Month: December 2020

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. 627-42-9, name is 2-Methoxyethyl chloride, A new synthetic method of this compound is introduced below., 627-42-9

General procedure: NaBH4 (23 mg, 0.60 mmol, 3.0 eq.) was portionwise added to a solution of 4,4′-diselanediyldibenzenesulfonamide 1 (94 mg, 0.20 mmol, 1.0 eq.) in EtOH (2 mL) at 0 C under inert atmosphere (N2). After 30 min, the halo-alkyl 2a-f (0.36 mmol, 2.1 eq.) was slowly added and the reaction mixture was stirred at reflux for 3 h, until complete consumption of the starting material was observed by TLC. The reaction was quenched by addition of saturated aq. NH4Cl (2 mL) and diluted with EtOAc (5 mL). The layers were separated and the aqueous layer was extracted with EtOAc (2 x 5 mL), dried over Na2SO4, filtered and concentrated under vacuum. The crude material was purified by flash chromatography to yield selenides (3a-f) bearing benzenesulfonamide moiety.

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:
Article; Angeli, Andrea; di Cesare Mannelli, Lorenzo; Lucarini, Elena; Peat, Thomas S.; Ghelardini, Carla; Supuran, Claudiu T.; European Journal of Medicinal Chemistry; vol. 154; (2018); p. 210 – 219;,
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

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. 112-26-5 name is 1,2-Bis(2-chloroethoxy)ethane, 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. 112-26-5

8-(9-chloro-1,4,7-trioxanon-1-yl) quinoline 8-hydroxyquinolinoe (1 g, 6.89 mmol) and potassium carbonate (1.43 g, 10.33 mmol) was stirred at room temperature in CH3CN for 2 h. The solution of 1,2 bis(2-chloroethoxy)ethane (2.58 g, 13.79 mmol) was added and the mixture was refluxed for 48 h. The solid residue was removed by filtration over filter paper. Then the filtrate was evaporated to dryness under rotary evaporator to yield brown oil. This was further purified by column chromatography through silica gel (EA/heaxane, 1:2) to give 8-(9-chloro-1,4,7-trioxanon-1-yl) quinoline as pale straw coloured oil (0.82 g, 40% yield). 1H NMR (500 MHz, CDCl3, 298 K): delta=8.89 (dd, J (H,H)=4 Hz, 1H, qu-CH), 8.10 (dd, J (H,H)=6 Hz, 1H, qu-CH), 7.39 (m, 3H, qu-CH), 7.07 (d, 1H, J (H,H)=8 Hz, qu-CH), 4.38 (t, 3J (H,H)=5 Hz, 2H, CH2), 4.05 (t, 3J (H,H)=5 Hz, 2H, alpha-CH2), 3.74 (m, 6H, CH2), 3.59 (t, 3J (H,H)=5 Hz, 2H, CH2).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1,2-Bis(2-chloroethoxy)ethane, and friends who are interested can also refer to it.

Reference:
Patent; National Dong Hwa University; LIN, Ivan Jyh Biau; HSU, Tina H. T.; CHOU, Shiu-Huey; (19 pag.)US2017/129907; (2017); 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

Into a vessel containing 3 mL of dioxane was added 60 mg of Exp-5-g24 prepared in Step 2 (0.19 mmol), 31 mg of 4-chloro-3-methoxy-phenylamine (0.2 mmol), 18 mg of Pd2dba3 (0.02 mmol), 23 mg of Xantphos (0.04 mmol) and 130 mg Cs2C03 (0.4 mmol). The reaction mixture thus provided was maintained under an 2 atmosphere, refluxed for 3 hours, then cooled to ambient temperature, filtered and concentrated under reduced pressure. The residue thus provided was purified by Prep-TLC (PE:EtOAc = 1 :2) yielding 65 mg of Exp-5-g25 (calculated yield 70 %).

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 SHARP & DOHME CORP.; LIVERTON, Nigel; JONES, Philip; LEI, Zhiyu; LIU, Fuqing; LUO, Yunfu; DONG, Jingchao; SOLL, Richard; WO2013/63100; (2013); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

118-69-4, Adding a certain compound to certain chemical reactions, such as: 118-69-4, name is 2,6-Dichlorotoluene, 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 118-69-4.

Ammoxidation runs were carried out in a fixed bed tubular quartz reactor, which is filled with 5g of catalyst particles prepared by the methods described in examples 1 to 3 and mixed with corundum particles of the same size in 1: 1 by weight ratio. A preheating zone is provided on the top of the catalyst bed. The catalyst was activated in a mixture of air and [NH3] at [400C] for 4 hours and then the catalytic runs were performed. The 2,6-DCT and [H20] were pumped in the mole ratio of 1: 15 to 20. The product stream was collected for every half-an-hour and analysed by gas chromatography. The reaction was carried out under the following reaction conditions. A reaction temperature of 350 to [400C] was used, and the GHSV comprised between 650-750 [H-‘.] The contact time consisted of 4.8 to 5.5 seconds. The mole ratio of 2,6-DCT : H20 : NH3: air was 1: 15: 3-4: 21, the molar concentration of 2,6-DCT was 2.4 % and the ratio of O/NH3 was 1. [1 %.]

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, 2,6-Dichlorotoluene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; TESSENDERLO CHEMIE S.A.; WO2003/101939; (2003); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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

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,
Chlorides – an overview | ScienceDirect Topics

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;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

57946-56-2, 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. 57946-56-2, name is 4-Chloro-2-fluoroaniline, This compound has unique chemical properties. The synthetic route is as follows.

4-Chloro-2-fluoroaniline (2.9 g, 20 mmol) was dissolved in ethanol (200 mL). Silver sulphate (6.22 g, 20 mmol) was added and then iodine (5.08 g, 20 mmol) was added in small portions. After the addition was complete the reaction mixture was stirred at ambient temperature for 90min. The reaction mixture was filtered through Celite and evaporated to leave a dark oil which was taken up in DCM (200 mL). and washed with 2M sodium hydroxide (2 x 50 mL), saturated sodium thiosulphate (2×50 mL) and water (2×50 mL). The solution was dried (MgSO4) and evaporated to leave the title compound as a dark oil (4.73g, 87%).1H NMR (400 MHz, DMSO-d6) delta 5.30 (2H, s), 7.25 – 7.29 (IH, m), 7.47 (IH, t)

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; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2006/82400; (2006); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

1996-29-8, These common heterocyclic compound, 1996-29-8, name is 1-Bromo-4-chloro-2-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.

1-bromo-4-chloro-2-fluorobenzene (5g, 23.9 mmol, 1 eq), 2-methylpiperazine (2.8 g, 1.15 eq), tris – dipalladium (O) (0.43g, 0,05 equiv), rac-BINAP (0.89g, 0.15 eq), sodium tert- butoxide (3.2 g, 1.4 eq) was slurried in toluene (60 mL), followed by the mixture was heated overnight at 65 C.. After cooling to room temperature, it was added ethyl acetate (100mL). The black precipitate was removed by filtration. The filtrate was washed twice with 3N potassium carbonate solution. The organic phase was dried over sodium sulfate, the solid was neutralized with 2N HCl-ether was collected by filtration, washed with ether, and dried in vacuo 1- (4-chloro-2-fluorophenyl) -3- It was obtained methyl piperazine as the dihydrochloride salt.

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 1996-29-8.

Reference:
Patent; CHEMOCENTRYX INCORPORATED; ZHANG, PENGLIE; ZENG, YIBIN; (41 pag.)JP5654467; (2015); B2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics