Category: chlorides-buliding-blocks

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. 2613-34-5, name is 3-Chloro-2,4-difluoroaniline, A new synthetic method of this compound is introduced below., name: 3-Chloro-2,4-difluoroaniline

Exapmle 35 (^-N-(4-((3-Chloro-2,4-difluorophenyl)amino)-7-methoxyquinazolin-6-yl)-4-((4aR,7aS)-tetrahydro- 2H-[l,4]dioxino[2,3-c]pyrrol-6( Step 1) N-(3-chloro-2,4-difluorophenyl)-7-fluoro-6-nitroquinazolin-4-amine A solution of 4-chloro-7-fluoro-6-nitroquinazoline (10.00 g, 44.0 mmol) and 3-chloro-2,4-difluoroaniline (8.40 g, 51.5 mmol) in isopropanol (150 mL) was heated to 70 C and stirred for 5.0 hours. The reaction mixture was then cooled to 25C, and a yellow solid precipitated out. The mixture was filtered. The filtered cake was washed with isopropanol (50 mL) and dried under vacuum to give the title compound as a yellow solid (10.8 g, 69.2%). The compound was characterized by the following spectroscopic data: MS (ESI, pos.ion) m/z : 354.1 [M+H]+.

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; SUNSHINE LAKE PHARMA CO., LTD.; ZHANG, Yingjun; LIU, Bing; LIU, Jinlei; ZHANG, Jiancun; ZHENG, Changchun; WO2014/177038; (2014); A1;,
Chloride – Wikipedia,
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These common heterocyclic compound, 2106-02-7, name is 2-Chloro-4-fluoroaniline, 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. Product Details of 2106-02-7

Step 1: 2-Chloro-4-fluoroaniline (3.0 g, 20.6 mmol) and 4-fluoro-1-bromo benzene (3.6 g, 20.6 mmol) were added to NaOfBu (9.9 g, 103.0 mmol), Pd(OAc)2 (0.231 g, 1.03 mmol) and [HPtBu3][BF4] (0.42 g, 1.4 mmol) suspended in toluene (120 mL). The reaction was then heated to reflux for 18 h, allowed to cool and concentrated to remove toluene. The residue was extracted with dichloromethane (2 X 100 mL), dried (Na2S04), then filtered and the solvent removed under reduced pressure. The crude product was purified by column chromatography using silica gel 230-400 mesh to get the desired colorless product 2-chloro-4-fluoro-A-(4- fluorophenyl)aniline (2.0 g, 41%). GC MS: (Method B) 239.0 (M+H), RT- 4.73 min H NMR (400 MHz, DMSO-d6): delta 7.28 (s, 1H), 7.01-7.16 (m, 5H), 6.89-6.88 (m, 1 H), 5.84 (s, 1H).

The synthetic route of 2-Chloro-4-fluoroaniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK PATENT GMBH; SPANGENBERG, Thomas; (129 pag.)WO2016/827; (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. 51419-59-1, name is p-Tolylmethanesulfonyl chloride, A new synthetic method of this compound is introduced below., Product Details of 51419-59-1

Potassium tert-butoxide (93.8 mg, 836 mumol) was added to a solution of 2-amino-5-(benzyloxy)-N,1-dimethyl-6-oxo-1,6-dihydropyrimidine-4-carboxamide (110 mg, 380 mumol) in THF (10 ml) in DMF (2 ml) [Comment: please check]. After 10 min., the reaction mixture was cooled by an ice bath and then a solution of (4-methylphenyl)methanesulfonyl chloride (93.7 mg, 458 mumol) in THF (2 ml) was added. After 70 min., EtOAc and 1 N NaOH aqueous solution were added. The organic phase was extracted with EtOAc and then with DCM. The combined organic phases were washed with water, and brine, dried over Na2SO4 and evaporated to dryness. Chromatography (silica gel, 0 to 2percent MeOH in DCM) provided the title compound as a pale yellow solid (0.080 g; 46percent). LCMS: m/z=457 (MH+).

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; SAVIRA PHARMACEUTICALS GMBH; EUROPEAN MOLECULAR BIOLOGY LABORATORY; F. HOFFMANN-LA ROCHE AG; BUSCHMANN, Helmut; WOLKERSTORFER, Andrea; SZOLAR, Oliver; HANDLER, Norbert; CUSACK, Stephen; SMITH, Mark; SO, Sung-Sau; US2014/38990; (2014); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 16799-05-6, 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. 16799-05-6, name is 3-Chlorophenethyl Bromide belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example 57; (3R)-1-[2-(3-Chlorophenyl)ethyl]-3-{[2-piperidin-1-yl-2-(2-thienyl)propanoyl]oxy}-1-azoniabicyclo[2.2.2]octane bromide (Isomer 1); (3R)-1-Azabicyclo[2.2.2]oct-3-yl 2-piperidin-1-yl-2-(2-thienyl)propanoate (Example 57b, Isomer 1, 0.5 g) in acetonitrile (3 mL) was treated with 1-(2-bromoethyl)-3-chlorobenzene (0.35 g) and the mixture stirred and heated at 80 C. for 4 h. The mixture was concentrated to dryness, and the residue purified on silica gel eluting with 5% methanol in dichloromethane. The product from the column was triturated with ether to afford title compound as a colourless solid (160 mg).m/e 487 [M]30 1H NMR (400 MHz, DMSO) delta 7.51 (1H, dd), 7.48-7.44 (1H, m), 7.41-7.32 (2H, m), 7.32-7.27 (1H, m), 7.10 (1H, dd), 6.97 (1H, dd), 5.17-5.13 (1H, m), 3.95-3.88 (1H, m), 3.65-3.56 (1H, m), 3.50-3.40 (4H, m), 3.33-3.26 (1H, m), 3.24-3.16 (1H, m), 3.04-2.97 (2H, m), 2.51-2.42 (2H, m), 2.41-2.32 (2H, m), 2.31-2.23 (1H, m), 2.04-1.83 (4H, m), 1.62 (3H, s), 1.56-1.38 (6H, m).; Preparation of Example 57 Bromide; (3R)-1-[2-(3-Chlorophenyl)ethyl]-3-{[2-piperidin-1-yl-2-(2-thienyl)propanoyl]oxy}-1-azoniabicyclo[2.2.2]octane bromide (Isomer 1) Crystalline Form A; (3R)-1-Azabicyclo[2.2.2]oct-3-yl 2-piperidin-1-yl-2-(2-thienyl)propanoate (Example 57b, Isomer 1, 0.5 g) in acetonitrile (3 mL) was treated with 1-(2-bromoethyl)-3-chlorobenzene (0.35 g) and the mixture stirred and heated at 80 C. for 4 h. The mixture was concentrated to dryness, and the residue purified on silica gel eluting with 5% methanol in dichloromethane. The product from the column was triturated with diethyl ether to afford title compound as a colourless solid (160 mg).m/e 487 [M]+ 1H NMR (400 MHz, DMSO) delta 7.51 (1H, dd), 7.48-7.44 (1H, m), 7.41-7.32 (2H, m), 7.32-7.27 (1H, m), 7.10 (1H, dd), 6.97 (1H, dd), 5.17-5.13 (1H, m), 3.95-3.88 (1H, m), 3.65-3.56 (1H, m), 3.50-3.40 (4H, m), 3.33-3.26 (1H, m), 3.24-3.16 (1H, m), 3.04-2.97 (2H, m), 2.51-2.42 (2H, m), 2.41-2.32 (2H, m), 2.31-2.23 (1H, m), 2.04-1.83 (4H, m), 1.62 (3H, s), 1.56-1.38 (6H, m).

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

Reference:
Patent; Ford, Rhonan; Mete, Antonio; Millichip, Ian; Teobald, Barry; US2010/113510; (2010); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 61881-19-4, name is 2,2,2-Trifluoro-N-phenylacetimidoyl chloride, 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 61881-19-4, Recommanded Product: 2,2,2-Trifluoro-N-phenylacetimidoyl chloride

In a flask with a dry inert atmosphere are introduced 260 ml of anhydrous THF, it is cooled to -78C and 225 ml are added of LDA 2M solution in THF/n-heptane at a rate allowing to maintain the temperature under -65C. After this diethylmethylphosphonate (34.25 g, 0.225 mol) is quickly added dropwise dissolved in 30 ml of THF and it is shaken for 30 minutes at -78C. N-phenyltrifluoroacetymidoyl chloride is then added dropwise (46.7 g, 0.225 mol) dissolved in 40 ml of THF and it is left with shaking in the same conditions for 1 hour. A solution is added of 2,4-difluorobenzaldehyde (33.6 g, 0.236 mol) in 40 ml of THF, the cold bath is removed and the temperature is allowed to rise to ambient temperature. It is left shaking overnight in these conditions. The following morning 450 ml of HCl 2N are added and the shaking continued for 24 hours. The THF is removed in the rotovapor and the resulting aqueous solution is extracted with AcOEt ( 2×200 ml), washed with a solution of 5% NaHCO3 and with a saturated NaCl solution, it is dried with sodium sulphate, filtered and the solvent evaporated with the rotovapor. In this way are obtained 54.6 g of a reddish liquid crude that solidifies. The crude is distilled at a pressure of 35 mbar and a fraction is collected of (E)-1,1,1-trifluoro-4-(2,4-difluorophenyl)-3-buten-2-one at 107-14C (43 g, 81%). Melting point : 50-1C IR (KBr, cm-1) : 1717, 1602, 1583, 1277, 1146, 1059, 7061H-RMN (CDCl3) : 6,9 (m, 2H), 7.05 (d, J=16 Hz, 1H), 7,6 (m, 1H), 8.0 (d, J=16Hz, 1H)13C-RMN (CDCl3): 105.1 (t,J=26Hz), 112,6(dd, J=4, 22Hz) , 116.4 (q, J=291Hz), 118.2, 118.5, 131.5 (dd, J=4, 11Hz), 141.5, 162.5 (dd, J=13, 193Hz), 165,7 (dd, J=13, 190Hz), 180 (q, J=36Hz)

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; LABORATORIOS DEL DR. ESTEVE, S.A.; EP1384477; (2004); 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. 2106-04-9, name is 3-Chloro-2-fluoroaniline, A new synthetic method of this compound is introduced below., name: 3-Chloro-2-fluoroaniline

Step 1: Synthesis of 1-(2-amino-4-chloro-3-fluorophenyl)-2-chloroethan-1-one (2) To a stirred solution of AlCl3 (10.0 g, 75.01 mmol) and BCl3 (1M in n-hexane) (74 mL, 75.01 mmol) in CH2Cl2 (80 mL) was added 3-chloro-2-fluoroaniline 1 (9.0 g, 6.18 mmol) followed by a solution of chloroacetonitrile (11.6 g, 153.64 mmol) in CH2Cl2 (20 mL) at 0 C. under inert atmosphere. The reaction mixture was allowed to stir at RT for 30 minutes; heated to reflux temperature and maintained for additional 14 h. The reaction mixture was then cooled to 0 C., added aqueous 3N HCl solution (100 mL) and raised the temperature to reflux and stirred for 3 h. After completion of the reaction by TLC, the reaction mixture was cooled RT, diluted with water (50 mL) and extracted with CH2Cl2 (2*150 mL). The combined organic extracts were dried over Na2SO4, filtered and concentrated under reduced pressure to obtain the crude. The crude was purified by triturating with n-pentane to afford compound 2 (4.5 g, 33%) as an off-white solid. 1H NMR (500 MHz, DMSO-d6): delta 7.61 (d, J=9.0 Hz, 1H), 7.35 (br s, 2H), 6.72 (d, J=9.0 Hz, 1H), 5.06 (s, 2H).

The synthetic route of 2106-04-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PHARMAKEA, INC.; Evans, Jillian Frances; US9051320; (2015); B1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 36556-52-2, 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. 36556-52-2, name is 2,3-Dichloro-4-fluoroaniline belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

EXAMPLE 67 7-[(2,3-dichloro-4-fluorophenyl)amino]-5-{[2-methoxy-4-(piperazin-l – yl)phenyl]amino}pyrido[3,4-d]pyridazin-4-ol EXAMPLE 67A tert-buty ] 4-(4-(7-(2,3-dichloro-4-fluorophenylamino)-4-oxo-3,4-dihydropyrido[3,4- c/|py ndazin-5-ylamino)-3-metho.xyphenyl)piperazine- l -carbox late A mixture of EXAMPLE 24A ( 162 mg, 0.33 mmol), 2,3-dichloro-4- fluorobenzenamine (90 mg, 0.50 mmol), tris(dibenzylideneacetone)dipalladium (3 1 mg, 0.03 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthenexanthene (20 mg, 0.03 mmol) and potassium 2-methylpropan-2-olate (1 12 mg, 1 mmol) in 2-methylpropan-2-ol (2 mL) was degassed with nitrogen twice and stirred in a sealed tube at 130C for 15 hours. After cooling to ambient temperature, the solution was concentrated and the residue was purified by flash chromatography on silica gel eluting with 100/1 dichloromethane/methanol to give the title compound. MS: 630 (M + H+).

The synthetic route of 2,3-Dichloro-4-fluoroaniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ABBOTT LABORATORIES; ABBOTT LABORATORIES TRADING (SHANGHAI) COMPANY, LTD.; VASUDEVAN, Anil; PENNING, Thomas Dale; CHEN, Huanming; LIANG, Bo; WANG, Shaohui; ZHAO, Zhongqiang; CHAI, Dikun; YANG, Leifu; GAO, Yingxiang; WO2012/97682; (2012); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 104-11-0, name is 1-(4-Chlorophenyl)-N-methylmethanamine, 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 104-11-0, Quality Control of 1-(4-Chlorophenyl)-N-methylmethanamine

General procedure: A solution of 0.17g (1.40mmol) of N-benzylmethylamine, 0.20g (1.40mmol) of K2CO3 and 0.40g of (R,S)-3(4-bromobutyl)-5-phenyloxazolidin-2-one 23 in ACN was allowed to stirring under reflux for 6-12h and monitored by TLC until the reaction was completed. The hot solution was filtered and concentrated in vacuo to afford 0.29g (85.0mmol) of a chromatography pure yellow oil 2a.

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, 1-(4-Chlorophenyl)-N-methylmethanamine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Zampieri, Daniele; Vio, Luciano; Fermeglia, Maurizio; Pricl, Sabrina; Wuensch, Bernhard; Schepmann, Dirk; Romano, Maurizio; Mamolo, Maria Grazia; Laurini, Erik; European Journal of Medicinal Chemistry; vol. 121; (2016); p. 712 – 726;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 2533-69-9, A common heterocyclic compound, 2533-69-9, name is Methyl 2,2,2-trichloroacetimidate, molecular formula is C3H4Cl3NO, 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.

General procedure: Preparation of 2-methyl-6-nitro-2H-indazole (5d). To a stirred mixture of 6-nitro-1H-indazole (1.0 g, 0.0061 mmol) in dichloromethane (25.0 mL) was added trifluoromethanesulfonic acid (0.54 mL, 0.0061 mmol), stirred for 5-10 min at 25-35 C. To this mixture was added methyl 2,2,2,-trichlroacetimidate (2.69 g, 0.015 mmol) at room temperature. The reaction mixture was stirred at room temperature for 16-18 h under N2. After reaction completion, chilled saturated NaHCO3 solution was added. The aqueous and organic phases were separated. Aqueous phase was extracted with dichloromethane 10 mL. Combined organic layers were washed with DM water (2 × 10 mL). Organic layer was dried over anhydrous Na2SO4, filtered, and evaporated completely under vacuum to obtain 2-methyl-6-nitro-2H-indazole (1.03 g, 95.0%) as a yellow solid.

The synthetic route of 2533-69-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Baddam, Sudhakar Reddy; Uday Kumar; Panasa Reddy; Bandichhor, Rakeshwar; Tetrahedron Letters; vol. 54; 13; (2013); p. 1661 – 1663;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 174913-12-3, 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. 174913-12-3 name is 1-Bromo-3-chloro-5-methoxybenzene, 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.

Step 2: 1 -Bromo-2,3-dichloro-5-methoxybenzene. To a solution of 1 -bromo-3-chloro-5-methoxybenzene (300 mg, 1 .35 mmol, 1 equiv.) in DMF (5 ml_) was added trichloro-1 ,3,5-triazinane-2,4,6-trione (1 15 mg, 0.49 mmol, 0.36 equiv.) and the reaction was stirred at 50 C for 3 h. The reaction mixture was concentrated and the crude product was purified by column chromatography (Heptane/EtOAc 100 %? 20: 1) to afford the desired product as a white solid (253 mg, 73 %). LCMS [M+H]+ 254; 1 H NMR (400 MHz, CD3CI) delta 7.09 (1 H, d, J = 3.0 Hz), 6.97 (1 H, d, J = 3.0 Hz), 3.77 (3H , s).

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

Reference:
Patent; THOMAS HELLEDAYS STIFTELSE FOeR MEDICINSK FORSKNING; SCOBIE, Martin; WALLNER, Olov; KOOLMEISTER, Tobias; VALLIN, Karl Sven Axel; HENRIKSSON, Carl Martin; HOMAN, Evert; HELLEDAY, Thomas; JACQUES, Sylvain; DESROSES, Matthieu; JACQUES-CORDONNIER, Marie-Caroline; FISKESUND, Roland Julius Yu; (359 pag.)WO2015/187089; (2015); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics