Month: September 2021

17061-62-0, name is Bis(4-methoxybenzyl)amine, belongs to ethers-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. SDS of cas: 17061-62-0

To a stirred solution of 100.1 (100 g, 0.39 mol) in DCM (1 L) was added TEA (71 mL, 0.51 mol), followed by dropwise addition of methanesulfonyl chloride (36 mL, 0.47 mol). The internal temperature was kept between 5-10 C during the addition of methane sulfonyl chloride. Once the addition was complete, the cooling bath was removed and the mixture was stirred at RT until TLC analysis indicated that the reaction was complete. Thereafter, water (1 L) was added, the layers were separated and the aqueous layer was extracted with DCM (2 x 500 mL). The combined organic layers were washed with brine (2 x 1 L), dried over Na2SO4, and concentrated in vacuo. The residue was purified on a silica gel column, employing a gradient of 10-80% EtOAc in hexanes, to afford 120 g (0.36 mol, 92%) of 101.0 as white solid.1H-NMR (400 MHz, CDCl3) delta 7.26 (dd, J=2.12, 6.60 Hz, 4H) 6.91 (dd, J=2.12, 6.62 Hz, 4H) 4.28 (s, 4H) 3.83 (s, 6H) 2.75 (s, 3H).

The synthetic route of 17061-62-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AMGEN INC.; CHEN, Ning; CHEN, Yinhong; DEBENEDETTO, Mikkel V.; DRANSFIELD, Paul John; HARVEY, James S.; HEATH, Julie Anne; HOUZE, Jonathan; KHAKOO, Aarif Yusuf; LAI, Su-Jen; MA, Zhihua; NISHIMURA, Nobuko; PATTAROPONG, Vatee; SWAMINATH, Gayathri; YEH, Wen-Chen; KREIMAN, Charles; (308 pag.)WO2018/93579; (2018); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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. 701-56-4, name is 4-Methoxy-N,N-dimethylaniline, A new synthetic method of this compound is introduced below., Application In Synthesis of 4-Methoxy-N,N-dimethylaniline

General procedure: Under an atmosphere of N2, KOt-Bu (2.2 mmol), dioxane (0.9 mL), DMSO (1.65 mmol), tertiary amine 1 (0.55 mmol), and aryl halide 2(1.65 mmol) were successively added to a Schlenk reaction tube. The mixture was stirred vigorously at 80-120 C for 12 h. Then the mixture was diluted with EtOAc, washed with sat. brine, and dried (anhyd Na2SO4). Then the solvent was removed under reduced pressure and the residue was purified by flash column chromatography (petroleum ether and petroleum ether-EtOAc, 100:1 for the methoxy group derived products) to give pure products 3.

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:
Article; Huang, Pei; He, Bang-Yue; Wang, Hui-Min; Lu, Jian-Mei; Synthesis; vol. 47; 2; (2015); p. 221 – 227;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Related Products of 702-24-9, These common heterocyclic compound, 702-24-9, name is 4-Methoxy-N-methylbenzylamine, 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.

Place ethyl 6,8-dichloroimidazo[ 1 ,2-bj pyridazine-3 -carboxylate (3 g, 11.54mmol), 1-(4-methoxyphenyl)-N-methylmethanamine (2.267 g, 15.00 mmol), and N,NDiisopropylethylamine (DIPEA) (4.03 mL, 23.07 mmol) in a 100 mL round bottle flask along with THF (15 mL). It was sealed and heated to 80°C for 6 hours. The reactionmixture was concentrated and purified with silica gel chromatography. The product came out when eluting with 35percent ethyl acetate in hexane. The fractions containing product was collected and concentrated to provide the product (3.7 g, 9.87 mmol, 86percent yield, 100percentpurity). LC retention time 1.06 mm [Al. MS (ES+) m/z: 375 (MH). ?H NMR (400MHz, CHLOROFORM-d):8.14 – 8.09 (m, 1H), 7.20 – 7.13 (m, 2H), 6.89 – 6.83 (m, 2H), 6.11 (s, 1H), 5.49 (s, 2H),4.44 (q, J=7.2 Hz, 2H), 3.84 – 3.77 (m, 3H), 3.17 (s, 3H), 1.42 (t, J=7.2 Hz, 3H)

Statistics shows that 4-Methoxy-N-methylbenzylamine is playing an increasingly important role. we look forward to future research findings about 702-24-9.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WEINSTEIN, David S.; DUNCIA, John V.; SPERGEL, Steven H.; (76 pag.)WO2018/93968; (2018); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Electric Literature of 349-65-5, The chemical industry reduces the impact on the environment during synthesis 349-65-5, name is 2-Methoxy-5-(trifluoromethyl)aniline, I believe this compound will play a more active role in future production and life.

5-(Trifluoromethyl)-2-methoxyaniline was treated with CDI, followed by 4-(1-oxoisoindolin-5-yloxy)aniline according to Method C2d to afford the urea. Entry 26: 4-Hydroxyacetophenone was reacted with 4-fluoronitrobenzene according to Method A13, Step 1 to give 4-(4-acetylphenoxy)nitrobenzene.

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, 2-Methoxy-5-(trifluoromethyl)aniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Riedl, Bernd; Dumas, Jacques; Khire, Uday; Lowinger, Timothy B.; Scott, William J.; Smith, Roger A.; Wood, Jill E.; Monahan, Mary-Katherine; Natero, Reina; Renick, Joel; Sibley, Robert N.; US2001/11135; (2001); A1;; ; Patent; BAYER CORPORATION; US2003/181442; (2003); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Adding a certain compound to certain chemical reactions, such as: 175278-17-8, name is 2-Bromo-4-(trifluoromethoxy)aniline, belongs to ethers-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 175278-17-8, Recommanded Product: 2-Bromo-4-(trifluoromethoxy)aniline

To a mixture of 2-bromo-4-(trifluoromethoxy)aniline (1.00 mmol), triethylamine (1.5 mmol) and P(o-tol)3 (0.40 mmol) in DMF (0.5 M) in a glass pressure tube under nitrogen gas were added ethyl acrylate (1.0 mmol) and palladium acetate (0.20 mmol). The tube was sealed and heated to 120 0C for 18 h. The resulting solution was concentrated under vacuum and purified by column chromatography. Retention time (min) = 2.467, method [1], MS(ESI) 276.1 (M+H).

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, 2-Bromo-4-(trifluoromethoxy)aniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ELAN PHARMACEUTICALS, INC.; SHAM, Hing, L.; KONRADI, Andrei, W.; HOM, Roy, K.; PROBST, Gary, D.; BOWERS, Simeon; TRUONG, Anh; NEITZ, R., Jeffrey; SEALY, Jennifer; TOTH, Gergely; WO2010/91310; (2010); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Adding a certain compound to certain chemical reactions, such as: 17715-69-4, name is 1-Bromo-2,4-dimethoxybenzene, belongs to ethers-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 17715-69-4, Safety of 1-Bromo-2,4-dimethoxybenzene

General procedure: Synthesis of 4′-methoxybiphenyl-4-carbonitrile. A reaction vessel equipped with filtration frit was charged with polystyrene resin-bound benzyl(di-tert-butyl)phosphonium chloride (6.20 mg, 4% mol, 100-200 mesh resin containing 1.60 mmol/g phosphonium hydrochloride) and flushed with argon. Next, 5mL of degassed dioxane was added followed by 20 mL of diisopropylamine and reaction mixture was agitated for 1 h at room temperature. Subsequently, the solvent was removed and the resin washed with degassed dioxane (3×5 mL). The resin was resupended in dioxane (5.0 mL) and Pd2(dba)3·CHCl3 (5.20 mg, 2% mol) added and the reaction mixture was agitated for 12 h at room temperature. The Pd-doped resin becomes black in colour. The solvent was removed and catalyst washed with degassed dioxane (3×5 mL). 4-Bromobenzonitrile (45.5 mg, 0.25 mmol), 4-methoxyphenylboronic acid (42.0 mg, 0.28 mmol), Cs2CO3 (179.2 mg, 0.55 mmol), 5 mL of degassed dioxane were added and the suspension agitated for 72h at room temperature. The solution was filtered and the Pd-doped catalyst re-suspended and washed with degassed dioxane (3 x 5 mL). Evaporation of the combined dioxane extracts under vacuum and purification by chromatography on silica gel (ethyl acetate/hexane 1:9) afforded the title compound (41 mg, 80%). All entries reported in table 2 were conducted under the above conditions.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Article; Ullah, Ehsan; McNulty, James; Sliwinski, Marcin; Robertson, Al; Tetrahedron Letters; vol. 53; 31; (2012); p. 3990 – 3993;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Adding a certain compound to certain chemical reactions, such as: 1663-61-2, name is (Triethoxymethyl)benzene, belongs to ethers-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 1663-61-2, Safety of (Triethoxymethyl)benzene

b. 1-Azidoethyl-2,4-dibenzoylmannose To a 1.0 L, 3-neck flask containing a stir bar, nitrogen inlet and 300 mL of anhydrous acetonitrile was added 25 gm 1-azidoethylmannose (100.4 mmole), and 50 mL triethyl orthobenzoate (220 mmole, 2.2 equiv.). The resulting slurry was stirred at room temperature and 0.8 mL (10 mmole) trifluoroacetic acid (TFA) was added neat. The solution cleared within 10 minutes and stirring was continued for an additional two hours, then 25 mL of 10percent aqueous TFA was added and stirring was continued for an additional 2 hours to hydrolyze the intermediate to the ester isomers. The solvent was evaporated under vacuum to a viscous oil, which was triturated with 50 mL DCM and again evaporated to a viscous oil. Toluene (70 mL) was added to the residue and the viscous solution was seeded with 2,4-dibenzoylazidoethylmannose. A fine precipitate formed within 15 minutes and stirring was continued overnight at room temperature. The resulting heavy suspension was set in the freezer for 2-4 hours, then filtered and the solid washed with ice cold toluene (2*10 mL). The solid was air dried to a constant weight to give 21 gm (TY 22.85 gm 50percent isomeric purity) of ?95percent isomeric purity. The product was taken into 40 mL toluene, stirred for 1 hour and then set in the freezer for an additional 2 hours. The solid was filtered and washed (2*10 mL) with ice cold toluene and air dried to a constant weight to give 18.5 gm of the single isomer product 2,4-dibenzoylazidoethylmannose in 83percent yield. The mother liquors contained the undesired isomer and a small amount of the desired isomer. The reaction was monitored by TLC: SG (Hexane/Ethyl Acetate 7/3) Starting Material Rf 0.0, orthoester intermediate Rf 0.9. (Hexane/Ethyl Acetate: 8/2) SM Rf 0.8, desired isomer Rf 0.4, un-desired isomer Rf 0.2 1H NMR 300 MHz (CDCl3) delta 8.12 (t, 4H), 7.66 (t, 2H), 7.5 (m, 4H), 5.56 (t, 1H), 5.48 (m, 1H), 5.14 (m 1H), 4.5 (dd, 1H), 4.0 (m, 2H), 3.8 (m, 3H), 3.56 (m, 1H), 3.44 (m, 1H).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; SMARTCELLS, INC.; Chen, Zhiyu; Lancaster, Thomas M.; Zion, Todd C.; US2013/190475; (2013); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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. 109-85-3, name is 2-Methoxyethylamine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. category: ethers-buliding-blocks

A solution of 6-amino-4-fluoronicotinonitrile (intermediate 21, 1.10 g, 8.02 mmol) in DMA (20 ml)was treated with 2-methoxyethylamine (2.07 ml, 24.1 mmol) and DIPEA (4.20 mL, 24.1 mmol),heated to 50 C and stirred for 15 h. The reaction mixture was cooled to room temperature and concentrated. The crude material was purified by normal phase chromatography (24 g silica gel cartridge, heptanes/EtOAc 100:0 to 0:100). The product containing fractions were concentrated and dried under vacuum to give the title compound as an off-white solid.

The synthetic route of 109-85-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; BUSCHMANN, Nicole; FAIRHURST, Robin Alec; FURET, Pascal; KNOePFEL, Thomas; LEBLANC, Catherine; MAH, Robert; NIMSGERN, Pierre; RIPOCHE, Sebastien; LIAO, Lv; XIONG, Jing; ZHAO, Xianglin; HAN, Bo; WANG, Can; WO2015/59668; (2015); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Adding a certain compound to certain chemical reactions, such as: 2734-70-5, name is 2,6-Dimethoxyaniline, belongs to ethers-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 2734-70-5, Safety of 2,6-Dimethoxyaniline

To a solution of pentanenitrile (310 mg, 3.7 mmol) and 2-methoxy-6-methylaniline (518 mg, 3.40 mmol) in toluene (13 mL) at RT was added a solution of trimethylaluminum in toluene (1.7 mL, 3.4 mmol) at 0 °C. The reaction mixture was heated at 110 °C for 1 h. The cooled reaction mixture was quenched by the addition of a saturated solution of Rochelle’s salt (5 mL) and stirred at RT for 30 min. The reaction mixture was extracted with EtOAc (3×20 mL). The combined organic portion was washed with brine, dried over MgS04, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography elution with 20-100percent EtOAc hexanes to give Compound la (450 mg, 56percent) as a brown oil. LCMS (Method D) retention time = 0.65 min, m/z = 237.1 (M+H)+. NMR (500MHz, chloroFORM-d)? 6.88 (t, J=8.4 Hz, 1H), 6.51 (d, J=8.3 Hz, 2H), 4.68 – 3.89 (m, 2H), 3.71 (s, 6H), 2.33 (br. s., 2H), 1.84 -1.52 (m, 2H), 1.49 -1.24 (m, 2H), 0.89 (br. s., 3H).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; TORA, George, O.; FINLAY, Heather; JIANG, Wen; MENG, Wei; ZHANG, Xiaojun; (303 pag.)WO2017/218633; (2017); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Application of 1484-26-0, These common heterocyclic compound, 1484-26-0, name is 3-Benzyloxyaniline, 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.

To a stirred solutionof 3-(benzyloxy)aniline 10b (1.0 equiv.) in ethylformate (3 mL),catalytic amount of pTsOH monohydrate was added. The reactionmixture was stirred at rt for 3 days and the resulting mixture wasextracted with ethyl acetate. Organic layers were collected, washedwith water and brine, dried over anhydrous MgSO4 and evaporatedgiving the product 11b as white solid in 80percent yield.xNMR: mixture of two rotamers (approx. 1:1) 1H (600 MHz,CDCl3): d 8.67 (d, J 10.0 Hz, 1H), 8.32 (s, 1H), 7.97e7.67 (m, 22H),5.05 (s, 2H), 5.03 (s, 2H).

Statistics shows that 3-Benzyloxyaniline is playing an increasingly important role. we look forward to future research findings about 1484-26-0.

Reference:
Article; Surmiak, Ewa; Neochoritis, Constantinos G.; Musielak, Bogdan; Twarda-Clapa, Aleksandra; Kurpiewska, Katarzyna; Dubin, Grzegorz; Camacho, Carlos; Holak, Tad A.; Doemling, Alexander; European Journal of Medicinal Chemistry; vol. 126; (2017); p. 384 – 407;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem