Tag: M.W=200-300

Application of 14862-52-3, The chemical industry reduces the impact on the environment during synthesis 14862-52-3, name is 3,5-Dibromochlorobenzene, I believe this compound will play a more active role in future production and life.

3,5-dibromochlorobenzene (2.7 g, 10 mmol)9-phenylcarbazole-3-boronic acid (6.0 g, 21 mmol)Sodium carbonate (10.2 g, 96 mmol),Pd2 (dba) 3 (0.4 g, 0.4 mmol), toluene,Ethanol, water 50ml in turn added to the reaction bottle,The reaction was refluxed under nitrogen for 10 hours, cooled to room temperature,The aqueous layer was extracted with ethyl acetate,The organic layers were combined, washed with saturated brine and water, respectively,The organic layer was dried over magnesium sulfate, filtered,Filtrate spin dry, over silicone column,4.4 g of product was obtained, HPLC purity 99.2%.

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, 3,5-Dibromochlorobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; CECEP Wanrun Co., Ltd.; Yu Kaichao; Zhang Zhaochao; Wang Lichun; (35 pag.)CN107056806; (2017); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Some common heterocyclic compound, 13526-66-4, name is 3-Bromo-6-chloroimidazo[1,2-b]pyridazine, molecular formula is C6H3BrClN3, 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. 13526-66-4

Example 70(£)-2-(1-(3-((1 -Methyl-1 H-indazol-5-yl)methyl)imidazo[1 ,2-b]pyridazin-6-yl)ethylidene) hydrazinecarboxamide(6-Chloroimidazo[1 ,2-b]pyridazin-3-yl)(1 -methyl-1 H-indazol-5-yl)methanol (70.1)To a solution of 3-bromo-6-chloroimidazo[1 ,2-b]pyridazine (232.0 mg, 1.00 mmol) in 5 ml_ THF, was added ethylmagnesium bromide (1.50 ml_, 1.50 mmol) at -10 0C. After stirring at – 10 0C for 1 hour, 1 -methyl-1 H-indazole-5-carbaldehyde (240.0 mg, 1.50 mmol) was added. The mixture was allowed to warm to room temperature slowly and stirred for additional 2 hours. The reaction was quenched with Sat. NH4CI solution and concentrated under reduced pressure. The residue was diluted with water, and extracted with EtOAc twice. The organic layers were combined, dried over Na2SO4 and concentrated. The crude product was washed with DCM to give the title compound as a white solid (230 mg, 70 %). 1H-NMR (400MHz, DMSO-Cf6) delta ppm 8.21 (d, 1 H), 8.02 (s, 1 H), 7.81 (s, 1 H), 7.59 (d, 1 H), 7.56 (s, 1 H), 7.49 (d, 1 H), 7.35 (d, 1 H), 6.29 (d, 1 H), 6.21 (d, 1 H), 4.02 (s, 3H). LCMS (method A): [MH]+ = 314, tR = 4.44 min

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 13526-66-4, its application will become more common.

Reference:
Patent; NOVARTIS AG; FU, Xingnian; HE, Feng; LI, Yue; LIU, Lei; MI, Yuan; XU, Yao-chang; XUN, Guoliang; YU, Zhengtian; ZHANG, Ji Yue (Jeff); DAI, Miao; WO2011/18454; (2011); A1;,
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Chlorides – an overview | ScienceDirect Topics

Reference of 51419-59-1,Some common heterocyclic compound, 51419-59-1, name is p-Tolylmethanesulfonyl chloride, molecular formula is C8H9ClO2S, 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: Sodium hydride (60percent dispersion in mineral oil) (18 mg, 0.45 mmol) was added to a solution of 2-(4-(Piperazine-1-carbonyl)phenyl)quinazolin-4(3H)-one (4) (50 mg, 0.15 mmol) in DMF (10 mL), and the mixture was heated at 100 °C. Appropriate sulfonyl chloride (0.22 mmol) in DMF (3 mL) was added slowly to the reaction mixture. The mixture was stirred at 100 °C for 16 h. After cooling, saturated NaHCO3 solution was added. The reaction mixture was extracted with ethyl acetate and the organic phase was washed with brine. The organic phase was dried over MgSO4 and evaporated in vacuo. The residue was washed with ethyl acetate/hexane (1:10) and purified by column chromatography (ethyl acetate) to provide 2-(4-(4-(substituted)-sulfonyl)piperazine-1-carbonyl)phenyl)quinazolin-4(3H)-one.

The synthetic route of 51419-59-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Rhee, Hee-Kyung; Yoo, Ji Hye; Lee, Eunyoung; Kwon, Young Joo; Seo, Hang-Rhan; Lee, Yun-Sil; Choo, Hea-Young Park; European Journal of Medicinal Chemistry; vol. 46; 9; (2011); p. 3900 – 3908;,
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1127-85-1, name is 2,4-Dichloro-5,6,7,8-tetrahydroquinazoline, belongs to chlorides-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Formula: C8H8Cl2N2

2,4-dichloro-5,6,7,8-tetrahydroquinazoline (0.5 g, 2.46 mmol) was added to a round bottom flask and dissolved in tetrahydrofuran (30 mL), and furfurylamine (0.23 mL, 2.46 mmol) and triethylamine (1.03 mL, 7.39 mmol) were added thereto, followed by stirring at 60 C. for 1 hour. After completion of the reaction, the solvent was removed by distillation under reduced pressure and water was added to the reaction mixture. The resulting mixture was extracted with dichloromethane and dried over anhydrous magnesium sulfate, and the solvent was removed by distillation under reduced pressure. The residue was purified by column chromatography (ethyl acetate:hexane, 1:1, v/v) to obtain a compound (0.22 g, 34%); 1H NMR (400 MHz, CDCl3) delta 1.82 (s, 4H), 2.28 (s, 2H), 2.68 (s, 2H), 4.68 (d, J=4.8 Hz, 2H), 4.99 (s, 1H), 6.32 (d, J=12.4 Hz, 2H), 7.37 (s, 1H); 13C NMR (400 MHz, CDCl3) delta 21.82, 21.86, 21.91, 31.63, 38.20, 108.01, 110.53, 110.55, 142.37, 151.08, 157.37, 161.42, 164.43.

The synthetic route of 1127-85-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KOREA INSTITUTE OF SCIENCE AND TECHNOLOGY; LEE, So Ha; YOO, Kyung Ho; ROH, Eun Joo; SIM, Tae Bo; KIM, Tae Young; KIM, Jae Ho; (30 pag.)US2019/315726; (2019); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 38762-41-3, 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 38762-41-3 as follows.

To a solution of 4-bromo-2-chloro-phenylamine (32 g, 0.15 mol) and pyridine (13.45 g, 0.17 mol) in DCM (200 mL) was added 3-chloropropionyl chloride (21.65 g, 0.17 mol) dropwise at 15 C. After stirring at room temperature for 1 hour, the mixture was washed with water and then aqueous 2N HC1. The organic layer was dried over anhy. Na2S04, filtered, and concentrated in vacuo to afford title compound (10.9 g, 90%) as a white solid.

According to the analysis of related databases, 38762-41-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; AEBI, Johannes; AMREIN, Kurt; HORNSPERGER, Benoit; KUHN, Bernd; MAERKI, Hans P.; MARTIN, Rainer E.; MAYWEG, Alexander V.; TAN, Xuefei; (77 pag.)WO2016/66597; (2016); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 328-84-7, 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. 328-84-7, name is 3,4-Dichlorobenzotrifluoride belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

a. 1,3-Bis(2-chloro-alpha,alpha,alpha-trifluoro-p-tolyloxy)benzene A solution of potassium hydroxide (3.26 g. 0.05 mole, 85%) in water (~3 g.) is added slowly dropwise to a solution of resorcinol (2.75 g. 0.025 mole) and 3,4-dichloro-alpha,alpha,alpha-trifluorotoluene (10.75 g. 0.05 mole) in sulfolane (125 ml) at 150-160 C., with stirring. When the addition is complete, the strongly colored reaction mixture is stirred at 150-160 C. overnight, then cooled, diluted with benzene (200 ml), and washed cautiously with water (700 ml). Hexane (200 ml) is added and the mixture washed with water (600 ml), dilute sulfuric acid (600 ml), dilute sodium hydroxide solution (600 ml), and water (600 ml), dried, and the solvent removed to give 1,3-bis(2-chloro-alpha,alpha,alpha-trifluoro-p-tolyloxy)benzene (8.6 g. 65%) b.p. 160-70 C./0.1 mm.

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

Reference:
Patent; Rohm and Haas Company; US31455; (1983); E1;; ; Patent; Rohm and Haas Company; US4063929; (1977); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 16793-91-2, Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 16793-91-2, name is 2-Chlorophenethyl Bromide, This compound has unique chemical properties. The synthetic route is as follows.

Compound 28. 1 -(2-chlorophenethyl)-4-(2-methoxyphenethyl)piperidine A 250 mL round bottom flask was equipped with a magnetic stir bar, and then charged with 5 grams (0.0537 mol) of 4-picoline, 8.77 grams (0.0644 mol) of 2- methoxybenzaldehyde, and 50 ml of acetic anhydride. The reaction mass was heated to reflux and maintained at that temperature for 72 hours. The reaction mixture was then cooled to room temperature, and subjected to silica chromatography. Yield of (E)-4-(2- methoxystyryl)pyridine was 7.15 grams (63%). The 7.15 grams of (E)-4-(2- methoxystyryl)pyridine was then charged into a 500 mL hydrogenation flask, to which was added 100 mL of acetic acid as well as 50 mg of Pt02. The reaction mass was subjected to 45 psi of hydrogen gas, and allowed to react at room temperature for 16 hours. The reaction mixture was then filtered through a pad of celite, evaporated, basified with aqueous Na2C03 solution, and extracted with dichloromethane. The combined extraction solvents were removed under reduced pressure via rotovap. The residue was then subjected to silica chromatography, yielding 6.1 grams (82.1 % yield) of 4-(2-methoxyphenethyl)piperidine. A 100 mL round bottom flask equipped with a magnetic stir bar was then charged with 1.0 grams of 4-(2-methoxyphenethyl)piperidine (0.0046 mol), 1 .41 grams of 2- chlorophenethyllbromide (0.0064 mol), 1.87 grams of K2C03 (0.0135 mol), and 20 mL of DMF as solvent. The reaction mass was then heated to 70 C for 24 hours. The excess DMF was removed via reduced pressure, partitioned with water and dichloromethane, the organic layer separated; excess solvent removed under reduced pressure and the residue was subjected to silica chromatography. Yield of l-(2-chlorophenethyl)-4-(2- methoxyphenethyl)piperidine was 1.12 grams (68.0% yield). 1H NMR (300 MHz, CDC13) delta 1.40-1.62 (m, 7H), 2.41-2.75 (m, 10H), 3.84 (s, 3H), 6.92-7.73 (m, 8H) ppm.

The chemical industry reduces the impact on the environment during synthesis 2-Chlorophenethyl Bromide. I believe this compound will play a more active role in future production and life.

Reference:
Patent; UNIVERSITY OF KENTUCKY RESEARCH FOUNDATION; CROOKS, Peter, A.; DWOSKIN, Linda, P.; CULVER, John; NICKELL, Justin, R.; ZHENG, Guangrong; WO2014/144064; (2014); A2;,
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Chlorides – an overview | ScienceDirect Topics

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 6579-54-0, name is 2,6-Dichlorobenzenesulfonyl chloride, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 6579-54-0

General procedure: Benzenesulfonyl chloride (1 mmol) in butanone (5 mL) was heated with stirring to 40C, and cyanamide solution (50%)was added dropwise, then the temperature was raised to 60C and stirring continued for 3 h. The compound 7 (0. 8 mmol)was added and heated to 80C for 3 h. After cooling to 40C, the reaction mixture was poured into cold water while stirring, white crystals or powders were precipitated, filtered,washed with water, and dried. Analytically pure samples were obtained by recrystallization from aqueous ethanol.

According to the analysis of related databases, 6579-54-0, the application of this compound in the production field has become more and more popular.

Reference:
Article; Li, Jie; Zheng, Tu-Cai; Jin, Yi; Xu, Jian-Guo; Yu, Jian-Gang; Lv, Yan-Wen; Chemical and Pharmaceutical Bulletin; vol. 66; 1; (2018); p. 55 – 60;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 3460-24-0, These common heterocyclic compound, 3460-24-0, name is 1,4-Dibromo-2-chlorobenzene, 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.

1,4-Dibromo-2-Chloro-Benzene 1eq(45.8 g), 2-aminophenylboronic acid 2eq (46.5 g), Pd (PPh3) 4 5 mol% (9.8 g) and K2CO3 2eq (46.9 g) were dissolved in toluene 1-fold, 550 ml) and distilled water (5 times as much as K2CO3, 235 ml), and the mixture was stirred under reflux for 18 hours under a nitrogen stream. After completion of the reaction, the reaction mixture was extracted with toluene and distilled water. The organic layer was dried with magnesium sulfate (MgSO4) and filtered, and the filtrate was concentrated under reduced pressure. The organic solution was removed, and the residue was subjected to silica gel column chromatography with hexane: dichloromethane = 7: 3 (v / v), and the resulting solid was recrystallized from dichloromethane and acetone to obtain intermediate d-1 (23.5 g, Y = 47%).

The synthetic route of 3460-24-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Samsung SDI Co., Ltd; Jang Gi-po; Kim Jun-seok; Lee Seung-jae; Hong Jin-seok; Kim Chang-u; Jeong Seong-hyeon; Kim Yeong-gwon; Ryu Eun-seon; Jeong Ho-guk; (30 pag.)KR2017/111538; (2017); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 67279-24-7, 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. 67279-24-7 name is 1,4-Dichloro-5,6,7,8-tetrahydrophthalazine, 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 1,4-dichloro-5,6,7,8-tetrahydro-phthalazine (compound 25, 100 mg, 0.492 mmol) in NMP (3 mL) is added 1-[5-trifluoromethyl)-pyrid-2-yl)-piperazine (114 mg, 0.492 mmol) followed by triethyl amine (218 muL, 1.57 mmol). The mixture was heated in a microwave reactor for 140 C. for 60 min. Water was added to the reaction mixture and extracted with EtOAc. The combined arganic extracts were washed with water, brine, dried over Na2SO4, filtered and concentrated. The crude product was purified by flash chromatography on silica gel (EtOAc/heptane 10% to 70%) to yield 96 mg (49%) of the title compound.1H NMR (400 MHz, CD2Cl2) delta=8.41 (s, 1H), 7.73 (dd, J=9.0 Hz, 2.5 Hz, 1H), 6.79 (d, J=9.0 Hz, 1H), 3.85 (m, 4H), 3.40 (m, 4H), 2.76-2.68 (m, 4H), 1.93 (m, 2H), 1.80 (m, 2H).HR MS (m/z, MH+) meas. 398.1359.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1,4-Dichloro-5,6,7,8-tetrahydrophthalazine, and friends who are interested can also refer to it.

Reference:
Patent; Novartis AG; US2010/41663; (2010); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics