-fluorobenzoate ( 1.867 g, 7.557 mmol) and potassium carbonate ( 1.899 g, 13.740 mmol) in acetonitrile ( 10 mL) was stirred at the room temperature for 15 hr, filtered to remove solids, and concentrated under the reduced pressure. The residue was chromatographed (Si02, 40 g cartridge; ethyl acetate / hexane = 0 % to 10 %) to give methyl 4-(((2-chloro-4-fluorophenyl)amino)methyl)-3-fluorobenzoate as green solid (0.974 g, 45.5 %).

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; CHONG KUN DANG PHARMACEUTICAL CORP.; LEE, Jaekwang; KIM, Yuntae; LEE, Chang Sik; SONG, Hyeseung; GWAK, Dal-Yong; LEE, Jaeyoung; OH, Jung Taek; LEE, Chang Gon; KIM, II Hyang; (1041 pag.)WO2017/23133; (2017); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 6276-54-6, A common heterocyclic compound, 6276-54-6, name is 3-Chloropropan-1-amine hydrochloride, molecular formula is C3H9Cl2N, 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.

Add 750 g of dimethyl sulfoxide to the reaction flask.420 g (2.196 mol) of compound 1 (prepared in Example 3) are added,Add 340g (8.5mol) of sodium hydroxide, heat, raise the temperature to about 90 C, add 14g of potassium iodide,Under stirring, 340 g (2.615 mol) of 3-chloropropylamine hydrochloride was added in portions, and the reaction was incubated at 100-110 C. for 20 hr.After confirmation of the reaction, 1000 g of water was added, pH=10~11 was adjusted with concentrated hydrochloric acid, and the mixture was stirred for about 1.5 hr. The mixture was allowed to stand for liquid separation. The aqueous phase was extracted once with 800 g of toluene. The organic phase was combined and used 50 kg of sodium chloride. The aqueous solution was washed once, and the liquid was separated. The organic solvent was concentrated and the solvent was weighed to obtain 500 g of an oil (theoretical amount: 545.38 g). Yield: 91.7%.

The synthetic route of 6276-54-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Inner Mongolia Jingdong Pharmaceutical Co., LTD.; Guo, Rong Yao; Wang, Xiao Feng; Inner Mongolia Jingdong Pharmaceutical Co., Ltd.; Guo Rongyao; Wang Xiaofeng; (11 pag.)CN107698538; (2018); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 627-42-9, These common heterocyclic compound, 627-42-9, name is 2-Methoxyethyl chloride, 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.

From the vacuum dryer D0201 out of 3,4-dihydroxybenzonitrile into the reactor R0301,Into the solvent acetone, the raw material 3,4-dihydroxybenzonitrile was dissolved under sufficient stirring,Then followed by adding potassium iodide and anhydrous potassium carbonate, the reaction was heated 9h after reflux, sample sampling by the sampling port 03001,The reaction was stopped completely after the reaction of the raw material, the reaction liquid through the material pump P0301 into the filter F0301,Remove the solid anhydrous potassium carbonate, the filtrate into the vacuum dryer D0301,After vacuum drying solvent acetone recovery, the acetone recovered into the acetone recovery tank V0301,After the acetone is recovered, the product 3,4-bis (2-methoxyethoxy) benzeneacetonitrile is obtained,The product 3,4-bis (2-methoxyethoxy) benzeneacetonitrile exits vacuum dryer D0301.

The synthetic route of 627-42-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Yancheng Normal College; Nanjing Tech University; Han Qing; Gu Huiwen; Sui Jingjiao; Yin Zijian; Sun Yaquan; (13 pag.)CN106957274; (2017); 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. 38762-41-3, name is 4-Bromo-2-chloroaniline, A new synthetic method of this compound is introduced below., HPLC of Formula: C6H5BrClN

2-Fluoro-4-bromoaniline (3.83 g, 18.55 mmol) was added to a reaction flask, then anhydrous tetrahydrofuran (20 ml) was added, and the mixture was cooled to -78 C with a dry ice ethanol bath, and LiHMDS (55.65 ml, 55.65 mmol), after reacting at -78 C for 30 minutes, methyl 2-chloro-1,5-dimethyl-6-oxo-1,6-dihydropyridine-3-carboxylate (4.00) was added. g, 18.55 mmol), after completion, the reaction was stirred at -78 C for 1 hour. After the completion of the reaction, the mixture was stirred at room temperature, and the reaction was quenched with saturated aqueous ammonium chloride.Column chromatography to obtain compounds(6.0 g, yield: 83.9%).

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; BINJIANG PHARMA INC; Tianjin Binjiang Pharmaceutical Research And Development Co., Ltd.; TIAN HONGQI; Tian Hongqi; (39 pag.)CN109988105; (2019); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Some common heterocyclic compound, 104-52-9, name is 3-Phenylpropyl Chloride, molecular formula is C9H11Cl, 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. name: 3-Phenylpropyl Chloride

General procedure: To a suspension of alkyl halide (1 mmol) and nucleophilic reagents(NaOAc or KSCN) (2 mmol) in water (5 mL), Fe3O4SiO2/DABCO(0.225 g) was added and the mixture was stirred at 90 C for the lengths of time shown in Table 1. After completion of the reaction as indicated by TLC [using n-hexane/ethyl acetate (5:1)], the reaction was allowed to cool to room temperature and the magnetic catalyst was concentrated on the side wall of the reaction vessel using an external magnet. The reaction mixture residue was poured into water (10 mL)and extracted with EtOAc (3 × 10 mL). The combined organic layers were dried over anhydrous Na2SO4, filtered and evaporated in vacuo to give the product in 74% to 91% isolated yields.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 104-52-9, its application will become more common.

Reference:
Article; Davarpanah, Jamal; Kiasat, Ali Reza; Catalysis Communications; vol. 42; (2013); p. 98 – 103;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 33786-89-9, name is 5-Chloro-m-phenylenediamine, 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 33786-89-9, Formula: C6H7ClN2

4-Chloro-6,7-dimethoxyquinazoline (200 mg, 0.89 mmol) and 5-amino-3-chloroaniline (253 mg, 1.78 mmol)were combined in isopropanol (3 mL) and heated to reflux for 16 hours under an atmosphere of dry nitrogen. After coolingto 20C the mixture was diluted with methanol (5 mL) and the resulting precipitate was filtered and dried, in vacuo, toafford 252 mg (77%) of (3-amino-5-chlorophenyl)-(6,7-dimethoxyquinazolin-4-yl)amine hydrochloride (mp. 298-301 C;LC-MS: 331 (MH+)). A portion of this product (175 mg, 0.476 mmol) was dissolved in 80% acetic acid/H2O (12 mL),cooled to 0C, and a solution of NaNO2 (36 mg, 0.516 mmol) in H2O (300 mL) was added. The solution was stirred for10 minutes at 0C and NaN3 (33 mg, 0.50 mmol) in H2O (300 mL) was added. The reaction mixture was allowed to warmto 20C and stirred 16 hours. The resulting precipitate was filtered and dissolved in 10% methanol in CHCl3 and thesolution was washed with saturated aqueous NaHCO3, and brine, dried over Na2SO4, filtered and concentrated in vacuoto yield 59 mg (35%) of the title product as a yellow solid; mp 205-206C.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Chloro-m-phenylenediamine, and friends who are interested can also refer to it.

Reference:
Patent; Pfizer Products Inc.; OSI Pharmaceuticals, LLC; Schnur, Rodney Caughren; Arnold, Lee Daniel; (28 pag.)EP2163546; (2016); B1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 39989-43-0, A common heterocyclic compound, 39989-43-0, name is 3,5-Dichlorobenzylamine, molecular formula is C7H7Cl2N, 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 45 Synthesis of Compound 46 (S)-9-fluorenylmethyl 10-(3,5-dichlorobenzyl)-2,2-dimethyl-4,9,13,16-tetraoxo-3,17-dioxa-5,10,15-triazaiscos-19-en-8-ylcarbamate To 3,5-dichlorobenzylamine (0.49 g, 2.8 mmol) in DCM (5 mL) was added the alpha,beta-unsaturated ketone 45 (2.12 mmol) in DCM (10 mL). After stirring at room temperature for 15 mins, Fmoc-diaminobutyric acid(Boc)-OH (1.35 g, 3.1 mmol) and DIC (0.5 mL, 3.2 mmol) was added. The reaction was stirred at room temperature overnight. The DCM was removed by rotary evaporation and the residue was subjected to column chromatography on silica gel using petroleum ether:EtOAc (1:1 to 0:1), providing compound 46 (0.48 g, 22%).

The synthetic route of 39989-43-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Blaskovich, Mark Arnold Thomas; Cassidy, Peter Joseph; US2009/221557; (2009); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics