Tag: M.W=100-200

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. 103-50-4, name is Benzyl ether belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Formula: C14H14O

General procedure: In the mixture of cyclic/acyclic ether (11 mmol) and acid chloride (10 mmol), nano-ZnO (5 mol%) was added at 0-5 C and stirred at room temperature for an appropriate time. After the TLC monitoring reaction, the ZnO was removed by filtration and washed repeatedly with dichloromethane and water. It was then dried at 60 C for 3 h and used for the next catalytic cycle. The solution was extracted three times with dichloromethane and water, and dried on anhydrous Na2SO4. The product was purified on a silica gel column chromatography using a mixture of petroleum ether/ethyl acetate (150:1, v/v). The product is obtained by vacuum distillation to remove the solvent. The compounds were characterized by 1H NMR and 13C NMR.

The synthetic route of 103-50-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Chen, Junqing; Feng, Chengliang; Ji, Min; Tang, Yuqi; Wang, Wei; Yang, Wanfeng; Chemical Papers; (2020);,
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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. name: 4-Fluoro-3-methoxyaniline

INTERMEDIATE PREPARATION 145-a nolTo a solution of 4-fluoro-3-(methyloxy)aniline (3.8 g, 26.92 mmol) in methylene chloride (50 mL) at 0C was added boron tribromide (20.2 g, 80.77 mmol). The mixture was quenched with methanol and concentrated in vacuo. The residue was dissolved in methanol and reconcentrated two times. The residue was dissolved in water and NaHC03 was added. The resulting solution was extracted with ethyl acetate, washed with brine, dried over MgS04, filtered and concentrated to afford 5-amino-2-fluorophenol (3.0 g).

The synthetic route of 4-Fluoro-3-methoxyaniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE LLC; BROOKS, Carl, A.; CHEUNG, Mui; EIDAM, Hilary, S.; FOX, Ryan, M; HILFKER, Mark, A.; MANAS, Eric, S.; YE, Guosen; WO2011/119704; (2011); A1;,
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Related Products of 876-32-4,Some common heterocyclic compound, 876-32-4, name is 4-Methoxy-N-methylbenzylamine hydrochloride, molecular formula is C9H14ClNO, 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.

In a sealed tube, mixture of benzamide 24b (38 mg, 0.11 mmol), formaldehyde (37% in water, 0.043 mL, 0.55 mmol), 1-(4-methoxyphenyl)-N-methylmethanamine hydrochloride (102 mg, 0.55 mmol), and 1N NaOH (0.5 mL) in H2O:THF (1 mL:0.5 mL) was heated at 65 C for 2 hours. After cooling to room temperature, the reaction mixture was diluted with ethyl acetate, washed with brine, dried over Na2SO4, and concentrated, then purified by column chromatography to afford the pure product (28 mg, 57% yield) as off white solid. 1H NMR (CDCl3, 300 MHz) delta: 7.73 (d, J= 1.8 Hz, 1H), 7.49 (d, J= 8.7 Hz, 1H), 7.36 (dd, J= 1.8, 8.7 Hz, 1H), 7.23 (d, J= 8.7 Hz, 2H), 7.20- 7.13 (m, 1H), 6.91-6.84 (m, 1H), 6.85 (d, J= 8.7 Hz, 2H), 6.17 (bs, 1H), 5.35 (s, 2H), 4.38 (d, J= 6.3 Hz, 2H), 3.79 (s, 3H), 3.59 (s, 2H), 2.32 (s, 3H).

The synthetic route of 876-32-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; RUTGERS, THE STATE UNIVERSITY OF NEW JERSEY; UNIVERSITY OF MEDICINE AND DENTISTRY OF NEW JERSEY; LAVOIE, Edmond J.; PARHI, Ajit; ZHANG, Yongzheng; PILCH, Daniel S.; KAUL, Malvika; WO2013/142712; (2013); A1;,
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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 10103-06-7 as follows. Application In Synthesis of 2,3-Dimethoxynaphthalene

EXAMPLE 9 2-(4-Chlorobutyl)-6,7-dimethoxynaphthalene Aluminum chloride (25.5 g, 0.19 mole) was added to a solution of 21.5 mL (0.19 mole) of 4-chlorobutyryl chloride in 225 mL of methylene chloride. To the resulting solution, cooled in an ice bath, was added dropwise a solution of 30.0 g (0.16 mole) of 2,3-dimethoxynaphthalene in 150 mL of methylene chloride over 30 minutes. The reaction mixture was stirred at 3 C. for 30 minutes and at 24 C. for 17 hours. The reaction mixture was worked up as Example 5 and the crude product was recrystallized from acetone-hexane, to give 31.5 g (68% yield), mp 98-99, of 4-chloro-1-(6,7-dimethoxy-2-naphthalenyl)-1-butanone. Anal Calcd. for C16 H17 ClO3: C, 65.64; H, 5.85; Cl, 12.11. Found: C, 65.33; H, 5.77; Cl, 12.16.

According to the analysis of related databases, 10103-06-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Hoffmann-La Roche Inc.; US4937371; (1990); A;,
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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, Computed Properties of C9H13NO2

Step 4 Preparation of 5-cyano-N-(2,3-dimethoxybenzyl)-8-hydroxy-1,6-naphthyridine-7-carboxamide To a solution of methyl 8-(benzoyloxy)-5-cyano-1,6-naphthyridine-7-carboxylate (264 mg, 0.792 mmol) in anhydrous toluene (12 ml) was added 2,3-dimethoxybenzyl amine (132 mg, 0.79 mmol) and the solution was stirred at reflux under argon overnight. The solvent was removed under reduced pressure to give a brown syrup which was subsequently taken up into ether (10 ml). After stirring for 4 hours the solids were collected by vacuum filtration and dried overnight on an aberhalden to give an off white solid. 1H NMR (CDCl3, 400 MHz) delta 9.26 (1H, d, J=2.8 Hz), 8.59-8.56 (1H, d, J=8.5 Hz), 8.39 (1H, b), 7.82-7.79 (1H, dd, J=4.2 and 8.5 Hz), 7.07 (1H, t, J=7.9 Hz), 6.98 (1H, d, J=6.6 Hz), 6.93 (1H, d, J=8.2 Hz), 4.72 (2H, d, J=6.0 Hz), 3.97 (3H, s) and 3.89(3H, s) ppm.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, (2,3-Dimethoxyphenyl)methanamine, and friends who are interested can also refer to it.

Reference:
Patent; Anthony, Neville J.; Gomez, Robert P.; Young, Steven D.; Egbertson, Melissa; Wai, John S.; Zhuang, Linghang; Embrey, Mark; Tran, LeKhanh; Melamed, Jeffrey Y.; Langford, H. Marie; Guare, James P.; Fisher, Thorsten E.; Jolly, Samson M.; Kuo, Michelle S.; Perlow, Debra S.; Bennett, Jennifer J.; Funk, Timothy W.; US2003/55071; (2003); 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. 107622-80-0, name is (4-Phenoxyphenyl)methanamine, A new synthetic method of this compound is introduced below., Computed Properties of C13H13NO

Example 71 3-Hydroxy-4-methoxy-N-(4′-phenoxybenzyl)picolinamide: The procedure of Example 39 was repeated, except that 4-benzyloxyaniline hydrochloride was changed to 4-phenoxybenzylamine. Thus, the title compound was prepared.

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; Meiji Seika Kaisha, Ltd.; EP1134214; (2001); A1;,
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Related Products of 22236-10-8, 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. 22236-10-8 name is 4-(Difluoromethoxy)aniline, 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.

To a solution of 5-bromo-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole-3-carboxylic acid (XLIX) (1 g, 3.08 mmol), 4-(difluoromethoxy)aniline (XLI) (0.420 mL, 3.38 mmol) and HATU (1.286 g, 3.38 mmol) in DMF (10 mL) was added DIPEA (1.343 mL, 7.69 mmol). The reaction mixture was stirred at 60 C. for 2 h. Water was then added to the reaction mixture and extracted with EtOAc. The organic layer was washed with water, saturated aqueous NaHCO3 and brine. The organic layer was dried, filtered and concentrated. The crude product was triturated in MeOH and the resulting solid filtered to give 5-bromo-N-(4-(difluoromethoxy)phenyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole-3-carboxamide as a white solid (CXLIII) (1.26 g, 2.70 mmol, 88% yield). ESIMS found C20H18BrF2N3O3 m/z 466.1 (M+H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-(Difluoromethoxy)aniline, and friends who are interested can also refer to it.

Reference:
Patent; Samumed, LLC; KC, Sunil Kumar; Mak, Chi Ching; Mittapalli, Gopi Kumar; Hofilena, Brian Joseph; Eastman, Brian Walter; Cao, Jianguo; Chiruta, Chandramouli; Bollu, Venkataiah; (145 pag.)US2019/263821; (2019); A1;,
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Electric Literature of 7252-83-7, A common heterocyclic compound, 7252-83-7, name is 2-Bromo-1,1-dimethoxyethane, molecular formula is C4H9BrO2, 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-hydroxythiobenzamide (30.64 g, 0.20 mol) and 2-bromo-1,1-dimethoxyethane (31.00 g, 0.20 mol) were stirred in ethanol (600 mL) at room temperature.P-toluenesulfonic acid (34.44 g, 0.20 mol) was added to the reaction solution.Heat to 90C for 24 hours.After the reaction was completed, it was cooled to room temperature, the solvent was distilled off under reduced pressure, water (200 mL) was added, and the pH was adjusted to 8 with saturated sodium bicarbonate solution.Dichloromethane (200 mL x 3) was extracted and the organic phases were combined and concentrated by evaporation under reduced pressure to give a yellow solid (21.3 g, 60%).

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; SUNSHINE LAKE PHARMA CO., LTD.; ZHANG, YINGJUN; ZHANG, JIANCUN; WANG, XIAOJUN; LIN, RUNFENG; CAO, SHENGTIAN; WANG, ZHAOHE; LI, JING; (226 pag.)TWI607995; (2017); B;,
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Synthetic Route of 1535-75-7, The chemical industry reduces the impact on the environment during synthesis 1535-75-7, name is 2-(Trifluoromethoxy)aniline, I believe this compound will play a more active role in future production and life.

To a stirred solution of 2, 4-dichloro-5-methoxypyrimidine (5 g, 28.08 mmol) in tertiary butyl alcohol (35 mL) under argon atmosphere were added 2-(trifluoromethoxy) aniline (4 g, 22.47 mmol) and diisopropylethylamine (35 mL) at RT. The reaction mixture was stirred at 160 C for 48 h in a sealed tube. After completion of the reaction (monitored by TLC), the volatile components were removed in vacuo. The crude material was purified by silica gel column chromatography using 10% EtOAc:hexanes to afford 2-chloro-5-methoxy- N-(2-(trifluoromethoxy) phenyl) pyrimidin-4-amine (2 g, 22%) as a colorless syrup. ?H-NMR (CDC13, 400 MHz): oe 8.64 (d, 1H), 7.79 (s, 1H), 7.72 (br s, 1H), 7.38 (t, 1H), 7.30-7.27 (m, 1H), 7.10-7.07 (m, 1H), 4.00 (s, 3H); LC-MS: 320.3 (M+1); (column; X Select CSH C-18 (50 x 3.0 mm, 3.5 .im); RT 4.63 mm. 0.05% Aq TFA: ACN; 0.80 ml/min); TLC: 15% EtOAc:hexanes (Rf 0.3).

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-(Trifluoromethoxy)aniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; FORUM PHARMACEUTICALS INC.; BURNETT, Duane, A.; BURSAVICH, Matthew, Gregory; MCRINER, Andrew, J.; WO2015/66696; (2015); A1;,
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Related Products of 7664-66-6,Some common heterocyclic compound, 7664-66-6, name is 4-Isopropoxyaniline, 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.

Step 4: 8-Hydroxy-2-(4-isopropoxy-phenyl)-2-aza-spiror4.51decan-l-one4-Isopropoxy-phenylamine (11.3 g) was added to a solution of 4-hydroxy-l-(2-methoxy- ethyl)-cyclohexanecarboxylic acid ethyl ester (11.5 g) in toluene (361 ml). The mixture was stirred for 10 minutes at RT. Then, dimethylaluminiumchloride (0.9 M in hexane, 99 ml) was added dropwise and the reaction mixture was heated to reflux for 4 h. The mixture was then cooled to 0C, water (50 ml) was added dropwise then AcOEt (300 ml). The mixture was stirred further 30 minutes, more AcOEt was added, the layers were then separated, the organic layer was dried over MgS04, filtered and the solvent was evaporated off . The crude product was triturated with diethyl ether/heptane to give the title compound as a mixture of cis/trans isomers as brown solid (14.3 g) which was used directly in the next step. MS (m/e): 304.190 [MH+].

The synthetic route of 7664-66-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HUNZIKER, Daniel; NEIDHART, Werner; WO2012/130679; (2012); A1;,
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