Tag: M.W=100-200

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. 95-81-8, name is 2-Chloro-5-methylaniline, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C7H8ClN

Preparation of (2-chloro-5-methyl-phenyl)urea (Intermediate 7) A solution of 2-chloro-5-methylaniline (10 g, 70.6 mmol) and potassium cyanate (14.3 g, 176 mmol) in a mixture of acetic acid (340 mL) and water (34 mL) was stirred at room temperature during 4 hours. The solvent was evaporated and the residue taken into a mixture of CH2Cl2 and an aqueous saturated solution of NaHCO3. The precipitate was filtered, washed with dichloromethane and dried under vacuum to give 12.6 g (97%) of intermediate 7. 1H NMR [(CD3)2SO] delta8.05 (s, 1H, NH), 7.96 (s, 1H), 7.23 (d, 1H), 6.75 (d, 1H), 6.37 (br s, 2H), 2.24 (s, 3H).

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 95-81-8.

Reference:
Patent; Bernardelli, Patrick; Ducrot, Pierre; Lorthiois, Edwige; Vergne, Fabrice; US2002/198198; (2002); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 2268-05-5, A common heterocyclic compound, 2268-05-5, name is 2,6-Dichlorofluorobenzene, molecular formula is C6H3Cl2F, 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 20 2-[3-(2,6-Dichloro-phenoxy)4-ethyl-phenyl]-N-(4-sulfamoyl-phenyl)-acetamide (I-20) step 1-To a solution of 12a (0.200 g; 0.960 mmol) and NMP (4 mL) was added K2CO3 (0.398 g; 2.88 mmol) and 1,3-dichloro-2-fluoro-benzene (0.174 g; 1.056 mmol). The reaction was heated to 120 C. and monitored by TLC. After 8 h the reaction was cooled to RT and 10% HCl was added. The mixture was extracted with EtOAc and the combined extracts were washed with H2O and brine. The extracts were dried (Na2SO4) filtered and evaporated. The crude product was purified by SiO2 chromatography eluding with a hexane/EtOAc gradient (0 to 40% EtOAc) to afford 144. steps 2 and 3-Hydrolysis and formation of the acid chloride were carried as described in step 7and 8 of Example 1 and used without additional purification. step 4-The acid chloride from step 3 (0.14 mmol) was dissolved in acetone (2 mL) and the flask was purged with nitrogen. NaHCO3 (0.024 g; 0.28 mmol) was added followed by 4-amino-benzenesulfonamide (0.024 g; 0.14 mmol) and water (4 mL). The mixture was sonicated for 5 min and allowed to stir for 12 h at RT. The reaction mixture was filtered and the crude product was washed sequentially with water and diethyl ether to afford I-20. Compound I-23 was prepared in the same manner except 4-amino-benzenesulfonamide was replaced by 2-chloro-phenylamine.

The synthetic route of 2268-05-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Roche Palo Alto LLC; US2005/239880; (2005); A1;,
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

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

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

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

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

Related Products of 918538-05-3,Some common heterocyclic compound, 918538-05-3, name is 2,4-Dichloropyrrolo[2,1-f][1,2,4]triazine, molecular formula is C6H3Cl2N3, 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 mixture of 2,4-dichloropyrrolo[1,2-f][1,2,4]triazine (150 mg, 0.8 mmol), 2-oxa-6-azaspiro[3.3]heptane (103mg, 1.04 mmol) and K2C03 (221 mg, 1.6 mmol) in DMF (4.5 mL) was stirred at room temperature for 2h. TLC showed the starting material was completely consumed and DCM (10 mL) was added to the mixture, and the mixture was washed with water (5 mL) and brine. The organic layer was dried over anhydrous Na2SO4 and concentrated in vacuo to give compound 35(160 mg, 8 1%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2,4-Dichloropyrrolo[2,1-f][1,2,4]triazine, its application will become more common.

Reference:
Patent; SUZHOU KINTOR PHARMACEUTICALS, INC.; GUO, Chuangxin; TONG, Youzhi; (160 pag.)WO2017/219800; (2017); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 363-51-9,Some common heterocyclic compound, 363-51-9, name is 2-Chloro-6-fluoroaniline, molecular formula is C6H5ClFN, 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 mixture of 2-chloro-6-fluoroaniline (2.23 g, 15.32 mmol) in propionic acid (7.66 ml) was treated with propionic anhydride (2.369 ml, 18.38 mmol), and the reaction mixture was stirred at 90 C. for 1 h. After cooling to r.t., water was added and the solid precipitate was collected by filtration, washed with water, and air dried. The crude product obtained was used directly in the next step without further purification. LCMS calculated for C9H10ClFNO (M+H)+: m/z=202.0; Found 202.1.

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-6-fluoroaniline, its application will become more common.

Reference:
Patent; Incyte Corporation; Hummel, Joshua; Vechorkin, Oleg; Sokolsky, Alexander; Ye, Qinda; Liu, Kai; Yao, Wenqing; (60 pag.)US2020/48241; (2020); 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