Month: July 2021

Electric Literature of 1663-61-2, A common heterocyclic compound, 1663-61-2, name is (Triethoxymethyl)benzene, molecular formula is C13H20O3, 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.

b. l-Azidoethyl-2,4-dibenzoylmannoseTo a 1.0L, 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 0.8mL (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 (at) 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 300MHz (CDCl3) delta 8.12(t, 4H), 7.66(t, 2H), 7.5(m, 4H), 5.56(t, IH), 5.48(m, IH), 5.14(m, IH), 4.5(dd, IH), 4.0(m, 2H), 3.8(m, 3H), 3.56(m, IH), 3.44(m, IH).

The synthetic route of 1663-61-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SMARTCELLS, INC.; ZION, Todd, C.; LANCASTER, Thomas, M.; WO2010/88261; (2010); A1;,
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Adding a certain compound to certain chemical reactions, such as: 494-99-5, name is 1,2-Dimethoxy-4-methylbenzene, 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 494-99-5, Recommanded Product: 1,2-Dimethoxy-4-methylbenzene

General procedure: A mixture of 3,4-disubstituetedtoluene (1 mmol), NBS(213 mg, 1.2 mmol) and AIBN(16 mg, 0.1 mmol) in anhydrous CCl4 (15 mL) was refluxed and monitored by TLC. After refluxing for 4 h, the reaction mixturewas filtered. The filtrate was concentrated to crude product, which was used inthe subsequent reaction without further purification

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, 1,2-Dimethoxy-4-methylbenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Ge, Bing-Chen; Feng, Hong-Fang; Cheng, Yu-Fang; Wang, Hai-Tao; Xi, Bao-Ming; Yang, Xue-Mei; Xu, Jiang-Ping; Zhou, Zhong-Zhen; European Journal of Medicinal Chemistry; vol. 141; (2017); p. 440 – 445;,
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Reference of 64465-53-8, These common heterocyclic compound, 64465-53-8, name is 4-Fluoro-3-methoxyaniline, 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.

4-Fluoro-3-methoxyaniline (Apollo-Chem, 0.0085g) was added to intermediate 30 (0. 021 G) in ethanol (3ML), pyridine hydrochloride 0.012g) was added, and the mixture was heated under reflux for 5h. The solvent was evaporated to give a brown gum (0.033g), which was purified by mass directed preparative HPLC (Method A); 2N hydrochloric acid (1ML) was added to the product fractions, and the solvents evaporated to give the title compound (0.0067g). LC/MS Rt 1. 91min m/z 504 [MH+]

The synthetic route of 64465-53-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; WO2005/30212; (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. 19056-40-7, name is 4-Bromo-3-methoxyaniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Quality Control of 4-Bromo-3-methoxyaniline

Intermediate Example Int26.013-(4-bromo-3-methoxyphenyl)-1 ,3-oxazolidin-2-oneTo a stirred solution of 4-Bromo-3-methoxy-aniline (10.0 g) in acetonitrile (176 mL) was added Hiinig Base (25 mL) and 2-chloroethyl chloroformate (10.6 g). The mixture was stirred at room temperature for 0.5 h . The solvent was removed in vaccuum. The residue was dissolved in tetrahydrofurane (250 mL), and potassium tert.-butoxide (16.2 g) was added. The mixture was stirred at room temperature for 2 h. The solvent was removed in vaccuum. The residue was dissolved in ethyl acetate and the mixture was washed with water and with saturated sodium chloride solution, dried (sodium sulfate) and the solvent was removed in vacuum. Silica gel chromatography gave a compound that was crystallized from ethanol. Yield: 7.7 g of the title compound. The mother liquor was concentrated in vaccuum and aminophase-silica-gel chromatography gave a solid that was recrystallized from ethanol to give further 2.3 g of the title compound.1H-NMR (300MHz, CHLOROFORM-d): delta [ppm]= 4.00 – 4.10 (m, 2H), 4.45 – 4.55 (m, 2H), 6.66 (dd, 1 H), 7.49 (d, 1 H), 7.63 (d, 1 H).

The synthetic route of 19056-40-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; SCHULZE, Volker; KOSEMUND, Dirk; SCHIROK, Hartmut; BADER, Benjamin; LIENAU, Philip; WENGNER, Antje Margret; BRIEM, Hans; HOLTON, Simon; SIEMEISTER, Gerhard; PRECHTL, Stefan; KOPPITZ, Marcus; STOeCKIGT, Detlef; PRIEN, Olaf; WO2011/157688; (2011); A1;,
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Related Products of 450-91-9, A common heterocyclic compound, 450-91-9, name is 4-Fluoro-2-methoxyaniline, molecular formula is C7H8FNO, 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.

iii: Intermediate 3 (1.0 eq) and cesium carbonate (2.0 eq) and corresponding phenylamine (1.2 eq) were added into a dry reaction flask. Dry DMF was used as reaction solvent, N2 was used to remove water vapor and oxygen. Then catalyst and ligand Pd(AcO)2 (0.1 eq) and Xantphos (0.1 eq) were added. The reaction mixture was transferred to a 60 C oil bath, 6~7 hours. After the reaction completed, the mixture was filtered and evaporated. Intermediate 4 was gained. The yield was 50%.

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; Rong, Juan; Feng, Zhan-Zhan; Shi, Yao-Jie; Ren, Jing; Xu, Ying; Wang, Ning-Yu; Xue, Qiang; Liu, Kun-Lin; Zhou, Shu-Yan; Wei, Wei; Yu, Luo-Ting; Bioorganic and Medicinal Chemistry Letters; vol. 29; 19; (2019);,
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Reference of 22483-09-6, 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. 22483-09-6, name is 2,2-Dimethoxyethanamine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a solution of isobenzofuran-i, 3-dione (80.Og, 0.540 mol) in toluene (1000 mL) added2, 2-dimethoxyethanamine (85.10 g, 0.811 mol), followed by N,N-diisopropylethylamine(0.187 mL, 1.080 mol) at room temperature. The reaction mixture was stirred at 120 C with dean stark apparatus for 16 h. After completion of the reaction, the reaction mixture was evaporated under reduced pressure. The residue obtained was diluted with in dichloromethane, filtered through pad of celite and dried over sodium sulfate and concentrated. The crude obtained was washed with petroleum ether to give the titled compound (100 g, 79%) as an off white solid. LCMS: m/z no ionization; ?H NMR (300 MHz, Chloroform-d) 7.89 – 7.81 (m, 2H), 7.76 – 7.68 (m, 2H), 4.77 (td, J = 5.8, 0.8 Hz, 1H), 3.82 (dd, J= 5.8, 0.8 Hz, 2H), 3.38 (d, J= 0.9 Hz, 6H).

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, 2,2-Dimethoxyethanamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; AURIGENE DISCOVERY TECHNOLOGIES LIMITED; CHIKKANNA, Dinesh; KHAIRNAR, Vinayak; PANIGRAHI, Sunil Kumar; WO2014/111871; (2014); 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. 1978-39-8, name is 5-Fluoro-2-methoxyaniline, A new synthetic method of this compound is introduced below., name: 5-Fluoro-2-methoxyaniline

To a THF (20 mL) solution of 5-fluoro-2-methoxyaniline (1.76 g), a THF (30 mL) solution of pyridinium bromide perbromide (4.36 g) was added dropwise under ice-cooling, and the reaction solution was agitated for 30 minutes at room temperature. The solid which deposited from the reaction mixture was separated by filtering and the solid was washed by THF. After the obtained solid was dissolved with water and ethyl acetate, the aqueous layer was neutralized with a saturated sodium bicarbonate water, and the organic layer was partitioned. After the obtained organic layer was washed with a saturated saline solution, it was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography (elution solvent:hexane-ethyl acetate system), and 1.83 mg of the title compound was obtained. 1H-NMR (CDCl3) delta (ppm): 3.82 (s, 3H), 3.91 (brs, 2H), 6.50 (d, J=9.6 Hz, 1H), 6.84 (d, J=6.0 Hz, 1H).

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; Eisai Co., Ltd.; US2006/4013; (2006); A1;,
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Reference of 588-63-6,Some common heterocyclic compound, 588-63-6, name is (3-Bromopropoxy)benzene, molecular formula is C9H11BrO, 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: NaN3 (0.42 g, 6.5 mmol) was added to a stirred solution of 1-bromo-4-(3-bromopropoxy)benzene (1.47 g, 5 mmol) in DMSO (25 mL). The mixture was stirred for 12 h at room temperature, diluted with H2O (50 mL), and extracted by EtOAc (50 mL .x. 3). The organic layer was separated, dried with Na2SO4, and concentrated under reduced pressure. The residue was white solid and reacted to the next step without further purification. The synthetic method for the compound 5b was similar to the synthesis of compound 5a.

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

Reference:
Article; Wang, Shengzheng; Jin, Gang; Wang, Wenya; Zhu, Lingjian; Zhang, Yongqiang; Dong, Guoqiang; Liu, Yang; Zhuang, Chunlin; Miao, Zhenyuan; Yao, Jianzhong; Zhang, Wannian; Sheng, Chunquan; European Journal of Medicinal Chemistry; vol. 53; (2012); p. 292 – 299;,
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Related Products of 321-28-8,Some common heterocyclic compound, 321-28-8, name is 1-Fluoro-2-methoxybenzene, molecular formula is C7H7FO, 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.

Add 3-fluoroanisole (85.0g, 0.67mol), tetrahydrofuran (3540mL), tetramethylethylenediamine (78.3g, 0.67mol) at room temperature,Replace with nitrogen three times, turn on stirring,Cooled to -50 ~ -78 , was added dropwise a solution of sec-butyllithium (870mL, 1.3M), after the addition was complete stirring incubated 2 to 3 hours, a solution of N, N- dimethylformamide (67.5g, 0.92 mol), heat and stir for 1 hour,After the reaction was completed, a 13% acetic acid aqueous solution (1464 g) was added dropwise at -50 to -78 C, and the layers were separated. The aqueous phase was extracted with ethyl acetate (350 mL * 3), and the organic phases were combined.After washing with water (500mL), 1N hydrochloric acid,The organic phase is concentrated to no droplets,A pale yellow mixture was obtained and crystallized from methyl tert-butyl ether (150 mL) to give a white solid,Drying gave compound II (57.7 g, 57.3%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Fluoro-2-methoxybenzene, its application will become more common.

Reference:
Patent; Shanghai Bopunuo Science And Technology Co., Ltd.; Guo Peng; Ji Changyou; Wang Jun; Zhang Dong; Liang Shoushan; Zhu Wenfeng; (15 pag.)CN110759870; (2020); A;,
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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. 37466-89-0, name is 3-Methoxybenzene-1,2-diamine, This compound has unique chemical properties. The synthetic route is as follows., name: 3-Methoxybenzene-1,2-diamine

4-Methoxy-2-trifluoromethyl-1H-benzimidazole The compound of Example 103 (6.49 g) was dissolved in trifluoroacetic acid (75.0 mL) under ice cooling, followed by stirring for 5 hours to heating under reflux. After evaporating the solvent, the residue was dissolved in ethyl acetate and poured into a saturated aqueous sodium hydrogen carbonate solution. The organic layer was collected by separation, washed with saturated brine, and then dried over anhydrous sodium sulfate. After evaporating the solvent, the resulting solid was suspended in hexane and collected by filtration to obtain the desired product (8.69 g) as a yellowish brown powder. 1H NMR (CD3OD, 400 MHz): delta 4.01 (3H, s), 6.89 (1H, d, J=8.0 Hz), 7.24 (1H, d, J=8.0 Hz), 7.32 (1H, dd, J=8.0, 8.0 Hz).

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 37466-89-0.

Reference:
Patent; Kyorin Pharmaceutical Co., Ltd.; EP2168959; (2010); A1;,
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