Month: November 2020

A common compound: 627-42-9, name is 2-Methoxyethyl chloride, 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. 627-42-9

(Ph2SiH)2 (0.10g, 0.27mmol) and B(C6F5)3 (0.015g, 0.029mmol) were combined with toluene (1mL) in a Schlenk flask. 2-Chloroethyl methyl ether (0.050mL, 0.55mmol) was added dropwise with stirring, and the resulting mixture was stirred under N2 (open to the nujol bubbler) for 16h, by which time it was cloudy white. The toluene was removed under vacuum and cold pentane (2mL) was added, giving a white precipitate. The precipitate was collected by filtration, washed with cold pentane (4mL), and dried under vacuum, giving a white powdery solid (0.094g, 65%). 1H NMR (300MHz, C6D6) delta 3.17 (t, 3JHH=6Hz, 4H, OCH2CH2Cl), 3.77 (t, 4H, OCH2CH2Cl), 7.14 (m, 12H, Hm/p-SiPh2), 7.75 (m, 8H, Ho-SiPh2); 13C NMR (75MHz, C6D6) delta 45.1 (OCH2CH2Cl), 64.8 (OCH2CH2Cl), 128.2 (Cm-SiPh2), 130.3 (Cp-SiPh2), 135.4 (Co-SiPh2). 29Si NMR (99MHz, C6D6) delta-7.7. M.p. 138-140C. Anal. (calcd for 93% C28H28O2Cl2Si2 (18) and 7% C2H6OSi (grease)): C 63.28 (63.23) H 5.17 (5.36).

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, 627-42-9, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Lee, Peter T.K.; Rosenberg, Lisa; Journal of Organometallic Chemistry; vol. 809; (2016); p. 86 – 93;,
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. 27139-97-5, name is 2-Bromo-4-chloro-1-methylbenzene, A new synthetic method of this compound is introduced below., 27139-97-5

To a suspension of magniesium (0.12 g) in THF (15 ml_) 2-bromo-4-chlorotoluene (0.125 g, commercially available) was added and the mixture stirred for a few minutes. Then a solution of 2-bromo-4-chlorotoluene (0.9 g) in THF (85 ml_) was added dropwise and the mixture stirred for 3h. The mixture was added dropwise to a solution of acetyl chloride(0.353 g) in THF (10 ml_) at 0 0C. The mixture was stirred at RT for 5h. Chilly water was added to the reaction mixture and the pH adjusted at pH 6 with HCI 10percent and the product extracted with EA. The organic phase was dried and the solvent evaporated under vacuum to give the title compound (0.676 g) that was used in next step without further purification.MS (m/z): 169 [MH]+

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; GLAXO GROUP LIMITED; WO2009/130231; (2009); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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. 13078-79-0, name is 2-(3-Chlorophenyl)ethanamine belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. 13078-79-0

Step iii) 3-(3-Chlorophenethylamino)-N-cyclohexyl-N-(2-(2-(8-hydroxy-2-oxo-l ,2- dihydroqumolin-5-yl)etliylamino)ethyl)rhoropanamide bis(trifluoroacetate)Benzyl 2-(N-cyclohexylacrylamido)ethyl(2-(8-hydroxy-2-oxo- 1 ,2-dihydroquinolin-5- yl)ethyl)carbamate (70 mg) [Step ii] and 2-(3-chlorophenyl)ethylamine (63 mg) were combined in ethanol (5.8 niL) and the resulting solution stirred at 50 0C for 18 h. The mixture was then concentrated in vacuo prior to addition of acetic acid (2 mL) followed by 33% HBr in acetic acid (3 mL). The resulting solution was stirred for 3 h then concentrated in vacuo and the residue partially purified by flash chromatography on silica (eluting with 10% methanol in dichloromethane). Product containaing fractions were combined and concentrated in vacuo. The residue was further purified by reverse phase preparative HPLC (eluting with 5-40% acetonitrile in 0.1% aqueous trifluoroacetic acid). Product containing fractions were combined and concentrated in vacuo to afford the title compound as a solid (5 mg) MS (APCI+) 539 [M+H]+1H NMR (399.825 MHz, CD3OD) delta 8.16 (d, J = 9.7 Hz5 IH)5 7.41 – 7.35 (m, 2H), 7.30 – 7.22 (m, 2H), 6.98 (dd, J = 22.2, 8.1 Hz52H), 6.66 (d, J= 10.0 Hz5 IH), 3.65 – 3.57 (m, 3H)5 3.38 – 3.27 (m, 4H), 3.23 – 3.14 (m, 8H), 2.91 (t, J = 6.0 Hz, 2H), 1.88 – 1.82 (m, 2H), 1.79 – 1.74 (m, 2H), 1.70 – 1.63 (m, IH), 1.56 – 1.26 (m, 4H), 1.22 – 1.09 (m, IH).

The synthetic route of 13078-79-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2008/75025; (2008); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

1996-30-1, Name is 3-Bromo-4-fluorochlorobenzene, 1996-30-1, belongs to chlorides-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows.

To a solution of 2-bromo-4-chloro-1 -fluorobenzene (1 .03 g, 4.94 mmol) in tetrahydrofuran (20 ml_) at -78 C was added n-butyllithium (4.0 ml_, 9.88 mmol) under nitrogen. The reaction mixture was stirred at -78 C for 2 h before a solution of 6-(4-methoxybenzylamino)pyridazine-3-carbaldehyde (0.800 g, 3.29 mmol) in tetrahydrofuran (3 ml_) was added dropwise. The reaction mixture was stirred for another 2 h and was warmed to 20 C. Aqueous ammonium chloride was added to quench the reaction and the volatiles were removed under reduced pressure. The aqueous layer was extracted with dichloromethane (50 ml_ x 2). The combined organic layers were dried over sodium sulfate, filtered and concentrated. The crude sample was purified by column chromatography (silica gel, petroleum ether/ethyl acetate = 4/1 to 1 /1 ) to give (5-chloro-2-fluorophenyl)(6-(4-methoxybenzylamino)pyridazin-3-yl)methanol (0.330 g, 0.888 mmol, 27%) as a yellow solid. LCMS (ESI) m/z: 374.0 [M+H]+.

Statistics shows that 3-Bromo-4-fluorochlorobenzene is playing an increasingly important role. we look forward to future research findings about 1996-30-1.

Reference:
Patent; YUMANITY THERAPEUTICS, INC.; LE BOURDONNEC, Bertrand; LUCAS, Matthew; OZBOYA, Kerem; PANDYA, Bhaumik; TARDIFF, Daniel; TIVITMAHAISOON, Parcharee; WRONA, Iwona; (475 pag.)WO2019/183587; (2019); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

The chemical industry reduces the impact on the environment during synthesis 933190-51-3, name is 8-Bromo-6-chloroimidazo[1,2-b]pyridazine, I believe this compound will play a more active role in future production and life. 933190-51-3

A mixture of 8-bromo-6-chloroimidazo[l ,2-b]pyridazine (300 mg, 1.3 mmol), 6-(3- methylcyclopentyl)pyridin-2-amine (277 mg, 1.56 mmol), Pd2(dba)3 (75 mg, 0.13 mmol), BINAP (324 mg, 0.52 mmol), Cs2C03 (1272 mg, 3.9 mmol) and dioxane (20 mL) was heated to 100 C with stirring for 16 h under N2. The solvent was removed in vacuo and the resulting mixture was purified by chromatography (silica gel, 200 – 300 mesh, petroleum ether : ethyl acetate = 5 : 1) to give 6-chloro-N-(6-(3-methylpyrrolidin-l-yl)pyridin-2-yl)imidazo[l ,2-b] pyridazin-8-amine (301 mg, 70 %) as a yellow solid. LC-MS : [M+H]+, 329.1 , tR = 1.949min.

The chemical industry reduces the impact on the environment during synthesis 933190-51-3. I believe this compound will play a more active role in future production and life.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HERMANN, Johannes Cornelius; KUGLSTATTER, Andreas; LUCAS, Matthew C.; PADILLA, Fernando; WANNER, Jutta; ZHANG, Xiaohu; WO2013/64445; (2013); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

A common compound: 452-83-5, name is 2-Chloro-5-fluoroaniline, 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. 452-83-5

To a mixture of (5.0 g) 2-chloro-5-fluoroaniline (commercially available, 6.0 g), glycerol (6.0 g) and m-nitrobenzene sulfonic acid sodium salt (11.0 g), was added 20 ml of 70% sulfuric acid dropwise. The reaction temperature was raised to 140 C. for 2 hr. The mixture was then cooled, poured on ice water and filtered through celite. The filtrate was neutralized with NaOH and extracted with CH2Cl2. The combined organic layers were dried over anhydrous MgSO4 and concentrated on a rotary evaporator. The crude product was purified by flash chromatography on silica gel using 100% CH2Cl2 to give 3.7 g of the desired product of a yellow solid; MP=74-76 C.; MS (ES) m/z (relative intensity): 182 (M+H)+ (100).

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, 452-83-5, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Wyeth; US2007/27160; (2007); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

29671-92-9, 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 29671-92-9 as follows.

Example 312-amino-N-hydroxy-4-oxo-3,4-dihydroquinazoline-7-carboxamide; Compound I-199 Step 1: methyl 2-amino-4-oxo-3,4-dihydroquinazoline-7-carboxylate; Intermediate-12Into a round bottom flask was added dimethyl 2-aminoterephthalate (1.0 g, 4.8 mmol) mixed with carbamimidic chloride-HCl (1.10 g, 9.6 mmol) and dimethyl sulfone (4.5 g, 47.8 mmol). The reaction mixture was heated to 150 C. and stirred overnight. The mixture was cooled to rt, water added and the solid was filtered. The solid was then washed with acetic acid to afford methyl 2-amino-4-oxo-3,4-dihydroquinazoline-7-carboxylate (1.0 g, 95%). LC-MS: (FA) ES+220

According to the analysis of related databases, 29671-92-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Millennium Pharmaceuticals, Inc.; US2012/94997; (2012); 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. 626-43-7, name is 3,5-Dichloroaniline, This compound has unique chemical properties. The synthetic route is as follows., 626-43-7

Benzoyl acetone (0.165 g, 1.017 mmol) was dispersed over Montmorillonite K-10 catalyst (1.5 g) and a mixture of 3.5-dichloroaniline (0.552 g, 3.407 mmol) with 20 ml THF was added dropwise, while stirring. The reaction was stirred at room temperature for 48 h. The catalyst was removed by filtration and the solvent was removed on a rotary evaporator, yielding a dark red oil.Yield 93%. Colour: dark red. UV: lambdamax 359 nm, epsilonmax 29453 mol-1dm3cm-1 (CH3CN), 1H NMR (300 MHz, CDCl3, 25C):delta 7.91-7.89 ppm (d, aromatic, 2H); 7.54-7.44 ppm (m, aromatic,3H); 6.75-6.74 ppm (t, aromatic, 1H); 6.56 ppm (d, aromatic, 2H);6.20 ppm (s, CH, 1H); 2.22 ppm (s, CH3, 3H).

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; Ngake, Tankiso Lawrence; Potgieter, Johannes Hermanus; Conradie, Jeanet; Electrochimica Acta; vol. 296; (2019); p. 1070 – 1082;,
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. 83121-15-7, name is 3,5-Dichloro-2,4-difluoroaniline, A new synthetic method of this compound is introduced below., 83121-15-7

To a mixture of 3,5-dichloro-2,4-difluoroaniline (5.0 g), an aqueous 57% solution of hydroiodic acid (20 ml) and water (20 ml), copper iodide (1.92 g) was added. The reaction liquid was maintained at 30C or less in a water bath.To the reaction mixture was added dropwise a water solution (2 mL) of sodium nitrite ( 1.74 g). The reaction mixture was stirred for 10 minutes, maintained at 30C or less in a water bath. To the reaction mixture was added dropwise a water solution (2 mL) of sodium nitrite (1.74 g), again. The reaction mixture was further stirred for 10 minutes, maintained at 30C or less in a water bath. To the reaction mixture was added dropwise a water solution (2 mL) of sodium nitrite (1.74 g), again. t-Butyl methyl ether was added and the mixture was washed with water and with an aqueous solution of sodium sulfite and brine, and dried over anhydrous magnesium sulfate. The drying agent was filtered off, the solvent was distilled off under reduced pressure and the residue was purified by silica gel chromatography (n- hexane) to obtain l,3-dichloro-2,4-difluoro-5-iodobenzene (6.0 g). i-NMR (CDC13) delta: 7.6-7.75 (1H, m).

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; BAYER CROPSCIENCE AG; MIHARA, Jun; HATAZAWA, Mamoru; YAMAZAKI, Daiei; KISHIKAWA, Hidetoshi; DOMON, Kei; WATANABE, Hidekazu; SASAKI, Norio; MURATA, Tetsuya; ARAKI, Koichi; SHIMOJO, Eiichi; ICHIHARA, Teruyuki; ISHIKAWA, Tadashi; SHIBUYA, Katsuhiko; GOeRGENS, Ulrich; BRUeCHNER, Peter; FISCHER, Reiner; JANSEN, Johannes-Rudolf; KAPFERER, Tobias; MAECHLING, Simon; MAUE, Michael; VOERSTE, Arnd; WO2012/35011; (2012); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

108-37-2, 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 108-37-2 as follows.

General procedure: Na2CO3 (212 mg, 2 mmol), 4-chloronitrobenzene (1 mmol) and styrene (1.5 mmol) were added successively into a dried Schlenk tube under nitrogen. Then the DMA (0.1mL) solution of DADPP (0.002mmol) and [Pd(C3H5)Cl]2 (0.0005mmol), which was reacted at 100C for 10 min prior to use, was added into the mixture. The reaction was performed at 130C. At the end of reaction, the mixture solution was extracted with ethyl acetate (3¡Á5 mL). Combined organic phase was washed with brine (3¡Á5mL) and dried over MgSO4. The dried solution was filtered and purified with silica gel chromatography (petroleum ether 60-90C) to give a corresponding product.

According to the analysis of related databases, 1-Bromo-3-chlorobenzene, the application of this compound in the production field has become more and more popular.

Reference:
Article; Jiang, Zhi-Jie; Wang, Wei; Zhou, Rong; Zhang, Lei; Fu, Hai-Yan; Zheng, Xue-Li; Chen, Hua; Li, Rui-Xiang; Catalysis Communications; vol. 57; (2013); p. 14 – 18;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics