Category: 363-51-9

Reference of 363-51-9, A common heterocyclic compound, 363-51-9, name is 2-Chloro-6-fluoroaniline, molecular formula is C6H5ClFN, 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: N, N-Diisopropylethylamine (1.86 g, 18.41 mmol) was added slowly to a stirred solution of 2, 6-dichloroaniline (2 g, 12.34 mmol) in DCM (25 mL) at room temperature and then cooled to 0 oC. Then, thiophosgene (11.4 g, 13.55 mmol) was added dropwise at that temperature and further stirred at room temperature for 3-4 h. After the reaction completion, the reaction mixture was diluted with water and extracted with DCM. The organic portion was dried over Na2SO4, concentrated and purified by flash column using 5% EtOAc in hexane to afford 1, 3-dichloro-2-isothiocyanatobenzene (1.75 g) in 70% yield.

The synthetic route of 363-51-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Muthukaman, Nagarajan; Tambe, Macchindra; Deshmukh, Sanjay; Pisal, Dnyandeo; Tondlekar, Shital; Shaikh, Mahamadhanif; Sarode, Neelam; Kattige, Vidya G.; Pisat, Monali; Sawant, Pooja; Honnegowda, Srinivasa; Karande, Vikas; Kulkarni, Abhay; Behera, Dayanidhi; Jadhav, Satyawan B.; Sangana, Ramchandra R.; Gudi, Girish S.; Khairatkar-Joshi, Neelima; Gharat, Laxmikant A.; Bioorganic and Medicinal Chemistry Letters; vol. 27; 23; (2017); p. 5131 – 5138;,
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. 363-51-9, name is 2-Chloro-6-fluoroaniline, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C6H5ClFN

General procedure: NaOt-Bu (0.240 g, 2.5 mmol), Pd(OAc)2 (0.006 g, 0.025 mmol) and [HPt-Bu3][BF4] (0.010 g, 0.035 mmol) were suspended in toluene (3 ml) in a 5 ml microwave vial. The appropriate 2-chloroaniline (0.50 mmol) and aryl bromide (0.50 mmol) were then added and the vial sealed. The reaction was then heated in the microwave reactor at 160 C for 3 h, allowed to cool, and then quenched by addition of aqueous HCl (2 M, 3 ml). The organic phase was extracted with CH2Cl2 (2¡Á20 ml), dried (MgSO4), then filtered and the solvent removed under reduced pressure. The crude product mixture was then subjected to column chromatography (SiO2).

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 363-51-9.

Reference:
Article; Bedford, Robin B.; Bowen, John G.; Weeks, Amanda L.; Tetrahedron; vol. 69; 22; (2013); p. 4389 – 4394;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 363-51-9, 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. 363-51-9, name is 2-Chloro-6-fluoroaniline, This compound has unique chemical properties. The synthetic route is as follows.

To a stirred solution of 4-bromo-2-butoxy-5-fluorobenzoic acid (Intermediate 2, 1.36 g, 4.67 mmol) and catalyticDMF in anhydrous DCM (25 mL) was added oxalyl chloride (490 ml, 5.6 mmol) dropwise. The resulting mixture wasstirred for 1 h and concentrated under reduced pressure. A solution of the residue in anhydrous DCM (20 mL) was addeddropwise to a stirred solution of 2-chloro-6-fluoroaniline (750 mg, 5.15 mmol) and triethylamine (720 ml, 5.2 mmol) inanhydrous DCM (30 mL). Following complete addition, the mixture stirred for 1 h. The mixture was concentrated underreduced pressure. The residue was dissolved in ethanol (15 mL) and precipitated by slow addition of water (30 mL).The solid was collected on a filter, washed with water and dried in a vacuum oven to yield 1.73 g (88 % yield) of thedesired product.LC-MS: Rt = 1.55 min; MS (ESIpos): m/z = 418 [M+H]+1H-NMR (400 MHz, DMSO-d6) delta [ppm]: 0.787 (0.48), 0.889 (6.64), 0.908 (16.00), 0.926 (7.83), 1.390 (0.52), 1.408(1.83), 1.427 (3.10), 1.446 (3.07), 1.464 (1.83), 1.483 (0.50), 1.731 (0.76), 1.747 (2.12), 1.767 (2.57), 1.784 (2.05), 1.801(0.67), 2.518 (3.81), 2.523 (2.64), 4.165 (2.33), 4.181 (4.62), 4.197 (2.31), 7.329 (0.79), 7.348 (1.90), 7.367 (1.26), 7.372(1.43), 7.380 (1.00), 7.395 (0.95), 7.400 (1.79), 7.414 (1.86), 7.421 (1.38), 7.433 (4.14), 7.438 (3.57), 7.453 (1.07), 7.458(0.93), 7.579 (2.69), 7.593 (2.74), 7.612 (3.05), 7.634 (2.88), 9.836 (4.40).

The chemical industry reduces the impact on the environment during synthesis 2-Chloro-6-fluoroaniline. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Bayer AG; Gradl, Stefan, Nikolaus; Niehues, Michael; Halfbrodt, Wolfgang; (43 pag.)EP3553052; (2019); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

A common heterocyclic compound, 363-51-9, name is 2-Chloro-6-fluoroaniline, molecular formula is C6H5ClFN, 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. 363-51-9.

Example 60A N-(2-chloro-6-fluorophenyl)-4-methyl-2-(methylthio)pyrimidine-5-carboxamide Example 21A (16.5 g, 90 mmol) was dissolved in a mixture of 358 mL of dioxane and thionyl chloride (7.84 ml, 107 mmol). Four drops of N,N-dimethylformamide were added. The reaction mixture was stirred for 30 minutes at ambient temperature then 2-chloro-6-fluoroaniline (17.41 g, 120 mmol) was added and the reaction mixture was stirred at 100 C. overnight. After cooling to room temperature, the reaction mixture was slowly poured into a 1000 mL separatory funnel containing 400 mL of saturated aqueous sodium bicarbonate and the mixture extracted with ethyl acetate (3*200 mL). The combined organic extracts were washed with aqueous sodium bicarbonate (10% wt, 200 mL) and saturated aqueous brine (200 mL), dried over magnesium sulfate, filtered and concentrated. Purification by silica gel flash chromatography (Isco, Redi-Sep column, 2-85% ethyl acetate/hexane, linear gradient) yielded the title compound.

The synthetic route of 2-Chloro-6-fluoroaniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AbbVie Inc.; Woods, Keith W.; Mastracchio, Anthony; Lai, Chunqiu; Gandhi, Viraj B.; Penning, Thomas D.; US2013/225589; (2013); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

363-51-9, 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. 363-51-9, name is 2-Chloro-6-fluoroaniline, This compound has unique chemical properties. The synthetic route is as follows.

Step B: Preparation of l-chloro-3-fluoro-2-isothiocyanatobenzene A solution of 2-chloro-6-fluorobenzenamine (29.2 g, 0.20 mol) in chlorobenzene (200 mL) was treated with N,N-dimethylformamide (0.10 mL) and then thiophosgene (27.6 g, 0.24 mol) dropwise at room temperature. The reaction mixture was heated to reflux for 2.5 hours and allowed to stir at room temperature for 18 hours. The suspension was filtered through a pad of silica gel and washed with hexane. The filtrate was concentrated under vacuum to give a crude oil which was chromatographed on silica gel with hexane to yield the title compound as a light yellow oil (31.5 g). H NMR (CDC13) delta 7.23-7.19 (m, 1H), 7.18-7.13 (td, 1H), 7.10-7.04 (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; E. I. DU PONT DE NEMOURS AND COMPANY; OBERHOLZER, Matthew, Richard; WO2014/189753; (2014); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

363-51-9, 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. 363-51-9, name is 2-Chloro-6-fluoroaniline, A new synthetic method of this compound is introduced below.

A solution of 5 -(2-(3,4-dimethoxyphenyl)propan-2-yl)-l -(4-fluorophenyl)- IH- imidazole-2-carbaldehyde (280 mg, 0.76 mmol), 2-chloro-6-fluoroaniline (332 mg, 2.28 mmol), TsOH (72 mg, 0.38 mmol) in THF (8 mL) was heated at reflux for 15 h over molecular sieves (4A). The solution was cooled to 0 0C, and NaBH4 (57 mg, 1.5 2mmol) was added in several portions. The resulting mixture was stirring for 1 h, and filtered through Celite to remove molecular sieves. The filtrate was quenched with H2O (5 mL), 2N NaOH (5 mL) and extracted with DCM (2 x 10 mL). The organic layers were dried over MgSO4 and concentrated to give a residue, which was purified by flash chromatography to provide the title compound as a white solid (157 mg, 0.315 mmol, 42%). 1H NMR (400 MHz, CDCl3) delta 1.49 (s, 6H), 3.72 (s, 3H), 3.85 (s, 3H), 4.13 (d, 2H), 4.65 (br, IH), 6.45 (dd, IH), 6.48 (m, 2H), 6.51 (d, IH), 6.60 (m, IH), 6.64 (d, IH), 6.76 (dd, IH), 6.80 (t, 2H), 7.00 (dt, IH), 7.13 (s, IH). MS (EI) m/z 498 [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; EXELIXIS, INC.; BOLLU, Venkataiah; BOREN, Brant, Clayton; DALGARD, Jackline, Eve; FLATT, Brenton, T.; HAQ, Nadia; HUDSON, Sarah; MOHAN, Raju; MORRISSEY, Michael; PRATT, Benjamin; WANG, Tie-lin; WO2010/93845; (2010); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

A common heterocyclic compound, 363-51-9, name is 2-Chloro-6-fluoroaniline, molecular formula is C6H5ClFN, 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. 363-51-9.

To a solution of 6.05 g (19.0 mmol) of ethyl 2-[(2,6-dichloropyridin-3-yl)carbonyl]-3-ethoxyacrylate (CAS 157373-27-8) and 3.88 g (26.6 mmol) of 2-chloro-6-fluoroaniline in 30.3 ml dichloromethane were added 23.2 ml (133 mmol) of DIPEA, and the mixture was stirred at RT for 4 h. Subsequently, 2.63 g (19.0 mmol) of potassium carbonate were added and the mixture was heated under reflux overnight. The mixture was diluted with 200 ml of DCM and washed twice with 75 ml of 1 M aqueous hydrochloric acid. The organic phase was dried over sodium sulphate and filtered, and the solvent was removed under reduced pressure. The suspension obtained was stirred with 40 ml of tert-butyl methyl ether, and the precipitate was filtered off with suction, washed with 10 ml of tert-butyl methyl ether and dried under high vacuum. 5.70 g (64% of theory, 81% purity) of the title compound were obtained. 1H-NMR (400 MHz, DMSO-d6): delta [ppm]=8.88 (s, 1H), 8.64 (d, 1H), 7.76-7.57 (m, 4H), 4.25 (q, 2H), 1.28 (t, 3H). LC-MS (Method 3): Rt=1.86 min; 381 [M+H]+.

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

Reference:
Patent; Bayer Pharma Aktiengesellschaft; TELLER, Henrik; STRAUB, Alexander; BRECHMANN, Markus; MUeLLER, Thomas; MEININGHAUS, Mark; NOWAK-REPPEL, Katrin; TINEL, Hanna; MUeNTER, Klaus; FLIEGNER, Daniela; MONDRITZKI, Thomas; BOULTADAKIS ARAPINIS, Melissa; MARQUARDT, Tobias; VAKALOPOULOS, Alexandros; REBSTOCK, Anne-Sophie; WITTWER, Matthias Beat; (342 pag.)US2018/297994; (2018); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

363-51-9, name is 2-Chloro-6-fluoroaniline, 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. 363-51-9

To a solution of 392 mg (0.890 mmol [calculation value with the purity defined as 100%]) of ethyl 5-(chioro- carbonyl)-6,6-dimethyl-3-[1 -(trimethylsilyl)cyclobutanecarboxamido]-5,6-dihydropyrrolo[3,4-c]pyrazole-2(4H)- carboxylate synthesized in the same way as in Reference Example 4 in 2.5 ml of 1,4-dioxane, 0.60 ml (3.4 mmol) of DIPEA and 807 mg (5.54 mmol) of 2-chloro-6-fluoroaniline were added at room temperature in a nitrogen atmosphere, reacted at 1000 C. for 1 hour with stirring, and then reacted at 130 C. for 0.5 hours and further at 150 C. for 2 hours in a microwave reaction apparatus. Subsequently, 0.50 ml (4.6 mmol) of N,N-dimethylethane-1 ,2-diamine was added thereto at room temperature and then reacted at room temperature for 1.5 hours with stirring.10718] After completion of the reaction, ethyl acetate was added to the reaction solution, followed by washing with a 5% aqueous potassium bisulfate solution. After separation into an organic layer and an aqueous layer, the aqueous layer was subjected to extraction twice with ethyl acetate. The whole organic layer thus obtained was dried over anhydrous magnesium sulfate, then filtered, and concentrated under reduced pressure. The obtained concentration residue was subjected to preparative column chromatography (apparatus 2, DIOL silica gel, elution solvent: n-hexane:ethyl acetate=80:20-65:35-50:50 (V/V)), and a fraction containing the compound of interest was concentrated under reduced pressure. The obtained concentration residue was subjected to preparative column chromatography (apparatus 2, silica gel, elution solvent: dichloromethane_methanol=100:0 99:1-98:2-97:3 (V/V)), and a fraction containing the compound of interest was concentrated under reduced pressure to obtain a white solid (approximately 70 mg). The obtained solid was subjected to preparative column chromatography (apparatus 3, ODS silica gel, elution solvent: acetonitrile: 1 mM aqueous dipotassium biphosphate solution=50:50-80:20 (V/V)), and a fraction containing the compound of interest was concentrated under reduced pressure, followed by the distilling oil of acetonitrile. The obtained concentration residue was subjected to extraction three times with ethyl acetate, and subsequently, the whole organic layer was washed with saturated saline, then dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The obtained concentration residue was dissolved in ethyl acetate, then n-hexane was added thereto, and the deposited solid was collected by filtration, washed with n-hexane, and then dried under reduced pressure to obtain 57.1 mg of the title compound (yield: 13% [calculation value with the purity of the starting material defined as 100%]) as a white solid.10719] Mass spectrum (CI, mlz): 478 [M+1].10720] ?H-NMR spectrum (400 MHz, DMSO-d5) oe: 12.27 & 11.69 (br s, total 1H), 9.64-9.54 (m, 1H), 8.09-7.89 (m, 1H), 7.38-7.19 (m, 3H), 4.69-4.52 (m, 2H), 2.56-2.39 (m, 2H), 2.28-2.13 (m, 2H), 1.93-1.73 (m, 2H), 1.70-1.54 (m, 6H), 0.15-0.04 (m, 9H).

Statistics shows that 363-51-9 is playing an increasingly important role. we look forward to future research findings about 2-Chloro-6-fluoroaniline.

Reference:
Patent; UBE INDUSTRIES, LTD.; IWASE, Noriaki; AGA, Yasuhiro; USHIYAMA, Shigeru; KONO, Shigeyuki; SUNAMOTO, Hidetoshi; MATSUSHITA, Takashi; OGI, Sayaka; UMEZAKI, Satoshi; KOJIMA, Masahiro; ONUMA, Kazuhiro; SHIRAISHI, Yusuke; OKUDO, Makoto; KIMURA, Tomio; (165 pag.)US2018/186818; (2018); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

363-51-9, These common heterocyclic compound, 363-51-9, name is 2-Chloro-6-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.

Acetic anhydride (10 mL, 106 mmol) was added to a solution of 2-chloro-6-fluoroaniline (12.81 g, 88 mmol) in AcOH (44 mL) and the mixture was stirred at 90 C. for 2 hrs. After cooling to r.t., water was added and the solid precipitate was collected by filtration, washed with water, and air dried to afford N-(2-chloro-6-fluorophenyl)acetamide (16.2 g, 98% yield) as a white solid. The crude product obtained was used directly in the next step without further purification. LCMS calculated for C8H8ClFNO (M+H)+: m/z=188.0; Found 188.0.

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 363-51-9.

Reference:
Patent; Incyte Corporation; Hummel, Joshua; Vechorkin, Oleg; Sokolsky, Alexander; Ye, Qinda; Liu, Kai; Yao, Wenqing; (60 pag.)US2020/48241; (2020); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

363-51-9,Some common heterocyclic compound, 363-51-9, name is 2-Chloro-6-fluoroaniline, molecular formula is C6H5ClFN, 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.

a) To a stirred suspension of (A7) as obtained from example 5 (60.0 g, 126 mmol) in acetonitrile (180 ml.) was added pyridine (35.6 ml_, 440 mmol) and 2-chloro-6-fluoroaniline (27.4 g, 188 mmol, CAS-no. 363-51-9 obtained from Combiblocks, product code OS-7812; alternatively a preparation of 2-chloro-6-fluoroaniline is described in US 4,089,958, example XVIII) at 22C. The cloudy solution was cooled to 0-5C and phosphoryl chloride (21.2 g, 138 mmol) was added over a period of 10 min. The reaction mixture was stirred for 1 h resulting in a clear solution. Methanol (360 ml.) and 85% phosphoric acid (12.8 ml_, 189 mmol) were added and the mixture was heated to 60C for 2 h. (0796) The reaction solvent was partially removed by distillation (95C bath, 64-72C internal temperature) to give 420 ml. distillate. The distillation residue was slowly cooled to 22C and stirred for 16 h. The resulting suspension was cooled to 0-5C and stirred for additional 2 h. The solid was isolated, washed two times with 2-propanol (30 ml.) and dried in vacuum at 50C for 16 h to give crude product Compound (I) as a white solid (55g, 106 mmol) in 84% yield. (0797) HPLC (method 1 ): Rt = 2.81 min (> 98% area) (0798) b) The reaction product (30.0 g, 57.6 mmol) was further purified by suspension in anhydrous ethanol (450 ml.) and heating to 60C. The resulting clear solution was filtered, the filter cake was washed two times with hot anhydrous ethanol (30 ml.) and the filtrate was concentrated by distillation of solvent (270 ml. distillate) at 100C bath temperature. The solution was cooled to 50C, seeded (I) (0.3 g), and cooled stepwise to 0-5C over 4h. The precipitated solid was isolated, washed two times with anhydrous ethanol (15 ml.) and dried in vacuum at 50C for 16h to give Compound (I) as a white solid (25.7 g, 49.3 mmol) in 86% yield from crude (0799) Compound (I). (0800) HPLC (method 1 ): Rt = 2.81 min (> 99% area) (0801) 1H NMR (400 MHz, DMSO-d6) d ppm 1.29 (t, J=7.15 Hz, 3 H) 1.45 (d, J=6.36 Hz, 3 H) 3.80 (q, J= 7.09 Hz, 2 H) 4.44 – 4.55 (m, 2 H) 5.36 (dt, J=12.78, 6.33 Hz, 1 H) 5.80 (t, J= 5.75 Hz, 1 H) (0802) 7.30 – 7.47 (m, 3 H) 7.50 – 7.66 (m, 2 H) 10.05 (s, 1 H) (0803) LCMS (method 1 ): Rt = 0.90 min; MS (ESIpos): m/z = 521 (M+H)+

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 363-51-9, its application will become more common.

Reference:
Patent; BAYER AKTIENGESELLSCHAFT; BAYER PHARMA AKTIENGESELLSCHAFT; HASSFELD, Jorma; GRADL, Stefan, Nikolaus; RUBENBAUER, Philipp; VAN DER HAAS, Henricus, Nicolaas, Sebastian; GIELING, Reinerus, Geradus; (127 pag.)WO2019/197239; (2019); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics