Month: January 2021

These common heterocyclic compound, 17061-62-0, name is Bis(4-methoxybenzyl)amine, 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. SDS of cas: 17061-62-0

To a solution of Example 4.11 (210 g, 816 mmol) in DCM (2000 mL) was added TEA (385 mL, 2856 mmol) and a solution of 2-chloroethanesulfonyl chloride (146 g, 898 mmol) in DCM (1000 mL) at 0 C, and the mixture was stirred for 2 h. The reaction mixture was then quenched with ice cold water (1000 mL) and extracted with DCM (2 x 1000 mL). The organic layer was washed with brine solution (1000 mL), dried over anhydrous Na2S04, filtered and concentrated under reduced pressure. The residue was absorbed onto a plug of silica gel (60-120 mesh) and purified by column chromatography over silica gel (60-120 mesh) using 50% to 80% EtOAc in hexanes as an eluent to give (0968) Example 144.11 (255 g, 90% yield) as an off-white solid. NMR (400 MHz, DMSO- ck) delta 7.16 (d, J = 8.8 Hz, 4H), 6.90 (d, J = 8.8 Hz, 4H), 6.73 (dd, J = 16.4, 10.0 Hz, 1H), 6.11 (d, 3.75 (m, 6H).

The synthetic route of Bis(4-methoxybenzyl)amine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AMGEN INC.; DRANSFIELD, Paul John; HARVEY, James S.; MA, Zhihua; SHARMA, Ankit; (281 pag.)WO2019/89335; (2019); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Some common heterocyclic compound, 454-90-0, name is 3-(Trifluoromethyl)anisole, molecular formula is C8H7F3O, 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. COA of Formula: C8H7F3O

A solution of n-butyllithium (20.4 mL, 51.1 mmol) and TMEDA (9.00 mL, 59.6 mmol) in anhydrous THF (50 mL) was cooled to -78 C. 1-Methoxy-3-(trifluoromethyl)benzene (1) (10 g, 57 mmol) was added dropwise and the reaction mixture was stirred at -78 C. for 15 min then allowed to warm to RT and stirred for 10 min. The reaction mixture was cooled to -78 C. and trimethyl borate (16.1 mL, 142 mmol) was added slowly, dropwise, and the reaction mixture was stirred at -78 C. for 15 min then allowed to warm to RT and stirred for 20 h. 7N NH3/MeOH (20 mL) was added and the solvent was removed in vacuo. The residue was dissolved in formic acid (20 mL) and cooled to 0 C. before hydrogen peroxide (6.00 mL, 68.5 mmol) was added and the solution was allowed to warm to RT and stirred for 2 h. The product was extracted with EtOAc (3*50 mL), and then the combined organics were shaken with NaOH (2*50 mL). The aq phase was acidified with 1M HCl and the product was extracted with DCM (2*30 mL). The organic solution was washed with brine (2*30 mL), dried over MgSO4 and filtered. The solvent was removed in vacuo and the residue was purified by silica gel chromatography (120 g, 0-5% MeOH in DCM) to afford 2-methoxy-6-(trifluoromethyl)phenol (2) (4.95 g, 45%) as a colourless oil: m/z 191 [M-H]- (ES-); 1H NMR (400 MHz, CDCl3) delta: 7.15-7.09 (1H, m), 7.04-6.98 (1H, m), 6.89 (1H, td), 6.14 (1H, br s), 3.91 (3H, s).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 454-90-0, its application will become more common.

Reference:
Patent; KING’S COLLEGE LONDON; US2012/149737; (2012); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Adding a certain compound to certain chemical reactions, such as: 6358-77-6, name is 5-Bromo-2-methoxyaniline, 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 6358-77-6, Recommanded Product: 5-Bromo-2-methoxyaniline

a) 4-bromo-2-isocvanato-1 -methoxybenzene5-bromo-2-methoxyaniline (11.4 g, 56.4 mmols) was dissolved in dioxane (115 mL) and a solution of trichloromethyl chloroformate (3.4 mL) in the same solvent (30 mL) was added dropwise. It was stirred at 6O0C for 18 hours. It was concentrated in vacuo and diethyl ether was added. The solid precipitated was filtered off and the mother liquors were concentrated in vacuo to give the title compound (13 g).

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, 5-Bromo-2-methoxyaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ALMIRALL PRODESFARMA, SA; WO2006/133802; (2006); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Application of 658-89-9, 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. 658-89-9, name is 4-(Trifluoromethoxy)benzene-1,2-diamine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example 18 (SV2-Nitro-6-f4-(5-trifluoromethoxy-1H-benzoimida2ol-2-yl)-benzyloxy1 -6.7-dihvdro-5H-imidazor2.1-bin .3l oxazine (23)23In an inert atmosphere, 4-((S)-2-nitro-6,7-dihydro-5H-imidazo[2,1-b)[1 ,3]oxazin-6- yloxymethyl)-benzoic acid (100 mol%) is dissolved in anhydrous CH2CI2 (0.20 M) and added HATU (120 mol%) and DIEA (120 mol%). Reaction is stirred at room temperature for 5 min followed by addition of 1,2-diamino-substituted benzene (120 mol%). Resulting reaction mixture is stirred at room temperature overnight. Reaction is concentrated and dissolved in EtOAc and washed with water three times. Organic layer is dried under anhydrous Na2SO4 and concentrated to yield pale brown solid, which is dissolved in glacial acetic acid (0.36 M). Reaction mixture is heated to 95 ‘C for 30 min. Crude reaction mixture is concentrated and residue obtained is purified by preparative reverse-phase LC to give final compound as fluffy solid. MS: M+ 476.4.1H NMR (CD3OH1 400 MHz): delta 8.05 (d. J = 8.18 Hz, 2H), 7.74 (s, 1 H), 7.62 (d, J = 8.76 Hz, 1H), 7.50 (m, 3H)1 7.18 (dd, J = 8.73, 1.24 Hz, 1H), 4.87 (s, 2H)1 4.73 (m, 2H)1 4.48 (d, J = 12.05 Hz, 1H), 4.30 (m, 2H). Melting Point: 98-99 ‘C. [Q]21D = -37.81 (C= 0.003, MeOH).

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-(Trifluoromethoxy)benzene-1,2-diamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NOVARTIS AG; NOVARTIS PHARMA GmbH; US DEPARTMENT OF HEALTH & HUMAN SERVICES; WO2007/75872; (2007); A2;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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. 24988-36-1, name is 1,5-Dibromo-2,4-dimethoxybenzene, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C8H8Br2O2

Under an argon atmosphere, 5.00 g of Compound A, 1.08 g of bis(4-biphenylyl)amine, 0.10 g of bis(dibenzylideneacetone)palladium(0), 0.14 g of tri-tert-butylphosphine and 0.49 g of sodium tert-butoxide were added to a 300 mL, three-necked flask, followed by heating and refluxing in a toluene solvent for 4 hours. After cooling in air, water was poured in the reaction mixture to separate an organic layer, and solvents were distilled. The crude product thus obtained was separated by silica gel column chromatography (toluene/hexane) to produce 1.38 g of Compound B as a white solid (yield 76%). The molecular weight of Compound B thus obtained was measured by FAB-MS and was 536 (C32H26BrNO2).

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 24988-36-1.

Reference:
Patent; SAMSUNG DISPLAY CO., LTD.; SAKAMOTO, Naoya; (55 pag.)US2015/376114; (2015); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Application of 74654-07-2, 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. 74654-07-2, name is 2-(2-(2-Methoxyethoxy)ethoxy)ethanamine, This compound has unique chemical properties. The synthetic route is as follows.

Benzhydryl 2-chloroethyl ether (2 mmol) and mPEGn-NH2 (3 mmol) were dissolved in 10 ml of acetonitrile, and then sodium hydroxide (2 mmol) in water (1 mL) was added to the solution. The mixture was stirred at 100 C for 16 hours. Dichloromethane (200 ml) was added to the reaction mixture, and the resulting solution was washed with water (200 mL x 3). The organic phase was dried and solvent was removed under reduced pressure. The crude product was purified by column chromatography (SiO2: DCM/CH3OH, 20:1) or alternatively using flash chromatography on silica gel using CAN/H2O (40M C-18RP column, Biotage, Inc., Charlottesville, VA). The desired product of mPEGn-NH- diphenhydramine obtained in -70% yield and mPEGn-N-(diphenhydramine)2 was also obtained in 15% yield.

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

Reference:
Patent; NEKTAR THERAPEUTICS AL, CORPORATION; WO2008/112257; (2008); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

These common heterocyclic compound, 5414-19-7, name is 1-Bromo-2-(2-bromoethoxy)ethane, 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. Application In Synthesis of 1-Bromo-2-(2-bromoethoxy)ethane

A 500 mL round-bottom flask was charged with the product from Part E (29.1 g, 76 mmol), dimethylformamide (125 mL), 18-crown-6 (6 g, 22.8 mmol), potassium carbonate (31.5 g, 228 mmol), and 2-bromoethyl ether (11.7 mL, 83.5 mmol). The resulting mixture was heated to 60 C. with vigorous stirring for 44 hr. After cooling to room temperature, the reaction mixture was poured into 500 mL ice water. The mixture was then extracted with ethyl acetate (300 mL). Afterward, the organic layer was washed with brine (400 ml). The organic layer was then dried over magnesium sulfate, filtered, and concentrated in vacuo to form 40 g of a dark yellow oil. Purification via flash column chromatography on silica gel (3*6 inch column) afforded 30.2 g of a yellow oil product (88% yield). 1H NMR (CDCl3) delta 1.30 (m, 2H), 1.50 (s, 9H), 1.77 (m, 3H), 2.10 (dt, J=4.6, 12.6 Hz,2H), 2.31 (d, J=11.6 Hz, 2H), 2.94 (t, J=12.4 Hz, 2H), 3.25-3.33 (m, 4H), 3.77-3.84 (m, 2H), 3.95 (dd, J=4.2, 11.1, 2H), 4.48 (s, 2H), 7.25-7.35 (m, 5H); Electrospray mass spectrometry showed m/z=454 (M+H).

The synthetic route of 1-Bromo-2-(2-bromoethoxy)ethane has been constantly updated, and we look forward to future research findings.

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;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Electric Literature of 6346-09-4, A common heterocyclic compound, 6346-09-4, name is 4,4-Diethoxybutan-1-amine, molecular formula is C8H19NO2, 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.

Hexahydroindolizin-7(1H)-one (140): Prepared according to WO0000487A1, U.S. Pat. No. 5,874,427, WO0017198A1.

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; Maddaford, Shawn; Ramnauth, Jailall; Rakhit, Suman; Patman, Joanne; Renton, Paul; Annedi, Subhash C.; US2006/258721; (2006); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

588-63-6, name is (3-Bromopropoxy)benzene, 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. Formula: C9H11BrO

The 148mgNa dissolved in 20ml of absolute ethanol until complete dissolution, 6-(3,5-difluoro)benzyl-2-thiouracil 234mg (0.92mmol) and 1- (3-bromo-propoxy) benzene 297mg (1.38mmol) was added thereto, TLC the reaction was complete after stirring overnight at room temperature; column chromatography, P:E = 5:1,2:1,1:1, the final product was 222mg, as a white solid, a yield of 62.14percent

The synthetic route of 588-63-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Peking University; Zhang, Liang; FU, YUHONG; Qin, Hua; Wang, Xiao Wei; Liu, Jun Yi; (30 pag.)CN103864699; (2016); B;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Some common heterocyclic compound, 592-55-2, name is 1-Bromo-2-ethoxyethane, molecular formula is C4H9BrO, 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. name: 1-Bromo-2-ethoxyethane

General procedure: To a mixture of 1,2,4-triazole 1 (1 mmol), triethylamine (1.1 mmol)and ethanol (20 ml) was added with stirring bromoethanol (2), chloropropanol(3), chloroglycerol (4), 2,3-O-isopropylidene-1-O-(p-tolylsulfonyl)-glycerol (5), bromoethylmethyl ether (6) and/or bromoethylethylether (7) (1.1 mmol). The mixture was stirred at reflux for8 h with 2-4 and for 6 h with 5-7. Ethanol was removed under pressureand the resulting solid was collected and recrystallized from ethanol toafford the targeted S-acyclonucleoside analogues 8-13.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 592-55-2, its application will become more common.

Reference:
Article; Aouad, Mohamed Reda; Al-Mohammadi, Hannan Musallam; Al-blewi, Fawzia Faleh; Ihmaid, Saleh; Elbadawy, Hossein Mostafa; Althagfan, Sultan Saad; Rezki, Nadjet; Bioorganic Chemistry; vol. 94; (2020);,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem