Month: December 2020

Reference of 19056-40-7,Some common heterocyclic compound, 19056-40-7, name is 4-Bromo-3-methoxyaniline, molecular formula is C7H8BrNO, 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 solution of 4-Bromo-3-methoxy-aniline (10.0 g) in acetonitrile (176 mL) was added Huenig 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 vacuum. 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 vacuum. 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 vacuum and aminophase-silica-gel chromatography gave a solid that was recrystallized from ethanol to give further 2.3 g of the title compound1H-NMR (300 MHz, CHLOROFORM-d): delta [ppm]=4.00-4.10 (m, 2H), 4.45-4.55 (m, 2H), 6.66 (dd, 1H), 7.49 (d, 1H), 7.63 (d, 1H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Bromo-3-methoxyaniline, its application will become more common.

Reference:
Patent; Schulze, Volker; Mais, Franz-Josef; US2015/148542; (2015); A1;,
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Application of 32338-02-6, These common heterocyclic compound, 32338-02-6, name is 2-Bromo-4-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.

General procedure: A round-bottomed flask was charged with 2-bromoaniline or 2-fluoro-aniline (>3 g, 1.0 equiv) and potassium O-ethyl carbonodithioate(1.5?1.7 equiv). The mixture was dissolved in DMF (10 volumes) andheated to 120?130 ¡ãC until the aniline was fully consumed (3?14 h).The reaction mixture was cooled to r.t. and filtered. The filtrate wasdiluted with H 2 O (50 volumes) and the pH was adjusted to 1?2 usingaqueous 2 M HCl. The solid precipitate was collected, washed withH 2 O and dried to yield the pure product.

Statistics shows that 2-Bromo-4-methoxyaniline is playing an increasingly important role. we look forward to future research findings about 32338-02-6.

Reference:
Article; Wimmer, Laurin; Parmentier, Michael; Riss, Bernard; Kapferer, Tobias; Ye, Chao; Li, Lei; Kim, Hongyong; Li, Jialiang; Synthesis; vol. 50; 10; (2018); p. 2027 – 2032;,
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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. 4316-51-2, name is 4-Methoxytriphenylamine, This compound has unique chemical properties. The synthetic route is as follows., Formula: C19H17NO

General procedure: Ni(cod)2 (3.4 mg, 0.025 mmol), ICy¡¤HBF4 (4.0 mg, 0.025 mmol), NaOtBu (48 mg, 0.50 mmol) and toluene (0.50 mL) were added to a 10 mL-sample vial with a Teflon-sealed screwcap in a glovebox filled with nitrogen. The resulting mixture was stirred at room temperature for 3 min. An aryl methyl ether (0.25 mmol) in toluene (0.50 mL) and AlMe3 (1.8 M in toluene solution, 0.14 mL, 0.25 mmol) were then added to the vial and the screw cap was closed. The contents of the vial were stirred at 80 C for 6 or 18 h. The reaction mixture was cooled to room temperature, and the crude mixture was then treated with EtOH. The resulting mixture was filtered through a pad of silica gel, and then analyzed by GC. The filtrate was concentrated in vacuo to give a residue, which was purified by flash column chromatography over silica gel.

According to the analysis of related databases, 4316-51-2, the application of this compound in the production field has become more and more popular.

Reference:
Article; Morioka, Toshifumi; Nishizawa, Akihiro; Nakamura, Keisuke; Tobisu, Mamoru; Chatani, Naoto; Chemistry Letters; vol. 44; 12; (2015); p. 1729 – 1731;,
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Electric Literature of 82830-49-7, These common heterocyclic compound, 82830-49-7, name is 2-Fluoro-1,4-dimethoxybenzene, 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 -78 0C solution of 1,4-dimethoxy-2-fluorobenzene (1.56 g, 10 mmol) in THF (15 mL) was added n-BuLi (5.0 mL of 2.5 M hexanes solution, 12 mmol). The mixture was stirred for 30 minutes before slow . addition of acetaldehyde (0.79 mL, 14 mmol). The reaction mixture was stirred for an additional 30 minutes before the reaction was quenched by addition of methanol and saturated aqueous NH4CI. The reaction mixture was warmed to room temperature and extracted with EtOAc. The organic extract was concentrated and purified by Biotage chromatography (40 S column, 15% acetone/heptane) to afford 1- (2-fluro-3,6-dimethoxyphenyl)ethanol (1.57 g, 79%).To an ice cooled solution of 1-(2-fluoro-3,6-dimethoxyphenyl)ethanol (1.57 g, 7.84 mmol) in acetone _C23_inL)jw.as_sloMy-^jd^d_JLQDes r_eagej3tjpj?p_aj_ed_by addition ofjLdeltaJ. Q CrO3InJ .6 mL of concentrated H2SO4 to 4.7 mL of ice cold water). The mixture was stirred for 30 minutes before the cooling bath was removed and addition of isopropanol (2 mL). The resultant green precipitate was removed by filtration through djatomaceous earth, and the diatomaceous earth was washed with ethyl acetate (“EtOAc”). The filtrate was concentrated and redissolved in EtOAc, washed with saturated aqueous NaHCO3, saturated aqueous NaCI, concentrated, and purified by Biotage chromatography (40 S column, 8% acetone/heptane) to provide the title compound as a yellow oil (1.06 g, 68%).

Statistics shows that 2-Fluoro-1,4-dimethoxybenzene is playing an increasingly important role. we look forward to future research findings about 82830-49-7.

Reference:
Patent; PFIZER PRODUCTS INC.; WO2008/65508; (2008); 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. 14804-31-0, name is 4-Bromo-1-methoxy-2-methylbenzene, A new synthetic method of this compound is introduced below., Application In Synthesis of 4-Bromo-1-methoxy-2-methylbenzene

Synthesis of VU6000181. To a suspension of Mg (936mg, 38.5mmol) and iodine (5mg) in THF (2mL) was added a part of a solution of 4-bromo-2-methylanisole (7.39g, 36.8mmol) in THF (9mL) at ambient temperature. After initiating the reaction, a solution of 4-bromo-2-methylanisole diluted with THF (19mL) was added dropwise to the mixture diluted with THF (10mL). After the mixture was allowed to stir at ambient temperature for 2h, resulting Grignard reagent was added to a suspension of phthalic anhydride 8 (5.18g, 35.0mmol) in THF (50mL) at -65C. The mixture was allowed to stir for 2.5h as temperature was elevated up to 0C. The reaction was quenched with cold water and the aqueous layer was separated. The organic layer was extracted with 1 N NaOH aqueous solution and the combined aqueous layer was acidified with 2N HCl solution. The aqueous layer was extracted with ethyl acetate twice and the combined organic layer was washed with brine and dried over magnesium sulfate. The filtrate was evaporated under reduced pressure. The residue was triturated with ethyl acetate/diethyl ether to give compound 3 as a white powder (5.61g, 59% yield). To a solution of compound 3 (1.0g, 3.7mmol) and para-toluene sulfonic acid monohydrate (10mg) in PhMe (8mL) and 1,4-dioxane (8mL) was added ethylenediamine (0.50mL, 7.4mmol) at ambient temperature. The resulting white suspension was subjected to microwave irradiation at 150C for 30min. After removing insoluble material, the filtrate was concentrated. The procedure above was repeated twice more and the three portions were combined and purified on silica gel using hexane/ethyl acetate as an eluent. Crude product was triturated with diethyl ether to give compound 4 as an off-white powder (1.69g, 52% yield). To a solution of compound 4 (500mg, 1.70mmol) in dichloromethane (8mL) was added DIPEA (0.74mL, 4.25mmol) and 3,4,5-trifluorobenzoyl chloride (0.33mL, 2.55mmol) at ambient temperature. After stirring for 30min, cold NaHCO3-aq was added to the mixture which was extracted with dichloromethane twice. The combined organic layer was concentrated under reduced pressure and the residue was purified on silica gel using hexane/ethyl acetate as an eluent. Crude product was triturated with diethyl ether/hexane to yield compound 7B-6 as a white powder (491mg, 64% yield). Chiral resolution by SFC (Agilent 1260, Column: LUX cellulose-3, Column dimensions: 10¡Á250mm, Co-solvent: MeOH, Modifier: none, Gradient Profile: 10% isocratic, Flow Rate: 15mL/min, Backpressure: 100, Column temperature: 40 degrees, retention time: 2.814min, dated on July 30th) followed by concentration afforded (S)-7B-6 (VU6000181) as a white powder.

The synthetic route of 14804-31-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Kurata, Haruto; Gentry, Patrick R.; Kokubo, Masaya; Cho, Hyekyung P.; Bridges, Thomas M.; Niswender, Colleen M.; Byers, Frank W.; Wood, Michael R.; Daniels, J. Scott; Conn, P. Jeffrey; Lindsley, Craig W.; Bioorganic and Medicinal Chemistry Letters; vol. 25; 3; (2015); p. 690 – 694;,
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Reference of 22094-18-4, These common heterocyclic compound, 22094-18-4, name is 1,3-Dibromo-2,2-dimethoxypropane, 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 -(3 ,4-dichlorophenyl)-3 ,3 -dimethoxycyclobutanecarboxamide[1 182] 3,4-Dichlorophenylacetonitrile (9.30 g, 50 mmol), l,3-dibromo-2,2- dimethoxypropane (13.10 g, 50 mmol), and sodium tert-butoxide (10.57 g, 110 mmol) in DMSO (100 mL) and water (5 mL) were heated at 125C for 1 hour, then stirred at ambient temperature for 20 hours. The reaction mixture was diluted with water and extracted three times with diethyl ether. The organic layers were combined, washed with brine, dried with MgS04, filtered, and concentrated. The crude product was triturated with 1 : 1 diethyl ether / hexanes, and the solid collected by filtration was Example 82A (7.16 g, 23.54 mmol, 47.1% yield). XH NMR (300 MHz, DMSO-d6) ? 7.61 – 7.55 (m, 2H), 7.37 (s, 1H), 7.29 (dd, J= 8.4, 2.2 Hz, 1H), 6.95 (s, 1H), 3.05 (s, 3H), 2.99 (s, 3H), 2.97 – 2.89 (m, 2H), 2.46 – 2.37 (m, 2H).

The synthetic route of 22094-18-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ABBVIE INC.; BAYBURT, Erol K.; CLAPHAM, Bruce; COX, Phil B.; DAANEN, Jerome F.; GOMTSYAN, Arthur; KORT, Michael E.; KYM, Philip R.; VOIGHT, Eric A.; SCHMIDT, Robert G.; DART, Michael J.; GFESSER, Gregory; WO2013/62964; (2013); A2;,
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Adding a certain compound to certain chemical reactions, such as: 4393-09-3, name is (2,3-Dimethoxyphenyl)methanamine, 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 4393-09-3, HPLC of Formula: C9H13NO2

EXAMPLE 30 2-[Trans-(4-aminocyclohexyl)amino]-6-[(2.3-dimethoxybenzyl)amino]-9-(2-propyl)purine dihydrochloride Scheme A, step b: 2-Chloro-6-[(2,3-dimethoxybenzyl)amino]-9-(2-propyl)purine 2-Chloro-6-[(2,3-dimethoxybenzyl)amino]-9-(2-propyl)purine is prepared from 2,6-dichloro-9-(2-propyl)purine (see Example 19 for preparation), 2,3-dimethoxybenzylamine, and triethylamine essentially as described above in Example 1, Scheme A, step b. Scheme A, step c: 2-[Trans-(4-aminocyclohexyl)amino]-6-[(2,3-dimethoxybenzyl)amino]-9-(2-propyl)purine dihydrochloride 2-[Trans-(4-aminocyclohexyl)amino]-6-[(2,3-dimethoxybenzyl)amino]-9-(2-propyl)purine dihydrochloride is prepared from 2-chloro-6-[(2,3-dimethoxybenzyl)amino]-9-(2-propyl)purine essentially as described in Example 1, Scheme A, step c.

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; Aventis Pharmaceuticals Inc.; US6479487; (2002); B1;,
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These common heterocyclic compound, 2930-05-4, name is 2-((Benzyloxy)methyl)oxirane, 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. Computed Properties of C10H12O2

General procedure: Five-membered cyclic carbonates were synthesized from carbondioxide and the corresponding substrates (10 mmol) in the appropriatemolar ratios by using 5.83 mg (0.01 mmol) of Co(II)-1-mesityl-1,2,3-1H-triazole-4-carboxylate (Co-TCA) as a catalyst in combination with aco-catalyst (tetrabutylammonium bromide (TBAB), tetrabutylammoniumchloride (TBAC), DMAP (4-(dimethylamino)pyridine)and TBAI (tetrabutylammonium iodide)) which were transferred intothe reactor. The reactor was charged with the reaction mixture (catalyst,cocatalyst, and substrate) and was purged with CO2 for 3 times atroom temperature. The reactor was heated to 120 C in the oil bath andthen pressurized to 1 bar of CO2. After completion, the reactor wasslowly cooled to room temperature. The catalyst (Co-TCA) was directlyused for the consecutive reaction cycles to identify the further usabilityand stability of the catalyst. In addition, column chromatography wasexecuted to isolate the product from the reaction mixture using petroleumether/ethyl acetate mixture (3:1) as eluent. After performing thecolumn chromatography, the solvent was evaporated to obtain thetarget-isolated product and the yield. Then, the sample was analyzed by1H, 13C-NMR and FTIR (Figure S3, S5, S7, S9, S11, S13, S15, S17, S19,S21, S23, S25, S27) analysis.

The synthetic route of 2-((Benzyloxy)methyl)oxirane has been constantly updated, and we look forward to future research findings.

Reference:
Article; Suleman, Suleman; Younus, Hussein A.; Ahmad, Nazir; Khattak, Zafar A.K.; Ullah, Habib; Park, Jihae; Han, Taejun; Yu, Baoyi; Verpoort, Francis; Applied Catalysis A: General; vol. 591; (2020);,
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Electric Literature of 24599-58-4, 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. 24599-58-4, name is 2,5-Dimethoxytoluene, This compound has unique chemical properties. The synthetic route is as follows.

Preparation 1; 2,5-Dimethoxy-4-methylbenzoic acid (Compound XII); a) 2,5-Dimethoxy-4-methylbenzaldehyde; 280 ml of phosphorus oxide trichloride are admixed with 212 ml of N-methylformanilide. After 4 hours at room temperature, 110 g of 2,5-dimethoxytoluene are added and the reaction mixture is brought to 70 C. for 2 hours. The reaction mixture is poured dropwise onto ice. The precipitate obtained is filtered, taken up in dichloromethane and decanted. The organic phase is dried over anhydrous sodium sulphate and the solvents are evaporated under reduced pressure. This gives 116 g of yellow crystals; m.p.=83 C.

The chemical industry reduces the impact on the environment during synthesis 2,5-Dimethoxytoluene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Bignon, Eric; Csikos, Eva; Frehel, Daniel; Gonczi, Csaba; Heja, Gergley; Morvai, Miklos; Podanyi, Benjamin; Schlovicsko Varkonyine, Erika; US2004/19091; (2004); A1;,
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Reference of 6298-96-0, 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. 6298-96-0, name is 1-(4-Methoxyphenyl)ethylamine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Examrle 22-[(S)-1 -(4-methoxyphenyl)-ethylamino]-cyclopent-1 -ene-carboxylic acid methylester(compound of formula (IV) wherein Ar = 4-methoxyphenyl, R1 = CO2Me) 10.37 g (70.0 mmol) of 2-oxo-cyclopentane-carboxylic acid methylester (purity 96%, Aldrich) were dissolved in 30 ml of toluene and 10.00 g (65.5 mmol) of (S)-1 -(4- methoxyphenyl)-ethylamine (purity >99%, BASE) were stirred under argon for 12 hours at ca. 25C. Water was completely removed by evaporation of toluene (3 x 50 ml) andthe product was dried at 80C/i mbar to give 18.1 g (100%) of the title product asyellow oil.LC-MS: MH 276;1H NMR: 1 .40 (d, 3H, Me), 1 .65 (m, 2H, H-4), 2.25, 2.37, 2.62 (3m, 4H, H-3, H-5), 3.57(5, 3H, CO2Me), 3.73 (5, 3H, OMe), 4.60 (m, 1 H, CHN), 6,90, 7.20 (2m, 4H, Ar-H), 7.70(d, 1H, NH).

The synthetic route of 1-(4-Methoxyphenyl)ethylamine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SANOFI-AVENTIS DEUTSCHLAND GMBH; KRETZSCHMAR, Gerhard; OEHME, Jan; ROSSEN, Kai; WO2015/189108; (2015); A1;,
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