Category: chlorides-buliding-blocks

933190-51-3, A common compound: 933190-51-3, name is 8-Bromo-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.

General procedure: To a solution of 6a-6c (1 mmol) in THF (5 mL) was addedmorpholine (or (S)-3-methylmorpholine, or 8-oxa-3-azabicyclo[3.2.1]octane) (1.2 mmol) and Et3N (2.2 mmol). The mixture washeated under reflux for 12 h. The crude product was extracted with CH2Cl2, dried over Na2SO4, purified over silica gel chromatographyeluting with PE and EtOAc to give 7a-7g [43].

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

Reference:
Article; Mao, Beibei; Gao, Shanyun; Weng, Yiran; Zhang, Liangren; Zhang, Lihe; European Journal of Medicinal Chemistry; vol. 129; (2017); p. 135 – 150;,
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6940-78-9, Adding some certain compound to certain chemical reactions, such as: 6940-78-9, name is 1-Bromo-4-chlorobutane, 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 6940-78-9.

General procedure: General procedure for the preparation of omega-naphthyloxyhalo alkanes (3a-c) involves refluxing of mixture of beta-naphthol (1) (20 g, 0.14 mol), anhydrous K2CO3 (100 g, in excess) and bromochloroalkane 2 (0.14 mol) in dry acetone (200 mL) for12-15 h. Reaction mixture was filtered and filtrate was concentrated to get oily compound, which was crystallized with benzene-hexane to give the colourless crystals of pure desired compound (Scheme-I) [48].

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 6940-78-9.

Reference:
Article; Zaidi, Sadaf; Chaturvedi, Devdutt; Saxena, Mridula; Srivastava, Richa; Asian Journal of Chemistry; vol. 31; 10; (2019); p. 2201 – 2210;,
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26487-67-2, 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. 26487-67-2, name is 1-(2-Chloroethyl)azepane hydrochloride belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 1,1-bis(4-hydroxyphenyl)-2-butylhex-1-ene (69.1 mg, 0.213 mmol) in DMF (2.13 mL) at 0 ¡ãC was added 55percent sodium hydride (dispersion in paraffin liquid, 74.4 mg, 1.71 mmol). The reaction mixture was stirred for 15 min at 50 ¡ãC and then N-(2-chloroethyl)hexahydro-1H-azepine hydrochloride (139 mg, 0.702 mmol) was added in portions at room temperature. After the reaction mixture had been stirred for 3 h at 50 ¡ãC, saturated aqueous ammonium chloride was added at 0 ¡ãC. The mixture was extracted with dichloromethane and the organic layer was dried over sodium sulfate. After filtration of the mixture and evaporation of the solvent, the crude product was purified by thin layer chromatography on silica (eluant; ammoniacal chloroform/methanol = 30/1) to afford RID-F-S*23 (compound 18) (118 mg, 96percent) as an orange oil

The synthetic route of 1-(2-Chloroethyl)azepane hydrochloride has been constantly updated, and we look forward to future research findings.

Reference:
Article; Hasegawa, Makoto; Yasuda, Yukari; Tanaka, Makoto; Nakata, Kenya; Umeda, Eri; Wang, Yanwen; Watanabe, Chihiro; Uetake, Shoko; Kunoh, Tatsuki; Shionyu, Masafumi; Sasaki, Ryuzo; Shiina, Isamu; Mizukami, Tamio; European Journal of Medicinal Chemistry; vol. 71; (2014); p. 290 – 305;,
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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 24279-39-8 as follows. 24279-39-8

Reference Production Example 10 First, 31.4 g (120 mmol) of triphenylphosphine and 4.9 g (48 mmol) of triethylamine were added to 20 ml of carbon tetrachloride, to which 3.8 g (40 mmol) of difluoroacetic acid was added dropwise under ice cooling. After completion of the dropwise addition, the mixture was stirred under ice cooling for 10 minutes. Then, a solution of 9.2 g (40 mmol) of 2,6-dichloro-4-trifluoromethylaniline in 20 ml of carbon tetrachloride was added dropwise to the reaction mixture, which was heated at 80 C. for 6 hours. The reaction mixture was concentrated under reduced pressure, followed by addition of hexane, and undissolved matter was removed by filtration. The filtrate was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 6.0 g of N-(2,6-dichloro-4-trifluoromethylphenyl)-2,2-difluoroacetimidoyl chloride. 1H-NMR (300 MHz, CDCl3/TMS): delta (ppm)=7.65 (s,21), 6.38 (t, J=54.1 Hz, 1H)

According to the analysis of related databases, 24279-39-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Matsumoto, Osamu; Uekawa, Toru; US2001/41740; (2001); A1;,
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Adding some certain compound to certain chemical reactions, such as: 2770-11-8, name is 2-(4-Chlorophenoxy)aniline, 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 2770-11-8. 2770-11-8

Preparation of {4-[2-(4-chlorophenoxy)phenylamino]-piperidin-l-yl}- cyclopentylmethanone STX1685 C23H27ClN2O2, MW: 398.94To a solution of 2-(4-cUorophenoxy)phenylarnine (100 mg, 0.45 mmol), 1- cyclopentylcarbonyl-4-piperidone (144 mg, 0.735 mmol) and acetic acid (147 mg, 2.45 mmol) in DCE (1.5 ml) was added sodium triacetoxyborohydride (260 mg, 1.23 mmol). This solution was then heated at 100C for 15 minutes hi a CEM discover microwave (fixed hold time set to on). The reaction mixture was then quenched with saturated aqueous sodium bicarbonate solution (5 ml) and extraction with ethyl acetate (3 x 5 ml) EPO followed. The combined organics were concentrated in vacuo and purification by flash chromatography proceeded (eluant: 8:2 hexane: ethyl acetate) to provide the title compound as a transparent oil (82 mg, 43%). 1H NMR (300 MHz, CDCl3): delta 1.16-1.36 (2H, m, 2 x CH)3 1.47-1.56 (2H, m, 2 x CH), 1.59-1.78 (6H, m, 6 x CH)5 1.93-2.08 (2H, m, 2 x CH), 2.76-2.87 (2H, m, 2 x CH), 3.07-3.18 (IH, m, CH), 3.43-3.52 (IH, sept, J = 3.9 Hz, CH), 3.78-3.89 (IH, bd, J = 13.8 Hz, CH), 3.97-4.10 (IH, m, CH), 4.31-4.42 (IH, bd, J = 13.5 Hz, NH), 6.55-6.62 (IH, td, J = 1.5, 1.2, 1.2, 7.7 Hz, ArH), 6.68-6.71 (IH, dd, J = 1.5, 8.1 Hz, ArH), 6.73-6.77 (IH, dd, J = 1.5, 8.1 Hz, ArH), 6.79-6.84 (2H, m, ArH), 6.95-7.01 (IH, td, J = 1.5, 0.6, 1.5, 7.7 Hz, ArH), 7.16-7.22 ppm (2H, m, ArH). 13C NMR (67.93 MHz, CDC13): delta 19.5, 19.6, 30.2, 32.2, 33.2, 40.6, 44.1, 49.9, 112.2, 117.2, 118.8, 119.6, 125.3, 127.9, 129.8, 138.9, 143.1, 156.1, 175.4 ppm LCMS: M+H: 421.46 HPLC: 98.41% (3.124 rnin, isocratic 90% acetonitrile, 10% water at 1 rnl/min).

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-(4-Chlorophenoxy)aniline.

Reference:
Patent; STERIX LIMITED; WO2007/3934; (2007); A2;,
Chloride – Wikipedia,
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54932-72-8, The chemical industry reduces the impact on the environment during synthesis 54932-72-8, name is 4-Bromo-1-chloro-2-methylbenzene, I believe this compound will play a more active role in future production and life.

To a solution of 4-bromo-1 -chloro-2-methyl-benzene (30 g, 146 mmol) and benzoyl peroxide (0.71 g, 3 mmol) in acetonitrile (70 mL) was added N-bromosuccinimide (28.6 g, 161 mmol) at 90C and the mixture was stirred overnight. The solution was evaporated under reduced pressure and the crude material was purified onsilica gel to give 4-bromo-2-(bromomethyl)-1 – chloro-benzene as a white solid (40.3 g, 95% yield).

The chemical industry reduces the impact on the environment during synthesis 4-Bromo-1-chloro-2-methylbenzene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; BASF SE; WINTER, Christian; RHEINHEIMER, Joachim; WOLF, Antje; POONOTH, Manojkumar; TERTERYAN, Violeta; WIEBE, Christine; KREMZOW-GRAW, Doris; ROeHL, Franz; GRAMMENOS, Wassilios; ROHRER, Sebastian Georgios; WIEJA, Andy; ROSENBAUM, Claudia; WO2014/207052; (2014); A1;,
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6775-78-6, A common heterocyclic compound, 6775-78-6, name is 6-Chloroimidazo[1,2-b]pyridazine, molecular formula is C6H4ClN3, 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.

[0517] Synthesis of methyl imidazo[l,2-b]pyridazine-6-carboxylate: [0518] To a stirred solution of 6-chloroimidazo[l,2-b]pyridazine (2.0 g, 13.15 mmol) in ACN:MeOH (60 mL, 1 : 1) under N2 bubbling atmosphere were added BINAP (818 mg, 1.31 mmol), Pd(ACN)2Cl2 (341 mg, 1.31 mmol) and Et3N (1.60 g, 15.78 mmol) in a steel bomb. The resultant reaction mixture was agitated under CO atmosphere (150 psi) at 100 C for 16 h. After full consumption of starting material by TLC, the reaction was diluted with water and extracted with EtOAc. The combined organic layer was dried over sodium sulphate, filtered and concentrated in vacuo to obtain the crude product. The crude material was purified by silica gel column chromatography to afford imidazo[l,2-b]pyridazine-6-carboxylate (1.3 g, 65%) as brown solid. 1H-NMR (DMSO-d6, 500 MHz): delta 8.51 (s, 1H), 8.27 (d, 1H), 7.94 (s, 1H), 7.72 (d, 1H), 3.97 (s, 3H); LC-MS: 91.14%; 178 (M++l) (column; X- bridge C-18, (50×3.0 mm, 3.5mu); RT 2.28 min. 5mM NH4OAc: ACN; 0.8 ml/min); TLC: 70% EtOAc/Hexane (Rf: 0.5).

The synthetic route of 6775-78-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ENVIVO PHARMACEUTICALS, INC.; RIPKA, Amy; SHAPIRO, Gideon; MCRINER, Andrew, J.; BURSAVICH, Matthew, Gregory; WO2013/142269; (2013); A1;,
Chloride – Wikipedia,
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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 39989-43-0 as follows. 39989-43-0

Step 8 Preparation of 8-hydroxy-6-methyl-[1,6]naphthyridine-7-carboxylic Acid 3,5-dichloro-benzylamide (124H) A mixture of 124G (150 mg, 0.64 mmol), 3,5-dichlorobenzylamine (153 mg, 0.87 mmol) and aluminum chloride (27 mg, 0.20 mmol) in toluene (8 mL) was refluxed for 4 h under nitrogen. After cooling to room temperature, the reaction mixture was treated with aqueous saturated NaHCO3 solution and ethylenediaminetetraacetic acid (1 g, 3.4 mmol) to pH 7. The mixture was extracted with chloroform four times. The combined organic phases were dried over Na2SO4 and concentrated. The residue was purified by preparative reverse-phase HPLC to give 124H. 1H NMR (400 MHz, DMSO) delta 13.2 (s, 1H), 9.73 (t, 1H), 9.15 (dd, 1H), 8.64 (dd, 1H), 7.83 (dd, 1H), 7.52 (s, 1H), 7.44 (s, 2H), 4.57 (d, 2H), 2.85 (s, 3H).

According to the analysis of related databases, 39989-43-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Anthony, Neville J.; Gomez, Robert P.; Young, Steven D.; Egbertson, Melissa; Wai, John S.; Zhuang, Linghang; Embrey, Mark; Tran, LeKhanh; Melamed, Jeffrey Y.; Langford, H. Marie; Guare, James P.; Fisher, Thorsten E.; Jolly, Samson M.; Kuo, Michelle S.; Perlow, Debra S.; Bennett, Jennifer J.; Funk, Timothy W.; US2003/55071; (2003); A1;,
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A common heterocyclic compound, 13078-79-0, name is 2-(3-Chlorophenyl)ethanamine, molecular formula is C8H10ClN, 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. 13078-79-0.

Example 23; 3-[5,6-Bis(methyloxy)-2-pyridinyll-Lambda/-[2-(3-chlorophenylkthyll-2,4-dioxo-l,2,3,4- tetrahydrothieno[3,2-Patent; GLAXOSMITHKLINE LLC; SCHULZ, Mark, James; WANG, Younghui; GHERGUROVICH, Jonathan M.; WO2010/59555; (2010); A1;,
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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 344-19-4 as follows. 344-19-4

General procedure: A solution of 2,4,6-trisubstitutedphenylamine (10, 0.8 mmol) in pyridine (10 mL) was added to the flask containingt he crude acyl chloride 8 (0.8 mmol) which was prepared from the procedure described above, and the mixture was refluxed for 3-5 h. After cooling down, the mixture was poured into water (50 mL) and extracted with ethyl acetate (3¡Á 15 mL). The extracts were combined and washed with hydrochloric acid (2 ¡Á 10 mL) and brine, successively. The organic phase was dried over anhydrous Na2SO4. After solvent removal, the residue was further purified by recrystallization from ethanol to afford the title compound 12(a-c) as a solid.

According to the analysis of related databases, 344-19-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; Wang, Baolei; Wang, Hongxue; Liu, Hang; Xiong, Lixia; Yang, Na; Zhang, Yan; Li, Zhengming; Chinese Chemical Letters; vol. 31; 3; (2020); p. 739 – 745;,
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