Tag: M.W=200-300

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 63624-28-2 as follows. Safety of 2,4-Dimethoxybenzene-1-sulfonyl chloride

A solution of 0.28 g of the compound from Preparation 2.1 in 10 ml of THF is cooled to -30 C., 0.073 g of potassium tert-butoxide is added and the mixture is left stirring while allowing the temperature to rise to 0 C. The reaction mixture is cooled to -60 C., 0.147 g of the compound from Preparation 3.1 is added and the mixture is left stirring at 20 C. overnight. The reaction mixture is hydrolyzed by addition of water, extraction is carried out with AcOEt, the organic phase is dried over Na2SO4 and the solvent is evaporated under vacuum. The expected compound is obtained.

According to the analysis of related databases, 63624-28-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SANOFI-AVENTIS; US2011/59955; (2011); A1;,
Chloride – Wikipedia,
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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. 33863-76-2, name is 1-Bromo-3-chloro-5-fluorobenzene belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Application In Synthesis of 1-Bromo-3-chloro-5-fluorobenzene

A solution of 1-bromo-3-chloro-5-fluorobenzene (50.0 g, 239 mmol) in DMF (300 ml.) was treated with sodium methoxide (15.5 g, 286 mmol) and the reaction was stirred overnight at rt. The mixture was diluted with ethyl acetate (500 ml.) and washed with water (700 ml_). The organic layer was isolated, washed with brine, dried over magnesium sulfate, filtered, and concentrated to give 51.0 g of the title compound which was used without purification. 1H NMR (DMSOd6) ¡ì 7.23 (t, 1 H), 7.13 – 7.15 (m, 1 H), 7.05 (t, 1 H), 3.77 (s, 3 H).

The synthetic route of 33863-76-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2008/157330; (2008); 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. 210532-25-5, name is 3,5-Difluorobenzene-1-sulfonyl chloride, A new synthetic method of this compound is introduced below., COA of Formula: C6H3ClF2O2S

0.3 g (1.0 mmol, 1.0 eq) of JD1001-002-8 was added to a 25 mL reactor under nitrogen protection. 3.2 mL (10.0 V) THF, 0.32 g (3 mmol, 3.1 eq) DMAP, 0.38 g (3.0 mmol, 3.0 eq) of 3,5-difluorobenzenesulfonyl chloride were added, and the reaction was stirred at room temperature for 3 hours. After completion of the reaction by TLC detection (developing agent: PE / EA = 1 / 1, UV254), the reaction was stopped, the reaction was quenched with saturated NaHCO3, and the organic phase was extracted with ethyl acetate .The organic phase was washed twice with 0.5 N hydrochloric acid, dried with anhydrous sodium sulfate, the organic phase was filtered out, the organic phase was concentrated to give a solid. The solid was separated and purified y HPLC (CH3CN/H2O=60:40) to afford 121 mg of JD 1001-1076. The yield was 40%.

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; Kunming Jida Pharmaceutical Co., Ltd.; Zhang Poyong; Xiao Xuzhi; Shen Changnian; Guo Kun; Lin Zhigang; Chen Mengran; Zhang Yun; Wang Lijiang; (24 pag.)CN109438297; (2019); A;,
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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. 849367-49-3, name is 3-Bromo-4-chlorobenzylamine, A new synthetic method of this compound is introduced below., category: chlorides-buliding-blocks

N-[(3-Bromo-4-chlorophenyl)methyl]-N’-{[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}propanediamide A solution of 3-({[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}amino)-3-oxopropanoic acid (600 mg, 1.541 mmol), 1-(3-bromo-4-chlorophenyl)methanamine (397 mg, 1.8 mmol), HATU (760 mg, 2.0 mmol), and triethylamine (0.488 ml, 3.5 mmol) in 25 mL of DCM was stirred at room temperature overnight. The reaction mixture was diluted with DCM, washed with saturated NaHCO3, water and saturated NaCl. The organic layer was dried over Na2SO4 and evaporated to a pale amber residue. This was purified on 80 g. Combi-Flash column with DCM [0-8% MeOH] to give N-[(3-bromo-4-chlorophenyl)methyl]-N’-{[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}propanediamide. LC-MS m/z 591.2 (M+H)+, 0.84 min (ret time).

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; Glaxo Group Limited; US2009/203677; (2009); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 50638-46-5, These common heterocyclic compound, 50638-46-5, name is 4-Bromo-3-chloroanisole, 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 1-bromo-2-chloro-4-methoxybenzene (6.6 g, 30 mmoL) in 1, 4-dioxane (150 mL) was added with 4, 4, 5, 5-tetramethyl-2- (1, 4-dioxaspiro [4.5] dec-7-en-8-yl) -1, 3, 2-dioxaborolane (8 g, 30 mmol) , Pd (dppf)2Cl2(2.2 g, 3 mmol) and Cs2CO3(14.7 g, 45 mmol) and the mixture was heated at 90 overnight. After evaporated the solvent under reduced pressure, the residue was added with water (80 mL) , extracted with ethyl acetate (80 mL) . The organic layer was dried, concentrated and purified by column chromatography (PE: EA=80: 1) to give product as a white solid (6.2 g in 74%yield) .1H NMR (CDCl3) deltaH7.12 (d, J = 12.0 Hz, 1H) , 6.90 (d, J = 1.2 Hz, 1H) , 6.75 (dd, J1=8.0 Hz, J2=4.0 Hz, 1H) , 5.56-5.54 (m, 1H) , 4.04-4.01 (m, 4H) , 3.79 (s, 3H) , 2.55-2.51 (m, 2H) , 2.45-2.42 (m, 2H) , 1.89 (t, J = 6.4 Hz, 2H) . [M+H]+=281.1.

Statistics shows that 4-Bromo-3-chloroanisole is playing an increasingly important role. we look forward to future research findings about 50638-46-5.

Reference:
Patent; BEIGENE, LTD.; WANG, Hexiang; GUO, Yunhang; REN, Bo; WANG, Zhiwei; ZHANG, Guoliang; ZHOU, Changyou; (353 pag.)WO2018/54365; (2018); A1;,
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Application of 16799-05-6,Some common heterocyclic compound, 16799-05-6, name is 3-Chlorophenethyl Bromide, molecular formula is C8H8BrCl, 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 compound 3 or 4, R-X (3 equiv.) and Cs2CO3 (3 equiv.) in acetone/DMF (10 mL/10mL) was stirred at proper temperature (25-80C) for 20h. The reaction was quenched with water (30mL) and extracted with ethyl acetate (¡Á3). The organic layer was collected and washed with brine, and then dried over anhydrous MgSO4. Solvent was removed under reduced pressure and residue was purified by silica gel column chromatography.5.4.10 1-(3-Chlorophenethoxy)-3-(oxiran-2-ylmethoxy)-9H-xanthen-9-one (14) Following the general method, compound 3 (0.19 g, 0.06 mmol), 3-chloro-1-phenethyl bromide (0.30 g, 1.37 mmol) and K2CO3 (0.26 g, 1.85 mmol) were used at 80 C. The purification was conducted with eluent (ethyl acetate/n-hexane = 1:3) to give compound 14 (0.04 g, 15.4%) as a white solid. m.p. 146-148 C; Rf 0.63 (eluent: ethyl acetate/n-hexane = 1:1); HPLC: RT 4.05 min (condition A, purity: 98.2%); 1H NMR (CDCl3, 400 MHz) delta 2.78 (dd, J = 2.4, 4.8 Hz, 1H), 2.95 (t, J = 4.4 Hz, 1H), 3.28 (t, J = 7.2 Hz, 2H), 3.36-3.40 (m, 1H), 4.00 (dd, J = 7.0, 11.2 Hz, 1H), 4.25 (t, J = 7.2 Hz, 2H), 4.35 (dd, J = 2.8, 11.2 Hz, 1H), 6.35 (d, J = 2.4 Hz, 1H), 6.51 (d, J = 2.4 Hz, 1H), 7.20-7.38 (m, 5H), 7.43 (dd, J = 2.0, 2.0 Hz, 1H), 7.64 (ddd, J = 1.6, 7.2, 8.8 Hz, 1H), 8.31 (dd, J = 2.0, 8.0 Hz, 1H); 13C NMR (CDCl3, 100 MHz) 35.5, 44.8, 50.0, 69.4, 70.1, 94.0, 96.6, 108.1, 117.2, 123.4, 124.9, 127.0, 127.9, 129.6, 130.0, 133.9, 134.4, 140.3, 155.2, 159.2, 161.4, 163.7, 175.3, 175.4 ppm.

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

Reference:
Article; Park, Seojeong; Hong, Eunji; Kwak, Soo Yeon; Jun, Kyu-Yeon; Lee, Eung-Seok; Kwon, Youngjoo; Na, Younghwa; European Journal of Medicinal Chemistry; vol. 123; (2016); p. 211 – 225;,
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Adding a certain compound to certain chemical reactions, such as: 51572-93-1, name is O-(2,4-Dichlorobenzyl)hydroxylamine hydrochloride, 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 51572-93-1, Computed Properties of C7H8Cl3NO

General procedure: To a solution of 3ae3e (1 mmol) in anhydrous ethanol (10 mL),corresponding O-benzylhydroxylamine hydrochloride (1 mmol)and NaOAc (1.2 mmol) were added and the resulting solution wasstirred at the room temperate for 3 h. The mixture was concentratedand taken in ethyl acetate (20 mL), washed with water(20 mL), saturated sodium chloride solution (20 mL) and dried oversodium sulfate. The resulting solution was concentrated and thepurification of the residue by recrystallization from ethanol yieldedthe desired compounds 4a-4t

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; Lv, Xian-Hai; Li, Qing-Shan; Ren, Zi-Li; Chu, Ming-Jie; Sun, Jian; Zhang, Xin; Xing, Man; Zhu, Hai-Liang; Cao, Hai-Qun; European Journal of Medicinal Chemistry; vol. 108; (2016); p. 586 – 593;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 326-64-7, These common heterocyclic compound, 326-64-7, name is 5-Chloro-2-(trifluoromethoxy)aniline, 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 suspension of 5-chloro-2- ( trifluorometnyl ) aniline (5.00 g, 23.6 mmol) and dibenzyl disulfide (4.66g, 18.9 mmol) in acetonitrile (75 mL) , Isoamyl nitrite (3.46 mL, 26.0 mmol) was slowly added at 60C in an oil bath, and the mixture was stirred at the same temperature as above for 2 hours. The reaction mixture was cooled and then concentrated under reduced pressure, and the residue was purified in an automatic chromatography apparatus (n-hexane/ethyl acetate = 100/0 – 95/5) to prepare 2- (benzylsulfanyl ) -4-chlorophenyl trifluoromethyl ether (3.86 g, yield: 51%) . To a mixture of the obtained 2- (benzylsulfanyl ) -4-chlorophenyl trifluoromethyl ether (4.84 g, 15.2 mmol), acetic acid(4.5 mL) and water (3 mL) in acetonitrile (120 mL) , 1, 3-dichloro-5, 5-dimethylhydantoin (5.98 g, 30.4 mmol) was added under ice cooling, and the mixture was stirred at the same temperature as above for 3 hours. The mixture was diluted by addition of a saturated aqueous solution of sodium bicarbonate, extracted with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate. After filtration, the solvent was distilled off under reduced pressure, and the residue was purified in an automatic chromatography apparatus(hexane/ethyl acetate = 100/0 – 85/15) to obtain the title compound (3.64 g, yield: 81%) . NMR spectrum (CDC13, 400MHz) delta: 8.09 (1H, d, J =2.3 Hz), 7.75 (1H, dd, J = 9.0, 2.7 Hz), 7.50-7.47 (1H, m) .

Statistics shows that 5-Chloro-2-(trifluoromethoxy)aniline is playing an increasingly important role. we look forward to future research findings about 326-64-7.

Reference:
Patent; DAIICHI SANKYO COMPANY, LIMITED; SANFORD BURNHAM PREBYS MEDICAL DISCOVERY INSTITUTE; MIYAZAKI, Shojiro; YAMAMOTO, Yuko; SUZUKI, Keisuke; INUI, Masaharu; IZUMI, Masanori; SOMA, Kaori; PINKERTON, Anthony; SHINOZAKI, Taeko; (243 pag.)WO2017/7943; (2017); A1;,
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Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 69695-61-0, name is 2-Chloro-4-(trifluoromethoxy)aniline, 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 69695-61-0, Safety of 2-Chloro-4-(trifluoromethoxy)aniline

Example 98: A mixture of N-[l-(6-bromonaphthalen-2-yl)ethyl]acetamide (80 mg, 0.274 mmol), 2-chloro-4-trifluoromethoxyphenylamine (69.5 mg, 0.330 mmol), potassium tert- butoxide (43 mg, 0.384 mmol), BINAP (1.28 mg, 0.002 mmol), and 20 ml of toluene was flushed with nitrogen for 10 minutes, and then tris(dibenzylidineacetone)dipalladium(0) (0.63 mg, 0.00068 mmol) was added. The mixture was heated at 120 0C for 15 h, cooled, and concentrated under reduced pressure. The residue was taken into EtOAc, washed with water and brine, dried over sodium sulfate, and concentrated under reduced pressure. The crude material was purified by preparative TLC to afford N-{l-[6-(4- trifluo romethoxyphenylamino)naphthalen-2-yl] ethyl} acetamide as a brown sticky solid. LC/MS [M+H] 389.2. 1H-NMR (400MHz, DMSOd6) delta 8.524 (bs, IH), 8.264-8.281 (d, IH, J=6.8 Hz), 7.740-7.762 (d, IH, J=8.8 Hz), 7.649-7.670 (d, IH, J=8.4 Hz), 7.616 (s, IH), 7.458 (s, IH), 7.336-7.357 (d, IH, J=8.4 Hz), 7.184-7.224 (m, 4H), 4.973-5.007 (m, IH), 1.831 (s, 3H), 1.373-1.390 (d, 3H, J=6.8 Hz) ppm.

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-Chloro-4-(trifluoromethoxy)aniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; FOREST LABORATORIES HOLDINGS LIMITED; SARMA, Pakala Kumara, Savithru; ACHARYA, Vinod, Parameshwaran; KASIBHATLA, Srinivas, Rao; TIWARI, Atul; REDDY, Vantaddu, Nagarjuna; BISCHOFF, Alexander; WO2010/127208; (2010); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 14862-52-3, 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. 14862-52-3, name is 3,5-Dibromochlorobenzene belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example 26: Preparation of 1-(3-bromo-5-chlorophenyl)ethan-1-one (C148) (0740) (0741) 656 1,3-Dibromo-5-chlorobenzene (5.0 g, 18.5 mmol) was dissolved in 167 diethyl ether (61.6 mL) and cooled to -78 C. Because the compound came out of solution, the mixture was removed from the cooling bath. As soon as stirring was again visible from temperature warming, 168 n-butyllithium (8.14 mL, 20.34 mmol) was added dropwise, and the solution was re-immersed in the cold bath. The solution took on a bright yellow color, and the mixture was stirred for 30 minutes. At this point a slight yellow precipitate was visible. 657 N-Methoxy-N-methylacetamide (2.359 mL, 22.19 mmol) was added dropwise, and the reaction mixture was stirred for 10 minutes, then warmed slowly to room temperature. The reaction mixture was quenched with 1 N hydrochloric acid and was extracted with diethyl ether. The combined organic extracts were washed with brine, dried over sodium sulfate and concentrated. The resulting oil was purified on silica running a 0-15% gradient of 110 acetone in hexanes. The 658 title compound was isolated as a white solid (3.7 g, 86%): mp 33-36 C.; 1H NMR (300 MHz, CDCl3) delta 7.97-7.95 (m, 1H), 7.85 (dd, J=1.5 Hz, 1H), 7.71 (t, J=1.8 Hz, 1H), 2.59 (s, 3H); IR (thin film) 1687 cm-1; ESIMS m/z 233 ([M+H]+).

The synthetic route of 3,5-Dibromochlorobenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Dow AgroSciences LLC; Barton, Thomas; Gao, Xin; Hunter, Jim; LePlae, Paul R.; Lo, William C.; Boruwa, Joshodeep; Tangirala, Raghuram; Watson, Gerald B.; Herbert, John; (176 pag.)US2017/208806; (2017); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics