Month: June 2021

Electric Literature of 120-61-6, A common heterocyclic compound, 120-61-6, name is Dimethyl terephthalate, molecular formula is C10H10O4, 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 synthetic procedure of the probe is illustrated in the Scheme 1. Methanolic solution (10 ml) of terephthalic acid in the presence of con.H2SO4 (10:1) was refluxed for 6 h. The reaction mixture was cooled to room temperature and evaporated under pressure, provided a dirty white colour solid. The solid formed was extracted with DCM for at least 3 times in order to completely remove the impurities and dried using MgSO4. The solution was then filtered and evaporated to give milky white solid (1 mmol). Subsequently, it was re-dissolved in methanol followed by slow addition of hydrazine monohydrate (2 mmol) and allowed to reflux for 3 h. The obtained white solid (bis-hydrazine derivative) was filtered,washed with water and dried under vacuum. A hot-aqueous solution of bis-hydrazine derivative (1 mmol) was mixed dropwise with pyridine-2-aldehyde (2 mmol) and again refluxed at 80 C for2 h. The probe (BPTH) was obtained as a white puffy solid which was filtered and dried in vacuum.

The synthetic route of 120-61-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Senthil Murugan, Arumugam; Abel Noelson, Enose Rajan; Annaraj, Jamespandi; Inorganica Chimica Acta; vol. 450; (2016); p. 131 – 139;,
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Reference of 55666-43-8, 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. 55666-43-8 name is tert-Butyl 3-bromopropanoate, 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.

The methodologies described in Example 36 substituting feri-butyl 3-bromopropanoate for 2-bromoethanol and additionally including acetone (0.4 mL) in the solution gave the title compound. MS (ESI+) m/z 554 (M+H)+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, tert-Butyl 3-bromopropanoate, and friends who are interested can also refer to it.

Reference:
Patent; CALICO LIFE SCIENCES LLC; ABBVIE INC.; MARTIN, Kathleen, Ann; SIDRAUSKI, Carmela; FROST, Jennifer, M.; TONG, Yunsong; XU, Xiangdong; CHUNG, Seungwon; ZHANG, Qingwei, I.; SHI, Lei; MURAUSKI, Kathleen; DART, Michael, J.; RANDOLPH, John, T.; (238 pag.)WO2019/90085; (2019); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 27492-84-8, The chemical industry reduces the impact on the environment during synthesis 27492-84-8, name is Methyl 4-amino-2-methoxybenzoate, I believe this compound will play a more active role in future production and life.

To a cooled (0°C) solution of phosgene (20percent solution in toluene, 2.76 ml, 5.52 MMOL) in dry DICHLOROMETHANE (75 ml) was added, under an argon atmosphere, methyl 4-amino-2- methoxybenzoate (1 G, 5.52 MMOL) in one portion, followed by a dropwise addition of diisopropylethylamine (1.92 ML, 11.04 MMOL). The mixture was stirred for 15 minutes at 0°C prior to the addition of 2-bromo-4 (trifluoromethoxy) aniline (0.83 ML, 5.52 MMOL). The reaction mixture was stirred at 0°C for a further 2 hours and then was allowed to stir at room temperature overnight. The organic phase was washed with 1 N aq. HCI (2x), sat. aq. NAHCO3, dried over MGS04 and concentrated in vacuo to give a solid residue which was recrystallized in hot acetonitrile. The fine crystalline solid was filtered off, washed with cold acetonitrile and dried in vacuo to give the title compound Ex 106 as a pale-orange solid (1. 64G, 3.54 mmol, 64percent). ‘H-NMR (DMSO-d6) : 6 3.74 (s, 3H), 3.80 (s, 3H), 7.02 (d, 1H), 7.38 (s, 1H), 7.42 (d, 1H), 7.69 (d, 1H), 7.74 (s, 1H), 8.17 (d, 1H), 8.36 (s, 1H), 9.85 (s, 1H)

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, Methyl 4-amino-2-methoxybenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; 7TM PHARMA A/S; LITTLE, Paul Brian; WO2004/48319; (2004); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Electric Literature of 120-61-6, 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. 120-61-6, name is Dimethyl terephthalate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

The reaction described in Example 1 was repeated, yielding the product from pure isobutyl alcohol.In a three-necked flask equipped with stirring blades0.3 mol of dimethyl terephthalate (DMT) was added,2 moles of isobutanol,The temperature was raised to 120 C,After the DMT was completely dissolved,17.46 g of Nafion resin was added,After the control reaction temperature between 127 ~ 137 ,So that the droplet dropping speed control in 3 to 6 drops per second,Every 7h add 2mol isobutanol,Add a total of two times,Reaction 21h after the end.After the ester interchange reaction is completed,The solid resin was filtered off,The crude product was then reactedWas added to the clean flask,And add a little porcelain pieces after vacuum distillation,Vacuum control in about 0.08MPa,Slowly increase the distillation temperature to no liquid drops,The distillation temperature did not exceed 142 C.The final product after vacuum distillation was analyzed by capillary gas chromatography,The composition is shown in Table 1 below.The isolated final product weighed 77.739 g,The theoretical amount of product was 83.50 g,The overall yield was therefore 93.1%

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, Dimethyl terephthalate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Shanghai Huayi Energy Chemical Co., Ltd.; Xu, Yunfeng; Zhao, Zhengkang; Ma, Jinqiang; Chen, Chen; Cui, Yunhue; Tan, Dong; (10 pag.)CN105693519; (2016); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 191478-99-6, 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. 191478-99-6, name is Methyl 4-amino-2,6-difluorobenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: Pyridine-4-thiol (16.7 g, 150 mmol) was dissolved in concentrated hydrochloric acid (110 ml) and water (30 ml). After cooling to 0 C., chlorine gas was bubbled for 1 hour. The reaction solution was diluted with ice-water (75 g), and neutralized by gradually adding sodium hydrogen carbonate. After extraction with methylene chloride (150 ml×3) cooled to 5 to 10 C., the organic layers were combined and dried over anhydrous sodium sulfate. Then, the solvent was removed under reduced pressure to obtain the corresponding sulfonyl chloride. In another reaction vessel, methyl 4-amino-2,6-difluorobenzoate (16.9 g, 90.3 mmol) and pyridine (10 ml) were dissolved in methylene chloride (200 ml). After cooling to -10 C., the above-described solution of the sulfonyl chloride in methylene chloride was added thereto, followed by stirring at room temperature for 6 hours. The organic layer was washed with 0.1 N hydrochloric acid (200 ml×2), and the solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography (petroleum ether/ethyl acetate=2:1 to 1:1) to obtain the title compound (11.2 g, 38% over two steps). [0839] MS (ESI) m/z 329 (M+H)+

The synthetic route of Methyl 4-amino-2,6-difluorobenzoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AJINOMOTO CO., LTD.; Ueno, Hirokazu; Yamamoto, Takashi; Takashita, Ryuta; Yokoyama, Ryohei; Sugiura, Toshihiko; Kageyama, Shunsuke; Ando, Ayatoshi; Eda, Hiroyuki; Eviryanti, Agung; Miyazawa, Tomoko; Kirihara, Aya; Tanabe, Itsuya; Nakamura, Tarou; Noguchi, Misato; Shuto, Manami; Sugiki, Masayuki; Dohi, Mizuki; US2015/51395; (2015); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 79383-44-1, The chemical industry reduces the impact on the environment during synthesis 79383-44-1, name is Methyl 2-methoxy-6-methylbenzoate, I believe this compound will play a more active role in future production and life.

Intermediate 4-A: (2-Methoxy-6-methylphenyl)methanolTo a solution of methyl 2-methoxy-6-methylbenzoate (CAS 79383-44-1, 500 mg, 2.77 mmol) in THF (5 ml) at 0 C was added LiAIH4 (211 mg, 5.55 mmol). The mixture was stirred at 0C for 2h and then at room temperature for 15h. The reaction mixture was then diluted with THF, and then quenched with sodium sulfate decahydrate. The mixture was then stirred for 1 h, dried over Na2504, filtered, and then concentrated to furnish the title compound. MS (ESl+) m/z 135.0 (M-OH).

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, Methyl 2-methoxy-6-methylbenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NOVARTIS AG; ADAMS, Christopher; EHARA, Takeru; JENDZA, Keith; JI, Nan; KAWANAMI, Toshio; MAINOLFI, Nello; POWERS, James J.; SERRANO-WU, Michael; ZHANG, Chun; WO2015/66241; (2015); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 135908-33-7, name is Methyl 4-aminobicyclo[2.2.2]octane-1-carboxylate, belongs to esters-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 135908-33-7, Formula: C10H17NO2

Example 8 : 4- (((2- ((trans-4- (tert-butyl)c clohexyl)oxy) -4-methylnaphthalen- l-yl)methyl)amino)bicyclo[2.2.2]octane-l-carboxylic acid To a mixture of 2-(cis-4-tert-butylcyclohexyloxy)-4-methyl-l-naphthaldehyde (lOOmg, 0.31 mmol, 1.0 eq) in toluene (1 mL) were added methyl 4- aminobicyclo[2.2.2]octane-l-carboxylate hydrochloride (81 mg, 0.37 mmol, 1.2 eq) and MgS04 (74 mg, 0.62 mmol, 2.0 eq). The resulting mixture was heated to reflux and stirred for 48 h. After being concentrated under reduced pressure, the residue was dissolved in THF (lmL). NaBH(OAc)3 (196 mg, 0.93 mmol, 3.0 eq) was added and the mixture was heated to reflux and stirred for 24 h. After cooling down to room temperature, the residue was diluted with EtOAc (5 mL). The suspension was filtered and the filtrate was concentrated under reduced pressure to give the residue, which was purified by column chromatography on silica gel (petroleum ether /EtOAc = 1/1) to yield the target ester (35 mg, 23 % yield) as a yellow oil. LCMS m/z 492.4 [M+H] +. Hydrolysis following standard condition gave the title compound as a white solid (20 mg, 69% yield). LCMS m/z 478.3 [M+H] +; 1H NMR (400 MHz, CD3OD) delta: 8.06- 8.01 (m, 2H), 7.61-7.59 (m, 1H), 7.49-7.47 (m, 1H), 7.36 (s, 1H), 4.54 (bs, 3H), 2.74 (s, 3H), 2.32-2.29 (m, 2H), 2.16 (bs, 12H), 1.99-1.94 (m, 2H), 1.54-1.51 (m, 2H), 1.34-1.24 (m, 2H), 1.20-1.14 (m, 1H), 0.91 (s, 9H).

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, Methyl 4-aminobicyclo[2.2.2]octane-1-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BIOGEN IDEC MA INC.; GUCKIAN, Kevin; KUMARAVEL, Gnanasambandam; LIU, Xiaogao; MA, Bin; PENG, Hairuo; WO2014/120764; (2014); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 110104-60-4, name is (E)-Methyl 4-chloro-3-methoxybut-2-enoate, A new synthetic method of this compound is introduced below., Safety of (E)-Methyl 4-chloro-3-methoxybut-2-enoate

Genera procedure: To a solution of the corresponding alkyl amine (1.2 equiv) in THF (2.0 M) was added simultaneously a solution of (E)-4-chloro-3-methoxy-but-2-enoic acid methyl ester (1 equiv) in acetonitrile (1.5 M) and a solution of triethylamine (1 equiv) in acetonitrile (3.6 M) over 30 min at room temperature. After stirring overnight at room temperature or 3 h at 55 C, the resulting precipitate in the reaction mixture was removed by filtration. The mother liquor was concentrated and purified by flash chromatography on silica gel eluting with a gradient of 20-100% ethyl acetate in hexanes to afford the title compound in greater than 75% yield.

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; Alhambra, Cristobal; Becker, Chris; Blake, Timothy; Chang, Amy; Damewood Jr., James R.; Daniels, Thalia; Dembofsky, Bruce T.; Gurley, David A.; Hall, James E.; Herzog, Keith J.; Horchler, Carey L.; Ohnmacht, Cyrus J.; Schmiesing, Richard Jon; Dudley, Adam; Ribadeneira, Maria D.; Knappenberger, Katherine S.; MacIag, Carla; Stein, Mark M.; Chopra, Maninder; Liu, Xiaodong F.; Christian, Edward P.; Arriza, Jeffrey L.; Chapdelaine, Marc J.; Bioorganic and Medicinal Chemistry; vol. 19; 9; (2011); p. 2927 – 2938;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 82702-31-6, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 82702-31-6 as follows.

Cesium carbonate (3.1 g, 9.6 mmol) was added to 4-fluoro-2,6-dimethylphenol (0.9 g, 6.4 mmol) and methyl 3-bromo-4-fluorobenzoate (1.57 g, 6.7 mmol) ) in a solution of dimethyl sulfoxide (10 mL). The reaction mixture was stirred at 80 C for 12 hr, then cooled to room temperature, then water (50mL), ethyl acetate (50mL*2). The organic phase was washed with brine (25 mL*4) and evaporated to dryness. The crude product was separated by column ( petroleum ether: ethyl acetate = 20:1) to give methyl 3-bromo-4-(4-fluoro-2,6-dimethylphenoxy) benzoate (1.4 g, yield 62%).

According to the analysis of related databases, 82702-31-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Shanghai Hansen Bio-pharmaceutical Technology Co., Ltd.; Jiangsu Haosen Pharmaceutical Group Co., Ltd.; Ye Guozhong; Liu Lei; Bao Rudi; Wu Shenghua; Deng Haining; (130 pag.)CN110041253; (2019); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 42726-73-8, name is tert-Butyl methyl malonate, A new synthetic method of this compound is introduced below., Application In Synthesis of tert-Butyl methyl malonate

To a solution of sodium hydride (4.60 g, 115 mmol) in DMSO (120 mL) was added tert-butyl methyl malonate dropwise. The resulting solution was heated to 100°C for 30 min then cooled to room temperature, where 3-cyano-4-fluorobenzotriflulide (9.86 g, 52.0 mmol) was added and the reaction reheated to 100°C. After 2 h the reaction was cooled to room temperature and poured into a mixture of saturated aqueous ammonium chloride (400 mL), EA (100 mL) and hexanes (100 mL). The organic layer was separated and washed once with saturated aqueous ammonium chloride, three times with water and once with brine. Filtration through a short plug of silica gel, followed by concentration under reduced pressure gave a crude yellow oil. This product was dissolved in ethyl alcohol (50 mL), treated with Raney Nickel (-1 g), and placed on a Parr shaker under 50 psi H2. After 18 h the reaction was filtered through celite and concentrated under reduced pressure to give 12.5 g of product (76 percent). ESI-MS calc. for C15H16F3N03 : 315; found 631 (2M+H). H NMR (CDC13, 500 MHz) 8 7.60 (d, J = 10.0 Hz, 1H), 7.50 (s, 1H), 7.44 (d, J = 10.0 Hz, 1H), 7.24 (bs, 1H), 4.86 (d, J = 14. 5 Hz, 1H), 4.46 (t, J = 14.5 Hz, 2H), 2.20 (bs, 1H), 1.45 (bs, 9H).

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; MERCK & CO., INC.; MERCK SHARP & DOHME LIMITED; WO2003/93231; (2003); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics