Month: July 2021

Application of 13526-66-4, A common heterocyclic compound, 13526-66-4, name is 3-Bromo-6-chloroimidazo[1,2-b]pyridazine, molecular formula is C6H3BrClN3, 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) ferf-Butyl 4-(imidazo[1 ,2 ine-1 -carboxylateTo a solution of 1-Boc-4-methylene-piperidine (1.29 g, 6.5 mmol, 2.0 eq) in dry THF (10 mL) under nitrogen was added 9-BBN (0.5M in THF, 16.3 mL, 8.16 mmol, 2.5 eq). The reaction mixture was heated at 75C for 3 h. After cooling, the resulting solution was added to a mixture of 6-chloroimidazo[1 ,2-b]pyridazine (0.5 g, 3.2 mmol), Pd(dppf)CI2 (133 mg, 0.16 mmol, 0.05 eq) and K2C03 (1.35 g, 9.8 mmol, 3.0 eq) in DMF (5 mL) and water (1 mL). The reaction mixture was heated at 75C for 16 h then concentrated in vacuo. The residue was dissolved in EtOAc and washed with water (50 mL) and brine (20 mL). The organics were dried over MgS04 and concentrated in vacuo. Purification by chromatography on silica gel gave a solid (0.406 g, 40%); 1H NMR (400 MHz, DMSO-d6) delta ppm 8.21 (s, 1 H), 8.03 (d, J=9.1 Hz, 1 H), 7.71 (s, 1 H), 7.16 (d, J=9.1 Hz, 1 H), 3.91 (m, 2H), 2.55-2.79 (m, 4H), 1.92 (m, 1 H), 1.52-1.65 (m, 2H), 1.38 (s, 9H), 0.99-1.22 (m, 2H); m/z (ES+APCI)+: 317 [M+H]+.

The synthetic route of 13526-66-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MEDICAL RESEARCH COUNCIL TECHNOLOGY; OSBORNE, Simon; CHAPMAN, Timothy; WALLACE, Claire; WO2012/127212; (2012); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 2401-24-3, name is 2-Chloro-5-methoxyaniline, 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 2401-24-3, COA of Formula: C7H8ClNO

To a solution of 2-chloro-5-methoxyaniline (500 mg) and TEA (0.49 mL) in MeCN (4 mL) was added phenylacetyl chloride (0.42 mL) at 0 C., and the mixture was stirred at room temperature for 30 minutes. To the reaction solution was added water, and the mixture was extracted with AcOEt and washed with brine. The organic layer was dried over anhydrous sodium sulfate, and then filtered. The filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (Hexane/AcOEt) to give N-(2-chloro-5-methoxyphenyl)-2-phenylacetamide (657 mg).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Chloro-5-methoxyaniline, and friends who are interested can also refer to it.

Reference:
Patent; OTSUKA PHARMACEUTICAL CO., LTD.; KAWANO, Yoshikazu; SHIMIZU, Hiroshi; ISHIKAWA, Shunpei; TAKEMURA, Isso; HARIGUCHI, Norimitsu; MATSUBA, Miki; MATSUMOTO, Makoto; (92 pag.)US2019/40039; (2019); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

These common heterocyclic compound, 63624-28-2, name is 2,4-Dimethoxybenzene-1-sulfonyl 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. COA of Formula: C8H9ClO4S

Example 148: N-(benzo[d]isoxazol-3-yl)-2,4-dimethoxybenzenesulfonamide 148 A solution of 2,4-dimethoxybenzenesulfonyl chloride (0.18 g, 0.75 mmol) and benzo[d]isoxazol-3-amine (0.10 g, 0.75 mmol) in pyridine (1 ml.) was irradiated in the microwave at 1 10 C for 2 hours. The resultant mixture was loaded onto silica gel and the product purified twice by column chromatography (4 g Si02 cartridge, 0-45% EtOAc in petroleum benzine 40-60 C then 4g Si02 cartridge, 0-35% EtOAc in petroleum benzine 40-60 C) to yield two batches (78 mg and 5 mg) of [183] the title compound (total mass 83 mg, 33 % yield) as white solids. 1H NMR (400 MHz, CDCI3) d 8.1 1 (d, J = 8.05 Hz, 1H), 7.79 (s, 1H), 7.70 (d, J = 8.81Hz, 1H), 7.57 – 7.50 (m, 1H), 7.47 – 7.40 (m, 1H), 7.37 – 7.29 (m, 1H), 6.50 (d, J = 2.27 Hz, 1H), 6.42 (dd, J = 2.25, 8.81Hz, 1H), 3.98 (s, 3H), 3.81 (s, 3H). LCMS-B: rt 3.20 min, m/z = 356.8 [M+Na]+, 334.8 [M+H]+.

The synthetic route of 2,4-Dimethoxybenzene-1-sulfonyl chloride has been constantly updated, and we look forward to future research findings.

Reference:
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;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 14862-52-3, name is 3,5-Dibromochlorobenzene, 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 14862-52-3, Computed Properties of C6H3Br2Cl

In a 200 mL three-neck flask, a mixture of 5.0 g (19 mmol) of 1,3-dibromo-5-chlorobenzene, 6.5 g (39 mmol) of carbazole, 370 mg (1.9 mmol) of copper iodide, 510 mg (1.94 mmol) of 18-crown-6-ether, 8.9 g (47 mmol) of potassium carbonate, and 20 mL of 1,3-dimethyl-3,4,5,6-tetrahydro-2-(1H)pyrimidinone was deaerated while being stirred under reduced pressure and then heated and stirred at 170 C. in a nitrogen atmosphere for 11 hours to cause a reaction. After the reaction, this reaction mixture was washed with water, and an organic layer and an aqueous layer were separated. Then, magnesium sulfate was added to the organic layer to remove moisture. This suspension was filtered to obtain a filtrate. The obtained filtrate was concentrated and purified by silica gel column chromatography. A mixed solvent of toluene and hexane (toluene: hexane=1:5) was used as a developing solvent for the chromatography. The Rf value of the substance that was the object of the synthesis was 0.35, which was obtained by silica gel thin layer chromatography (TLC) (with a developing solvent containing ethyl acetate and hexane in a 10:1 ratio). The obtained fraction was concentrated, and hexane was added thereto. The mixture was irradiated with ultrasonic waves and then recrystallized to give 6.6 g of white powder that was the object of the synthesis in a yield of 80%. A scheme of the synthesis of Step 1 is shown in (a-1). The compound obtained in Step 1 was subjected to a nuclear magnetic resonance (NMR) measurement. The measurement data are as follows: 1H NMR (CDCl3, 300 MHz): delta(ppm)=7.31-7.64 (m, 12H), 7.71-7.72 (m, 1H), 7.75-7.76 (m, 1H), 7.84-7.85 (m, 1H), 8.15(d, J=7.8 Hz, 4H). are 1H NMR charts. Note that is a chart where the range of from 7.00 ppm to 8.50 ppm in is enlarged. The above results reveal that 9-[3-(9H-carbazol-9-yl)-5-chloro]phenyl-9H-carbazole (abbreviation: mCP-Cl) that was the object of the synthesis was obtained.

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, 3,5-Dibromochlorobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Semiconductor Energy Laboratory Co., Ltd.; TAKASU, Takako; OHSAWA, Nobuharu; US2013/75705; (2013); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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. 2533-69-9, name is Methyl 2,2,2-trichloroacetimidate, This compound has unique chemical properties. The synthetic route is as follows., Safety of Methyl 2,2,2-trichloroacetimidate

500 mg (2.31 mmol) 3,4-diamino-benzene-sulfonylethan-2-ol were dissolved in 10 ml concentrated acetic acid. 0.4 ml (1.4 equiv.) methyl-2,2,2-trichloroacetimidate were added slowly and the resulting mixture was stirred at room temperature for 4 h. The mixture was diluted with 100 ml toluene and the solvent was removed under reduced pressure. The residue was rinsed with toluene, filtered and dried under vacuo to give a brown crystalline solid pure enough for all further reactions. Yield: 680 mg MS (ES+): m/e = 345, chloro pattern.

According to the analysis of related databases, 2533-69-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Aventis Pharma Deutschland GmbH; EP1479676; (2004); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 19752-55-7, The chemical industry reduces the impact on the environment during synthesis 19752-55-7, name is 1-Bromo-3,5-dichlorobenzene, I believe this compound will play a more active role in future production and life.

N*3*-(3,5-Dichloro-phenyl)-l,N*5*-bis-(4-methoxy-benzyl)-N*5*-methyl-lH- [l,2,4]triazole-3,5-diamine In a 25 mL sealed tube, sodium tert-butoxide (97.9 mg, 1.02 mmol, Eq: 1.20), bis(dibenzylideneacetone)palladium (48.8 mg, 84.9 muiotaetaomicron, Eq: 0.1) and 2-di-tert-butylphosphino- 2′,4′,6′-triisopropylbiphenyl (36.0 mg, 84.9 muiotaetaomicron, Eq: 0.1) were combined with toluene (5 mL) to give a dark brown suspension. N5,l-bis(4-methoxybenzyl)-N5-methyl-lH-l,2,4-triazole-3,5- diamine (300 mg, 849 muiotaetaomicron, Eq: 1.00) and l-bromo-3,5-dichlorobenzene (230 mg, 1.02 mmol, Eq: 1.20) were added. The reaction mixture was degassed with argon for 15 min, and then heated to 110°C for 3 hours. The reaction mixture was cooled and diluted with EtOAc (50 mL), washed with H20 (25 mL) and brine (25 mL). The organic layer was dried over anhydrous MgS04, filtered and volatiles were removed under reduced pressure to yield an oil from which the compound was isolated by column chromatography (Hexanes/EtOAc = 70/30) to give an off- white solid 140 mg (33percent). MH+ 498.2

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, 1-Bromo-3,5-dichlorobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; DING, Qingjie; JIANG, Nan; WEIKERT, Robert James; WO2014/135472; (2014); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 19752-55-7,Some common heterocyclic compound, 19752-55-7, name is 1-Bromo-3,5-dichlorobenzene, molecular formula is C6H3BrCl2, 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.

It was dissolved in I-2 (68 g, 140 mmol) in a nitrogen environment in 500 mL tetrahydrofuran (THF), where the 1-bromo-3, 5-dichlorobenzene (38.0 g, 168.1 mmol) and tetrakis( triphenylphosphine) palladium was stirred into the (1.62 g, 1.4 mmol). Into a potassium carbonate (48.4 g, 350 mmol) in saturated water it was heated to reflux at 80°C for 12 hours. After the reaction was completed, the reaction solution into water and extracted with dichloromethane (DCM) and then water was removed with anhydrous MgSO4, filter and was concentrated under reduced pressure. Thus separated and purified the resulting residue was purified by flash column chromatography gave Compound I-3 (61.4 g, 87percent).

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-3,5-dichlorobenzene, its application will become more common.

Reference:
Patent; Cheil Industries Co., Ltd; Lee, Han Ir; Yu, Uhn Sun; Kang, Dong Min; Kang, Uii Soo; Yang, Yong Tak; Oh, Jae Jin; Yu, Dong Gyu; Lee, Sang Sin; Jang, Yuna; Jung, Su Young; Han, Su Jin; Hong, Jin Suk; (59 pag.)KR2015/6758; (2015); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 102-49-8, name is 3,4-Dichlorobenzylamine, 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 102-49-8, Application In Synthesis of 3,4-Dichlorobenzylamine

A mixture of 3,4-dichlorobenzylamine (440 mg, 2.5 mmol) and acrylimide (185 mg, 2.6 mmol) was treated with silicon tetrachloride (6 mul, 0.05 mmol) under solvent-free conditions at 0°C. The mixture was heated to 60°C and stirred for 4 hr. The reaction was allowed to cool to rt and ethyl acetate (20 mL) and water (20 mL) were added. The layers were separated and the aqueous layer was further extracted with ethyl acetate (2 x 20 mL) and the combined organic layers were dried over sodium sulfate and concentrated in vacuo. The crude product was purified by flash column chromatography eluting with a gradient of dichloromethane: methanol (95:5 ? 85:15) to yield the product as a white solid (378 mg, 61percent).

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, 3,4-Dichlorobenzylamine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Brear, Paul; North, Andrew; Iegre, Jessica; Hadje Georgiou, Kathy; Lubin, Alexandra; Carro, Laura; Green, William; Sore, Hannah F.; Hyvoenen, Marko; Spring, David R.; Bioorganic and Medicinal Chemistry; vol. 26; 11; (2018); p. 3016 – 3020;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 202197-26-0, 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. 202197-26-0, name is 3-Chloro-4-((3-fluorobenzyl)oxy)aniline belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: A mixture of 14 (1.03 g, 5 mmol), 10 mL SOCl2 and five drops of DMF was stirred and refluxed for 6 h. Excess SOCl2 was removed under reduced pressure, gave the intermediate 15 without further purification. A mixture of intermediate 15 and aniline (5 mmol) dissolved in 15 mL isopropanol, 1 mL Et3N was added, the mixture was stirred at reflux for 4 h. the reaction mixture was allowed to cool to room temperature. The precipitate was collected and washed with isopropanol, water and ether in order, dried to provide the products 16a-c.

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, 3-Chloro-4-((3-fluorobenzyl)oxy)aniline, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Li, Ri-Dong; Zhang, Xin; Li, Qiao-Yan; Ge, Ze-Mei; Li, Run-Tao; Bioorganic and Medicinal Chemistry Letters; vol. 21; 12; (2011); p. 3637 – 3640;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 363-51-9, 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. 363-51-9 name is 2-Chloro-6-fluoroaniline, 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.

To 2-chloro-6-fluoroaniline (24.8 g, 165 mmol) in HOAc (90 mL) is added Ac2O (18 mL, 189 mmol) and the mixture is stirred at 90 C. for 1 h. After cooling to rt H2O is added and the mixture is neutralized with 2 M NaOH solution with stirring. The aqueous layer is extracted twice with DCM. The combined organic layer is washed with semi-saturated NaHCO3 solution and brine, dried over MgSO4 and evaporated to give the acetanilide which is used without further purification

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Chloro-6-fluoroaniline, and friends who are interested can also refer to it.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; US2012/322803; (2012); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics