Month: March 2021

Application of 5414-19-7, 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. 5414-19-7, name is 1-Bromo-2-(2-bromoethoxy)ethane belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A solution of the ethyl 3-amino-1-methyl-1H-pyrazole-4-carboxylate (500 mg, 2.95 mmol), C52CO3 (2.9 g, 8.87 mmol), 1-bromo-2-(2-bromoethoxy) ethane (1.37 g, 5.90 mmol) in DMA(lOmL) as stirred at 120C overnight. Then H20 (20 mL) was added to the mixture and it was extracted with EA(x3). The organic layer was dried and purified by flash to give desired compound as yellow oil (610 mg, 87%). ESI-MS m/z: 240.0 [M+Hjt

The synthetic route of 1-Bromo-2-(2-bromoethoxy)ethane has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ENANTA PHARMACEUTICALS, INC.; SHOOK, Brian, C.; KIM, In, Jong; BLAISDELL, Thomas, P.; YU, Jianming; PANARESE, Joseph; OR, Yat, Sun; (434 pag.)WO2017/15449; (2017); A1;,
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Application of 1978-39-8, 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 1978-39-8 as follows.

Example 1 (3) obtained in 2 – [[5-phenyl-4-(lH-pyrrol-1-yl)-4H-1,2,4-triazol-3-yl] thio] acetic acid (90 mg, 0.3mmol),1-hydroxybenzotriazole (40mg, 0.3mmol),1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride (60 mg, 0.3 mmol)Of N, N-dimethylformamide (2 ml)Was added triethylamine (0.09ml, 0.6mmol)When the 5-fluoro-2-methoxy aniline (0.04ml, 0.36mmol)Was stirred for 16 hours at room temperature added.The reaction solution was extracted by adding aqueous sodium bicarbonate solution and ethyl acetate, and extracted twice further the aqueous layer with ethyl acetate. After acidification with 1N hydrochloric acid was added to the organic layer, extracted, extracted twice further the aqueous layer with ethyl acetate. The organic layer was washed with saturated brine, and dried with anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, the residue was purified by column (hexane: ethyl acetate = 1: 3-1: 5) to give to N-(5-fluoro-2-methoxyphenyl) -2 – [[5-phenyl to give-4- (lH-pyrrol-1-yl) -4H-1,2,4- triazol-3-yl] thio] acetamide (20mg, 16%) as a pale brown solid.

According to the analysis of related databases, 1978-39-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Chiba Prefecture; Nakagawara, Akira; Hoshino, Tadatsugu; Nakamura, Yoko; (15 pag.)JP2015/117182; (2015); A;,
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Reference of 20781-20-8,Some common heterocyclic compound, 20781-20-8, name is (2,4-Dimethoxyphenyl)methanamine, molecular formula is C9H13NO2, 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.

Step 1: N-(2-((tert-Butyldimethylsilyloxy)methyl)- l-methyl-6,7,8,9-tetrahydrocyclohepta[f]indol-5( lH)-ylidene)- 1 -(2,4-dimethoxyphenyl)methanamine To solution of 2-((tert-butyldimethylsilyloxy)methyl)-l-methyl-6,7,8,9-tetrahydrocyclohepta[f]indol-5(lH)-one (Intermediate 4, 7.458 g, 20.86 mmol) in CH2C12(65 mL) was added 2,4-dimethoxybenzylamine (3.30 mL, 21.97 mmol) and NEt3(7.80 mL, 55.96 mmol). The mixture was cooled to 0 C before TiCl4solution (1M CH2C12, 13.60 mL, 13.60 mmol) was added dropwise via syringe pump over 30 min. The reaction was allowed to warm to room temperature and stirred overnight. The mixture was diluted with CH2C12(150 mL) and then quenched with NaHC03(aq. satd., 50 mL). Upon vigorous shaking, the organic phase was separated with a PTFE phase separator and then dried over Na2S04. Removal of the solvent afforded the product (10.6 g, quant.) as yellow oil which was taken directly into next step without purification.

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-Dimethoxyphenyl)methanamine, its application will become more common.

Reference:
Patent; PTC THERAPEUTICS, INC.; GERASYUTO, Aleksey, Igorevich; ARNOLD, Michael, A.; CHEN, Guangming; KARP, Gary, Mitchell; QI, Hongyan; TURPOFF, Anthony, A.; WANG, Jiashi; WOLL, Matthew, G.; ZHANG, Nanjing; ZHANG, Xiaoyan; BRANSTROM, Arthur, A.; NARASIMHAN, Jana; DUMBLE, Melissa, L.; HEDRICK, Jean; WEETALL, Marla, L.; (229 pag.)WO2016/25932; (2016); A1;,
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Synthetic Route of 2752-17-2,Some common heterocyclic compound, 2752-17-2, name is 2,2′-Oxydiethanamine, molecular formula is C4H12N2O, 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 for the preparation of compounds 10-15 (B) (0016) The appropriate diamines were added to compound 1a and Na2CO3 (2eq.) with stirring in DMF (5mL). The mixture was stirred overnight at room temperature. After completion, as judged by TLC, the solvent was evaporated under reduced pressure. The mixture was resolved in EtOAc and washed twice with water and brine. The organic layer was dried over Na2SO4, then filtered and concentrated. The crude product was purified by column chromatography (CH2Cl2/MeOH, 25/1 v/v) to give the target compound as a white solid.

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

Reference:
Article; Yu, Fei; Peng, Yiyun; Wang, Qi; Shi, Yongying; Si, Longlong; Wang, Han; Zheng, Yongxiang; Lee, Emily; Xiao, Sulong; Yu, Maorong; Li, Yingbo; Zhang, Chuanling; Tang, Hengli; Wang, Chunguang; Zhang, Lihe; Zhou, Demin; European Journal of Medicinal Chemistry; vol. 77; (2014); p. 258 – 268;,
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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. 20469-65-2, name is 1-Bromo-3,5-dimethoxybenzene, A new synthetic method of this compound is introduced below., HPLC of Formula: C8H9BrO2

To magnesium (290 g, 12 mmol), 1-bromo-3,5-dimethoxybenzene(0.86 g 4.0 mmol) in THF (20 mL) was added dropwise under nitrogen atmosphere. The mixture was refluxed until magnesium was consumed and cooled to 0C subsequently. To the solution allylbromide (1.2 mL, 15 mmol) was added dropwise. After stirring for 2 h at room temperature the mixture was quenched with sat. NH4Cl aq. was added and extracted with ether and the subsequent purification by flash column chromatography (hexane-ethyl acetate=19 : 1) afforded 1-allyl-3,5-dimethoxybenzene (356 mg, 50%). The mixture of CS2 (35 mL), Al (0.40 g 74 mmol) and I2 (3 g 118 mmol) was refluxed for 2 hs and cooled down to room temperature. To the stirred solution, a solution of 1-allyl-3,5-dimethoxybenzene (0.75 g, 4.2 mmol) in CS2 (35 mL) was added dropwise. The reaction mixture was stirred under reflux for 12 h. The reaction mixture was quenched with water and extracted with Et2O. The combined organic phase washed with 1 M Na2S2O3 aqueous solution and dried over Na2SO4. The solvent was removed and the resulting residue was dissolved in THF, subsequent purification by flash column chromatography (CHCl3-methanol=5 : 1) afforded 2-allylhydroquinone (34 mg, 6%).

The synthetic route of 20469-65-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Nishiwaki, Keiji; Ohigashi, Kanae; Deguchi, Takahiro; Murata, Kazuya; Nakamura, Shinya; Matsuda, Hideaki; Nakanishi, Isao; Chemical and Pharmaceutical Bulletin; vol. 66; 7; (2018); p. 741 – 747;,
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Adding a certain compound to certain chemical reactions, such as: 6876-00-2, name is 1-Bromo-3-phenoxybenzene, belongs to ethers-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 6876-00-2, HPLC of Formula: C12H9BrO

STEP A 1-(m-phenoxy-phenyl)-2,2,2-trifluoro-ethanone A few drops of m-phenoxy-bromobenzene were added to a mixture of 16.6 g of magnesium (50% turnings) in 53 ml of tetrahydrofuran and the mixture was heated to 40-45 C. Crystallization began and the rest of 62.2 g of m-phenoxy-bromobenzene was added dropwise at reflux over 45 minutes. 183 ml of tetrahydrofuran were added and the mixture was refluxed for one hour and was cooled to 0 C. to obtain a solution of a magnesium compound. The said solution was then added at 0 C. over 40 minutes to a mixture of 40.8 g of sodium trifluoroacetate in 240 ml of tetrahydrofuran and the mixture was stirred for two hours and was poured into aqueous 0.1N hydrochloric acid solution. The mixture was extracted with ether and the ether phase was washed with water, with aqueous N sodium hydroxide and with water. The ether phase was added to two liters of methylene chloride and the mixture was evaporated to dryness under reduced pressure to obtain 56.2 g of raw 1-(m-phenoxy-phenyl)-2,2,2-trifluoro-ethanone which was used as is for the next step.

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

Reference:
Patent; Roussel Uclaf; US4833163; (1989); A;,
Ether – 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 6346-09-4 as follows. Product Details of 6346-09-4

General procedure: The reaction mixture containing 0.5 g (1.8 mmol) of 4-(dibromomethyl)benzenecarbaldehyde (7), 0.11 g (0.0018 mmol) of isopropylamine (12) and 0.2 g of molecular sieves 3 A in 10 mL of dry benzene was thermostated at room temperature for 24 h. N-Isopropyl-4-(dibromomethyl)benzenecarbimine (14) (0.44 g, 77%) in the form of yellow oil was obtained by filtration through the molecular sieves followed by the removal of the solvent in vacuo provided by water jetpump.

According to the analysis of related databases, 6346-09-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; Gazizov; Ivanova, S. Yu.; Karimova; Bagauva; Gazizova; Karimova; Russian Chemical Bulletin; vol. 65; 1; (2016); p. 191 – 194; Izv. Akad. Nauk, Ser. Khim.; 1; (2016); p. 191 – 194,4;,
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Related Products of 2930-05-4, These common heterocyclic compound, 2930-05-4, name is 2-((Benzyloxy)methyl)oxirane, 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: IL/DFNS NPs (5mg) and epoxide derivatives (1mmol) werecharged into the reactor vessel without using any co-solvent. The reactor vessel was placed under a constant pressure ofcarbon dioxide and then heated to 70C for 2h. Then thereactor was cooled to ambient temperature, and the resultingmixture was transferred to a 50mL round bottom flask.Upon completion, the progress of the reaction was monitoredby TLC when the reaction was completed, EtOH wasadded to the reaction mixture and the KCC-1/IL/HPW NPswas separated by filteration. Then the solvent was removedfrom solution under reduced pressure and the resulting productpurifed by recrystallization using n-hexane/ethyl acetate.

Statistics shows that 2-((Benzyloxy)methyl)oxirane is playing an increasingly important role. we look forward to future research findings about 2930-05-4.

Reference:
Article; Zhang, Pu; Zhiani, Rahele; Catalysis Letters; vol. 150; 8; (2020); p. 2254 – 2266;,
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Application of 38197-43-2, These common heterocyclic compound, 38197-43-2, name is 2-Bromo-1-methoxy-3-methylbenzene, 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: To a mixture of 1-bromo-2-methoxynaphthalene (2.3mmol) and magnesium turnings (9.0mmol) in diethyl ether (10mL) was stirred at room temperature under argon atmosphere until white slurry was formed. To the resulting mixture was added benzene (10mL) to dissolve the material, and the mixture was stirred for 2h at room temperature under argon atmosphere. The solution of resulting Grignard reagent was added dropwise to a solution of 2-methoxy-1,3-dinitrobenzene (1.5mmol) in benzene (15mL), and the mixture was stirred for 8h at 50C. The reaction mixture was quenched with water and extracted with ethyl acetate (3¡Á15mL). The combined extracts were dried over Na2SO4, and concentrated. The residue was purified by column chromatography on silica gel (ethyl acetate/hexane as eluent) to give a precursor of the starting material, which was the corresponding dinitro compound (1.1mmol, 73% yield). A mixture of the corresponding dinitro compound (1.0mmol) and Pd/C (80mg; 10wt%) in ethanol (10mL) was stirred for 12h at room temperature under hydrogen atmosphere (H2 balloon). The reaction mixture was filtered over Celite and concentrated to give a diamino compound. To a solution of the resulting diamino compound and pyridine (30mmol) in dichloromethane (20mL) was added dropwise a solution of benzenesulfonyl chloride (3.0mmol) in dichloromethane (10mL), and the reaction mixture was stirred for 24h at room temperature. The mixture was concentrated, and the residue was purified by column chromatography on silica gel (dichloromethane/ethyl acetate/hexane as eluent) to give starting material 8a (0.98mmol, 98% yield). Compounds 8b and 8c were synthesized by the same procedure.

The synthetic route of 38197-43-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Shirakawa, Seiji; Wu, Xiangfei; Liu, Shiyao; Maruoka, Keiji; Tetrahedron; vol. 72; 34; (2016); p. 5163 – 5171;,
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These common heterocyclic compound, 126-38-5, name is 1-Bromo-2,2-dimethoxypropane, 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 C5H11BrO2

EXAMPLE 10 (+-)CIS AND (+-)-TRANS-1-[[2-(BROMOMETHYL)-4-(2,4-DICHLOROPHENYL)-2-METHYL-1,3-DIOXOLAN-4-YL]METHYL]-1H-IMIDAZOLE To a well stirred suspension of 2-(2,4-dichlorophenyl)-3-(1H-imidazol-1-yl)-1,2-propanediol (3.4 g), in toluene (500 mL) and n-butanol (4 mL), add successively with p-toluenesulfonic acid monohydrate (2.47 g) and 2,2-dimethoxybromopropane (3.2 g). Heat the mixture gently at reflux for 36 hr. Treat the reaction mixture in a manner described in Example 7 to give a mixture of the title compounds. Chromatograph on silica gel to provide the title compound, cis-isomer (less polar) m.p. 145-147 C., and trans-isomer (more polar) m.p. 128-130 C.

The synthetic route of 1-Bromo-2,2-dimethoxypropane has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Schering Corporation; US4788190; (1988); A;,
Ether – Wikipedia,
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