Tag: M.W=200-300

Reference of 13745-86-3,Some common heterocyclic compound, 13745-86-3, name is 11-Chlorodibenzo[b,f][1,4]thiazepine, molecular formula is C13H8ClNS, 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.

(b) 11-Piperazinyl-dibenzo[b,f][1,4]thiazepine. Piperazine (1.7 mole) was dissolved in warm toluene (about 50C) (750 ml) and 11-chloro-dibenzo[b,f][1,4]thiazepine added. The reaction was heated to reflux and maintained at this temperature for 5 hr. After cooling to ambient temperature the reaction was filtered to remove piperazine hydrochloride, the organic phase was washed several times with water to remove excess piperazine. The organic phase was dried over magnesium sulphate and after filtration the solvent was removed in vacuo to give the product as an oil. The oil was dissolved in ethanol and treated with a solution of hydrogen chloride in ethanol. 11-Piperazinyl-dibenzo[b,f][1,4]thiazepine was isolated as the dihydrochloride salt in ca 88% yield, m.pt. 103-105 (softens), 135-140C (decomp).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 11-Chlorodibenzo[b,f][1,4]thiazepine, its application will become more common.

Reference:
Patent; IMPERIAL CHEMICAL INDUSTRIES PLC; EP282236; (1988); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 1205-71-6, name is 4-Chloro-N-phenylaniline, 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 1205-71-6, Recommanded Product: 4-Chloro-N-phenylaniline

General procedure: To a 50 mL of two-neck round-bottomed flask charged with a magnetic stirrer bar, were successively added 1-Bromo(2-diphenylphosphoryl)ethyne (1) (305 mg, 1.0 mmol), diphenylamine(203 mg, 1.2 mmol, 1.2 equiv), K3PO4 (637 mg, 3.0 mmol, 3.0 equiv) and dehydrated toluene (5mL). After the mixture was stirred at 80 C for 15 h, the reaction mixture was quenched with 1 mL of saturated NH4Cl aq., and extracted with ethyl acetate and H2O, and dried over brine and MgSO4. The crude product was purified by flash chromatography (hexane/EtOAc, 1:2) to afford the corresponding phosphoryl ynamine 2a (240 mg) in 61% yield.

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:
Article; Okuda, Yasuhiro; Seo, Tomoyo; Shigezane, Yuki; Watanabe, Hikaru; Akashi, Haruo; Iwanaga, Tetsuo; Orita, Akihiro; Chemistry Letters; vol. 48; 12; (2019); p. 1484 – 1487;,
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Electric Literature of 96558-78-0, The chemical industry reduces the impact on the environment during synthesis 96558-78-0, name is 3-Bromo-5-chlorophenylamine, I believe this compound will play a more active role in future production and life.

Preparation of starting material 3-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (SM-17) This material was prepared from 3-bromo-5-chloroaniline following a similar procedure used for SM-9, step 3. The crude product was purified by flash chromatography (RediSep Cyano, Teledyne ISCO, 0-50% EtOAc in hexanes) to afford 3-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (48%) as a pale orange solid: LCMS(m/z) 172.1 (MH+), tR=0.33 minute.

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, 3-Bromo-5-chlorophenylamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Costales, Abran Q.; Huang, Shenlin; Jin, Jeff (Xianming); Liu, Zuosheng; Pecchi, Sabina; Poon, Daniel; Tellew, John; US2011/52578; (2011); A1;,
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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. 13918-92-8, name is 2,4-Difluorobenzene-1-sulfonyl chloride, A new synthetic method of this compound is introduced below., Safety of 2,4-Difluorobenzene-1-sulfonyl chloride

General procedure: To a solution of 5-bromo-2-methoxypyridin-3-amine (2.01 g,10 mmol) in pyridine (50 mL) at 0 C was added methanesulfonylchloride (1.72 g, 11 mmol). Then the mixture was stirred at 25 C for24 h. Pyridine was removed at reduced pressure and add water (100 mL), extracted with ethyl acetate (3×100 mL), the organic layerwas washed with water (50 mL), dried with Na2SO4 and evaporated togive compound 6a as a white solid. Yield 78.4%, m.p. 150-151 C. 1HNMR (400 MHz, DMSO-d6) 9.51 (s, 1H, NH), 8.09 (d, J=2.4 Hz, 1H,Ar-H), 7.77 (d, J=2.4 Hz, 1H, Ar-H), 3.91 (s, 3H, OCH3), 3.16 (t,J=7.6 Hz, 2H, CH2), 1.73-1.65 (m, 2H, CH2), 1.42-1.33 (m, 2H, CH2),0.87 (t, J=7.2 Hz, 3H, CH3). ESI-MS: m/z 384.1 [M+H]+.Compounds 6b was synthesized according to the procedure describedin 6a.

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; Dong, Fu-Dan; Liu, Dan-Dan; Deng, Cheng-Long; Qin, Xiao-chun; Chen, Kai; Wang, Jian; Song, Hong-Rui; Ding, Huai-Wei; Bioorganic and Medicinal Chemistry; vol. 26; 14; (2018); p. 3982 – 3991;,
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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. 1996-29-8, name is 1-Bromo-4-chloro-2-fluorobenzene belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Computed Properties of C6H3BrClF

To a stirred solution of l-Bromo-4-chloro-2-fluorobenzene Al (200 g, 0.955 mol, 1.0 equiv.) in anhydrous THF (2.0 L) was added 2.0 M lithium diisopropylamide (LDA) in THF (620 mL, 1.24 mol, 1.3 equiv.) at -50 C, the reaction mixture was allowed to -20 C and stirred for 1 h. Then it was re-cooled to -50 C and slowly added DMF (184.8 mL, 2.48 mol, 2.6 equiv.) at the same temperature. The mixture was allowed to 0 C and stirred for 30-45 min. After completion of the reaction (monitored by TLC), it was quenched with the slow addition of ice cold water (2.0 L); then diluted with ethyl acetate (2.0 L) and stirred for 15 min at room temperature. The organic layer was separated and aqueous layer was extracted with ethyl acetate (2 x 1.0 L). The combined organic layers were washed with water (2 x 1 0 L); 1.0 N HC1 (1 0 L) and 1 % NaCl solution (2.0 L). The organic layer was dried over anhydrous Na2SC , concentrated under vacuum. The resultant crude solid was directly used for next step without further purification. Yield: 210.0 g, 93% (reported 78%). NMR (400 MHz, CDCb): delta 10.39 (d, J= 0.8 Hz, 1H), 7.69 (dd, Ji = 7.2 Hz, J2 = 8.8 Hz, 1H), 7.19 (dd, Ji = 1.2 Hz, J2 = 8.4 Hz, 1H).

The synthetic route of 1996-29-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VIIV HEALTHCARE UK (NO.5) LIMITED; BABU, Suresh; BELEMA, Makonen; BENDER, John A; IWUAGWU, Christiana; KADOW, John F.; KUMARAVEL, Selvakumar; NAGALAKSHMI, Pulicharla; NAIDU, B. Narasimhulu; PATEL, Manoj; PEESE, Kevin M; RAJAMANI, Ramkumar; SAULNIER, Mark; WANG, Alan Xiangdong; (536 pag.)WO2018/203235; (2018); A1;,
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Chlorides – an overview | ScienceDirect Topics

These common heterocyclic compound, 110407-59-5, name is 2-Chloro-4-fluorobromobenzene, 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. Computed Properties of C6H3BrClF

Step 1 Ethyl 2′-chloro-4′-fluorobiphenyl-2-carboxylate To a reaction vessel were added 1-bromo-2-chloro-4-fluorobenzene (25 g), ethyl 2-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)benzoate (46 g), toluene (125 ml), water (125 ml) and tripotassium phosphate (50.5 g), and the reaction vessel was substituted with argon. To this mixture was added dichlorobis(triphenylphosphine)palladium(II) (1.67 g) and the mixture was stirred at an oil bath temperature 110 C. for 3 hr. The reaction vessel was removed from the oil bath, and water (125 ml) was added to the reaction mixture. The mixture was stirred at room temperature for 1 hr and filtered through celite. The filtrate was partitioned by pouring into a separating funnel. The aqueous layer was extracted with toluene, and combined with the organic layer. The organic layer was washed twice with water (125 ml), dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to give the title compound (41.8 g). The obtained solid was used for the next reaction without further purification. 1H-NMR (400 MHz, CDCl3) delta: 8.06-8.02 (1H, m), 7.60-7.54 (1H, m), 7.52-7.45 (1H, m), 7.27-7.16 (3H, m), 7.06-7.00 (1H, m), 4.18-4.09 (2H, m), 1.11-1.06 (3H, m).

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

Reference:
Patent; JAPAN TOBACCO INC.; Motomura, Takahisa; US2014/296316; (2014); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 883499-24-9, name is 1-Bromo-2-chloro-3-fluorobenzene, 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 883499-24-9, SDS of cas: 883499-24-9

Under nitrogen environment,And at reflux temperature, 7-(diphenylamino)-9,9′-dimethyl-9H-fluoren-3-ol (100 g),1-bromo-2-chloro-3-fluorobenzene (58.3 g),The flask of potassium carbonate (91.5 g) and NMP (500 ml) was heated and stirred for 4 hours.After the reaction stopped, the reaction solution was cooled to room temperature, and water was added,The precipitate deposited was extracted by suction filtration. Use water in turn,After washing the obtained precipitate with methanol,Refined with silicone tubing (dissolved solution: toluene),Thus, 6-(3-bromo-2-chlorophenoxy)-9,9-dimethyl-N,N-diphenyl-9H-fluoren-2-amine (150 g) was obtained.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Bromo-2-chloro-3-fluorobenzene, and friends who are interested can also refer to it.

Reference:
Patent; KWANSEI GAKUIN EDUCATIONAL FOUNDATION; JNC CORPORATION; HATAKEYAMA, TAKUJI; MASUDA, KATSUYA; YAMAGA, YUKO; YANAI, MOTOKI; (214 pag.)TW2019/4977; (2019); A;,
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Synthetic Route of 220227-21-4,Some common heterocyclic compound, 220227-21-4, name is 2,4,5-Trifluorobenzene-1-sulfonyl chloride, molecular formula is C6H2ClF3O2S, 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.

Intermediate 19 1,1 -dimethylethyl (2S,4R)-2-methyl-4-{[(2,4,5-trifluorophenyl)sulfonyl]amino}-1- pyrrolidinecarboxylateTo 1 ,1-dimethylethyl (2S,4R)-4-amino-2-methyl-1-pyrrolidinecarboxylate (0.075 g, 0.38 mmol) in DCM (~5 mL) was added a solution of 2,4,5-trifluorobenzenesulfonyl chloride (0.075 g, 0.38 mmol) in DCM (~5 mL) and DIPEA (0.13 mL, 0.75 mmol). The resultant mixture was stirred at room temperature overnight, evaporated and loaded onto a 5 g silica SPE cartridge, eluting sequentially with DCM and ethyl acetate. The ethyl acetate fractions were combined and evaporated to afford the title compound (0.0942 g). LC-MS: m/z, 395 (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 2,4,5-Trifluorobenzene-1-sulfonyl chloride, its application will become more common.

Reference:
Patent; GLAXO GROUP LIMITED; WO2009/26197; (2009); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 63624-28-2 as follows. Product Details of 63624-28-2

Example 199; 1 -(2,4-Dimethoxybenzensulfonyl)-2-oxo-3-{2-oxo-1 -phenyl-2-[(S)-3-(4- propylpiperazin-1 -yl)pyrrolidin-1 -yl]ethyl}-2,3-dihydro-1 H-benzimidazole-5- carbonitrile; To a solution of 2-oxo-3-{2-oxo-1-phenyl-2-[(S)-3-(4-propyl-piperazin-1-yl)-pyrrolidin- 1-yl]-ethyl}-2,3-dihydro-1 H-benzoimidazole-5-carbonitrile (32 mg, 0.07 mmol), triethylamine (0.02 ml_, 0.13 mmol) and DMAP (catalytic amount) in CH2CI2 (2 ml.) 2,4-dimethoxybenzenesulfonyl chloride (17 mg, 0.077 mmol) was added. The reaction mixture was stirred at room temperature for 24 hours, diluted with water and extracted the aqueous phase with CH2CI2 (3 x). The combined organic phase was washed with saturated NaHCO3 aqueous solution, dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by flash chromatography in silica gel using 4% methanol in CH2CI2 as eluent to afford 1-(2,4-dimethoxy- benzenesulfonyl)-2-oxo-3-{2-oxo-1-phenyl-2-[(S)-3-(4-propyl-piperazin-1-yl)- pyrrolidin-1-yl]ethyl}-2,3-dihydro-1 H-benzoimidazole-5-carbonitrile (29 mg, 66%) as a white solid. 1H-NMR (400 MHz, CDCI3): delta 0.88-0.94 (m, 3H), 1.28 (m, 2H), 1.84 (m, 1 H), 2.14 (m, 1 H), 2.25-2.59 (m, 9H), 2.79-3.12 (m, 2H), 3.23-3.58 (m, 2H), 3.48 (s, 3H), 3.73- 3.99 (m, 2H), 3.89 (s, 3H), 6.36-6.44 (m, 2H), 6.65 (d, 8.9 Hz, 1 H), 7.00-7.10 (m, 1 H), 7.22-7.26 (m, 2H), 7.34-7.39 (m, 4H), 7.94 (d, 8.5 Hz, 1 H), 8.14 (d, 8.9 Hz, 1 H). MS (API-ES, pos) m/z = 673

According to the analysis of related databases, 63624-28-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ABBOTT GMBH & CO. KG; WO2008/25736; (2008); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 831-81-2, A common heterocyclic compound, 831-81-2, name is 4-Chlorodiphenylmethane, molecular formula is C13H11Cl, 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: In around-bottom flask, diarylmethanes (1.0 mmol), NBS (889.9 mg, 5.0 mmol) andwater (0 or 5.0 mmol) were dissolved in CHCl3 (4.0 mL). After refluxingfor 3 h in the air, the reaction mixture was quenched withNa2S2O3·5H2O, cooled to roomtemperature, washed with 5mL CH2Cl2, dried with MgSO4,and filtered to get clear organic solution. The solvent was removed reducedpressure by a rotary evaporator, and the resulting residue was subjected tocolumn chromatography on silica gel using co-solvent(ethyl acetate / petroleum ether, v/v) as eluent to give the correspondingdiaryllketones.

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; He, Chao; Zhang, Xiaohui; Huang, Ruofeng; Pan, Jing; Li, Jiaqiang; Ling, Xuege; Xiong, Yan; Zhu, Xiangming; Tetrahedron Letters; vol. 55; 32; (2014); p. 4458 – 4462;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics