Tag: M.W=100-200

Reference of 446-61-7, A common heterocyclic compound, 446-61-7, name is 2-Fluoro-6-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.

(1) 2-Fluoro-6-methoxyaniline (7.80 g) and 17.23 g of di-(2-bromoethyl)amine hydrobromide were dissolved in 5 ml of water and, by heating at about 110 C. on a bath, 10 ml of 30% potassium hydroxide solution was added thereto (each about 3.5 ml once an hour). Heating was further continued (7 hours in total). After cooled, the reaction solution was made alkaline with aqueous solution of sodium hydroxide to salt out and extracted with chloroform twice. The extract was washed with saturated sodium chloride solution, dried over sodium sulfate, the solvent was evaporated therefrom, and the residue was purified by a column chromatography to give 8.95 g of oily 1-(2-fluoro-6-methoxyphenyl)piperazine in 34.94 g yield or 94%.

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; Nippon Shinyaku Co., Ltd.; US4843070; (1989); A;,
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Adding a certain compound to certain chemical reactions, such as: 113421-98-0, name is 4-Fluoro-3-(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 113421-98-0, name: 4-Fluoro-3-(trifluoromethoxy)aniline

General procedure: Ethyl 4-bromo-1H-indole-2-carboxylate (1 eq), Pd2(dba)3 (0.1 eq), X-phos(0.2 eq), Cs2CO3 (3 eq) and aryl amine (3 eq) was added to a microwave tube,dissolved in 1,4-dioxane, and filled with argon gas. The microwave reaction wascarried out at 100 C for 0.5-1.5 h, and the starting material disappeared. The mixturewas cooled to room temperature and concentrated. Ethyl acetate was added todissolve the residue, and the mixture was washed with saturated brine and water, driedover anhydrous Na2SO4, and concentrated in vacuo. The crude product was purifiedby column chromatography to afford the target compound. Compounds 8m-8o, 8s,8a-3 ~ 8a-5, 8a-13, 8a-15 ~ 8a-17, 8o-1 ~ 8o-24 were prepared with method 3.

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; Cui, Guonan; Lai, Fangfang; Wang, Xiaoyu; Chen, Xiaoguang; Xu, Bailing; European Journal of Medicinal Chemistry; vol. 188; (2020);,
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Reference of 321-28-8, A common heterocyclic compound, 321-28-8, name is 1-Fluoro-2-methoxybenzene, molecular formula is C7H7FO, 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.

(A) 3-fluoro-4-methoxybenzaldehyde. To a solution of o-fluoroanisole, 101 g. (0.80 mole) in 500 ml. dry methylene chloride is added dropwise over 30 minutes a solution of titanium tetrachloride, 182 g. (0.96 mole, 1.2 equiv.) and alpha,alpha-dichloromethylmethyl ether, 110 g. (0.96 mole) in an equal volume of methylene chloride. The temperature is maintained at 10-20 C. with an ice-bath. The mixture is stirred at room temperature for 1 hour longer and then poured over crushed ice-water with stirring. Ether (1 l.) is added,and the mixture stirred under nitrogen until solution occurs. The organic layer is extracted with water (3X), sodium bicarbonate solution (3X) and dried (MgSO4). The solvent is evaporated off at 30 to give crude product as an oil. The oil is vacuum distilled through a jacketed Vigreux column when it gives 3-fluoro-4-methoxybenzaldehyde, B.P. 120-121 C, at 10 mm. Hg; Rf0.6 on a silica-gel G plate with methylene chloride.

The synthetic route of 321-28-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FGN, INC.; THE UNIVERSITY OF ARIZONA; EP485172; (1992); A2;,
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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. 6781-17-5, name is 2-(2-Ethoxyphenoxy)ethanamine, A new synthetic method of this compound is introduced below., Recommanded Product: 2-(2-Ethoxyphenoxy)ethanamine

a) 2-Methoxy-5-(2-oxopropyl)-benzene sulfonamide (37.3 gm, 153.3 mmol), 2-(2-ethoxyphenoxy)-1-ethanamine (29.8 gm, 164.4 mmol) and methanol (250 mL) were taken into a one liter stainless steel flask and mixed well. Catalyst Raney nickel (8 gm) was added to the flask and the mixture hydrogenated at 50 C. at hydrogen pressure of 40 psi for 30 hrs. The catalyst was removed by filtration and solvent from the filtrate was distilled off completely at 50 C. under vacuum. The dark brown crude obtained was treated with methanolic hydrochloric acid (175 mL) at 0-5 C. under stirring. Tamsulosin hydrochloride formed as a solid was filtered, washed with ethyl acetate (200 mL), suspended in methanol (120 mL) and the methanol slurry filtered to obtain off white solid material. It was dried for 3 hrs at 80 C. to give racemic tamsulosin hydrochloride. Melting point 255-257 C., chemical purity of 98.8 area % (by HPLC) and R,S ratio of 51.45:48.55 (by chiral HPLC).

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; DIVI’S LABORATORIES LIMITED; US2006/79714; (2006); 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. 707-07-3, name is (Trimethoxymethyl)benzene, A new synthetic method of this compound is introduced below., HPLC of Formula: C10H14O3

To a suspension of known p-tolyl 2-O-benzyl-1-thio-beta-L-fucopyranoside 2 (3.5 g, 9.7 mmol) in dry CH3CN (20 mL), trimethyl orthobenzoate (2.2 mL, 12.6 mmol) was added followed by the addition of CSA (25 mg). The reaction mixture was allowed to stir at room temperature for 2 h until the TLC (n-hexane-EtOAc; 2:1) showed complete conversion of the starting material. Then the solvents were evaporated in vacuo and the crude mixture was diluted with CH2Cl2 (25 mL) and washed with 1 M HCl (2 25 mL). The organic layer was then collected, dried (Na2SO4) and filtered. The solvents were then evaporated and the crude mixture was purified by flash chromatography to give the pure product 3 (3.9 g, 87%) asa colourless syrup.

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; Das, Rituparna; Mahanti, Mukul; Mukhopadhyay, Balaram; Carbohydrate Research; vol. 399; (2014); p. 15 – 20;,
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Some common heterocyclic compound, 1535-73-5, name is 3-Trifluoromethoxyaniline, molecular formula is C7H6F3NO, 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: 3-Trifluoromethoxyaniline

To a solution of 1.5 mmol N-(3-dimethylaminopropyl)-N’-ethylcarbodiimide hydrochloride (EDC*HCl) and 1 mmol 4-dimethylaminopyridine (DMAP) in 2 ml dichloromethane were added 1.5 mmol 3-substituted aniline and the solution stirred at ambient temperature for 5 min. This solution was then added to 1 mmol of substituted benzoic or nicotinic acid and the solution stirred at ambient temperature for 18 hours. The reaction mixture was filtered through a cartridge filled with 5g SCX/silica gel 2:3, pre-washed with 10 ml methanol and 20 ml dichloromethane, and the reaction product eluted with 50 ml dichloromethane. Evaporation provided the benzanilides or nicotinanilides typically as solids.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1535-73-5, its application will become more common.

Reference:
Article; Stalder, Henri; Hoener, Marius C.; Norcross, Roger D.; Bioorganic and Medicinal Chemistry Letters; vol. 21; 4; (2011); p. 1227 – 1231;,
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Application of 41789-95-1,Some common heterocyclic compound, 41789-95-1, name is 1-(3-Methoxyphenyl)-N-methylmethanamine, molecular formula is C9H13NO, 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 mixture of Pd(OAc)2 (6.7 mg, 0.030 mmol, 10 mmol%), Cu(OAc)2 (54.45 mg, 0.30 mmol, 1 equiv.), 1a (32.1 mg, 0.30 mmol, 1equiv.), CsF (136.7 mg, 0.90 mmol, 3 equiv.) was dissolved in a solvent of acetonitrile (3 mL) followed by addition of 2a (179 mg,0.60 mmol, 2 equiv.). The reaction mixture was stirred at 120 C for 24 h and progress of the reaction was monitored continuously byTLC with ethyl acetate: hexane eluent system. Upon completion of reaction the mixture was cooled to room temperature, poured into brine, and extracted with EtOAc. The combined extracts were dried over MgSO4 and filtered through pad of Celite eluting with ethylacetate. The filtrate was concentrated under reduced pressure and was purified by column chromatography (EtOAc/hexane) on silicagel to afford the 5,6-dihydrophenanthridine 3a. Compound 1i was synthesized in accordance with reported literature [25]. Characterization data of compounds 3a, 3c, and 3e were found exactly similar as reported in the literature (References of above compounds are mentioned in Supplementary data).

The synthetic route of 41789-95-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Asamdi, Manjoorahmed; Chauhan, Prakashsingh M.; Patel, Janki J.; Chikhalia, Kishor H.; Tetrahedron; vol. 75; 25; (2019); p. 3485 – 3494;,
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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. 592-55-2, name is 1-Bromo-2-ethoxyethane, A new synthetic method of this compound is introduced below., Safety of 1-Bromo-2-ethoxyethane

Take 30.0g of compound A and 19.6g of K2CO3,162mL of N, N-dimethylformamide in a reaction flask, stir,25.3g of 2-bromoethylethyl ether was added, the temperature was raised to 60 C, and the reaction was performed for 2h. The reaction solution was poured into 270 mL of water, stirred for 0.5 h, and the solid was precipitated and filtered. The obtained filter cake was slurried with 540 mL of water for 1 h, filtered, and the filter cake was slurried with 240 mL of n-heptane for 1 h. The product was filtered and dried at 60 C to obtain product B1 43.5 g, yield 93%, HPLC purity: 99.0%.

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; Sichuan Kelun Pharmaceutical Institute Co., Ltd.; Zha Zhongyun; Pan Junzhu; Cao Zhi; Liu Zhiqiang; Feng Liejiang; Wang Lichun; Wang Jingyi; (9 pag.)CN110396063; (2019); A;,
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Electric Literature of 24599-58-4, 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. 24599-58-4 name is 2,5-Dimethoxytoluene, 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.

2,5-dimethoxy toluene 1 (9.0 g, 59.21 mmol) in diethyl ether (90 cm3) was added to a stirred solution of iodine monochloride (10.17 g, 62.65 mmol) in chloroform (30 cm) over 30 minutes. The mixture was stirred overnight before 10% sodium thiosulfate (150 cm3) was added. The organics were extracted with 2×75 cm3) of diethyl ether. The organics were combined, washed with saturated aqueous NaHCO3 (150 cm3), brine (100 cm3), dried (MgSO4) and dried under vacuum. The resultant solid was recrystallised from methanol to yield the title compound as red solid 2 (11.3 g, 69%). [0085] Rf 0.52 (SiO2, Hex 3:1 EtOAc). [0086] Mp 80-82 C. (Literature 81-82 C. (Reed et al., JACS, 120(38): 9729-9734, 1998) [0087] 1H NMR (400 MHz, CDCl3) 2.12 (3H, s, CH), 3.72 (3H, s, OCH), 3.75 (3H, s, OCH), 6.60 (1H, s, ArH), 7.10 (1H, s, ArH) ppm.

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

Reference:
Patent; Onco-NX Limited; Mcgown, Alan; Hadfield, John; Butler, John; US2015/210639; (2015); A1;,
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Adding a certain compound to certain chemical reactions, such as: 592-55-2, name is 1-Bromo-2-ethoxyethane, 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 592-55-2, category: ethers-buliding-blocks

General procedure: To a solution of 2 (0.28 g, 1.132 mmol) in DMF (5 mL) was added potassium carbonate (0.438 g, 3.17 mmol) and 1-bromobutane (0.340 ml, 3.17 mmol). The mixture was heated at 90 C for 4 h, then cooled to rt and aq. HCl (0.2 M, 50 mL) was added. The mixture was extracted with CH2Cl2 (3 x 5 mL) and the combined organic layers were dried over MgSO4. Solvents were removed under reduced pressure and the residue was purified by silica gel chromatography using hexane:EtOAc (2:1) as eluent to give 3a (0.33 g, 91% yield).

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; Slavik, Roger; Herde, Adrienne Mueller; Bieri, Daniel; Weber, Markus; Schibli, Roger; Kraemer, Stefanie D.; Ametamey, Simon M.; Mu, Linjing; European Journal of Medicinal Chemistry; vol. 92; (2015); p. 554 – 564;,
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