Author: Jessica.F

Reference of 93919-56-3,Some common heterocyclic compound, 93919-56-3, name is (4-(Trifluoromethoxy)phenyl)methanamine, molecular formula is C8H8F3NO, 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: Approximately 0.5 mmol of 2 and 0.5 mmol of HATU were dispensed in 24 reaction wells (MiniBlock XT) using a dispensing spatula and funnel. To each well were added 10 mL of anhydrous MeCN, (0.5 mmol) of the appropriate amine in MeCN, and then 0.13 mL of DIPEA (0.75 mmol) through the septa sheet. The reaction block was covered and shaken at room temperature for 180 minutes (TLC monitored). Two grams of silica gel were added to each well and the reaction block was placed on a parallel centrifugal evaporator. After automated flash chromatography, the obtained pure intermediate (0.25 mmol) and 4 mL of formic acid (50%) were dispensed in 24 reaction wells (MiniBlock XT), heated to 70 C and shaken vigorously for 2 h whereupon TLC showed no remaining starting material. Silica gel (1 g) was added to each well and the mixture was evaporated, dried on a parallel centrifugal evaporator and the dry solid was chromatographed to give the desired product.

The synthetic route of 93919-56-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Moukha-Chafiq, Omar; Reynolds, Robert C.; Nucleosides, nucleotides and nucleic acids; vol. 33; 11; (2014); p. 709 – 729;,
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Electric Literature of 5414-19-7, 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. 5414-19-7, name is 1-Bromo-2-(2-bromoethoxy)ethane, This compound has unique chemical properties. The synthetic route is as follows.

The product of Part F (5.0 g, 10.6 mmol), 18-crown-6 (Aldrich, 0.5 g, catalytic amount), potassium carbonate (Aldrich, 4.4 g, 31.8 mmol), and bis(bromoethyl)ether (Aldrich, 4.9 g, 21.2 mmol) were slurried in N,N-dimethylformamide (20 ml) and stirred at 65 C. for 15 hr. Afterward, the mixture was diluted with water (50 ml) and extracted with ethyl acetate (3?100 ml). The organics were combined and washed with water (twice), washed with brine (twice), dried over Na2SO4, and concentrated for a tan oil. The oil was washed with hexanes, and then dried to afford a tan oil. The tan oil was recrystallized from methanol to afford the desired intermediate in the form of a white solid (2.5 g, 44% yield). 1H NMR and LCMS showed desired intermediate.

The chemical industry reduces the impact on the environment during synthesis 1-Bromo-2-(2-bromoethoxy)ethane. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Barta, Thomas E.; Becker, Daniel P.; Bedell, Louis J.; Boehm, Terri L.; Brown, David L.; Carroll, Jeffery N.; Chen, Yiyuan; Fobian, Yvette M.; Freskos, John N.; Gasiecki, Alan F.; Grapperhaus, Margaret L.; Heintz, Robert M.; Hockerman, Susan L.; Kassab, Darren J.; Khanna, Ish K.; Kolodziej, Stephen A.; Massa, Mark A.; McDonald, Joseph J.; Mischke, Brent V.; Mischke, Deborah A.; Mullins, Patrick B.; Nagy, Mark A.; Norton, Monica B.; Rico, Joseph G.; Schmidt, Michelle A.; Stehle, Nathan W.; Talley, John J.; Vernier, William F.; Villamil, Clara I.; Wang, Lijuan J.; Wynn, Thomas A.; US2005/9838; (2005); A1;,
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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. 1515-81-7, name is 1-Methoxy-4-(methoxymethyl)benzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Quality Control of 1-Methoxy-4-(methoxymethyl)benzene

General procedure: To a test tube charged with CuCl (2.0 mg, 0.02 mmol) andisochroman (1a; 251 muL, 2.0 mmol) in t-BuOH (20 mL) wasadded TBHP (5.0-6.0 M in decane, 10.9 muL, 0.6 mmol) and themixture was stirred and heated at 50 C for 12 h under open air.After cooling to room temperature, the reaction was quenchedwith 25% aqueous ammonia solution and water then themixture was extracted with EtOAc. The separated organic layerwas dried over Na2SO4 and products were concentrated after filtration.The residue was purified by silica gel column chromatography(EtOAc/hexane, 1:10) to give isochromanone (2a) as acolorless oil in 83% yield.

The synthetic route of 1515-81-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Tanaka, Hirotaka; Oisaki, Kounosuke; Kanai, Motomu; Synlett; vol. 28; 13; (2017); p. 1576 – 1580;,
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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. 92248-06-1, name is Bis(3-methoxyphenyl)amine, A new synthetic method of this compound is introduced below., category: ethers-buliding-blocks

(3) The third step: under argon protection, add to the double-mouth bottle4,4 ‘, 4 “, 4” -tetrabromostatrene,3,3’-dimethoxydianiline, palladium acetate, sodium tert-butoxide and tri-tert-butylphosphine, adding 5 mL of toluene, stirring and placing at 130 C., reacting for 12 hours, stopping the reaction, adding saturated chlorinated The ammonium solution was extracted three times with dichloromethane and the organic layer was dried over anhydrous MgSO4. The crude product was subjected to silica gel column chromatography (petroleum ether: dichloromethane = 2: 3, v / v)A yellow solid was obtained,Recrystallization from tetrahydrofuran / petroleum ether. The product TPE-OMe-mm, the product of the formula as shown in formula (VI):

The synthetic route of 92248-06-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sun Yat-sen University; Shao Guang; Kuang Daibin; He Yanjian; Chen Jian; (17 pag.)CN105037179; (2017); B;,
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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. 2688-84-8, name is 2-Phenoxyaniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 2688-84-8

To a 1 L four-necked round bottom flask equipped with a stirrer, a Liebig condenser fitted with a calcium chloride tube, a nitrogen inlet tube, a 50 mL isobaric dropping funnel and a thermometer, 50.0 g (0.6 mmol) of 2′-phenoxyaniline was added. 27 mol) and 500 mL of DCM, and the mixture was stirred at room temperature under a nitrogen stream. Subsequently, 42.8 g (0.41 mol) of triethylamine was added, and the mixture was cooled to -10 C. with an ice water bath, and 30.3 g (0.38 mol) of acetyl chloride was added dropwise from the dropping funnel at 0 C. or less while paying attention to heat generation . The mixture was further stirred at the same temperature for 30 minutes, returned to room temperature, and allowed to react after 5 hours to obtain a reaction solution.Next, 250 g of pulverized ice was added to a 1 L four-necked round bottom flask equipped with a stirrer, a Liebig condenser fitted with a calcium chloride tube, a 1 L dropping funnel and a thermometer, and while stirring, the above reaction solution The whole amount was added dropwise. Next, the dropping funnel was washed with 100 mL of DCM and added to the reaction solution, followed by stirring at room temperature for one day and night.The obtained reaction solution was transferred to a 1 L separating funnel, the organic layer was separated, washed three times with 250 mL of water, dried with magnesium sulfate, magnesium sulfate was suction filtered and removed, And the solvent was distilled off to obtain 73.2 g (yield 119.8%) of the target compound. The obtained compound was directly used for the next reaction.

The synthetic route of 2688-84-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; YAMAGATA UNIVERSITY; CHEMIPRO KASEI KAISHA LIMITED; KIDO, JUNJI; SASABE, HISAHIRO; TAKAHASHI, JUN; NAGAI, NAGAI; (723 pag.)JP2018/90561; (2018); A;,
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Application of 123652-95-9, A common heterocyclic compound, 123652-95-9, name is (3-Fluoro-4-methoxyphenyl)methanamine, molecular formula is C8H10FNO, 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: Generally, the procedure for the synthesis of 8 (a-w) was as follows. A mixture of substituted acridine (1) and benzylamine(2 equiv) in ethanol (8 mL) was added potassium carbonate(2 equiv) and potassium iodide (2% equiv). The reaction mixturewas stirred for 30 min at room temperature and refluxed in oil bathfor 24-48 h. Then the mixturewas extracted with absolute ethanolto give the crude products, which were purified by column chromatography with petroleum ether and ethyl acetate (5:1 v/v).

The synthetic route of 123652-95-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhang, Wei; Zhang, Bin; Zhang, Wei; Yang, Ti; Wang, Ning; Gao, Chunmei; Tan, Chunyan; Liu, Hongxia; Jiang, Yuyang; European Journal of Medicinal Chemistry; vol. 116; (2016); p. 59 – 70;,
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Electric Literature of 13468-02-5,Some common heterocyclic compound, 13468-02-5, name is N,N-Dimethyl-2-phenoxyethanamine, molecular formula is C10H15NO, 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 5 – Sodium 4-(2-dimethylaminoethoxy)-benzenesulfonate 7.00 g (42.4 mmol) of dimethyl-(2-phenoxyethyl)-amine were dissolved in 35 mL of glacial acetic acid and cooled in an ice bath. 9.63 g (93.3 mmol) of 95% sulfuric acid were dropped in while maintaining an internal temperature of 10C or lower followed by stirring for 1 hour at room temperature. The solution was concentrated followed by the gradual addition of the concentrated residue to 1 mol/L sodium hydroxide to bring pH10, after which the solution was concentrated and dried. After extracting the residue with methanol, concentrating and drying, the residue was suspended in 100 mL of ethanol followed by cooling and filtration. The filtrate was concentrated and the precipitated crystals were filtered to obtain 8.36 g of the target substance (yield: 74%). 1H-NMR (400 MHz, D2O): delta = 7.68 (d,2H,J=8.8 Hz), 7.01 (d,2H,J=8.8 Hz), 4.33 (t,2H,J=5.0 Hz), 3.53 (t,2H,J=5.2 Hz) 13C-NMR (400 MHz, D2O): delta = 158.12, 133.61, 125.61, 112.90, 61.79, 59.66, 41.70 IR (KBr): nu = 3431, 3097, 2770, 1599, 1180, 1032, 844 cm-1

The synthetic route of 13468-02-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Dainippon Ink and Chemicals, Incorporated; EP1736464; (2006); A1;,
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Application of 19500-02-8, 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. 19500-02-8, name is 3-Methoxy-2-methylaniline, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 2-methyl-3-(methyloxy)aniline (5.0 g, 36.5 mmol) in p-xylene (80 mL) and cooled to 0¡ã C., added BCl3 (36.5 mL) as a 1M solution in dichloromethane and stirred for 30 min at 0¡ã C. under a nitrogen atmosphere. Acetonitrile (2.6 mL, 54.7 mmol) was added and the solution was stirred for an additional 30 min at 0¡ã C. AlCl3 (4.87 g, 36.5 mmol) was suspended in anhydrous dichloromethane (50 mL) under a nitrogen atmosphere and cooled to 0¡ã C. The xylene solution was transferred to an addition funnel and added to the dichloromethane reaction dropwise. The reaction was stirred at 0¡ã C. for 45 min and the dichloromethane was removed in vacuo. The xylene solution was heated to 70¡ã C. for 18 h and cooled to room temperature. Water (80 mL) was added and the solution was heated to 70¡ã C. for 1 h and cooled to room temperature. The reaction was diluted with ethyl acetate and the aqueous layer separated. The organic layer was washed with an equal volume of water, brine and dried (MgSO4) and concentrated in vacuo. To the residue was added 5:1 hexanes:diethyl ether and the precipitate collected by filtration to afford intermediate 9 as a white solid (4.66 g, 71percent yield). 1H NMR (400 MHz, DMSO-d6) delta ppm 1.87 (s, 3H) 2.42 (s, 3H) 3.77 (s, 3H) 6.30 (d, J=9.04 Hz, 1H) 7.03 (br. s., 2H) 7.65 (d, J=9.04 Hz, 1H). LC-MS (ESI): m/z 180.10 (M+H)+.

The chemical industry reduces the impact on the environment during synthesis 3-Methoxy-2-methylaniline. I believe this compound will play a more active role in future production and life.

Reference:
Patent; GLAXOSMITHKLINE LLC; US2010/196321; (2010); A1;,
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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 954235-83-7 as follows. HPLC of Formula: C7H4BrF3O

A mixture of l-bromo-2-(difluoromethoxy)-4-fluorobenzene (intermediate 176a, 150 mg), (4-(2- (4-(ethylsulfonyI)phenyl)acetamido)-2,6-difluorophenyl)boronic acid (intermediate 122a, 404 mg), tri-ierf-butylphosphine, tetrafluoroboric acid salt (217 mg), Pd2(dba)j (171 mg) and sodium carbonate solution (2 M, 1.245 mL) in 1,4-dioxane (4.5 mL) was sealed in a vessel and heated in the microwave at 100C for 45 mins. The reaction mixture was filtered through celite and silica gel. The filtrate was concentrated under reduced pressure and the residue was purified by MDAP to afford N-(2′- (difluoromethoxy) -2,4′,6-trifiuoro-[ 1 , 1 ‘-biphenyl] -4-yl) -2-(4-(ethylsulfonyl)phenyl) acetamide ( 133 mg) as a yellow solid. ?-NMR (400 MHz, DMSO-Patent; GLAXO GROUP LIMITED; WANG, Yonghui; CAI, Wei; LIU, Qian; MENG, Qinghua; CHENG, Yaobang; YANG, Ting; ZHANG, Guifeng; XIANG, Jianing; WU, Chengde; WO2013/29338; (2013); A1;,
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Application of 91-16-7, 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. 91-16-7 name is 1,2-Dimethoxybenzene, 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.

Under nitrogen atmosphere, to a suspension of 4-chlorobutyrylchloride (4.0 mL, 36.1 mmol), 1,2-dimethoxybenzene (23.1 mL,180.9 mmol) in dichloromethane (60 mL) was added portionwisealuminum chloride (5.8 g, 43.4 mmol) at 0 C. The resulting suspensionwas stirred for 3 h at 25 C. The reaction was quenched bypouring the reaction mixture into an ice/water mixture. Theresulting aqueous solution was extracted with dichloromethane(3), and the organic layer was washed with water and brine, driedwith Na2SO4, and concentrated in vacuo. The crude residue wasthen purified by chromatography on silica gel (gradient of EtOAc inpetroleum ether) to afford the title compound 26 as a pale yellowsolid. (Yield 7.9 g, 90%). Rf 0.4 (EtOAc/petroleum ether 1:4).1HNMR (300 MHz, CDCl3, d): 2.13e2.22 (m, 2H), 3.09 (t, 2H, J 6.9 Hz),3.63 (t, 2H, J 6.0 Hz), 3.89 (s, 3H), 3.91 (s, 3H), 6.85 (d, 1H,J 8.4 Hz), 7.49 (d, 1H, J 2.1 Hz), 7.57 (dd, 1H, J 8.4 Hz, J 1.8 Hz).13C NMR (75 MHz, CDCl3, d): 27.1, 34.8, 44.8, 56.0, 56.7, 110.0, 110.6,122.7, 130.0, 149.0, 153.3, 197.5. HRMS (ESI): m/z calcd forC12H16O3Cl [MH]: 243.0788; found 243.0787.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1,2-Dimethoxybenzene, and friends who are interested can also refer to it.

Reference:
Article; Azzouz, Rabah; Peauger, Ludovic; Gembus, Vincent; ?in?a?, Mihaela-Liliana; Papamicael, Cyril; Levacher, Vincent; Sopkova-de Oliveira Santos, Jana; European Journal of Medicinal Chemistry; vol. 145; (2018); p. 165 – 190;,
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