Category: chlorides-buliding-blocks

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 69411-05-8 as follows. Quality Control of 3-Chloro-5-trifluoromethylaniline

Intermediate E (120 mg, 0.25 mmol), 3-chloro-5-(trifluoromethyl)benzenamine (49 mg, 0.27 mmol) and DMAP (16 mg, 0.125 mmol) were dissolved in THF (15 mL). The reaction mixture was heated to 85 C for 16 hours. The solvent was removed and the crude product was purified by column chromatography (DCM: methanol 100/0 to 98/2) to give 5-((4-((4-(3-(3-chloro-5- (trifluoromethyl)phenyl)ureido)phenyl)(methyl)amino)pyrimidin-2-yl) amino)-N,2- dimethylbenzamide (38 mg, 26%) as a white solid. LCMS (method B): 2.74 min [MH]+=584.1. 1H NMR (400 MHz, DMSO-d6) delta ppm 2.23 (s, 3 H) 2.74 (d, J=4.8 Hz, 3 H) 3.41 (s, 3 H) 5.77 (d, J= 7.0 Hz, 1 H) 7.07 (d, J= 8.4 Hz, 1 H) 7.28 (d, J= 8.8 Hz, 2 H) 7.43 (s, 1 H) 7.59 (d, J= 8.8 Hz, 2 H) 7.67 (dd, J=8.4 2.0 Hz, 1 H) 7.87 (m, 4 H) 8.11 (m, 1 H) 9.15 (s, 1 H) 9.19 (s, 1 H) 9.37( s, 1 H).

According to the analysis of related databases, 69411-05-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CATALYST THERAPEUTICS PTY LTD; LESSENE, Guillaume Laurent; GARNIER, Jean-Marc; CUZZUPE, Anthony Nicholas; FEUTRILL, John Thomas; CZABOTAR, Peter Edward; SHARMA, Pooja; (142 pag.)WO2016/127213; (2016); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 29027-17-6, These common heterocyclic compound, 29027-17-6, name is 2-Chloro-3-methylaniline, 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.

2-Chloro-1-isothiocyanato-3-methylbenzene To 2-chloro-3-methylaniline (1 equiv.) in DCM/water (0.5 M, 1/2) at 0 C. was added NaOH (3 equiv.), the solution was stirred at 0 C. for 5 min, then CSCl2 (3 equiv.) was added. The reaction was stirred at room temperature overnight. The reaction was extracted with DCM. The combined organic layers were concentrated to dryness to give crude 2-chloro-1-isothiocyanato-3-methylbenzene. The crude product was purified by column chromatography on silica gel with petroleum ether to give 2-chloro-1-isothiocyanato-3-methylbenzene (61%) as a colorless oil. 1H NMR (400 MHz, CDCl3) delta ppm: 7.19-7.09 (m, 3H), 2.42 (s, 3H).

Statistics shows that 2-Chloro-3-methylaniline is playing an increasingly important role. we look forward to future research findings about 29027-17-6.

Reference:
Patent; Signal Pharmaceuticals, LLC; Alexander, Matthew; Bahmanyar, Sogole; Hansen, Joshua; Huang, Dehua; Hubbard, Robert; Jeffy, Brandon; Leisten, Jim; Moghaddam, Mehran; Raheja, Raj K.; Raymon, Heather; Schwarz, Kimberly; Sloss, Marianne; Torres, Eduardo; Tran, Tam Minh; Xu, Shuichan; Zhao, JingJing; Boylan, John Frederick; (317 pag.)US2016/96841; (2016); 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. 348-65-2, name is 5-Chloro-2,4-difluoroaniline, A new synthetic method of this compound is introduced below., Recommanded Product: 5-Chloro-2,4-difluoroaniline

j00283j A solution of 5-chloro-2,4-difluoro-aniline (5.0 g, 31 mmol) and potassium 0-ethyl carbonodithioate (12 g, 73 mmol) in 1V N-dimethylformamide (50 mL) was stirred at 130 C for 16hours. On completion, the reaction was cooled to room temperature, and iN hydrochloric acid (100 mL) was added. The mixture was stirred for 1 hour, resulting in formation of a solid. The solid was collected by filtration, washed with water (2×100 mL) and dried under vacuum to give compound B- 5(5.6 g, 79% yield) as a white solid. LCMS (B): tR=0.759 mi, (ES)m/z(M+H)=220.1.

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; FORUM PHARMACEUTICALS, INC.; ACHARYA, Raksha; BURNETT, Duane, A.; BURSAVICH, Matthew, Gregory; COOK, Andrew, Simon; HARRISON, Bryce, Alden; McRINER, Andrew, J.; (267 pag.)WO2017/69980; (2017); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 1000577-58-1, name is 1-Bromo-2,3-dichloro-5-fluorobenzene, 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 1000577-58-1, Recommanded Product: 1000577-58-1

A mixture of l-bromo-2,3-dichloro-5-fluorobenzene (3.1304 g, 12.94 mmol), bis(pinacolato)diboron (5.7397 g, 22.38 mmol), potassium acetate (3.9788 g, 40.1 mmol) in DMSO (60 mL) was stirred at room temperature for about 30 min. The mixture was degassed with nitrogen for a few minutes and l ,l’-[bis(diphenylphosphino)ferrocene]dichloro- palladium (II) (0.7953 g, 1.09 mmol) was added. The mixture was degassed again with nitrogen, was heated to 80 oc with stirring and kept at 80 oC for 4 h 20 min. The mixture was cooled to room temperature and poured into ice. The mixture was extracted with ethyl acetate (3 x 150 mL). The combined organic solution was washed with saturated sodium chloride solution (150 mL), dried over anhydrous sodium sulfate, and concentrated. The residue was separated with flash column chromatography on silica gel using ethyl acetate/hexane to afford product as white solid (2.6156 g, Yield: 70%). NMR (500 MHz, Chloroform-d) delta 7.070 (d, J= 3.0 Hz, lH), 7.029 (d, J= 3.0 Hz, 1H), 1.238 (s, 12H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Bromo-2,3-dichloro-5-fluorobenzene, and friends who are interested can also refer to it.

Reference:
Patent; NEKTAR THERAPEUTICS (INDIA) PVT. LTD.; NEKTAR THERAPEUTICS; SHARMA, PANKAJ; KHATRI, VIJAY KUMAR; GU, XUYUAN; SONG, YUAN; SHEN, MICHAEL LIXIN; SAUTHIER, JENNIFER RIGGS; ANAND, NEEL K.; KOZLOWSKI, ANTONI; ODINECS, ALEKSANDRS; RILEY, TIMOTHY A.; REN, ZHONGXU; MU. YONGQI; SHEN, XIAOMING; YUAN. XUEJUN; AURRECOECHEA, NATALIA; O’MAHONY, DONOGH JOHN ROGER; WO2015/92819; (2015); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 167404-32-2, A common heterocyclic compound, 167404-32-2, name is 4-Cyclopropylbenzene-1-sulfonyl chloride, molecular formula is C9H9ClO2S, 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.

Compound 46. Crude compound 45 (13.3 g) was dissolved in 200 mL of acetone and 60 mL of water. Potassium fluoride (7.12 g, 122 mmol) was added and the reaction mixture was stirred overnight at rt. The reaction mixture was diluted with EtOAc and washed with water. The organic layer was dried with Na2SO4, filtered, and concentrated to dryness to give 9.80 g (97%) of crude p-cyclopropyl benzenesulfonyl fluoride (Compound 46).

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; Schering Corporation; US2003/232859; (2003); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 697-88-1,Some common heterocyclic compound, 697-88-1, name is 4-Bromo-2,6-dichloroaniline, molecular formula is C6H4BrCl2N, 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.

Pd (OAc) 2 (186 mg), P (o-Tol) 3 (505 mg), Et3N (1.73 ml), 4-bromo-2,6- dichlorobenzeneamine (2.0 g) and acrylamide (885 mg) were dissolved in MECN (15 ml) and N2 was bubbled through the reaction mixture for at least 20 minutes. Then a cooler was mounted strictly under nitrogen atmosphere. The reaction mixture was heated at 70 C overnight. The reaction mixture was allowed to cool to 20 C and was diluted with CH2CI2 and washed with saturated aqueous NAHC03 (2x) and dried with brine and NA2SO4. The residue was sonicated in diisopropyl ether and filtered off. Yield: 0.55 g of intermediate 18 (30%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Bromo-2,6-dichloroaniline, its application will become more common.

Reference:
Patent; JANSSEN PHARMACEUTICA N.V.; ARTS, Theodora, Joanna, Francisca; JANSSEN, Graziella, Maria, Constantina; JANSSEN, Herwig, Josephus, Margareta; JANSSEN, Jasmine, Josee, Werner; JANSSEN, Paul, Peter, Maria; JANSSEN, Maroussia, Godelieve, Frank; WO2004/74266; (2004); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 327-76-4, name is 1-Chloro-2,4-bis(trifluoromethyl)benzene, 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 327-76-4, HPLC of Formula: C8H3ClF6

[0199] To a solution of 95 (25.0 g, 0.10 mol) in anhy. THF (150 mL) was added NaOCH3 (7.0 g, 0.13 mol) at 0C. The mixture was then heated at 50C for 6 h. After cooling to 25C, the reaction mixture was quenched with sat. NH4C1, diluted with EtOAc, washed with brine, and concentrated in vacuo to afford crude methyl ether 96 (17.93 g, 73%) as a colorless liquid. This product was sufficiently pure to be used directly in subsequent reaction. 1H NMR (400 MHz, CDC13) : 8 7.83 (1H, s), 7.77 (1H, d, J = 8. 4 Hz), 7.09 (1H, d, J= 8.4 Hz), 3.97 (3H, s) ppm. A solution of methyl ether 96 (9.98 g, 0.04 mol) in anhyrous CH2C12 (150 mL) was cooled to-78C and treated with BBr3 (6.0 mL, 0.063 mol). The resultant brown mixture was stirred for 1 h at-78C, and then warmed up to 25C over 4 h, and then quenched with water. The organic layer was separated and washed with sat. NaHCO3 and brine, dried over Na2S04, concentrated to-13 mL in vacuo below 0C and used directly in the following substitution reaction. Take this solution (ca. 1.15 mL) and diluted with DMF (8 mL), and then treated with K2CO3 (1.27 g) and bromide 79 (1.72 g). The resultant mixture was stirred at room temperature for 1 h, diluted with EtOAc, washed with water and brine, dried over Na2S04, and concentrated in vacuum. The residue was purified by flash chromatography (5: 95 EtOAc/hexanes) on silica gel and then recrystallized with 10 % EtOAc/hexanes to give pure ester 97 as a white solid. 1H NMR (400 MHz, DMSO-d6) : No. 8. 60 (1H, d, J= 2.2 Hz), 8.17 (1H, dd, J= 8.6, 2.2 Hz), 7.96 (1H, s), 7.91 (1H, d, J= 8.6 Hz), 7. 84 (1H, d, J= 8.2 Hz), 7.74 (1H, t, J= 7.8 Hz), 7.38 (1H, d, J= 9.0 Hz), 6.40 (1H, s), 4.19 (2H, m), 1.11 (3H, t, J = 7.2 Hz) ppm.

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; METABOLEX, INC.; WO2005/80340; (2005); 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. 2729-36-4, name is 4,5-Dichloro-2-fluoroaniline, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C6H4Cl2FN

In brief, 3,4-Dicliloro-6-fluoroaniline (1 equivalent, prepared as described in U.S. Patent No. 6,126,917) was reacted with 4-chloro-7-fluoro-6-nitroquinazoline (3.5 equivalents, Compound 24, prepared as described hereinabove), in a mixture of iso-propylalcohol/ dichloromethane. After filtration, 4,5-dichloro-2-fluoro-phenyl-(7-fluoro-6-nitro- quinazolin-4-yl)-amine was obtained.

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 2729-36-4.

Reference:
Patent; T.K. SIGNAL LTD.; WO2007/29251; (2007); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 1000572-88-2, 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. 1000572-88-2 name is 2,5-Dibromo-1-chloro-3-fluorobenzene, 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.

An autoclave equipped with a stir bar was charged with 2,5-dibromo- l-chloro-3-fluorobenzene (5.0 g, 17.3 mmol), triethylamine (12.1 mL, 86.7 mmol), bis(diphenylphosphino)ferrocene)palladium(II) Chloride (0.86 mmol, 708 mg) and methanol (100 mL) was degassed with nitrogen for 10 min. Then the container was sealed and filled with CO to 400 psi. The reaction mixture was heated at 100 C with stirring for 12 hours. The reaction mixture was filtered through Celite, washed with MeOH, and the filtrate was concentrated. The crude product was purified by silica gel chromatography (0-10% EtOAc/hexane) to afford the title compound as a colorless oil which solidified in high vacuum (3.06 g, 71% yield). ¾ NMR (400 MHz, CDC13) delta 7.90 (s, 1H), 7.69 (dd, J = 9.0, 1.2 Hz, 1H), 3.99 (s, 3H), 3.95 (s, 3H). LCMS (APCI+) 247.0[M+H]+

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2,5-Dibromo-1-chloro-3-fluorobenzene, and friends who are interested can also refer to it.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; BLENCH, Toby; ELLWOOD, Charles; GOODACRE, Simon; LAI, Yingjie; LIANG, Jun; MACLEOD, Calum; MAGNUSON, Steven; TSUI, Vickie; WILLIAMS, Karen; ZHANG, Birong; WO2012/35039; (2012); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 21397-08-0, name is 2-Chloro-3-fluoroaniline, 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 21397-08-0, Recommanded Product: 21397-08-0

c) 2-Chloro-3-fluorophenylisothiocyanate Into a solution of 2-chloro-3-fluoroaniline (2.61 g, 17.94 mmol) in 50 mL of toluene at room temperature, thiophosgene (2.1 mL, 26.91 mmol) and triethylamine (3.02 mL, 26.91 mmol) was added. The mixture was stirred at room temperature for 16 hours. The mixture was partitioned between ethyl acetate and water. The combined organic layer was then concentrated to give the desired product (2.99 g, 89%). 1H NMR (CDCl3) delta 7.10 (m, 1H), 7.22 (m, 1H).

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; Palovich, Michael R.; Widdowson, Katherine L.; Nie, Hong; US2003/216375; (2003); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics