Month: September 2021

Related Products of 4090-55-5,Some common heterocyclic compound, 4090-55-5, name is 2-Chloro-5,5-dimethyl-1,3,2-dioxaphosphorinane 2-oxide, molecular formula is C5H10ClO3P, 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: Ph(But)P(O)Cl or 2-chloro-5,5-dimethyl-1,3,2-dioxaphosphinane 2-oxide (5.0mmol) was added to the suspension of NaH (0.133g, 5.5mmol) in THF (25mL). Subsequently, 5,7-dibromo-2-methylquinolin-8-ol (1a), 5-fluoro-2-methylquinolin-8-ol (1i) (5.0mmol) in THF (5mL), was added. The reaction was carried out for 24 h under reflux. The mixture was allowed to cool to room temperature. The reaction was neutralized with aqueous solution of KHSO4. After extraction with CH2Cl2 (3×50mL), the organic phase was dried over MgSO4, followed by filtration and solvent evaporation. The crude product was purified by chromatography and crystallization.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Chloro-5,5-dimethyl-1,3,2-dioxaphosphorinane 2-oxide, its application will become more common.

Reference:
Article; Nycz, Jacek E.; Szala, Marcin; Malecki, Grzegorz J.; Nowak, Maria; Kusz, Joachim; Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy; vol. 117; (2014); p. 351 – 359;,
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Synthetic Route of 467435-07-0, These common heterocyclic compound, 467435-07-0, name is 4-Bromo-2-chlorobenzotrifluoride, 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.

Example 1677 Production of (4aS,8aS)-3,3-dimethyl-l-(3-chloro-4-trifluoromethylphenyl)decahydroquinoxali ne dihydrochloride n A toluene (5 mL) suspension of (4aS,8aS)-2,2-dimethyldecahydroquinoxaline (200 mg, 1.19 mmol), 4-bromo-2-chloro-l-trifluoromethylbenzene (370 mg, 1.43 mmol), sodium tert-butoxide (137 mg, 1.43 mmol), palladium (II) acetate (21.3 mg, 0.0951 mmol), and tri-tert- butylphosphine tetrafluoroborate (27.6 mg, 0.0951 mmol) was stirred for 4 hours at 100 C in a nitrogen atmosphere. After the reaction mixture was cooled to room temperature, insoluble matter was filtered through celite, and the filtrate was then concentrated under reduced pressure. The obtained residue was purified by NH-silica gel column chromatography (n-hexane: ethyl acetate) to obtain pale yellow oil. 1 N hydrochloric acid/ethyl acetate (5.0 mL) was added to an ethanol solution of the obtained oil with stirring at room temperature, and, after sufficient stirring, the mixed solution was concentrated under reduced pressure. The obtained oil was added with an appropriate amount of ethanol/ethyl acetate and the deposited crystal was collected by filtration. The obtained crystal was washed with ethyl acetate and then dried under reduced pressure to obtain (4aS,8aS)-3,3-dimethyl-l-(3-chloro-4- trifluoromethylphenyl)decahydroquinoxaline dihydrochloride (348 mg, yield: 70%) in a white powder form.

The synthetic route of 467435-07-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; OTSUKA PHARMACEUTICAL CO., LTD.; SHINOHARA, Tomoichi; SASAKI, Hirofumi; TAI, Kuninori; ITO, Nobuaki; WO2013/137479; (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 367-22-6 as follows. Recommanded Product: 4-Chloro-3-fluoroaniline

Into a 500-mL round-bottom flask was placed 4-chloro-3-fluoroaniline (5.08 g, 34.9 mmol), ACN (200 mL), and NBS (18.69 g, 105.0 mmol). The resulting solution was stirred for 12 h at RT and then was concentrated under vacuum. The residue was applied onto a silica gel column and eluted with a gradient of ethyl acetate/petroleum ether (1 :200 to 1 : 100). This resulted in 9.7 g (92%) of the title compound as a light yellow solid. MS-ESI: 303.8/305.8/301.8 (M+l).

According to the analysis of related databases, 367-22-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; IFM TRE, INC.; GLICK, Gary; ROUSH, William R.; VENKATRAMAN, Shankar; SHEN, Dong-Ming; GHOSH, Shomir; KATZ, Jason; SEIDEL, Hans Martin; FRANCHI, Luigi; WINKLER, David Guenther; OPIPARI JR., Anthony William; (783 pag.)WO2019/23147; (2019); A1;,
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Some common heterocyclic compound, 873-38-1, name is 2-Bromo-4-chloroaniline, molecular formula is C6H5BrClN, 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. SDS of cas: 873-38-1

A mixture of 2-bromo-4-chloroaniline (4g), sodium carbonate (6.Ig) phenylboronic acid (2.93g) and tetrakis(triphenylphosphine)palladium(0) (0.5g) in dioxane (30ml) was heated under reflux for 48h then cooled. The mixture was partitioned between ethyl acetate and water, the organic layer was washed with water, dried, and the solvent evaporated under reduced pressure. The residue was purified by chromatography on silica eluting with 5-10% ethyl acetate/isohexane, yield 0.99g. MS: APCI (+ve) 204/6

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 873-38-1, its application will become more common.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2006/37982; (2006); A2;,
Chloride – Wikipedia,
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Related Products of 1127-85-1, A common heterocyclic compound, 1127-85-1, name is 2,4-Dichloro-5,6,7,8-tetrahydroquinazoline, molecular formula is C8H8Cl2N2, 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 solution of NaOH (79.2 mg, 1.98 mmol) in 90% aqueous methanol solution (1.8 mL)A solution of thiophenol (193 muL, 1.89 mmol) in methanol (2.9 mL) was slowly added dropwise at 0 C., The mixture was stirred at room temperature for 1 hour. To the reaction mixture was added 2,4-dichloro-5,6,7,8-tetrahydroquinazoline (350 mg, 1.72 mmol) in methanol (2.9 mL) was slowly added dropwise at 0 C,The mixture was stirred at room temperature for one day.After completion of the reaction was confirmed by TLC,After diluting with ethyl acetate,And extracted with brine. The organic layer was dried over anhydrous Na2SO4,Filtered and concentrated. The concentrated filtrate was separated and purified by silica gel column chromatography (Hex: EtOAc = 20: 1) to obtain the desired compound (475 mg, 99%) as a white solid.

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; KOREA INSTITUTE OF SCIENCE AND TECHNOLOGY; Nam, Ghil-Soo; Choo, Hyun-Ah; Choi, Kyung-Il; (40 pag.)KR101730790; (2017); B1;,
Chloride – Wikipedia,
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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 622-86-6 as follows. Application In Synthesis of (2-Chloroethoxy)benzene

To a stirred solution of l-(2-chloroethoxy)benzene (48 g, 1.0 eq) in 400 mL CH2CI2 at 0 C was added dropwise a solution of 4-methoxybenzoyl chloride (62 g, 1.2 eq) and AICI3 (49 g, 1.2 eq) in 400 mL CH2CI2 while maintaining the temperature at 0 C. After the addition, the reaction was stirred at rt for 1 h. Then added ice water to quench the reaction and extracted with CH2CI2. The extract was washed with brine, dried and evaporated in vacuo. Hexane (500 mL) was added to the residue, cooled to 0 C and stirred for 30 min, then filtered and washed with cold hexane and dried to give the product as a white solid (85 g, 96%). NMR (400 MHz, CDC13) 67.79 (dd, J = 6.8 Hz, 2.0 Hz, 4H), 6.97 (dd, J = 8.8 Hz, 2.0 Hz, 4H), 4.32 (t, J = 6.0 Hz, 2H), 3.89 (s, 3H), 3.86 (t, J = 6.0 Hz, 2H).

According to the analysis of related databases, 622-86-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CENTAURUS BIOPHARMA CO., LTD.; XIAO, Dengming; ZHU, Li; HU, Yuandong; YU, Rong; HU, Wei; ZHAO, Na; PENG, Yong; LUO, Hong; HAN, Yongxin; WO2013/97773; (2013); A1;,
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Adding a certain compound to certain chemical reactions, such as: 39989-43-0, name is 3,5-Dichlorobenzylamine, belongs to chlorides-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 39989-43-0, Recommanded Product: 39989-43-0

EXAMPLE 125 8-hydroxy-6-methyl-[1,6]naphthyridine-7-carboxylic acid 4-fluoro-benzylamide (125) In a manner similar to that for the compound 124H in Example 124, Step 8, substituting 3,5-dichlorobenzylamine with 4-fluorobenzylamine in Step 8, 8-hydroxy-6-methyl-[1,6]naphthyridine-7-carboxylic acid the 4-fluoro-benzylamide (125) was prepared. 1H NMR (400 MHz, CD3OD) delta 9.10 (d, 1H), 8.72 (d, 1H), 7.84 (dd, 1H), 7.43 (dd, 2H), 7.06 (t, 2H), 4.64 (s, 2H), 2.88 (s, 3H).

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; 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;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 2533-69-9, 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. 2533-69-9, name is Methyl 2,2,2-trichloroacetimidate belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Step B4-bromo-6-( 1, 1-dimethylethyl)-2-(trichloromethyl)- 1H-benzimidazole[00244] 3-bromo-5-(1 ,1-dimethylethyl)-1 ,2-benzenediamine (1.2 g, 4.9 mmol) was dissolved in acetic acid (25 mL) and methyl 2,2,2-trichloromethylacetimidatate (0.94 mL, 7.4 mmol) was added drop-wise. The reaction was stirred for 3 hours. The mixture was diluted with ethyl ether and washed with water. The aqueous layer was extracted again with ether. The combined organic layers were washed with water, washed with brine, dried over sodium sulfate, and concentrated to give the title compound (0.91 g, 50%). LCMS: m/z 369, 371 , 373 (M+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, Methyl 2,2,2-trichloroacetimidate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GLAXOSMITHKLINE LLC; BANKA, Anna; CATALANO, John G; FANG, Jing; PEAT, Andrew James; TAI, Vincent; TURNER, Elizabeth; WO2011/97491; (2011); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 41965-95-1, 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. 41965-95-1, name is 3-Chloro-4-methoxybenzylamine Hydrochloride belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

9-((3-chloro-4-methoxybenzyl)amino)-2-ethyl-7-methoxy-2,3-dihydro-lH- pyrrolo[3,4-b]quinolin-l-one L [00289] A solution of 43 (0.11 mmol), 3-chloro-4-methoxybenzylamine hydrochloride (0.16 mmol) and (‘pr)2NEt (0.66 mmol) in n-propanol (1.5 mL) was heated to 90 C for lh. The solvent was evaporated off and the residue was purified by flash chromatography (AcOEt: MeOH 19: 1) to give the final product L. MS ESI (m/z) 412 (M+H)+; 1H NMR (400 MHz, CDC13) delta 8.14 (t, 1H, J=6.4 Hz), 7.85 (d, 1H, J=9.6 Hz), 7.48 (d, 1H, J=2.4 Hz), 7.37-7.29 (m, 3H), 6.95 (d, 1H, J=8.8 Hz), 4.95 (d, 2H, J=6.8 Hz), 4.38 (s, 2H), 3.90 (s, 3H), 3.66 (q, 2H, J=7.2 Hz), 3.59 (s, 3H), 1.28 (t, 3H, J=7.2 Hz)

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

Reference:
Patent; THE TRUSTEES OF COLUMBIA UNIVERSITY IN THE CITY OF NEW YORK; LANDRY, Donald, W.; DENG, Shixian; FIORITO, Jole; ARANCIO, Ottavio; WASMUTH, Andrew; WO2015/9930; (2015); A2;,
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Chlorides – an overview | ScienceDirect Topics

Reference of 7051-16-3,Some common heterocyclic compound, 7051-16-3, name is 1-Chloro-3,5-dimethoxybenzene, molecular formula is C8H9ClO2, 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 solution of 1-chloro-3,5-dimethoxybenzene (5 g, 29.0 mmol) and TMEDA (4.37 mL, 29.0 mmol) in diethyl ether (100 mL, 962 mmol) at -78 C under N2 atmosphere was charged with BuLi (19.91 mL, 31.9 mmol) dropwise over a period of 30 minutes using a syringe pump. After stirring for 4 hours at -78 C, DMF was added and the reaction mixture continued to stir for 1.5 hours after which 1N HCl (~30 mL) was added (all at -78 C). The reaction mixture was warmed to room temperature and extracted withy ethyl acetate. The organic phase was dried (MgSO4), filtered and concentrated to dryness. The residue was purified by ISCO using hexanes/EtOAc as eluent. Fractions containing the desired product were concentrated to dryness to give the title material (1.97 g, 9.82 mmol, 33.9% yield) as a light yellow solid. LC (Method B): 1.924 min. LCMS (APCI): calcd for C9H10ClO3 [M+H]+ m/z 201.03, found 201.0. 1H NMR (CDCl3, 400 MHz): delta ppm 10.28 (s, 1H), 6.87 (s, 2H), 3.86 (s, 6H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Chloro-3,5-dimethoxybenzene, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; UNIVERSITE DE MONTREAL; PRIESTLEY, Eldon Scott; POSY, Shoshana L.; TREMBLAY, Francois Tremblay; MARTEL, Alain; MARINIER, Anne; WO2013/163241; (2013); A1;,
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