Chlorides-buliding-blocks

6775-78-6, A common compound: 6775-78-6, name is 6-Chloroimidazo[1,2-b]pyridazine, belongs to chlorides-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

A mixture of 6-chloro-imidazo[ l ,2-b]pyridazine (200 mg, 1 .30 mmol, 1.00 equiv), bis(triphenylphosphine)palladium(Il) dichlonde (200 mg, 0 28 mmol, 0.22 equiv), and tnethylamine (0.5 mL) in methanol (4 mL) was stirred under carbon monoxide ( 10 atm) in a 50-mL pressure reactor overnight at 1 10 C. The solid material was removed by filtration. The filtrate was concentrated under vacuum and the residue was purified on a silica gel column eluted with ethyl acetate/petroleum ether (1 /1 ) to give 1 00 mg (43%) of the title compound as a yellow solid. NMR (300 MHz, CDCL) 5 8.16 (s, l H), 8.08 (d, J = 9,6 Hz, 1 H), 7.94 (s, 1 H), 7.77 (d, J = 9.6 Hz, 1 H), 4.09 (s, 3H).

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, 6-Chloroimidazo[1,2-b]pyridazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GENENTECH, INC.; FORMA TM, LLC; BAIR, Kenneth W.; BAUMEISTER, Timm R.; DRAGOVICH, Peter; GOSSELIN, Francis; YUEN, Po-Wai; ZAK, Mark; ZHENG, Xiaozhang; WO2013/127267; (2013); 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

60811-21-4, These common heterocyclic compound, 60811-21-4, name is 4-Bromo-2-chloro-1-fluorobenzene, 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.

EXAMPLE 21 6(3-Chloro-4-fluoro-phenyl)-4-isopropyl-3,4-dihydro-1H-quinoxalin-2-one A mixture of (3,4-dihydro-4-isopropyl-2-oxoquinoxalin-6-yl)boronic acid (2.4 g, 10 mmol), 4-bromo-2-chlorofluorobenzene (2 g, 10 mmol), potassium carbonate (4 g, 30 mmol), and tetrakis(triphenylphosphine)palladium(0) (0.46 g, 0.4 mmol) in dimethoxyethane (100 ml), ethanol (25 ml) and water (25 mol) was heated to reflux for 6 hrs. After cooling to room temperature the mixture was diluted with water and extracted with ethyl acetate (3*). The combined organic layers were washed with water, then brine, dried (MgSO4) and evaporated to obtain crude product (2.9 g, 91%). Recrystallization from EtOAc/hexane afforded the title compound, mp 208-213 C.: 1H-NMR (DMSO-d6) delta 1.16 (d, J=6.59 Hz, 6H), 3.56 (s, 2H), 4.22 (septet, J=6.59 Hz, 1H), 6.86 (d, J=7.91 Hz, 1H), 6.96 (dd, J=7.91, 1.76 Hz, 1H), 7.01 (d, J=1.76 Hz, 1H), 7.43 (t, J=9.01 Hz, 1H), 7.61 (m, 1H), 7.82 (dd, J=7.14, 2.31 Hz, 1H), 10.47 (s, 1H). MS (EI) m/z 318 [M]++ 1 chlorine.

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 60811-21-4.

Reference:
Patent; American Home Products Corporation; Ligand Pharmaceutical, Inc.; US6423699; (2002); B1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

4535-90-4, Adding some certain compound to certain chemical reactions, such as: 4535-90-4, name is 2-Chloro-N-methylethanamine hydrochloride, 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 4535-90-4.

Example 23trans-{2-[1-(4-Benzo[d]isothiazol-3-yl-cyclohexyl)-8-chloro-4H,6H-2,3,5,10b-tetraaza-benzo[e]azulen-5-yl]-ethyl}-methyl-amineA mixture of trans-1-(4-benzo[d]isothiazol-3-yl-cyclohexyl)-8-chloro-5,6-dihydro-4H-2,3,5,10b-tetraaza-benzo[e]azulene (35.0 mg, 0.0803 mmol), cesium carbonate (105 mg, 0.321 mmol) and 2-methylaminoethyl chloride hydrochloride (41.8 mg, 0.321 mmol) in acetonitrile (0.8 ml) was heated at 70 C. for 20 h. After cooling to room temperature the reaction mixture was partitioned between 1 M aqueous sodium hydroxide solution (2 ml) and ethyl acetate (5 ml). The layers were separated. The aqueous layer was extracted with three 5-ml portions of ethyl acetate. The combined organic layers were concentrated in vacuo. Preparative RP-HPLC with water (0.05% formic acid)/methanol as eluent gave title compound (19 mg, 48%) as off-white solid. MS m/e: 493 ([M+H]+)

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 4535-90-4.

Reference:
Patent; Dolente, Cosimo; Schnider, Patrick; US2011/263573; (2011); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

13726-14-2, These common heterocyclic compound, 13726-14-2, name is 4-Chloro-3-methoxyaniline, 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.

A solution of 4-chloro-3-methoxyaniline (1.0 equivalent) dissolved in CH2CI2 (15 volumes) at 5 C was treated portion wise with N-bromosuccinimide (1.03 equivalents), warmed to 20 C and mixed for 5 minutes. A 5% aqueous Na2S03 solution (10 volumes) was added and the mixture was stirred for 10 minutes. The layers were separated and the organic layer was washed with water and saturated brine, dried (Na2S04), filtered and concentrated. The resulting solid was triturated with a minimal volume of heptane and the solid was collected by filtration and dried to constant mass (80 % yield).

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 13726-14-2.

Reference:
Patent; ABBOTT LABORATORIES; ABBOTT GMBH & CO.KG; MARING, Clarence J.; PRATT, John K.; CARROLL, William A.; LIU, Dachun; BETEBENNER, David A.; HUTCHINSON, Douglas K.; TUFANO, Michael D.; ROCKWAY, Todd W.; SCHOEN, Uwe; PAHL, Axel; WITTE, Adreas; WO2012/87833; (2012); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

A common compound: 13726-14-2, name is 4-Chloro-3-methoxyaniline, belongs to chlorides-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 13726-14-2

Step 1 : 4-choro-3-methoxy aniline (2.0 g, 12.6 mmol), 1-chloro-4-iodobenzene (3.33 g, 13.9 mmol, and sodium-tert-butoxide (6.04 g, 63 mmol) were taken in toluene (15 mL). The resulting mixture was purged with nitrogen, added Pd(OAc)2 (0.141 g, 0.63 mmol), [HPtBu3][BF4] ( 0.255 g, 0.88 mmol) and heated at 110 C for 12 h. After completion of the reaction, the reaction mixture was filtered through celite bed and concentrated under vacuum. The residue obtained was diluted with ethyl acetate (200 mL) washed with water, brine solution and dried over anhydrous Na2S04. The organic phase was concentrated and purified by the column chromatography (230-400 size mesh) to get the white solid 4-chloro-N-(4_chlorophenyl)-3- methoxy aniline (1.2 g, 35.2%). 1H NMR (400 MHz, DMSO-d6): delta 8.46 (s, 1H), 7.22-7.28 (m, 3H), 7.08-7.10 (m, 2H), 6.75 (s, 1H), 6.64 (d, J = 8.68 Hz, 1H), 3.80 (s, 3H).

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, 13726-14-2, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK PATENT GMBH; SPANGENBERG, Thomas; (129 pag.)WO2016/827; (2016); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

The chemical industry reduces the impact on the environment during synthesis 821-99-8, name is 1,9-Dichlorononane, I believe this compound will play a more active role in future production and life. 821-99-8

General procedure: To a DMF solution (63 mL) of 3b (1.06 g, 6.31 mmol) was added sodium hydride (55% oil dispersion, 340 mg, 7.8 mmol) at rt. After being stirred for 2 h at rt, the suspension was cooled to 0 C, and 1,8-dichlorooctane (3.40 mL, 3.47 g, 18.9 mmol) was added to the suspension. The mixture was allowed to warm to rt and stirred at rt for 2 h and then at 55 C for 10 h. After adding aqueous HCl solution (35%, 0.7 mL) at rt, the mixture was concentrated under reduced pressure and diluted with water (30 mL). The aqueous solution was washed with hexane (320 mL), treated with NaHCO3 until the pH reached to 9, and extracted with AcOEt (3*150 mL). The organic layers combined were washed with water (3500 mL), dried over anhydrous Na2SO4, concentrated under reduced pressure, and subjected to silica gel column chromatography (CHCl3/MeOH 100:0 to 96:4, v/v) to afford 4b[11] as a colorless oil (1.25 g, 3.97 mmol, 63%). Because 4b[11] tends to undergo inter- and intramolecular quaternization during storage, the obtained material was characterized only by 1H NMR and used for the next reaction immediately after the purification. 1H NMR (300 MHz, CDCl3, 25 C, TMS): delta=0.73 (3H, d, 3JH-H=6.6 Hz), 1.05 (3H, d,3JH-H=6.9 Hz), 1.24-1.34 (5H, m), 1.36-1.44 (2H, m), 1.47-1.51 (2H, m), 1.67-1.81 (3H, m), 2.08-2.19 (1H, m), 2.37 (3H, s), 3.24-3.39 (2H, m), 3.53 (2H, t, 3JH-H=6.9 Hz), 3.63-3.75 (3H, m), 6.92-6.93 ppm (2H, m).

The chemical industry reduces the impact on the environment during synthesis 821-99-8. I believe this compound will play a more active role in future production and life.

Reference:
Article; Noguchi, Tomohisa; Li, Chunji; Sasaki, Daisuke; Yamada, Kuniyo; Saigo, Kazuhiko; Ishida, Yasuhiro; Tetrahedron; vol. 72; 11; (2016); p. 1493 – 1504;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

72235-56-4, These common heterocyclic compound, 72235-56-4, name is 3-Chloro-4-fluorobenzylamine, 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.

Preparation of 3-[(3-chloro-4-fluorobenzyl)amino]-1-propanesulfonic acid To a solution of 3-chloro-4-fluorobenzy]amine (1.0 g, 7.8 mmol) in Acetone (2 mL) and Toluene (2 mL) was added 1,3-propane sultone solution (1.5 M in THF, 4.0 mL, 6.0 mmol). The solution was stirred at reflux for 4 hours. The reaction mixture was cooled to room temperature. The solid material was collected by filtration and washed with acetone (2*5 mL) and dried in a vacuum oven at 50 C., affording the title compound, 0.041 g (2%). 1H NMR (D2O, 300 MHz) delta ppm 7.44 (dd, 1H, J=2.2 Hz, 6.9 Hz), 7.25 (m, 1H), 7.15 (t, 2H, J=8.6 Hz), 4.07 (s, 2H), 3.07 (t, 2H, J=7.8 Hz), 2.83 (t, 2H, J=7.5 Hz), 1.98 (m, 2H). 13C (D2O, 75 MHz) delta ppm 160.07, 156.77, 132.18, 130.43, 130.22, 127.90, 120.94, 117.58, 117.29, 50.20, 48.17, 46.09, 21.67. 19F (D2O, 282 MHz) delta ppm -115.33. ES-MS 280 (M-1).

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 72235-56-4.

Reference:
Patent; Kong, Xianqi; Wu, Xinfu; Bouzide, Abderrahim; Valade, Isabelle; Migneault, David; Bellini, Francesco; US2006/183800; (2006); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

A common compound: 626-43-7, name is 3,5-Dichloroaniline, belongs to chlorides-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 626-43-7

General procedure: To a solution of alcohol (1.1 mmol) in a mixture of solvents EtOAc: DMSO (4 ml: 2 ml), was added T3P (2.5 mmol, 50% solution in ethyl acetate) at 0 C, and the resulting mixture was stirred at room temperature for 1-2 h under nitrogen atmosphere. The reaction was monitored by TLC, amine (1.0 mmol) and thioglycolic acid (1.0 mmol) were added once and stirred further for 1-3 h at room temperature. After completion of the reaction, the mixture was diluted with water (20 ml) and neutralized by adding 10% NaHCO3 solution. The product was extracted with ethyl acetate (10 ml 2) and the combined organic layers were washed with water followed by brine solution. The organic phase was dried over anhydrous Na2SO4. The solvent was removed under reduced pressure to afford a crude product which was purified by column chromatography using hexane: ethyl acetate mixture (8:2) as an eluent.

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, 626-43-7, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Sharath Kumar, Kothanahally S.; Swaroop, Toreshettahally R.; Harsha, Kachigere B.; Narasimhamurthy, Kereyagalahally H.; Rangappa, Kanchugarakoppal S.; Tetrahedron Letters; vol. 53; 42; (2012); p. 5619 – 5623;,
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. 627-42-9, name is 2-Methoxyethyl chloride, This compound has unique chemical properties. The synthetic route is as follows., 627-42-9

146.5 g (1.2 mol) of 4-hydroxybenzaldehyde are dissolved in DMF, and 2O g (0.12 mol) of potassium iodide, 134.6 g (1.2 mol) of potassium tert-butoxide and 170.2 g (1.8 mol) of 2- chloroethyl methyl ether are added. The reaction mixture is stirred at 800C for 16 h. For work-up, the reaction mixture is concentrated under reduced pressure. The residue is taken up in 1 1 of ethyl acetate and extracted with 0.5 1 of IN aqueous sodium hydroxide solution. The ethyl acetate phase is dried using magnesium sulphate and concentrated under reduced pressure. The residue obtained after concentration is distilled under high vacuum (b.p. = 1000C at 0.45 mbar). This gives 184.2 g (85% of theory) of product.MS (ESIpos): m/z = 181 (M+H)+1H-NMR (300 MHz, CDCl3): delta = 3.5 (s, 3H); 3.8 (tr, 2H); 4.2 (tr, 2H); 7.0 (d, 2H); 7.8 (d, IH); 9.9 (s, IH).

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; BAYER HEALTHCARE AG; WO2007/73855; (2007); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics