Category: ethers-buliding-blocks

Electric Literature of 37466-89-0, These common heterocyclic compound, 37466-89-0, name is 3-Methoxybenzene-1,2-diamine, 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.

The reaction mixture of 3-methoxy-o-phenylenediamine (2, 190mg, 1.37mmol)and HCOOH (5mL) was refluxed for 4h, then cooled to room temperature and poured into ice/ water (20mL). The mixture was treated with 10% NaOH aqueous solution to pH?8 and then extracted with ethyl ether (15mL×3). The combined extracts were washed with water and brine, then dried over anhydrous MgSO4. The organic phase was concentrated to give the crude product, which was purified by column chromatography with CH2Cl2-MeOH (v/v=60/1). The desired product 4-methoxy-1H-benzo[d]imidazole (162mg) was afforded as white powder with 83.9% yield. M.p. 165-167C; 1H NMR (acetone-d6, 300MHz, delta ppm): 8.08 (1H, s), 7.21 (1H, d, J=7.8Hz), 7.11 (1H, t, J=7.8Hz), 6.73 (1H, d, J=7.8Hz), 3.97 (3H, s); HRMS (ESI): m/z, calcd. For C8H9N2O [M+H]+ 149.0709 found 149.0707.

The synthetic route of 37466-89-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhou, Jie; Jin, Jing; Zhang, Yi; Yin, Yuwen; Chen, Xiaoguang; Xu, Bailing; European Journal of Medicinal Chemistry; vol. 68; (2013); p. 222 – 232;,
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Reference of 4316-51-2, A common heterocyclic compound, 4316-51-2, name is 4-Methoxytriphenylamine, molecular formula is C19H17NO, 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.

(1) Synthesis of 4,4′-Diformyl-4″-methoxytriphenylamine (8c) Reactions were conducted in the same manner as in (4) in Example 2 except that 20.0 g (0.075 mol) of 4-methoxytriphenylamine (7c) was used in place of triphenylamine (7a). Thus, 19.0 g of 4,4′-diformyl-4″-methoxytriphenylamine (8c) was obtained. Theoretical yield, 76.5%; m.p., 113-114 C. Spectral data for this compound are as follows. 1 H-NMR spectrum (400 MHz, CDCl3, deltappm): 3.85 (3H, s), 6.94 (2H, d, J=9.0 Hz), 7.12 (2H, d, J=9.0 Hz), 7.17 (4H, d, J=8.7 Hz), 7.56 (4H, d, J=8.7 Hz), 9.88 (2H, s)

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; Takasago International Corporation; US5573878; (1996); A;,
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Adding a certain compound to certain chemical reactions, such as: 589-10-6, name is (2-Bromoethoxy)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 589-10-6, name: (2-Bromoethoxy)benzene

Compound 99 (100 mg, 0.371 mmol) to DCM (2 mL) the solution was dissolved in methyl isothiocyanate (30.0 , 0.446 mmol) was slowly added dropwise in a 0 and then, at room temperature two hours then stirred dongan. After checking the completion of the reaction by TLC, the solution was diluted with DCM and extracted with brine. The organic layer was dried over anhydrous Na2SO4, concentrated and filtered. The concentrated filtrate was purified by column chromatography (Hex: EtOAc = 1: 2) to give Compound 101 was synthesized via a (69.3 mg, 55%, colorless oil).

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

Reference:
Patent; Korea Institute of Science and Technology; Ulsan University Academic Cooperation; Kim, Dong Jin; Nam, Gil Soo; Choe, Gyung Ir; Park, Woong Saw; Kim, Young Soo; Pyeon, Sung Lim; Hwang, Hyun Suk; Mun, Doo Hyun; Hwang, Ohn Yu; Sim, Young Sun; Kim, Jin Woo; Kim, Yun Gyung; Kang, Yong Gu; Park, Gi Tuk; (106 pag.)KR101525019; (2015); B1;,
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62257-15-2, name is 2-Fluoro-5-methoxyaniline, 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. Computed Properties of C7H8FNO

E. Preparation of N-benzyl-2-fluoro-5-methoxyaniline This procedure was patterned after that of Tietze and Grote, Chem Ber. 126(12), 2733 (1993). A solution of 2.73 g of 2-fluoro-5-methoxyaniline and 2.67 g of benzaldehyde in 48 ml of methanol was treated with 3.43 g of zinc chloride and then cooled in an ice bath. Sodium cyanoborohydride (1.58 g) was added in small poroom temperature ions over 30 minutes and the reaction was stirred for five hours at room temperature. After evaporation of the solvent, the residue was slurried in 40 ml of 1 N sodium hydroxide solution and then extracted twice with ether. The extracts were washed with water and then with brine, dried over magnesium sulfate and concentrated. The residue was recrystallized from hexane to afford 2.61 g and the mother liquors were chromatographed on silica gel using 20:1 hexane/ether to afford another 1.4 g of the subtitle compound (90%). mp. 56-58C

The synthetic route of 62257-15-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ELI LILLY AND COMPANY; EP950657; (1999); A2;,
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Some common heterocyclic compound, 53087-13-1, name is 1-(Benzyloxy)-3-bromobenzene, molecular formula is C13H11BrO, 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-(Benzyloxy)-3-bromobenzene

Preparation 3 3-Benzyloxyphenyl boronic acid A solution of 3-benzyloxy-bromobenzene 10 g (38 mmol) in 150 mL of anhydrous THF was cooled to -70C under a nitrogen atmosphere. 28.5 mL of n-butyl lithium (1.6 M in hexanes) was added dropwise to the solution. The reaction mixture was stirred for 30 minutes, then tri-isopropyl borate 10.6 mL (45.6 mmol) was added. The reaction mixture was allowed to warm to ambient temperature over a two hour period. The reaction was quenched by the addition of 200 mL of 1 N HCl andthe reaction mixture was stirred for an additional hour. The slurry was extracted twice with EtOAc and the organic layer separated and combined. The EtOAc solution was washed twice with brine, dried with Na2SO4, and evaporated to a yellow oil. The product was crystallized from ether-hexane. This yielded 4.85 g of the title compound as white solid. PMR: Consistent with the proposed structure.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 53087-13-1, its application will become more common.

Reference:
Patent; ELI LILLY AND COMPANY; EP838461; (1998); A2;,
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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. 1836-62-0, name is 2-(2-Methoxyphenoxy)ethylamine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Computed Properties of C9H13NO2

General procedure: To a solution of 2-phenoxy-ethylamine (5 eq.) or 2-(2-methoxyphenoxy-)ethylamine (5 eq.) in 2-methoxyethanol(25 mL per mmol of amine) the appropriate aliphatic chloride33-39 (1 eq.) and KI (cat.) was added. The mixturewas refluxed for18-48 h and concentrated. The residue was suspended in CHCl3and washed with 1M NaOH, brine, dried over anhydrous Na2SO4and concentrated. The crude was purified by flash chromatographyto give the titled compound.

The synthetic route of 1836-62-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Franchini, Silvia; Sorbi, Claudia; Linciano, Pasquale; Carnevale, Gianluca; Tait, Annalisa; Ronsisvalle, Simone; Buccioni, Michela; Del Bello, Fabio; Cilia, Antonio; Pirona, Lorenza; Denora, Nunzio; Iacobazzi, Rosa Maria; Brasili, Livio; European Journal of Medicinal Chemistry; vol. 176; (2019); p. 310 – 325;,
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Application of 62257-15-2, 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. 62257-15-2 name is 2-Fluoro-5-methoxyaniline, 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.

A. 2-Azido-1-fluoro-4-methoxybenzene, 5a To a mixture of 2-fluoro-5-methoxyaniline (5.0 g, 35 mmol), sulfuric acid (7.5 mL), trifluoroacetic acid (37.5 mL) and water (45 mL) was added NaNO2 (3.7 g, 53 mmol) portionwise at 0 qC. The mixture was stirred for 30 min at 0 qC and NaN3 (4.6 g, 71 mmol) was added. The resulting solution was stirred overnight at RT and extracted with EtOAc (2 x 200 mL). The combined organic layers were dried over Na2SO4 and concentrated. The residue obtained was purified by column chromatography on silica gel (EtOAc/petroleum ether, 1:100) to give compound 5a as a light yellow oil. 1H-NMR (300 MHz, DMSO-d6) (ppm): 7.23 (dd, J1 = 9.0 Hz, J2 = 10.8 Hz, 1H), 6.72 – 6.80 (m, 2H), 3.76 (s, 3H). Mass Spectrum (GCMS, EI): Calcd. for C7H6FN3O: 167.0 (M); found: 167.2.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Fluoro-5-methoxyaniline, and friends who are interested can also refer to it.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; HUANG, Hui; MEEGALLA, Sanath; PLAYER, Mark R.; (196 pag.)WO2017/27310; (2017); A1;,
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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. 1535-75-7, name is 2-(Trifluoromethoxy)aniline, A new synthetic method of this compound is introduced below., Application In Synthesis of 2-(Trifluoromethoxy)aniline

Add in a 25 ml two-neck round bottom flask2-methylaniline(53.5 mg, 0.5 mmol), Pd2(dba)3 (0.05 g, 10 mol%), NaHCO3 (12.5 mg, 30 mol%), pivalic acid 0.44 g and stirring magnet, after replacing oxygenN,N-dimethylacetamide 2 ml and methyl trifluoromethyl propyrate (91.2 mg, 0.6 mmol) were added. Stir at 120CAfter 12h, TLC was followed by a complete reaction and column chromatography gave a white solid, ie 7-methyl-2-trifluoromethyl-1H-indole-3-carboxylic acid.Methyl esters.

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; Shanghai Maikelin Biochemical Technology Co., Ltd.; Shen Dandan; Han Jing; Chen Jie; Zhang Hui; Cao Weiguo; (23 pag.)CN104892485; (2018); B;,
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Electric Literature of 578-57-4, The chemical industry reduces the impact on the environment during synthesis 578-57-4, name is 1-Bromo-2-methoxybenzene, I believe this compound will play a more active role in future production and life.

A screw-cap vial equipped with a magnetic stir bar was charged with aryl halide (1 mmol), hexa-n-butylditin (0.5 mmol),palladium acetate (0.01 mmol) and tricyclohexylphosphine (0.02 mmol),followed by anhydrous cesium fluoride (1.5 mmol). The resulting mixture was manually homogenized with a magnet. A vial was transferred to a preheated oil bath (110 C). After 24 h, the mixture was cooled, dissolved in CH2Cl2-H2O mixture (1:1), the organic phase was separated, the solvent was evaporated in vacuo and the product was isolated by flash chromatography on a silica gel by elution with hexane-CH2Cl2 mixture.

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, 1-Bromo-2-methoxybenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Gribanov, Pavel S.; Golenko, Yulia D.; Topchiy, Maxim A.; Philippova, Anna N.; Kirilenko, Nikita Yu.; Krivoshchapov, Nikolai V.; Sterligov, Grigorii K.; Asachenko, Andrey F.; Bermeshev, Maxim V.; Nechaev, Mikhail S.; Mendeleev Communications; vol. 28; 3; (2018); p. 323 – 325;,
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Related Products of 102-52-3,Some common heterocyclic compound, 102-52-3, name is 1,1,3,3-Tetramethoxypropane, molecular formula is C7H16O4, 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.

70.67 grams of piperidine are condensed with 1,1,3,3-tetramethoxypropane in acetic acid, concentrated and treated with 59.72 grams of 2-ethoxyethyl cyanoacetate cyanoacetate in the presence of an organic base and a solvent. After silica gel column chromatography (eluent: toluene/acetone) the pure product is obtained yielding dark yellow crystals. Melting point: 66-67 C.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1,1,3,3-Tetramethoxypropane, its application will become more common.

Reference:
Patent; L’OREAL; Richard, Herve; Marat, Xavier; L’Alloret, Florence; Candau, Didier; Songeur-Geney, Julie; Grumelard, Julie; Winkler, Barbara; Huglin, Dietmar; US2014/294743; (2014); A1;,
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