Month: July 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. 6579-54-0, name is 2,6-Dichlorobenzenesulfonyl chloride, A new synthetic method of this compound is introduced below., SDS of cas: 6579-54-0

The methyl 4-(morpholine-2-carboxamido)adamantine-1-carboxylate compound (174.0 mg, 0.54 mmol) was dissolved in CH2Cl2 (4 ml), and 2,6-dichlorobenzenesulfonyl chloride (132.6 mg, 0.54 mmol) and triethylamine (120.2 mg, 1.19 mmol) were added thereto, followed by stirring at room temperature for 3 hours. H2O was added to the reaction solution, which was then extracted three times with CH2Cl2. The extract was dried with MgSO4, filtered and distilled under reduced pressure to remove the solvent. The residue was separated by column chromatography, thereby obtaining a methyl 4-(4-((2,6-dichlorophenyl)sulfonyl)morpholine-2-carboxamido)adamantane-1-carboxylate compound (243.9 mg, 0.46 mmol, 85 %).[2013] 1H NMR (400 MHz, CDCl3) delta7.53-7.48 (m, 2H), 7.39-7.33 (m, 1H), 6.92 (br, -CONH), 4.15-4.00 (m, 4H), 3.85-3.63 (m, 5H), 3.13-3.06 (m, 1H), 2.90-2.84 (m, 1H), 2.07-1.54 (m, 13H).

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; HYUNDAI PHARM CO., LTD.; LEE, In Hee; PARK, Chang Min; KIM, Se Hoan; CHAE, Hee Il; PYEON, Doo Hyeok; SHIN, Myoung Hyeon; HWANG, Jeong Un; MOON, Soon Young; HA, Tae Young; KIM, So Youn; CHOI, Hyuk Joon; YOO, Myoung Hyun; LEE, Jong Chan; KIM, Young Seok; RHEE, Jae Keol; WO2012/128582; (2012); A2;,
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. 118-69-4, name is 2,6-Dichlorotoluene, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 2,6-Dichlorotoluene

This Example demonstrates the preparation of 2,6-dichloro-3,5-dinitrotoluene.To a 1 L 4-neck round bottom flask equipped with external ice cooling, mechanical stirrer, addition funnel, N2 inlet, and thermometer was added 118 g (1.872 mmol) fuming nitric acid (d=1.54). With cooling, 745 g (1863 mmol SO3) 20% oleum was added over a period of 30 minutes while maintaining a temperature below 30 C. The acid solution was cooled to 0-5 C. and 150 g (932 mmol) 2,6-dichlorotoluene was slowly added over 2 h while maintaining a temperature below 20 C. When addition was complete, the ice bath was removed and the reaction mixture was slowly allowed to warm to room temperature. It was then heated from room temperature to 110 C. over a time period of 45 min. After 15 min at 110 C., the reaction mixture was allowed to cool to room temperature and then cooled to 5 C. It was then filtered through a glass flitted funnel and washed with 250 mL water followed by 250 mL 10% aqueous NH3 solution to yield a pale yellow crystalline wet cake. A small sample was dried in vacuum and analyzed by both H1-NMR and GC and found to be 99.9% pure. The wet cake (219 g) contained about 201.5 g 2,6-dichloro-3,5-dinitrotoluene and 17.5 g water. The net yield of 2,6-dichloro-3,5-dinitrotoluene amounted to about 86%.

According to the analysis of related databases, 118-69-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; E.I. DU PONT DE NEMOURS AND COMPANY; US2010/160675; (2010); A1;,
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, category: chlorides-buliding-blocks

To a solution of methyl 1-(2-chloro-5-methylpyrimidin-4-yl)-1H-pyrrole-3-carboxylate (0.3 g, 0.1195 mmol) in dioxane (10 mL) were added 2-chloro-4-fluoroaniline (0.17 g, 0.1195 mmol) and potassium carbonate (0.24 g, 1.17 mmol). The resulting reaction mixture was purged with nitrogen gas for 15 min, then 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl(0.074 g, 0.119 mmol) and palladium(dibenzylidineacetone)dipalladium(0) (0.054 g, 0.059 mmol) were added. The reaction mixture was stirred at 100 C. for 12 h. The reaction mixture was diluted with ethyl acetate (200 mL) and filtered through Celite bed. The bed was washed with ethyl acetate (2*50 mL). The filtrate was washed several times with cold water and then with brine. The organic layer was dried over sodium sulfate, filtered and evaporated under reduced pressure. The residue was purified by gradient column chromatography using ethyl acetate in hexane as eluent to afford methyl 1-(2-((2-chloro-4-fluorophenyl)amino)-5-methylpyrimidin-4-yl)-1H-pyrrole-3-carboxylate as an off-white solid (0.25 g, 58%). 1HNMR (400 MHz, CDCl3): delta 8.40-8.36 (m, 2H), 7.95 (s, 1H), 7.51 (s, 1H), 7.40-7.34 (m, 1H), 7.19-7.16 (m, 1H), 7.07-6.99 (m, 1H), 6.77-6.76 (m, 1H), 3.86 (s, 3H), 2.40 (s, 3H). LC-MS calcd exact mass 360.08, found m/z 361.3 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Chloro-4-fluoroaniline, and friends who are interested can also refer to it.

Reference:
Patent; Asana Biosciences, LLC; Venkatesan, Aranapakam M.; Thompson, Scott K.; Smith, Roger A.; Reddy, Sanjeeva P.; (166 pag.)US2016/362407; (2016); 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. 932-32-1, name is 2-Chloro-N-methylaniline, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C7H8ClN

Examples; General Description General description of the reaction conditions; In a microwave reaction vial (size 0.5-2 ml) fitted with a magnet stirring bar, a solution of 0.5-1.5 mg of the starting ortho-bromo anilines in 250 muL of dry acetonitrile was introduced, followed by the addition of 50 muL of an anhydrous solution of [18F]TBAF in acetonitrile. To the reaction solution, 500 muL of dry acetonitrile was added. The microwave vial was crimped with a Teflon septum, and thereafter purged with argon for 5 min. The resulting reaction vial was kept in the microwave cavity of a microwave system (Initiator EXP, Biotage, Sweden), and heated for 30 min at 180C. The reaction was quenched by cooling the vial with compressed air, after which the contents of the vial were subjected to chromatographic analysis (HPLC with RP18e Chromolith column, internal diameter 4.6 mm; length of 100 mm) eluted with a mixture of acetonitrile/water (27.5 : 72.5% v/v).; Example 1: Model Compounds and Examples of the General Method; Labeling reactions were carried out in acetonitrile in the presence of a tetrabutylammonium salt (TBA+) and [18F]fluoride. Various leaving groups were evaluated. Reaction times were 20-40 minutes, and the reaction temperature was in the range of 150C-200C to result in yields in the range of 7-68% at. The highest yields of 61 +/- 5 % resulted from the use of a ortho-bromo-leaving group and a combination of a reaction temperature of 180C and a reaction time of 30 min. No radioactive by-product except for the desired ortho-[18F]fluorinated aniline derivative has been observed as measured by analytical HPLC. The reactions were according to the general reaction scheme of Scheme 2 below and are summarized in Table 1.

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 932-32-1.

Reference:
Patent; Technische Universitaet Muenchen; EP1944281; (2008); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 76958-07-1, 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 76958-07-1 as follows.

[00378] N-[(6-chloro-1 ,3-benzodioxol-5-yl)carbamothioyl]benzamideImage available on “Original document”[00379] To 1 .88g ( 0.025 mol) of anhydrous ammonium thiocyanate in 40 ml acetone was added dropwise 3.2 g (0.023 mol) of benzoyl chloride. The resulting mixture was heated to reflux. Heating was removed and a solution of 3.8g (0.022 mol) of the amine in 15 ml dry acetone was added at a rate to maintain the mixture at boiling. After an additional 15 minutes reflux the reaction was cooled and the precipitate was filtered off. The precipitate was washed with acetone and dried to yield 5.5 g of the product.

According to the analysis of related databases, 76958-07-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; KINEATA INC; Ladonato, Shawn P.; Bedard, Kristin M.; Munoz, Ernesto J.; Imanaka, Myra W.; Fowler, Kerry W.; (122 pag.)WO2014/113492; (2014); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Some common heterocyclic compound, 59681-66-2, name is 4-Chloro-N1-methylbenzene-1,2-diamine, molecular formula is C7H9ClN2, 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. Product Details of 59681-66-2

General procedure: A solution of compound 5 (R1=H, 100mg, 0.657mmol), 1,3-bis(tert-butoxycarbonyl)-2-methyl-2-thiopseudourea 6 (209mg, 0.722mmol), and p-toluene sulfonic acid (12mg, 0.065mmol) in isopropanol was heated at 65C for 16h. The reaction mixture was concentrated in vacuo and diluted with ethyl acetate. The organic layer was successively washed with 1N sodium hydroxide and brine, and dried over sodium sulfate. After concentration in vacuo, the crude product was purified by silica gel column chromatography (eluent : n-Hex/EA=5 : 1) to give the compound 7 (R1=H, 121mg, yield 75%) as solid. 1H NMR (400MHz, DMSO-d6) delta 11.9 (NH, 1H), 7.38 (m, 2H), 7.14 (m, 2H), 3.65 (s, 3H), 1.45 (s, 9H); LC/MS (electrospray) m/z (M+H)+ 248.03.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 59681-66-2, its application will become more common.

Reference:
Article; Windisch, Marc Peter; Jo, Suyeon; Kim, Hee-Young; Kim, Soo-Hyun; Kim, Keumhyun; Kong, Sunju; Jeong, Hyangsuk; Ahn, Sujin; No, Zaesung; Hwang, Jong Yeon; European Journal of Medicinal Chemistry; vol. 78; (2014); p. 35 – 42;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 1939-99-7, name is Phenylmethanesulfonyl 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 1939-99-7, Formula: C7H7ClO2S

A solution of phenylmethanesulfonyl chloride (2.19 g, 10 mmol) was added into a suspension of 3-bromopropan-l-amine hydrobromide (2.19 g, 10 mmol) and Et3N (2.02 g, 20 mmol) in THF (50 mL) at 0 C. The mixture was stirred at 0 C for 5 min. TLC confirmed the completion of reaction. Solid was filtered out with suction, and the filtrate was concentrated to provide compound N-(3- bromopropyl)(phenyl)methanesulfonamide (2.7 g, quant.) as a pale yellow solid which was used in the next step without further purification. NMR (300 MHz, CDC13) delta 7.40 (m, 5H), 4.48 (m, IH), 4.27 (s, 2H), 3.41 (t, J = 6.6 Hz, 2H), 3.16 (q, 2H), 2.01 (m, 2H). LCMS (ESI), m/z, 314 and 316 [M+Na]+, Br pattern found.

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, Phenylmethanesulfonyl chloride, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; FAUBER, Benjamin; LADDYWAHETTY, Tammy; RENE, Olivier; (105 pag.)WO2016/96936; (2016); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 6781-98-2, 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 6781-98-2 as follows.

General procedure: Under N2 atmosphere, KOtBu (114.0 mg, 1.0 mmol), NHC-Pd(II)-Im complex 1 (5.2 mg, 1.0 mol percent), dry toluene (1.0 mL), chlorobenzene 2a (0.8 mmol), and aniline 3a (0.96 mmol) were successively added into a Schlenk reaction tube. The reaction mixture was stirred under reflux for 4 h. Then the solvent was removed under reduced pressure and the residue was purified by a flash chromatography on silica gel to give the pure product 4a.

According to the analysis of related databases, 6781-98-2, the application of this compound in the production field has become more and more popular.

Reference:
Article; Zhu, Lei; Ye, Yue-Mei; Shao, Li-Xiong; Tetrahedron; vol. 68; 10; (2012); p. 2414 – 2420;,
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. 108-70-3, name is 1,3,5-Trichlorobenzene, A new synthetic method of this compound is introduced below., COA of Formula: C6H3Cl3

To a 250 ml one-necked flask was added 10.0 g (55.1 mmol) of 1,3,5-trichlorobenzene and 100 ml of ultra-dry tetrahydrofuran under argon gas protection and minus 78 degrees Celsius. Then, 23 ml (2.4 M, 55.2 mmol) of n-butyllithium in n-hexane was added dropwise, and the mixture was stirred at minus 78 C for 30 minutes. Then, 7.44 ml (107.3 mmol) of ultra-dry DMF was added dropwise, and stirring was continued for 1.5 hours at minus 78 C. The reaction was then slowly warmed to room temperature and quenched by the addition of 200 mL (3M) hydrochloric acid. The combined organic layers were washed with brine (25 mL) After evaporating the solvent, it was purified by column chromatography using methylene chloride: petroleum ether 1:1 (yield ratio) as eluent to afford 11.0 g of product A1, yield 95%.

The synthetic route of 108-70-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Jilin University; Li Feng; Ai Xin; Zhang Ming; (25 pag.)CN108191739; (2018); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

1205-71-6, name is 4-Chloro-N-phenylaniline, 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. COA of Formula: C12H10ClN

Example 1.106: Preparation of Sodium 2-(((lr,4r)-4-(((4- Chlorophenyl)(phenyl)carbamoyloxy)methyl)cyclohexyl)methoxy)acetate.; Method 1.; Step A: Preparation of ((lr,4r)-4-(hydroxymethyl)cyciohexyI)methyl 4- chlorophenyl(phenyl)carbamate.; 4-Chloro-N-phenylaniline (15.0 g, 73.6 mmol), tribasic potassium phosphate, (fine powder, 4.69 g, 22.1 mmol), N^V-carbonyldiimidazole (13.14 g, 81 mmol) and acetonitrile (75 mL) were charged to a 500-mL, jacketed, four-necked cylindrical reaction flask equipped with a mechanical stirrer and a condenser. The reaction mixture was heated at 65 0C under nitrogen and monitored by HPLC. After about 2.5 h HPLC showed > 98% conversion to the intermediate N-(4-chlorophenyl)-N-phenyl-lH-imidazole-l-carboxamide. After about 5.5 h a solution of (lr,4r)-cyclohexane-l,4-diyldimethanol (37.2 g, 258 mmol) in acetonitrile (150 mL) at 65 0C was added to the reaction mixture over 20 min. The resulting mixture was heated at 65 0C overnight. etaPLC showed about 98% conversion to the required product. The mixture was filtered, and the cake was rinsed with acetonitrile (2 x 25 mL). The filtrate was concentrated under reduced pressure (40 0C, 32 torr) 124.125 g of distillate was collected. The residue was diluted with water (50 mL) and this mixture was concentrated under reduced pressure (400C, 32 torr) and 35.184 g of distillate was collected. The residue was diluted with water (50 mL) and the resulting mixture was allowed to stir overnight to give a white paste. The mixture was filtered, and the cake was rinsed with 25% acetonitrile/water (2 x 75 mL). The solid was dried in a vacuum oven to leave a white solid (22.271 g); 94.8% purity by etaPLC peak area. LCMS m/z = 374.3 [M+eta]+; 1H nuMR (400 MHz, DMSO-^6) delta ppm 0.77 – 0.93 (m, 4 H) 1.23 (dd, J = 6.22, 3.51 Hz, 1 H) 1.47 (dd, J = 6.32, 2.91 Hz, 1 H) 1.56 – 1.76 (m, 4 H) 3.20 (t, J= 5.78 Hz, 2 H) 3.92 (d, J = 6.13 Hz, 2 H) 4.33 (t, J = 5.31 Hz, 1 H) 7.28 – 7.35 (m, 5 H) 7.38 – 7.47 (m, 4 H).

The synthetic route of 1205-71-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ARENA PHARMACEUTICALS, INC.; WO2009/117095; (2009); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics