Month: March 2021

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 589-10-6 as follows. SDS of cas: 589-10-6

Example 101 N’-[1-imidazol-1-yl-1-[3-(2-phenoxyethoxy)thiophen-2-yl]methylidene]-N,N-dimethylhydrazine (compound No. 101) To a solution of methyl 3-hydroxythiophene-2-carboxylate (0.992 g, 6.27 mmol) in N,N-dimethylformamide (12 ml) were added beta-bromophenetole (1.268 g, 6.31 mmol) and potassium carbonate (1.059 g, 7.66 mmol), and the mixture was stirred at 80C for 4.5 hr. Ethyl acetate was added to the reaction mixture, the mixture was washed with water, and the organic layer was dried over sodium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate) to give methyl 3-(2-phenoxyethoxy)thiophene-2-carboxylate (1.624 g, 5.83 mmol, yield 93%).

According to the analysis of related databases, 589-10-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; KAKEN PHARMACEUTICAL CO., LTD.; EP2168951; (2010); A1;,
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Application of 162705-07-9,Some common heterocyclic compound, 162705-07-9, name is (Z)-2-Methoxy-5-(3,4,5-trimethoxystyryl)aniline, molecular formula is C18H21NO4, 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: The corresponding N-(1-oxyl-2,2,6,6-tetramethyl-4-piperidinyl-oxycarbonyl) amino acids 20a-h (0.47 mmol) were dissolved in 50 mL of anhydrous CH2Cl2 and cooled to 0 C. 1-Hydroxybenzotriazole (HOBt) (0.7 mmol) and EDCI (0.56 mmol) were added, and the mixture was stirred for 30 min at 0 C. Subsequently, 0.39 mmol of compound 3 and finally 2.4 mL of N-ethyl diisopropylamine were added. The mixture was stirred for 16 h at ambient temperature. The solvent was removed under reduced pressure and the residue was purified by flask-column chromatography (gradient elution with mixtures of chloroform/methanol) on silica gel as monitored by TLC. Synthesized target compounds 21a-h were characterized by mp, IR, ESR and HRMS analyses.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route (Z)-2-Methoxy-5-(3,4,5-trimethoxystyryl)aniline, its application will become more common.

Reference:
Article; Liu, Ying-Qian; Li, Xiao-Jing; Zhao, Chun-Yan; Nan, Xiang; Tian, Jing; Morris-Natschke, Susan L.; Zhang, Zhi-Jun; Yang, Xiao-Ming; Yang, Liu; Li, Lin-Hai; Zhou, Xing-Wen; Lee, Kuo-Hsiung; Bioorganic and Medicinal Chemistry; vol. 21; 5; (2013); p. 1248 – 1256;,
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These common heterocyclic compound, 59557-91-4, name is 4-Bromo-2-methoxyaniline, 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. Quality Control of 4-Bromo-2-methoxyaniline

EXAMPLE 175B tert-butyl 4-bromo-2-methoxyphenylcarbamate A mixture of Example 175A (36.4 g, 180 mmol), and di-tert-butyl dicarbonate (47.2 g, 216 mmol) in THF (500 mL) was heated to reflux for 20 hours and cooled to ambient temperature. HPLC (using the conditions from Example 175A, product Rt=13.55 min and TLC (8:2 heptane/ethyl acetate, Rf of product=0.53, Rf of 4-bromo-2-methoxyaniline=0.27) indicated approximately 10% starting material was remaining. Additional di-tert-butyl dicarbonate (3.9 g, 18 mmol) was added and heating was continued for another 5 hours. The mixture was cooled and evaporated under reduced pressure. The residue was applied to a 400 gram silica gel column and eluted with 8:2 heptane/ethyl acetate. The fractions showing the desired product were combined and washed with saturated NaHCO3 and then brine. The organic solution was dried (MgSO4), filtered, and concentrated to provide 61.3 g of a mixture of the desired product and di-tert-butyl dicarbonate which was used directly in the next step.

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

Reference:
Patent; Betschmann, Patrick; Burchat, Andrew F.; Calderwood, David J.; Curtin, Michael L.; Davidsen, Steven K.; Davis, Heather M.; Frey, Robin R.; Heyman, Howard R.; Hirst, Gavin C.; Hrnciar, Peter; Michaelides, Michael R.; Muckey, Melanie A.; Rafferty, Paul; Wada, Carol K.; US2005/43347; (2005); A1;,
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Adding a certain compound to certain chemical reactions, such as: 37466-89-0, name is 3-Methoxybenzene-1,2-diamine, 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 37466-89-0, name: 3-Methoxybenzene-1,2-diamine

At room temperature, a solution of oxaldehyde in H20 (40%, 4 mL) was added to a solution of 3-methoxybenzene-1,2-diamine (3.66 g, 26.53 minol) in water (100.00 mL). Then NaHSO3 (7.59 g, 72.94 minol) was added slowly. The resulting solution was stirred for 15 min at room temperature. When the reaction was done, the insoluable solids in the reactionminxture were filtered out. The filtrate was extracted with DCM (300 mL x 3), and the organic phases were combined, washed with brine and dried over Na2SO4. The solvent was removed under reduced pressure and the residue was purified by flash chromatography eluting with EtOAc in hexane (0% to 100% gradient) to yield 5-methoxyquinoxaline as dark red oil (3.02 g, 71%). MS: m/z = 161.0 [M+Hj.

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; MERCK PATENT GMBH; SHERER, Brian A.; BRUGGER, Nadia; (546 pag.)WO2017/106607; (2017); A1;,
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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. 2734-70-5, name is 2,6-Dimethoxyaniline, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 2,6-Dimethoxyaniline

To a solution of 5-methylfuran-2-carboxylic acid (1.0 g, 8.0 mmol, 1 equiv) and 2,6- dimethoxyaniline (1.46 g, 9.5 mmol, 1.2 equiv) in DCM (10 mL) were added DMAP (44 mg, 0.4 mmol, 0.05 equiv) and EDCI (1.5 g, 9.6 mmol, 1.2 equiv) successively at room temperature. The resulting mixture was stirred at room temperature overnight. The reaction mixture was diluted with EtOAc (100 mL), washed with water (3*20 mL) and brine (50 mL), dried over anhydrous Na2S04, and concentrated in vacuo. The residue was purified by flash column chromatography (eluted with PE/EtOAc = 20/1 ~ 1/1) to afford the title compound N-(2,6-dimethoxyphenyl)-5-methylfuran-2-carboxamide as a white solid (1.23 g, 59 % yield). LC-MS: m/z 262.1 (M+H)+

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 2734-70-5.

Reference:
Patent; ANNAPURNA BIO INC.; TANG, Haifeng; BOYCE, Sarah; HANSON, Michael; NIE, Zhe; (213 pag.)WO2019/169193; (2019); A1;,
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Application of 104197-14-0, 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 104197-14-0 as follows.

To a 200 mL flask which had been sufficiently dried under argon atmosphere, 30 mL of anhydrous pentane and 22.1 g (0.10 mol) of 4-bromo-2,6,-difluoroanisole were added and the mixture was cooled to -78 C. in a dry ice/acetone bath. Dropped thereto over 50 minutes was 61.2 mL of 1.6 mol/L n-butyl lithium hexane solution and the thus obtained mixture was subsequently stirred for 5 hours at -78 C. Thereto dropped over 30 minutes was 24.5 mL of 1 mol/L boron trichloride/hexane solution and the thus obtained reaction solution was stirred for 5 hours at -20 C. To this reaction solution, 80 mL of water was slowly added to hydrolyze the reaction mixture and the formed crystals were collected, which were then washed with 80 mL of hexane and 80 mL of water to obtain 13.0 g of tetrakis(3,5-difluoro-4-methoxyphenyl) lithium borate having an HPLC purity of 98.8% (Yield: 90%). The thus obtained product was subjected to measurements by 1H-NMR (heavy methanol solvent) and MALDI TOF-MS to confirm that it was the desired product. (Measurement Results)(1H-NMR (shift; ppm: multiplicity: number of protons)(3.8: s: 12) (6.5-6.6: m: 8)(0177)MALDI TOF-MS (m/z)mass: 583.25 (Theoretical value: 583.27)

According to the analysis of related databases, 104197-14-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Adeka Corporation; Kimura, Kentaro; Fujita, Shohei; Tamachi, Tomoya; US8383862; (2013); B2;,
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Adding a certain compound to certain chemical reactions, such as: 74137-36-3, name is 1,3-Dibromo-5-methoxybenzene, 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 74137-36-3, category: ethers-buliding-blocks

Tris (dibenzylideneacetone) [DIPALLADIUM (0)] (6.53g, 7. [15MMOL)] was added in one portion to a stirred solution of the bromide of Preparation 1 (38. [0G,] [143MMOL),] 1,1′-bis (diphenylphosphino) ferrocene (9.3g, 16. [8MMOL)] and zinc cyanide (20. 0g, [172MMOL)] in [NN-DIMETHYLFORMAMIDE (300ML)] at room temperature under nitrogen. The reaction was heated at [100¡ãC] for 14 hours and cooled to room temperature. Water [(1500ML)] was added and the mixture was extracted with ethyl acetate [(3X500M1).] The combined organics were filtered and the filtrate was washed with water [(500MOI),] dried over magnesium sulphate, filtered and concentrated under reduced pressure. The resulting solid was triturated with toluene [(1000MOL)] to provide the [TITLE COMPOUND (1 8. 0G)] as a tan solid. [1H-NMR] [(300MHZ,] [CDC13)] : [8] = 3.83 (3H, s), 7.31 (2H, s), 7.48 [(1 H,] s).

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; PFIZER LIMITED; PFIZER INC.; WO2004/29051; (2004); A1;,
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Synthetic Route of 156573-09-0, 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. 156573-09-0, name is 1-Bromo-4-ethoxy-2,3-difluorobenzene, This compound has unique chemical properties. The synthetic route is as follows.

Third Step 4-Bromo-2,3-difluoroethoxybenzene (s-5) (45.2 g), 2, 3-difluorophenyllboronic acid (s-6) (36.1 g), potassium carbonate (79.1 g), Pd (Ph3P)2Cl2 (4.0 g), toluene (200 ml), Solmix A-11 (200 ml) and water (200 ml) were placed in a reaction vessel under an atmosphere of nitrogen, and heated to reflux for 2 hours. After the reaction solution had been cooled to 25C, it was poured into water (200 ml) and toluene (200 ml) and mixed with them. The mixture was then allowed to stand until it had separated into two layers of organic and aqueous layers, and the extraction into an organic layer was carried out. The resulting organic layers were separated, and washed with water, and then dried over anhydrous magnesium sulfate. The resulting solution was concentrated under reduced pressure. The resulting residue was purified by column chromatography using silica gel as a stationary phase powder and a mixed solvent of toluene and heptane (toluene: heptane= 2:1 by volume) as an eluent, and further purified by recrystallization from Solmix A-11 and dried to give 4-ethoxy-2,2′,3,3′-tetrafluoro-1,1′-biphenyl (s-7) (40.1 g).

The chemical industry reduces the impact on the environment during synthesis 1-Bromo-4-ethoxy-2,3-difluorobenzene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; JNC Corporation; JNC Petrochemical Corporation; EP2479162; (2012); A1;,
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These common heterocyclic compound, 52411-34-4, name is 1,2-Bis(o-aminophenoxy)ethane, 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. Safety of 1,2-Bis(o-aminophenoxy)ethane

Diacetylpyridine (0.134 g, 0.82 mmol) was added in one portion to a solution of MnCl2-4H2O (0.142 g, 0.82 mmol) in EtOH (30 mL). The solution was heated to 50 C., and then 1,4-bis-(2-aminophenyl)-1,4-dioxabutane (0.200 g, 0.82 mmol) was added in one portion. The reaction mixture was heated to 85 C. and refluxed for 4 h. The solvent volume was reduced by half, and the mixture was cooled to r.t. An excess of Et2O was added, and the resulting precipitate was collected by Buchner filtration and washed well with cold Et2O to give 3 as an orange solid (62 mg, 14.2%). IR (cm-1) 3351, 3072, 2968, 2924, 1671, 1592, 1503, 1362, 1249, 1210, 1087. FAB-MS: m/z=461 [M-Cl]+ (10%). Anal. calcd. for (C23H21N3O2C1-2Mn)0-2H2O C, 55.55; H, 4.26; N, 8.45. found C, 55.72; H, 4.65; N, 8.39%

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

Reference:
Patent; Brock University; Pilkington, Melanie; Stares, Emma Louise; (51 pag.)US2016/362434; (2016); A1;,
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Electric Literature of 707-07-3,Some common heterocyclic compound, 707-07-3, name is (Trimethoxymethyl)benzene, molecular formula is C10H14O3, 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: 2-Nitroaniline derivative (1 mmol) was added to a mixture of indium powder (574 mg, 5.0 mmol for 2-nitroaniline, 918 mg 8.0 mmol for 1,2-dinitroarene), and acetic acid (0.572 mL, 10 mmol) in ethyl acetate (2 mL), followed by the addition of trimethyl orthoester (2.0 mmol) in ethyl acetate (3 mL for 2-nitroaniline; 8 mL for 1,2-dinitroarene). The reaction mixture was stirred at reflux under a nitrogen atmosphere. After the reaction was completed, the reaction mixture was diluted with ethyl acetate (30 mL), filtered through Celite, poured into 10% NaHCO3 (30 mL), and then extracted with ethyl acetate (30 mL¡Á3). The combined organic extracts were dried over MgSO4, filtered, and concentrated. The residue was eluted with ethyl acetate/hexane (v/v=10/90) for 2-phenylbenzimidazole derivatives or methanol/dichloromethane (v/v=1/99) for 2-methylbenzimidazole derivatives through a silica gel column to give the corresponding benzimidazoles. The structures of the benzimidazoles were characterized by 1H NMR, 13C NMR, FTIR, and GC-MS, and were mostly known compounds. HRMS data were reported in addition for unknown compounds.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route (Trimethoxymethyl)benzene, its application will become more common.

Reference:
Article; Kim, Jaeho; Kim, Jihye; Lee, Hyunseung; Lee, Byung Min; Kim, Byeong Hyo; Tetrahedron; vol. 67; 41; (2011); p. 8027 – 8033;,
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