Month: June 2021

Adding a certain compound to certain chemical reactions, such as: 53531-69-4, name is (4-Bromophenyl)methanesulfonyl chloride, 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 53531-69-4, Product Details of 53531-69-4

C-(4-Bromophenyl)-N-(2,4-dimethoxybenzyl)methanesulfonamide While cooling with ice, 20.0 g of 4-bromobenzylsulfonyl chloride were initially charged in 200 ml of dichloromethane, and a solution of 24 ml of 2,4-dimethoxybenzylamine in 100 ml of dichloromethane was slowly added dropwise. For improved stirrability, a further 100 ml of dichloromethane were added, and the reaction mixture was allowed to come to room temperature. After stirring for 2 hours, the reaction mixture was washed with 100 ml of water, with 100 ml of 0.2 N aqueous hydrochloric acid, with 100 ml of saturated aqueous sodium hydrogencarbonate solution and finally once more with 100 ml of water. The organic phase was dried over Na2SO4, concentrated by rotary evaporation and dried under high vacuum. The residue (30 g) was used in the next reaction without further purification.

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, (4-Bromophenyl)methanesulfonyl chloride, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SANOFI; Boehme, Thomas; Ritter, Kurt; Engel, Christian; Haack, Torsten; Guessregen, Stefan; Tschank, Georg; US2013/345127; (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. 108-41-8, name is 1-Chloro-3-methylbenzene, This compound has unique chemical properties. The synthetic route is as follows., category: chlorides-buliding-blocks

General procedure: In a glovebox with an N2 atmosphere, to a vial containing bis(pinacolato)diboron (0.6 mmol, 3 equiv.), complex 1 (8.5 mg, 0.01 mmol, 0.05 equiv.), potassium acetate (78.5 mg, 0.8 mmol, 4 equiv.), THF (1 mL), was added aryl chloride (0.2 mmol, 1 equiv.). The mixture was allowed to react at room temperature for 24-48 h. After quenching with water, the reaction mixture was extracted with ethyl acetate. The organic layer was washed with brine and then evaporated under vacuum. Flash chromatography on silica gel Flash chromatography on silica gel (hexane:ethyl acetate = 100:0 to 85:15) yielded the product.

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 reaction routes of 108-41-8.

Reference:
Article; Dong, Jie; Guo, Hui; Peng, Wei; Hu, Qiao-Sheng; Tetrahedron Letters; vol. 60; 11; (2019); p. 760 – 763;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 110407-59-5, These common heterocyclic compound, 110407-59-5, name is 2-Chloro-4-fluorobromobenzene, 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: NiCl2(PCy3)2 (17 mg, 0.025 mmol) was added to a substrate (0.5 mmol) in dry THF (4 mL – 10 mL) and then LiAl(O-t-Bu)3H (2 mmol – 8 mmol, ) was added to this solution slowly under argon atmosphere. The mixture was then heated to reflux and left to stir while being periodically monitored by GC and GC/MS. All products were identified by GC/MS and GC.

Statistics shows that 2-Chloro-4-fluorobromobenzene is playing an increasingly important role. we look forward to future research findings about 110407-59-5.

Reference:
Article; Xiao, Juan; Wu, Jingjing; Zhao, Wenwen; Cao, Song; Journal of Fluorine Chemistry; vol. 146; (2013); p. 76 – 79;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

4090-55-5, name is 2-Chloro-5,5-dimethyl-1,3,2-dioxaphosphorinane 2-oxide, belongs to chlorides-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. HPLC of Formula: C5H10ClO3P

In a 250-mL three-necked flask with a flux condenser, thermometer, a mechanical stirrer and dropping funnel, neopentyl glycol (20.8 g, 0.2 mol) and chloroform (100 mL) were mixed. After the solids were dissolved completely in ice-water bath, 39.8 g (0.26 mol) of phosphorus oxychloride was then slowly dropped into the above reaction vessel within 2 h, and then, the temperature of the mixtures was increased to refluxing temperature for 4 h. After that, the solvent was removed by a rotary evaporator; then, the white powders were obtained (intermediate II) [17]. The schematic processes for the reactions are presented in Scheme 1(a). The intermediate II 73.8 g (0.4 mol) and acetonitrile (300 mL) were added into a three-necked flask with an ice bath equipped with a mechanical stirrer, flux condenser, dropping funnel and drying tube with calcium chloride. Then, 35.0 g of 9,9-bis (4-hydroxyphenyl)fluorene (0.1 mol) was added to the mixtures and the mixtures were kept stirring in the ice-water bath. Triethylamine (1.5 mL) was then slowly dropped into the above reactants, and the temperatures of the mixtures were increased to 60 C for another 10 h. After that, the acetonitrile was removed by rotary evaporator and the white products were obtained. The white products were washed by distilled water and further recrystallized from distilled water and ethyl alcohol for two times. Then, the white products were obtained (49.46 g, 76.6%). The schematic processes of the reaction are presented in Scheme 1(b). 1H NMR: 7.742-6.662 ppm, -C6H2- in the benzene ring; 4.252-3.957 ppm, OCH2; 1.325, 0.918, 1.325 and 0.918 ppm -CH3. MS: [M + K]+ = 687.4; thus, the molecular weight of the FRs is 648.4.

The synthetic route of 4090-55-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Qian, Xiaodong; Guo, Nan; Zhao, Yanhua; Lu, Lingang; Wang, Huiya; Wang, Xuebao; Jin, Jing; Shao, Gaosong; Hu, Zhijia; Journal of Thermal Analysis and Calorimetry; vol. 131; 3; (2018); p. 2625 – 2636;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 2533-69-9, 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. 2533-69-9, name is Methyl 2,2,2-trichloroacetimidate belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: Preparation of 2-methyl-6-nitro-2H-indazole (5d). To a stirred mixture of 6-nitro-1H-indazole (1.0 g, 0.0061 mmol) in dichloromethane (25.0 mL) was added trifluoromethanesulfonic acid (0.54 mL, 0.0061 mmol), stirred for 5-10 min at 25-35 C. To this mixture was added methyl 2,2,2,-trichlroacetimidate (2.69 g, 0.015 mmol) at room temperature. The reaction mixture was stirred at room temperature for 16-18 h under N2. After reaction completion, chilled saturated NaHCO3 solution was added. The aqueous and organic phases were separated. Aqueous phase was extracted with dichloromethane 10 mL. Combined organic layers were washed with DM water (2 × 10 mL). Organic layer was dried over anhydrous Na2SO4, filtered, and evaporated completely under vacuum to obtain 2-methyl-6-nitro-2H-indazole (1.03 g, 95.0%) as a yellow solid.

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, Methyl 2,2,2-trichloroacetimidate, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Baddam, Sudhakar Reddy; Uday Kumar; Panasa Reddy; Bandichhor, Rakeshwar; Tetrahedron Letters; vol. 54; 13; (2013); p. 1661 – 1663;,
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. 6223-78-5, name is 2,5-Dichloro-2,5-dimethylhexane, A new synthetic method of this compound is introduced below., Application In Synthesis of 2,5-Dichloro-2,5-dimethylhexane

10351] A flame-dried 50-mE pressure vessel, equipped with a Teflon stir bar, was charged with phenol SO (2 g, 21.25 mmol, 1 equiv.), 2,5-dichloro-2,5-dimethylhexane (4.28 g, 23.38 mmol, 1.1 eqiuv.) and CH2C12 (20 mE). Aluminum trichloride (2.83 g, 21.25 mmol, 1 equiv.) was added to this reaction mixture and the reaction was stirred at 500 C. for 12 h. The reaction mixture was quenched by the addition of distilled H20 (20 mE), and the phases were separated. The aqueous phase was washed with CH2C12 (3×20 mE). The combined organic fractions were dried over Mg504, filtered and concentrated in vacuo to afford a crude residue, which was purified using flash column chromatography (silica gel with 15% EtOAc in hexanes as eluant) to afford Si as white powder in 70% isolated yield.

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; THE ROYAL INSTITUTION FOR THE ADVANCEMENT OF LEARNING/MCGILL UNIVERSITY; LUMB, JEAN-PHILIP; ESGUERRA, KENNETH V.N.; (118 pag.)US2017/66711; (2017); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 1005-56-7, 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 1005-56-7 as follows.

In a 30 ml eggplant type flask, 194.2 mg (1.0 mmol) of methyl beta-D-glucopyranoside, 22.0 mg (0.10 mmol) of dimethyldichlorotin, 36.9 mg (0.10 mmol) of tetrabutylammonium iodide,Tetrahydrofuran (10 ml) was added and stirred. To this mixed solution, 0.175 ml (1.3 mmol) of phenyl chlorothionoformate was added, then 0.271 ml (1.5 mmol) of 1,2,2,6,6-pentamethylpiperidine was added and the mixture was stirred at 20 C. for 6 hours And reacted. After completion of the reaction, 20 ml of a saturated aqueous solution of ammonium chloride was added to the reaction solution, and extraction operation was carried out three times with 20 ml of ethyl acetate. The organic phase (ethyl acetate phase) was washed with 20 ml of water and 20 ml of an aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, filtered, and the solvent (ethyl acetate) was distilled off under reduced pressure. The residue was purified by silica gel chromatography (developing solvent n-hexane: ethyl acetate = 5: 1) to obtain 331.05 mg (100% yield) of methyl 6-0-phenoxythiocarbonyl-? – D-glucopyranoside did. Since the beta-D-glucopyranoside in which the hydroxyl group other than the 6-position was phenoxythiocarbonylated could not be obtained, the selectivity of 6-O-phenoxythiocarbonyl-beta-D-glucopyranoside was 100%.

According to the analysis of related databases, 1005-56-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Nagasaki University; Tokuyama Corporation; Onomura, Osamu; Muramatsu, Wataru; Tanigawa, Tomoko; Iwasaki, shitetsu; (14 pag.)JP5669618; (2015); B2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 2106-04-9, The chemical industry reduces the impact on the environment during synthesis 2106-04-9, name is 3-Chloro-2-fluoroaniline, I believe this compound will play a more active role in future production and life.

Example 7; (2S,4R)-4-({4-[(3-chloro-2-fluorophenyl)amino]-7-methoxyquinazolin-6-yl}oxy)-N,l- dimethylpiperidine-2-carboxamide; The title compound was prepared as shown in Scheme DExample 7 (15)Scheme D (25,42?)-4-({4-[(3-cMoro-2-fluorophenyl)amiQo]-7-methoxyquinazolin~6-yl}oxy)-l- methylpiperidine-2-carboxylic acid (15) (145mg, 0.32mmol) was dissolved in DMF (10ml) under nitrogen. Triethylamine (0.13ml, 0.95mmol) was added, followed by DEPEA (0.055ml, 0.32mmol) and methylamine hydrocMoride (0.043g, 0.63mmol). The mixture was cooled in an ice/water bath and HATU (180mg, 0.47mmol) was then added portionwise such that the temperature remained < 1O0C. The reaction mixture was stirred at room temperature overnight and evaporated to dryness. The residues were dissolved in EtOAc, washed with water (10ml), brine (10ml), dried over MgSO4, filtered and evaporated. The crudes were purified by column chromatography eluting with increasingly polar mixtures of methylene chloride/methanol (100/0-90/10). Fractions containing the desired product were combined and evaporated. The resulting solids were dissolved in methanol, loaded onto an SCX column and eluted with MeOH (20ml) followed by 7N NH3 in MeOH. Appropriate fractions were combined and evaporated to give the title product as a white solid (69mg, 40%): 1H NMR Spectrum: (DMSO-dg) deltal.63 - 1.69 (2H, m), 2.15 - 2.21 (6H, m), 2.55 - 2.62 (4H, m), 2.93 - 2.98 (IH, m), 3.94 (3H, s), 4.43 - 4.51 (IH, m), 7.23 (IH, s), 7.28 - 7.33 (IH, m), 7.49 - 7.56 (2H, m), 7.68 - 7.72 (IH, m), 7.86 (IH, s), 8.39 (IH, s), 9.57 (IH, s); Mass Spectrum: (M+H)+ 474.The starting material (25,4i?)-4-({4-[(3-cMoro-2-fluorophenyl)arnino]-7- methoxyquinazoHn-6-yl}oxy)-l-methylpiperidine-2-carboxync acid (15) was prepared as follows:(2S, 4S)-N Boc-4-hydroxy pirhoeridine-2 carboxylic acid benyzlamine salt (0.5g) was dissolved in methanol and loaded onto a SCX column. This was eluted with methanol (20ml). The combined filtrates were evaporated in vacuo to give a gum (405mg). This was dissolved in DMF (5ml). Iodomethane (0.107ml, 1.7mmol) was added and the resulting mixture cooled to 00C. Cesium carbonate (647mg, 1.98mmol) was added in one portion and the mixture stirred overnight at room temperature. The reaction mixture was partitioned between water (10ml) and DCM (3xlthetaml). The combined organics were washed with brine (10ml), dried over MgSO4, filtered and evaporated to give 1-tert-bntyl 2-methyl (IS, AS)A- hydroxypiperidine-l,2-dicarboxylate (11) as a clear gum (347mg, 81%): 1H NMR Spectrum: (CDCl3) 51.39 - 1.50 (1OH, m), 1.60 - 1.66 (IH, m), 1.86 - 1.96 (2H, m), 2.40 - 2.49 (IH, m), 2.96 - 3.10 (IH, m), 3.65 (IH, t), 3.73 (3H, s), 3.95 - 4.18 (IH, m), 4.82 - 5.06 (IH, m). A solution of DEAD (0.329ml, 2.08mmol) in DCM (2ml) was added to as stirred suspension of 4-chloro-7-methoxyquinazohn-6-ol (283mg, 1.74mmol prepared as described in Example 16 of WO03/082831), 1-te/t-butyl 2-methyl (2S,4S)~4-hydroxypirhoeridine-l,2- dicarboxylate (11) (450mg, 2.08mmol) and triphenylphosphine (547mg, 2.098mmol) in DCM (10ml), such that the internal temperature remained < 3O0C. The reaction mixture was stirred overnight and evaporated to dryness. The residues were purified by column chromatography on SiO2 eluting with increasingly polar mixtures of DCM/methanol (100/0-95/5). The fractions containing the desired product were combined and evaporated to give 1-fetaut-butyl 2- methyl (25,4i?)-4-[(4-chloro-7-methoxyquinazohn-6-yl)oxy]piperidine-l,2-dicarboxylate (12) as a gum (478mg, 79%): 1H NMR Spectrum: (DMSO-d6) deltal.39 - 1.46 (1OH, m), 1.73 - 1.84 (IH, m), 1.92 - 2.03 (IH, m), 2.10 - 2.18 (IH, m), 2.60 - 2.69 (IH, m), 3.15 - 3.40 (3H, m), 3.74 - 3.85 (IH, m), 4.01 (3H, s), 4.61 - 4.73 (IH, m), 5.06 (IH, s), 7.43 (IH, s), 7.47 (IH, s), 8.89 (IH, s), 8.97 (IH, s); Mass Spectrum: (M+H)+452. l-te^butyl 2-methyl (25',4i2)-4-[(4-cliloro-7-metlioxyquinazolialpha-6-yl)oxy]piperidiiie- 1,2-dicarboxylate (12) (0.45g, l.Ommol) was dissolved in MeCN (11ml) under nitrogen. 3- Chloro-2-fluoro aniline (153mg, 1.05mmol) was then added followed by 4M HCl in dioxane (1.2ml). The resulting mixture was heated overnight at 6O0C. The reaction mixture was cooled to -80C and the resulting solids collected "by filtration and washed with diethylether. The solids were dissolved in methanol, loaded onto an SCX column and eluted with methanol followed by 7N NH3 in MeOH. Appropriate fractions were combined and evaporated. The residues were purified by column chromatography on SiO2 eluting with increasingly polar mixtures of DCM/methanol (100/0-95/5). The fractions containing the desired product were combined and evaporated to give methyl (25r,4i?)-4-({4-[(3-chloro-2-fluorophenyl)amino]-7- methoxyquinazonn-6-yl}oxy)piperidine-2-carboxylate (13) as a clear gum (316mg, 69%): 1H NMR Spectrum: (DMSO-d6) 51.45 - 1.58 (2H, m), 2.02 - 2.11 (IH, m), 2.32 - 2.40 (IH, m), 2.57 - 2.67 (IH, m), 3.08 - 3.13 (IH, m), 3.42 - 3.48 (IH, m), 3.64 (3H, s),... 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-2-fluoroaniline, other downstream synthetic routes, hurry up and to see. Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2006/90163; (2006); A1;,
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. 16799-05-6, name is 3-Chlorophenethyl Bromide, A new synthetic method of this compound is introduced below., Formula: C8H8BrCl

Example 15: Preparation of 8-r2-(3-chlorophenyl)ethvn-3-methyl-4-((4-r3- (trifluoromethyl)phenvnpiperazin-1-yl}carbonyl)-1-oxa-8-azaspiror4.5ldec-3-en-2-oneA mixture of 3-methyl-4-({4-[3-(trifluoromethyl)phenyl]piperazin-1-yl}carbonyl)-1 -oxa-8- azaspiro[4.5]dec-3-en-2-one dihydrochloride (Example 1 , 200 mg, 0.40 mmol), anhydrous potassium carbonate (180 mg, 1.30 mmol) and 1-(2-bromo-ethyl)-3-chloro-benzene (0.07 mL, 0.22 mmol) in anhydrous Nu,Nu-dimethylformamide (3 mL) was heated at 90C for 1.5 hours under microwave irradiation. The reaction mixture was concentrated under vacuum. The residue was taken up in dichloromethane (20 mL), washed with water (20 mL) and brine (20 mL), dried (MgS04) and concentrated under vacuum. After purification by flash chromatography (silica), the title compound was obtained as a white solid. 1H NMR (DMSO-d6, 400 MHz): delta 7.46-7.42 (m, 1 H), 7.30-7.17 (m, 6H), 7.11 (d, J = 7.5 Hz, 1H), 3.79-3.78 (m, 1H), 3.68-3.67 (m, 1H), 3.55 (s, 3H), 3.55 (d, J = 4.9 Hz, 2H), 2.89-2.88 (m, 3H), 2.73-2.71 (m, 2H), 2.49-2.48 (m, 2H), 2.23-2.21 (m, 3H), 1.82-1.81 (m, 1 H), 1.75 (s, 3H), 1.67-1.66 (m, 1 H), 1.51-1.49 (d, J = 7.3 Hz, 1H). LCMS (Method D): Mass found (M+ 562), Rt (min): 4.75, Area (%): 99.6 (Max), 99.5 (254 nm). HPLC (Method A): Rt (min): 4.72, Area (%): 99.3 (Max), 99.2 (254 nm).

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; ARES TRADING S.A.; JORAND-LEBRUN, Catherine; SWINNEN, Dominique; GERBER, Patrick; KULKARNI, Santosh; WO2012/130915; (2012); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 766545-20-4, 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. 766545-20-4 name is 2-Chloro-5,6,7,8-tetrahydro-1,6-naphthyridine hydrochloride, 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.

2-Chloro-5,6,7,8-tetrahydro-1,6-naphthyridine hydrochloride (2.00 g, 9.75 mmol, 1.00 eq) was dissolved in DCM (20.00 mL) and triethylamine (2.47 g, 24.38 mmol, 2.50 eq) and di-tert-butyl dicarbonate (3.19 g, 14.63 mmol, 1.50 eq) were added at 15 C under the nitrogen gas atmosphere. The mixture was stirred at 15 C for 12 hours. The mixture was poured into water (30 mL) and the aqueous phase was extracted with dichloromethane (100 mL * 4). The combined organic phases were washed with saturated brine (100 mL), dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to deliver tert-butyl 2-chloro-7,8-dihydro-5H-1,6-naphthyridine-6-carboxylate (2.50 g, 9.30 mmol, 95.41% yield) as a white solid. LCMS (ESI) m / z: 269 (M + 1).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Chloro-5,6,7,8-tetrahydro-1,6-naphthyridine hydrochloride, and friends who are interested can also refer to it.

Reference:
Patent; Medshine Discovery Inc.; LUO, Wei; DING, Charles Z.; HUANG, Zhigang; CHEN, Shuhui; (162 pag.)EP3252059; (2017); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics