Tag: M.W=200-300

96558-78-0, 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. 96558-78-0, name is 3-Bromo-5-chlorophenylamine belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a mixture of intermediate 459 and intermediate 460 (1 g) in acetone ( 10 mL) was added a solution of oxone ( 1 .25 g 2.03 mmol) in H20 ( 10 mL ) dropwise under N2 at 0 C. The reaction mixture was stirred at 0 C for 1 hour. Water (20 ml ) was added and the mixture was extracted with EtOAc (3 x 30 ml ). The organic layer was combined, dried over Na2S04, filtered and concentrated. The residue was triturated under EtOAc/ petroleum ether (1/10). The precipitate was filtered off and dried give a mixture of intermediate 220a and intermediate 220b ( 1 50 mg ) as a yellow solid.A mixture of intermediate 457 and intermediate 458 (750 mg), bi.s( pi naco lato )d iboron (942.5 mg, 3.7 mmol ), Pd(dppf)Cl2 (1 13.1 mg, 0. 1 55 mmol ) and KOAc ( 910.6 mg, 9.28 mmol) in THF (20 niL) was stirred at 60C for 2 hours unde N2. Water (30 ml ) was added and extracted with EtOAc (30 niL x 3 ). The organic layers were combined, dried over Na2S04, filtered and concentrated to give a mixture of intermediate 459 and intermediate 460 (1.0 g) as a yellow oil. Step 3 A mixture of intermediate 457 and intermediate 458 (750 mg), bi.s( pi naco lato )d iboron (942.5 mg, 3.7 mmol ), Pd(dppf)Cl2 (1 13.1 mg, 0. 1 55 mmol ) and KOAc ( 910.6 mg, 9.28 mmol) in THF (20 niL) was stirred at 60C for 2 hours unde N2. Water (30 ml ) was added and extracted with EtOAc (30 niL x 3 ). The organic layers were combined, dried over Na2S04, filtered and concentrated to give a mixture of intermediate 459 and intermediate 460 (1.0 g) as a yellow oil. Step 3 3-chloro-5-bromoaniline (1 g, 4.84 mmol) was dissolv ed in 75% I LSO ( 10 mL). Then glycerol (1.1 1 g, 12.1 mmol ) and nitrobenzene (0.59 g. 4.84 mmol ) were added. The reaction mixture was stirred at 150C for 3 hours under N2. EtOAc (50 ml ) was added and the mixture was adjusted to pH to 6-7 with a 30% solution of NaOH in water. The solid was filtered off over celite and the organic layer was separated and ev aporated. The residue was purified by flash column chromatograph over silica gel (gradient eiuent: petroleum ether EtOAc from 20/ 1 to 5/1). The desired fractions were collected and the solvent was evaporated to give a mixture of intermediate 457 and intermediate 458 (750 mg) as a white solid.

The synthetic route of 96558-78-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; WU, Tongfei; BREHMER, Dirk; BEKE, Lijs; BOECKX, An; DIELS, Gaston, Stanislas, Marcella; GILISSEN, Ronaldus, Arnodus, Hendrika, Joseph; LAWSON, Edward, Charles; PANDE, Vineet; PARADE, Marcus, Cornelis, Bernardus, Catharina; SCHEPENS, Wim, Bert, Griet; THURING, Johannes, Wilhelmus, John, F; VIELLEVOYE, Marcel; SUN, Weimei; MEERPOEL, Lieven; (375 pag.)WO2017/32840; (2017); A1;,
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A common heterocyclic compound, 2770-11-8, name is 2-(4-Chlorophenoxy)aniline, molecular formula is C12H10ClNO, 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. 2770-11-8.

To a stirred and cooled solution of 2-(4-chlorophenoxy)aniline (330 mg, 1.50 mmol) and triethylamine (230 muL, 1.65 mmol) in toluene (5 mL), the appropriate acid chloride (pivaloyl chloride, 2,2-dimethylbutyryl chloride, 3-methylbutyryl chloride, propyl chloride, cyclopropanecarbonyl chloride, cyclobutanecarbonyl chloride, methyl succinyl chloride, 4-methoxybenzoyl chloride) (1.65 mmol) was added. Subsequently the reaction mixture was allowed to warm to room temperature. The progress of the reaction was monitored by TLC. After 2-9 h the reaction mixture was extracted with a saturated sodium hydrogen carbonate solution, with a hydrogen chloride solution (10%), with brine and finally with water. Afterwards the organic solution was dried over sodium sulfate and evaporated under reduced pressure. The residue was further purified by recrystallization or column chromatography over silica gel. N-[2-(4-Chlorophenoxy)phenyl]-2,2-dimethylpropanamide (1): Crystallization from ethanol (70%) yielded slightly brown needles (277 mg, 0.92 mmol, 61%); m.p.: 99-100 C ; IR (KBr): [cm-1] nu = 3336 (br, N-H), 1663 (s, C=O); 1H-NMR: (400 MHz, DMSO-d6) delta [ppm] = 1.05 (s, 9H, C(CH3)3), 6.80-7.01 (m, 2H, arom. H), 6.99-7.15 (m, 1H, arom. H), 7.15-7.32 (m, 2H, arom. H), 7.27-7.48 (m, 2H, arom. H), 7.56-7.78 (m, 1H, arom. H), 8.72 (s, 1H, NH); 13C-NMR: (101 MHz, DMSO-d6) delta [ppm] = 26.95 (3C, CH3), 118.40 (2C), 120.46, 124.63, 126.13, 126.62, 129.49 (2C) (CH), 38.12, 126.38, 130.28, 147.84, 155.91 (C), 176.13 (C=O); C17H18ClNO2 (303.78): calcd. C 67.21, H 5.97, N 4.61, found C 67.13, H 6.00, N 4.51; EI-MS: m/z (%): 303.1 [M]+ (28), 176.1 [M – 127]+ (100); HPLC: 99.7% at 254 nm, 99.9% at 280 nm; tR = 7.42 min, tM(DMSO) = 1.06 min (ACN/H2O 60:40), lambdamax [nm] = 230, 275; HPLC-gradient: 99.4%, tR = 13.62 min, tM(DMSO) = 1.28 min.

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

Reference:
Article; Weidner, Thomas; Nasereddin, Abed; Preu, Lutz; Gruenefeld, Johann; Dzikowski, Ron; Kunick, Conrad; Molecules; vol. 21; 2; (2016);,
Chloride – Wikipedia,
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Adding some certain compound to certain chemical reactions, such as: 41965-95-1, name is 3-Chloro-4-methoxybenzylamine 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 41965-95-1. 41965-95-1

tert-butyl 8-bromo-10-((3-chloro-4-methoxybenzyl)amino)-3,4-dihydrobenzo[b][1,6]naphthyridine-2(1H)-carboxylate, 21 A mixture of 20 (0.075 mmol), 3-chloro-4-methoxybenzyl amine hydrochloride (0.38 mmol), TEA (0.38 mmol) and NaI (0.0037 mmol) in NMP (1 mL) was heated to 130 C. and stirred overnight. The reaction was diluted with Et2O (10 mL) and washed with H2O (2*20 mL) and brine (20 mL). The organic layers were dried over Na2SO4, filtered and evaporated under reduced pressure to give the desired intermediate 21 (40% yield). 1H NMR (300 MHz, CDCl3) delta 8.08 (s, 1H), 7.84 (s, 1H), 7.68 (d, 1H, J=9.0 Hz), 7.35 (s, 1H), 7.19 (d, 1H, J=8.1 Hz), 6.93 (d, 1H, J=8.1 Hz), 4.57 (s, 4H), 3.91 (s, 3H), 3.76 (t, 2H, J=6.0 Hz), 3.19 (t, 2H, J=5.7 Hz), 1.49 (s, 9H).

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 3-Chloro-4-methoxybenzylamine Hydrochloride.

Reference:
Patent; THE TRUSTEES OF COLUMBIA UNIVERSITY IN THE CITY OF NEW YORK; Landry, Donald W.; Deng, Shixian; Arancio, Ottavio; Fiorito, Jole; Wasmuth, Andrew; (41 pag.)US10626113; (2020); B2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding some certain compound to certain chemical reactions, such as: 6579-54-0, name is 2,6-Dichlorobenzenesulfonyl chloride, 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 6579-54-0. 6579-54-0

General procedure: A mixture of N-Boc-aminol (1 eq.) and KOH (3eq) in THF was stirred vigorously for 15 min. It was followed by the addition of required benzenesulfonyl chloride derivative (1.2eq) and subsiquent stirring of the reaction for 4-5h. After completion of the reaction (as per TLC), the reaction mixture was filtered to expel out the precipitated salt and the filterate thus obtained was concentrated under reduced pressure to obtain the crude product which was further purified by column chromatography (eluent EtOAc:Hexane).

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 2,6-Dichlorobenzenesulfonyl chloride.

Reference:
Article; Saxena, Anil K.; Sharma, Sugandha; Pandey, Atindra K.; Shukla, Praveen K.; Bioorganic and Medicinal Chemistry Letters; vol. 21; 21; (2011); p. 6476 – 6481;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

81927-55-1,Some common heterocyclic compound, 81927-55-1, name is Benzyl 2,2,2-trichloroacetimidate, molecular formula is C9H8Cl3NO, 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.

To a solution of alcohol 5 (1.00 g, 8.61 mol) and benzyl 2,2,2-trichloroacetimidate26 (4.34 g, 17.2 mmol, 2.0 equiv) in 1,4-dioxane (15 mL) was added trifluoromethanesulfonic acid (0.15 mL, 1.72 mmol, 0.2 equiv) dropwise at room temperature under nitrogen. The reaction was stirred at room temperature for 1.5 h. The mixture was diluted with dichloromethane (35 mL), washed with saturated aqueous solution of sodium bicarbonate (25 mL*2) and brine (25 mL*3), dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by flash column chromatography over silica gel (petroleum ether/ethyl acetate 5:1 to 2:1) to afford the titled compound as colorless oil (1.60 g, 90%). The 1H NMR spectrum was identical to literature data. 1H NMR (400 MHz, CDCl3) delta 7.30-7.19 (m, 5H), 4.62-4.54 (m, 1H), 4.56 (d, J=2.9 Hz, 2H), 3.59 and 3.49 (ABX, JAB=10.8 Hz, JAx=3.3 Hz, JBx=4.3 Hz, 2H), 2.59-2.34 (m, 2H), 2.26-2.13 (m, 1H), 2.09-1.97 (m, 1H).

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

Reference:
Article; Yang, Fan; Feng, Liang; Wang, Nengzhong; Liu, Xuge; Li, Jun; Shen, Yuehai; Tetrahedron; vol. 69; 45; (2013); p. 9463 – 9468;,
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. 96558-78-0, name is 3-Bromo-5-chlorophenylamine, This compound has unique chemical properties. The synthetic route is as follows., 96558-78-0

To a solution of 3-bromo-5-chloro-aniline (0.2 g, 968.7 pmol, 1 eq), 2-isopropenyl- 4,4,5,5-tetramethyl-l,3,2-dioxaborolane (195.3 mg, 1.2 mmol, 1.2 eq) and K2CO3 (267.8 mg, 1.9 mmol, 2 eq) in 2 mL of dioxane and 0.2 mL of H2O was added Pd(dppf)Ch (70.9 mg, 96.9 pmol, 0.1 eq) and purged with N2 for 3 times. The mixture was stirred at 100C for 12 hours. The reaction mixture was partitioned between 3 mL of water and 5 mL of ethyl acetate. The organic phase was separated, washed twice with 2 mL of brine, dried over Na2SC>4, filtered and concentrated under reduced pressure to give a residue, which was purified by prep-TLC (S1O2, eluting with Petroleum ether : Ethyl acetate = 5: 1) to give 83 mg of compound 2 (495.1 pmol, 51.1 % yield) as a green oil

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; AQUINNAH PHARMACEUTICALS, INC.; VACCA, Joseph, P.; WAGER, Travis, T.; (383 pag.)WO2020/117877; (2020); 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. 13526-66-4, name is 3-Bromo-6-chloroimidazo[1,2-b]pyridazine, This compound has unique chemical properties. The synthetic route is as follows., 13526-66-4

mixture of 2.0 g (16.8 mmol) furo[3,2-b]pyridine and anhydrous THF (100 mL) was cooled to -78 C. 10.1 mL (25.2 mmol) of a 1 .6 M solution of n-butyllithium in hexane was added and the resulting mixture stirred for 1 h at -78 C. 6.8 mL (25.2 mmol) of tributyltin chloride was added at -78 C. The cooling bath was removed and the reaction was stirred at room temperature over night. Methanol was carefully added and the solvent evaporated. The obtained residue was purified by flash chromatography to yield 7.4 g of crude product of the corresponding 2-stannylbenzofurane, which was used without further purification. In an inert atmosphere, 3.0 g (12.9 mmol) of 3-bromo-6-chloro-imidazo[1 ,2-b]- pyridazine, 6.85 g (16.8 mmol) of the crude 2-stannylfuro[3,2-b]pyridine, 246 mg (1 .29 mmol) copper (I) iodide and 453 mg (0.645 mmol) bis(triphenylphosphine) palladium(ll)chloride in 100 mL of THF was stirred over night at 85 C in a sealed pressure tube. The solvent was evaporated, the obtained solid was digested in dichloromethane/methanol and filtered off. The solid was washed with methanol and hexane to give 2 g of the title compound as solid material. 1H-NMR (300 MHz, DMSO-de), delta [ppm]= 7.35-7.45 (1 H), 7.57-7.64 (1 H), 7.65-7.70 (1 H), 8.08-8.15 (1 H), 8.40-8.47 (1 H), 8.47-8.52 (1 H), 8.54-8.62 (1 H). LCMS (Method 3): Rt = 0.91 min; MS (ESIpos) m/z = 271 [M+H]+.

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 PHARMA AKTIENGESELLSCHAFT; ZORN, Ludwig; EIS, Knut; SCHULZE, Volker; SUeLZLE, Detlev; PUeHLER, Florian; LIENAU, Philip; BOeMER, Ulf; PETERSEN, Kirstin; HAeGEBARTH, Andrea; WO2014/118135; (2014); 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. 6579-54-0, name is 2,6-Dichlorobenzenesulfonyl chloride, A new synthetic method of this compound is introduced below., 6579-54-0

2,6-Dichloro-3-nitrobenzenesulfonic acid Lithium hydroxide hydrate (12.64 g, 0.301 mol) was added to a solution of 2,6-dichlorobenzenesulfonyl chloride (35.53 g, 0.146 mol) in MeOH (600 mL) and the reaction was allowed to stir at room temperature for 3 hr. The reaction mixture was filtered to remove suspended solids and then concentrated. The resulting solid was dried in vacuo overnight to remove any residual MeOH. The solid was then dissolved in H2SO4 (300 mL) and chilled in an ice bath. A solution of H2S04 (35 mL) and HNO3 (13.2 mL) was slowly added to the above reaction over 90 min. The reaction was allowed to warm up to room temperature overnight and then slowly poured into ice water (1200 mL) and extracted with EtOAc. The combined organic layers were dried (MgSO4) and concentrated to yield 2,6-dichloro-3-nitrobenzenesulfonic acid (44.35 g, 99%) as the dihydrate. EI-MS (m/z) 270 (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; SmithKline Beecham Corporation; US6500863; (2002); B1;,
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. 823-57-4, name is 2-Bromo-5-chloroaniline, A new synthetic method of this compound is introduced below., 823-57-4

Intermediate 129 4-Chloro-4′-fluorobiphenyl-2-amine 2-Bromo-5-chloroaniline (CAS 823-57-4; 5 g), 4-fluorophenylboronic acid (3.56 g) and cesium carbonate (31.6 g) were combined in THF (70 ml) and water (35 ml). The mixture was degassed by bubbling argon through the solution. After addition of [Iota, – bis(diphenylphosphino)ferrocene]dichloropalladium(II) (886 mg) the reaction mixture was stirred 1 h at 80 ¡ãC in a sealed tube. The reaction mixture was diluted with EtOAc, washed with water, dried over Na2S04, evaporated and purified by chromatography (silica gel, 0percent to 30percent EtOAc in heptane). The product was finally bulb-to-bulb distilled at 0.3 mbar and 120-130 ¡ãC oven temperature to give the title compound (5.07 g) as a light yellow liquid. In analogy to the synthesis of Intermediate 129, the following intermediates were prepared:

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; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; BUETTELMANN, Bernd; CECCARELLI, Simona M.; CONTE, Aurelia; KUEHNE, Holger; KUHN, Bernd; NEIDHART, Werner; OBST SANDER, Ulrike; RICHTER, Hans; WO2014/146994; (2014); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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. 6579-54-0 name is 2,6-Dichlorobenzenesulfonyl chloride, 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. 6579-54-0

a) 2-[(Cyclopropylcarbamoyl)amino]-1H-benzimidazol-5-yl 2,6-dichlorobenzenesulfonate may be prepared in the following manner:To a suspension of 300 mg of 1-cyclopropyl-3-(5-hydroxy-1H-benzimidazol-2-yl)urea in 100 cm3 of acetone are added 186 mg of triethylamine and 349 mg of 2,6-dichlorobenzenesulfonyl chloride. After stirring overnight at a temperature in the region of 20 C., 90 mg of 2,6-dichlorobenzenesulfonyl chloride are added and the mixture is stirred for a further 24 hours. The reaction medium is evaporated to dryness under reduced pressure (2 kPa). The residue is taken up in 50 cm3 of water and then extracted with three times 40 cm3 of ethyl acetate. The combined organic phases are dried over magnesium sulfate, filtered and evaporated to dryness under reduced pressure (0.5 kPa). After flash chromatography on a column of silica [eluent: dichloromethane/methanol (96.5/3.5 by volume)], the product obtained is solidified in 10 cm3 of diethyl ether and then filtered off, washed with three times 5 cm3 of diethyl ether and dried under reduced pressure over phosphorus pentoxide. 130 mg of 2-[(cyclopropylcarbamoyl)amino]-1H-benzimidazol-5-yl 2,6-dichlorobenzenesulfonate are obtained in the form of a cream-coloured powder, the characteristics of which are as follows:Melting point: melting at 160-165 C. (Koefler block)1H NMR spectrum at 400 MHz: 0.47 (m, 2H); 0.68 (m, 2H); 2.62 (m, 1H); 6.75 (dd, J=2.5 and 8.5 Hz, 1H); 7.09 (broad m, 1H); 7.24 (broad m, 1H); 7.30 (broad d, J=8.5 Hz, 1H); from 7.68 to 7.79 (m, 3H); 9.82 (broad m, 1H); 11.75 (broad m, 1H)Mass spectrum: MS (ES+): m/z=441 [MH+]

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2,6-Dichlorobenzenesulfonyl chloride, and friends who are interested can also refer to it.

Reference:
Patent; AVENTIS PHARMA S.A.; US2008/194555; (2008); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics