Month: May 2021

Related Products of 928-50-7,Some common heterocyclic compound, 928-50-7, name is 5-Chloropent-1-ene, molecular formula is C5H9Cl, 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 an oven-dried two-neck round-bottom flask equipped with a condenser and a magnetic stirrer were successively added oxime1b(193 mg, 0.92 mmol), xanthate20(75 mg, 0.46 mmol) and the desired chloroolefin21b(202 mg, 1.93 mmol) in benzene (5 mL). Argon was then bubbled directly into the flask for 30 min. (Bu3Sn)2(0.3 mL, 0.58 mmol) was then injected and the flask was heated to 60C. After 5min., DTBHN was added. After total consumption of the starting material, the resulting mixture was concentrated in vacuo and purified by silica gel chromatography (Petroleum ether/EtOAc 90-10->80:20) to afford the desired product22bas a yellow oil (63 mg, 52%).Rf = 0.32 (Petroleum ether/EtOAc90:10)IR (neat, NaCl)nmax(cm-1) 2953, 2247, 1453, 1378, 1248, 1144, 1089, 1004, 837.1H-NMR (300 MHz, CDCl3)delta(ppm) 7.23 (d,J= 7.5 Hz, 1 H), 5.04(s, 2 H), 3.63 (t,J= 8.3 Hz, 2 H), 3.50 (t,J= 6.4 Hz, 2 H), 2.47-2.27 (m, 3 H), 1.87-1.49 (m, 6 H), 0.90 (t,J= 8.3 Hz, 2 H), -0.02(s, 9 H).13C-NMR (75 MHz, CDCl3)delta(ppm) 152.6, 119.0, 96.7, 66.0, 44.9, 38.6, 29.6, 29.5, 28.1, 17.9, 14.9, -1.5.HRMS (ESI) calcd for C14H27ClN2O2SiNa [M+Na+]:341.1422,found:341.1431.

The synthetic route of 928-50-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Landais, Yannick; Robert, Frederic; Godineau, Edouard; Huet, Laurent; Likhite, Nachiket; Tetrahedron; vol. 69; 47; (2013); p. 10073 – 10080;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 348-65-2, 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. 348-65-2 name is 5-Chloro-2,4-difluoroaniline, 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.

In a 500 mL two-neck round-bottomed flask equipped with magnetic stirrer, 5-chloro-2,4-difluoroaniline (10 g,61 mmol, 1 eq) was dissolved in DCM (150 mL, HPLC grade). Then, prop-2-ynoic acid (5.5 g, 78 mmol, 1.3 eq) wasadded dropwise (the salt of the amine appeared). Next EDC·HCl (14 g, 78 mmol, 1.3 eq) was added in several portions(during the addition the reaction flask was cooled in an ice bath to maintain the room temperature. After full addition ofEDC·HCl, the reaction mixture was stirred for an additional 1 h at room temperature. After that time 150 ml of water wasadded and the mixture was transferred into a separatory funnel. The phases were separated. The water phase wasextracted twice with the DCM (2 x 100 mL). The organic fractions were combined, washed with brine, dried over MgSO4and concentrated to approximately 50 ml in vacuo, resulting a thick suspension. The solids were filtered and dried tofurnish 8 g of cream crystals. The filtrate was concentrated and then purified by flash chromatography (n-hexane/AcOEt;8:1 ? 5:1) giving additional 4.4 g of the amide C-6F. As a result, expected amide C-6F was obtained as a cream solid(12.4 g, 94 % yield, 100 % purity according to UPLCMS analysis).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Chloro-2,4-difluoroaniline, and friends who are interested can also refer to it.

Reference:
Patent; Adamed sp. z o.o.; FEDER, Marcin; MAZUR, Maria; KALINOWSKA, Iwona; JASZCZEWSKA, Joanna; LEWANDOWSKI, Wojciech; WITKOWSKI, Jakub; JELEN, Sabina; WOS-LATOSI, Katarzyna; (56 pag.)EP3511334; (2019); A1;,
Chloride – Wikipedia,
Chlorides – 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. 60956-24-3, name is 1,2-Dibromo-4-chlorobenzene, A new synthetic method of this compound is introduced below., Recommanded Product: 1,2-Dibromo-4-chlorobenzene

General procedure: 2-aminobenzenethiol (10 g, 80mmol), 3, 4-difluorobenzonitrile (11.12, 80mmol) and ferric citrate (19.59g, 80mmol) were added in DMF (50.00 mL) at 25-30 0C. The reaction mixture was heated to 110C. Reaction mixture was monitored for the synthesis of compound 3 by TLC. (2ml of reaction mixture was withdrawn and separated in ethylacetate and water. Ethyl acetate solution concentrated and crystallised in isopropyl ether to give compound 3 for characterization). After completion of reaction by TLC, powdered potassium carbonate (16.58 g, 120mmol) was added to the solution and stirred for 1 hr. The mixture was heated to 110C till completion by TLC. After completion of reaction, the mass was cooled to 25-30 C. Ethyl acetate (150 mL) and DM water (150 mL) were added. Layers separated. Organic layer washed with water (150 mL), dried over sodium sulfate and concentrated. Isopropyl ether (IPE; 150 mL) was added to the slurry, filtered, washed with IPE. Dried under vacuum at 50 C (16.84g, 94%)

The synthetic route of 60956-24-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Das, Tonmoy Chitta; Quadri, Syed Aziz Imam; Farooqui, Mazahar; Letters in Organic Chemistry; vol. 16; 1; (2019); p. 16 – 24;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 1298031-94-3, name is 8-Bromo-6-chloro-2-methylimidazo[1,2-b]pyridazine, 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 1298031-94-3, SDS of cas: 1298031-94-3

8-Bromo-6-chloro-2-methylimidazo[l,2-b]pyridazine (1.2 g, 4.9 mmol) was combined with Zn(CN)2 (850 mg, 7.3 mmol) and Pd(PPh3)4 (570 mg, 0.49 mmol ) in DMF (20 mL). The reaction vessel was degassed and then charged with nitrogen three times. The mixture was stirred at 100 C for 1 h under muwave irradiation. The mixture was partitioned between EtOAc and H20. The organic layer was washed with brine, dried over Na2S04, filtered and concentrated. The residue was chromatographed on silica gel, eluting with 0-35% EtOAc in petroleum ether to yield 6- chloro-2-methylimidazo [l,2-b]pyridazine-8-carbonitrile (0.5 g, 53%). MS m/z 193.0, 195.0 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 8-Bromo-6-chloro-2-methylimidazo[1,2-b]pyridazine, and friends who are interested can also refer to it.

Reference:
Patent; PTC THERAPEUTICS, INC.; WOLL, Matthew, G.; AMEDZO, Lukiana; BABU, Suresh; BARRAZA, Scott, J.; BHATTACHARYYA, Anuradha; KARP, Gary, Mitchell; MAZZOTTI, Anthony, R.; NARASIMHAN, Jana; PATEL, Jigar; TURPOFF, Anthony; XU, Zhenrong; (251 pag.)WO2018/226622; (2018); A1;,
Chloride – Wikipedia,
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. 16429-44-0, name is 5-Bromo-3-chlorobenzene-1,2-diamine, This compound has unique chemical properties. The synthetic route is as follows., category: chlorides-buliding-blocks

5-bromo-7-chloro-1H-benzimidazole A solution of 5-bromo-3-chlorobenzene-1,2-diamine (2 g, 9.03 mmol) in formic acid (30 ml) was heated at reflux for 16 hours. The reaction progress was monitored by LCMS. Reaction mixture was concentrated under vacuum to yield brown oil. The mixture was extracted by EtOAc from a saturated aqueous solution of NaHCO3, dried over MgSO4 and evaporated under vacuum to yield 5-bromo-7-chloro-1H-benzo[d]imidazole as a pale yellow solid. Mass spectrum (EI, m/z): Calculated for C7H4BrClN2, 232.5 (M+H), found 233.0.

According to the analysis of related databases, 16429-44-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Janssen Pharmaceutica NV; Zhang, Xuqing; Macielag, Mark J.; (184 pag.)US2019/47960; (2019); A1;,
Chloride – Wikipedia,
Chlorides – 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. 87-63-8, name is 2-Chloro-6-methylaniline, A new synthetic method of this compound is introduced below., Product Details of 87-63-8

Ethyl vinyl ether compound of formula-5 (500 gm) was slowly added to oxalyl chloride compound of formula-4 (670 ml) at 10-15C. Raised the temperature of the reaction mixture to 25-30C and stirred for 12 hours at the same temperature. Heated the reaction mixture to 120- 125C and stirred for 90 minutes at the same temperature. Cooled the reaction mixture to 30-35 C and (E)-3-ethoxyacryloyl chloride compound of formula-7 was collected by fractional distillation. Added tetrahydrofuran (1160 ml) to the obtained compound of formula-7 and cooled the reaction mixture to 10-15C. Slowly added a solution of 2-methyl-6-chloroaniline compound of formula-9 (290 gm), pyridine (248ml) & tetrahydrofuran (1160 ml) to the reaction mixture at same temperature. Raised the temperature of the reaction mixture to 25-30C and stirred the reaction mixture for 4 hours at the same temperature. Cooled the reaction mixture to 5-10C and acidified the reaction mixture using aqueous HC1 solution. Water and ethyl acetate were added to the reaction mixture and stirred for 10 minutes. Separated the both aqueous & organic layers and extracted the aqueous layer with ethyl acetate. Washed the total organic layer with aqueous sodium bicarbonate solution followed by with water. Distilled off the solvent completely from the organic layer under reduced pressure. Ethyl acetate was added to the obtained compound at 25-30C and cooled the reaction mixture to 0-5C. Stirred the reaction mixture for 2 hours at the same temperature. Filtered the precipitated solid, washed with chilled ethyl acetate and dried the material to get the title compound. Yield: 300 gm; M.R.: 160-164C; HPLC Purity: 99.66%.

The synthetic route of 87-63-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MSN LABORATORIES PRIVATE LIMITED; THIRUMALAI RAJAN, Srinivasan; ESWARAIAH, Sajja; MADHUSUDHAN, Gutta; SEETHA RAMA SARMA, Peri; KHALIL AHAMED, Mogal; (38 pag.)WO2017/2131; (2017); A1;,
Chloride – Wikipedia,
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. 54730-35-7, name is 3,5-Dichloro-4-methylaniline, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 3,5-Dichloro-4-methylaniline

To a solution of HBr (40percent in water, 3.4 mL) in water (3 mL) was added 3,5-dichloro-4-methylaniline (2.0 g, 11.4 mmol). The suspension was heated to dissolve as much of the solid as possible, then the mixture was cooled to 0 degrees C. and a solution of sodium nitrite (0.83 g, 12.0 mmol) in water (2 mL) was added dropwise (temperature was maintained <5 degrees C.). After 10 min., the diazonium salt mixture was poured into a mixture of CuBr (8.2 g, 57.0 mmol) in 40percent aq. HBr (13 mL) at room temperature. The resulting mixture was heated at 50 degrees C. for 45 min., then cooled to room temperature. The mixture was diluted with water and extracted with dichloromethane (3.x.). The combined organics were filtered through Celite and dried over sodium sulfate, then concentrated in vacuo to provide the product, 5-bromo-1,3-dichloro-2-methylbenzene, as an orange solid. 1H NMR (400 MHz, CDCl3) delta 2.40 (s, 3H), 7.43 (s, 2H). Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 54730-35-7. Reference:
Patent; Diaz, Caroline Jean; Haffner, Curt Dale; Speake, Jason Daniel; Zhang, Cunyu; Mills, Wendy Yoon; Spearing, Paul Kenneth; Cowan, David John; Green, Gary Martin; US2010/222345; (2010); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

69411-05-8, name is 3-Chloro-5-trifluoromethylaniline, 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. HPLC of Formula: C7H5ClF3N

General procedure: To a solution of 3-chloroaniline 5a (37mg, 0.33mmol) in H2O (10mL cooled to-5C) was added 0.2mL of 2N HCl (aq.). To the resulting acidic aniline solution, 1N solution of sodium nitrite (0.33mL, 0.33mmol) was added dropwise to generate the aryldiazonium salt solution 6a. To the aryldiazonium salt solution was added sodium acetate (54mg, 0.66mmol), followed by 1mL solution of crude 3-oxo-3-(3-phenylisoxazol-5-yl)propanenitrile 4a (88mg, 0.33mmol) in ethanol. The reaction mixture was stirred at 0C for 5min, and then poured onto H2O (10mL) and extracted with ethyl acetate (20mL). The organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by short column chromatography on silica gel, eluting with hexane/ethyl acetate (2/1) to provide the desired product 7 (67mg, 50% for two steps from 3a) as a yellow solid.

The synthetic route of 69411-05-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Ye, Na; Zhu, Yingmin; Liu, Zhiqing; Mei, Fang C.; Chen, Haiying; Wang, Pingyuan; Cheng, Xiaodong; Zhou, Jia; European Journal of Medicinal Chemistry; vol. 134; (2017); p. 62 – 71;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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. 69411-05-8, name is 3-Chloro-5-trifluoromethylaniline belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. COA of Formula: C7H5ClF3N

A 1.0 M solution of lithium bis(trimethyldisilyl)amide in THF (i3 mL, i2 mmol, 2.0 equiv) was added through an addition funnel at 10-i5 C to a solution of 3-chloro-5-(trifluoromethyl)aniline (i5 g, 78 mmol, i.2 equiv) in THF (i3 mL). The mixture was allowed to stir at room temperature for 20 mm and a solution of crude trans-i ?-tert-butyl-4?-ethyl-3 -iodo-2-oxo-[ i ,3 ?-bipiperidine]- i ?,4?- dicarboxylate 9 (3.7 g, 65 mmol, i.0 equiv) in THF (i3 mL) was added through an addition funnel at iO-i5 C over 30 mm. After addition, the reaction was allowed to stir at the temperature for 30 mm. Upon completion, the reaction was cooled to 5 C and quenched slowly with water (iO mL), keeping the temperature below 20 C. The quenched reaction was extracted with EtOAc (2 x 30 mL). The combined organic layers were washed with saturated brine (30 mL), dried (Na2504), filtered, and concentrated in vacuo. The resulting crude product was purified over silica gel eluting with a gradient of iO% to 75% of EtOAc in heptanes to give the desire product iO. ESIMS (M+H-56): 463.i. ?H NMR (400 MHz, CDC13) 5. 6.92 (s, iH), 6.7i-6.69 (m, 2H), 4.i7- 4.06 (m, 4H), 3.78-3.68 (m, 2H), 3.46-3.36 (m, 3H), 3.23-3.07 (m, 2H), 2.73-2.65 (m, iH), 2.44-2.37 (m, iH), 2.03-i.85 (m, 3H), i.7i-i.6i (m, 2H), i.46 (s, 9H), i.27-i.i9 (m, 3H).

The synthetic route of 69411-05-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BIOGEN MA INC.; SUNESIS PHARMACEUTICALS, INC.; MACPHEE, J. Michael; NEUMAN, Linda L.; (89 pag.)WO2018/17153; (2018); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 1298031-94-3, 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 1298031-94-3 as follows.

Preparation of intermediate 31 : 6-Chloro-3-iodo-2-methyl-8-morpholin-l-yl- imidazo [ 1 ,2-&”|pyridazineN-Iodosuccinimide (0.95 g, 4.36 mmol) was added to a stirred solution of a mixture 70/30 of intermediate 3 (0.95 g, 3.36 mmol) in a mixture of dichloromethane (9 ml) and acetic acid (1 ml). The mixture was stirred at room temperature for 16 h. and then washed with a saturated solution of sodium carbonate. The organic layer was separated, dried (Na2S04), filtered and the solvents evaporated in vacuo to yield 1.33 g of crude product. A portion of this crude product (0.5 g) was dissolved in acetonitrile (8 ml) and morpholine (0.140 ml, 1.6 mmol) and N,N-diisopropylethylamine (0.393 ml, 2.29 mmol) were added. The mixture was stirred at 150 C for 10 min in a sealed tube, under microwave irradiation. The mixture was diluted with ethyl acetate and washed with a saturated solution of ammonium chloride. The organic layer was separated, dried (Na2S04), filtered and the solvents evaporated in vacuo to yield intermediate 31 (0.53 g, 69%).

According to the analysis of related databases, 1298031-94-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; PASTOR-FERNANDEZ, Joaquin; BARTOLOME-NEBREDA, Jose, Manuel; MACDONALD, Gregor, James; CONDE-CEIDE, Susana; DELGADO-GONZALEZ, Oscar; VANHOOF, Greta, Constantia, Peter; VAN GOOL, Michiel, Luc, Maria; MARTIN-MARTIN, Maria, Luz; ALONSO-DE DIEGO, Sergio-Alvar; WO2011/51342; (2011); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics