Month: July 2021

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

Related Products of 3401-47-6,Some common heterocyclic compound, 3401-47-6, name is 1-Bromo-2-methoxynaphthalene, molecular formula is C11H9BrO, 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: The mixture of anisole(1c, 0.216 mg, 2 mmol) and acetyl chloride (2a, 0.157 mg, 2 mmol) was treated with CTAB/CTAC, (0.001 mol), in dichloroethane and the resulting reaction mixture was heated in a controlled microwave synthesizer (BiotageInitiator+SP Wave model (0.200W at 2.45 GHz, capped at 60W duringsteady state) for 5 min (attains temperature 100 C and 2 bar pressure). The final product (3o) was isolated by absorbing the reaction mixture into silica geland purifying it by column chromatography using ethyl acetate-petroleumether as the eluent.

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

Reference:
Article; Rajendar Reddy; Rajanna; Uppalaiah; Tetrahedron Letters; vol. 54; 26; (2013); p. 3431 – 3436;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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

Synthetic Route of 2674-34-2, The chemical industry reduces the impact on the environment during synthesis 2674-34-2, name is 1,4-Dibromo-2,5-dimethoxybenzene, I believe this compound will play a more active role in future production and life.

Example 6: Preparation of 4-bromo-2,2′,5,5′- tetramethoxybiphenyl (6); [00111] In an argon flushed two-neck round-bottom flask, a mixture of 1.02 g (5.0 mmol) of sodium 2,5-dimethoxyphenylboronate, 3.0 g (10 mmol) of 2,5-dibromo-1 ,4-dimethoxybenzene, 60 mg (1 mol%) of tetrakis(triphenylphosphine)palladium, 20 ml of 2 M sodium carbonate and 50 ml of THF was added and heated at reflux for two hours. After cooling, the reaction mixture was extracted with ethyl acetate and the organic phase was EPO washed with brine and dried over magnesium sulfate. After the solvent was removed on a rotary evaporator, the residue was purified by column chromatography eluted with hexane/CH2CI2 (4:1) to give 1.0 g 4-bromo- 2,25,5′-tetramethoxybiphenyl (yield 63%). 1HNMR (CDCI3) 57.187 (s, 1 H), 6.836-6.951 (m, 4 H), 3.869 (s, 3 H), 3,814 (s, 3 H), 3.757 (s, 6 H). 13CNMR (CDCI3) 5153.788, 151.830, 151.596, 150.278, 128.277, 127.995, 117.615, 117.293, 115.897, 113.924, 112.933, 110.019, 57.291 , 57.042, 56.897, 56.171.

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, 1,4-Dibromo-2,5-dimethoxybenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; AGENCY FOR SCIENCE, TECHNOLOGY AND RESEARCH; NATIONAL UNIVERSITY OF SINGAPORE; WO2006/93467; (2006); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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

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

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

Reference of 332-48-9,Some common heterocyclic compound, 332-48-9, name is 1-(2-Bromoethoxy)-4-fluorobenzene, molecular formula is C8H8BrFO, 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.

Example 90 4-[2-(4-fluorophenoxy)ethoxy]-1-{2-[isopropyl(methyl)amino]-1H-benzimidazol-6-yl}pyridin-2(1H)-one Potassium carbonate (60 mg) and 1-(2-bromoethoxy)-4-fluorobenzene (60 mg) were added to a DMF solution (5 mL) of the compound (60 mg) obtained in Production Example 41-2, and stirred overnight at room temperature. Ethyl acetate was added to the reaction liquid, washed successively with water and saturated saline water, and dried with anhydrous magnesium sulfate. The solvent was evaporated off under reduced pressure, and the obtained residue was purified by silica gel column chromatography (NH silica gel, chloroform) to obtain the entitled compound (14.6 mg). 1H-NMR (400 MHz, DMSO-d6, delta ppm): 1.17 (6H, d, J=6.7 Hz), 2.90 (3H, s), 4.29-4.35 (4H, m), 4.49 (1H, septet, J=6.7 Hz), 5.92 (1H, d, J=2.7 Hz), 6.03 (1H, dd, J=7.6 Hz, 2.7 Hz), 6.79 (1H, brs), 6.99-7.05 (3H, m), 7.11-7.19 (3H, m), 7.52 (1H, d, J=7.4 Hz), 11.32 (1H, brs). ESI-MS Found: m/z 437 [M+H]+

The synthetic route of 332-48-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sakuraba, Shunji; Kameda, Minoru; Kishino, Hiroyuki; Haga, Yuji; Otake, Norikazu; Moriya, Minoru; US2009/264426; (2009); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

These common heterocyclic compound, 1462-37-9, name is ((2-Bromoethoxy)methyl)benzene, 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. Safety of ((2-Bromoethoxy)methyl)benzene

506 mg (60percent in oil, 13 mmol equivalents) of sodium hydride was added to 5.0 mL of tetrahydrofuran, and the mixture was cooled to about 0°C in an ice bath. 3.2 mL (20.7 mmol equivalents) of diethyl malonate was added thereto (solution A). 2.3 g (10.7 mmol equivalents) of 2-benzyloxy-1-bromoethane was dissolved in 3.0 mL of tetrahydrofuran, this was added dropwise to solution A over 10 minutes, and the mixture was refluxed while heating overnight. After completion of the reaction, a 0.5 mol/L aqueous solution of hydrochloric acid was added dropwise to the reaction liquid, and the mixture was extracted three times with diethyl ether. The combined diethyl ether layers were washed with brine, then dried with anhydrous magnesium sulfate, and subsequently concentrated under vacuum, and the obtained crude product was purified by silica gel column chromatography (eluent: hexane/ethyl acetate (v/v) = 20/1) to give 2.85 g (9.67 mmol equivalents) of diethyl 2-(2-benzyloxyethyl)malonate. [0115] 1H-NMR (solvent: deuterated chloroform) of diethyl 2-(2-benzyloxyethyl)malonate: delta 7.36-7.28 (m, 5H), 4.48 (s, 2H), 4.21-4.14 (m, 4H), 3.60 (d, J = 7.3 Hz, 1H), 3.53 (t, J = 5.5 Hz, 2H), 2.22 (dt, J = 5.5, 7.3 Hz, 2H), 1.25 (t, J = 7.3 Hz, 6H)

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

Reference:
Patent; Nihon Medi-Physics Co., Ltd.; National University Corporation Hokkaido University; NAKATA, Norihito; OKUMURA, Yuki; KIRIU, Masato; NAGATA, Eriko; MATSUMOTO, Hiroki; KUGE, Yuji; ZHAO, Songji; NISHIJIMA, Ken-Ichi; EP2759538; (2014); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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