Month: May 2021

Application of 54149-17-6, 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. 54149-17-6, name is 1-Bromo-2-(2-methoxyethoxy)ethane belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Synthetic procedures of the zwitterionic compounds reported in previously published papers (Kuroda, K.; Satria, H.; Miyamura, K.; Tsuge, Y.; Ninomiya, K.; Takahashi, K. Journal of the American Chemical Society 2017, 139, 16052-16055; Yoshizawa-Fujita, M.; Tamura, T.; Takeoka, Y.; Rikukawa, M. Chemical Communications 2011, 47, 2345-2347) were used for this Example. Briefly, 0.2 mol sodium hydride was suspended in tetrahydrofuran (THF) under argon gas. Imidazole (0.1 mol), which was dissolved in 30 mL THF, was added dropwise to the sodium hydride solution. After stirring for 24 h at room temperature, 1-bromo-2-(2-methoxyethoxy)ethane (0.1 mol) was added to the solution. The resulting suspension was filtered after stirring for 6 h at 70 C. to remove the white precipitate. The solvent was removed by rotary evaporation to yield the crude product. The product was further purified by distillation under reduced pressure. A fraction was collected at 105 C. under reduced pressure to obtain 1-(2-(2-methoxyethoxy)ethyl)-1H-imidazole (OE2im). OE2im (0.1 mol) was subsequently dissolved in 40 mL acetonitrile. 1,4-butanesultone (0.1 mol) was added dropwise to the solution under a nitrogen atmosphere. The mixture was then refluxed for 40 h. The solvent was then removed by rotary evaporation. The residue was washed several times with diethyl ether by decantation followed by drying of the product under vacuum at 50 C. for 24 h to obtain IL 1, 3-(1-(2-Methoxyethyl)-1H-imidazol-3-ium-3-yl)butane-1-sulfonate (OE2imC4S) as a colorless viscous liquid. The zwitterionic compounds IL 2, 3-(1-octyl-1H-imidazol-3-ium-3-yl)propane-1-sulfonate (C8imC3S), and IL 4, 3-(1-octyl-1H-imidazol-3-ium-3-yl)butane-1-sulfonate (C8imC4S), were prepared in similar procedure using octylimidazole with 1,3-propanesultone or 1,4-butanesultone.

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, 1-Bromo-2-(2-methoxyethoxy)ethane, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Iowa State University Research Foundation, Inc.; Anderson, Jared L.; Kuroda, Kosuke; Nan, He; (27 pag.)US2019/360979; (2019); 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. 592-55-2, name is 1-Bromo-2-ethoxyethane, A new synthetic method of this compound is introduced below., category: ethers-buliding-blocks

10.0 g (0.061 mol) of 6-nitro-2,3-dihydro-1H-indole (16) was dispersed in 100 ml of dimethylformamide under nitrogen atmosphere, stirred for about 10 minutes at room temperature and then dissolved in 2-bromoethyl 15.3 g (0.01 mol) of ether and 15.0 ml (0.088 mol) of diisopropylethylamine (DIPEA) were added in this order. The reaction solution was gradually heated and stirred at 140 C for 5 hours to complete the reaction. After cooling the reaction solution to room temperature, 100 ml of distilled water and 200 ml of ethyl acetate were added and the mixture was stirred for 30 minutes. The organic layer was separated and washed with H 2 O. The recovered organic layer was dried over anhydrous magnesium sulfate, The resulting product was purified by silica gel column chromatography (developing solvent; ethyl acetate: hexane = 1: 3) to obtain 6-nitro-2,3-dihydro-1- (2-ethoxyethyl) 12.0 g (83.3%) of indole (43) was obtained.

The synthetic route of 592-55-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Korea Research Institute of Chemical Technology; Shin Seung-rim; Jeon Geun; Shin Jong-il; Park Yeong-il; Ahn Gyeong-ryong; (48 pag.)KR101842495; (2018); B1;,
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These common heterocyclic compound, 405-06-1, name is 2-Fluoro-4-methoxy-1-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. HPLC of Formula: C8H9FO

To a -70 C. solution of 3-fluoro-4-methyl anisole (1.62 g; 11.6 mmol) in CH2Cl2 (10 mL) was added dropwise BBr3 (10 mL; 12 mmol). The reaction mixture was stirred at -70 C. for 10 min, then allowed to warm to 0 C. and stirred at 0 C. for 2 h. The reaction was allowed to warm to RT and concentrated in vacuo and the residue was partitioned between H2O and EtOAc. The organic phase was washed with H2O, dried (Na2SO4) and concentrated in vacuo to give 3-fluoro-4-methyl phenol (1.1 g; 75%) as an oil.

The synthetic route of 2-Fluoro-4-methoxy-1-methylbenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bristol-Myers Squibb Company; US6414002; (2002); B1;,
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Application of 3616-56-6,Some common heterocyclic compound, 3616-56-6, name is 2,2-Diethoxy-N,N-dimethylethanamine, molecular formula is C8H19NO2, 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.

Under a nitrogen atmosphere, 14.1 g (0.061 mol) of the intermediate A, 11.4 g (0.071 mol) ofN,N’-dimethylaminoacetaldehyde diethyl acetal, and 110.0 g of acetic acid were stirred for 8 hours while being heated at 118°C to reflux. After the reaction solution was cooled to room temperature, the precipitated crystal was collected by filtration and washed with acetic acid (30 ml) . The resultant crystal was subjected to purification by reslurrying to afford 10.4 g (67percent yield) of IC-2 as a white crystal.

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-Diethoxy-N,N-dimethylethanamine, its application will become more common.

Reference:
Patent; Nippon Steel Chemical Co., Ltd.; EP2415772; (2012); A1;,
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Application of 1579-40-4, These common heterocyclic compound, 1579-40-4, name is Di-p-tolyl Ether, 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.

Representative Experimental Protocol: 2,7-Dimethyl-9-(4-nitro)phenyl xanthen-9-ol (R = NO2: 3e): Di-p-tolyl ether (1, 5 g, 25.5 mmol), 4-nitro benzoic acid (5.13 g, 30.7 mmol) and ZnCl2 (10 g, 73.4 mmol) are taken into a 100 ml double neck RB flask and charged with POCl3 (7.5 mL) and heated to 95 C for 4 h. The reaction mixture turned into a brown viscous mass that was difficult to stir. The reaction mixture was then cooled to room temperature and crushed ice was added slowly while keeping the low temperature. To the above mixture was added H2O (75 mL) and stirred for 12 h. The above reaction mixture was filtered and the residue was washed with H2O (20 mL) and hexane (20 mL) to afford 4-nitro-DMPx 3e as white powder. The crude product was dissolved in EtOAc and washed with NaHCO3 to remove the excess of 4-nitro benzoic acid. The EtOAc layer was evaporated under reduced pressure to furnish the desired product as fine powder 7.5 g (86%).

The synthetic route of 1579-40-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Banerjee, Shyamapada; Srishylam; Rajendra Prasad; Migawa, Michael T.; Swayze, Eric E.; Sanghvi, Yogesh S.; Tetrahedron Letters; vol. 53; 35; (2012); p. 4669 – 4672;,
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Synthetic Route of 1462-37-9,Some common heterocyclic compound, 1462-37-9, name is ((2-Bromoethoxy)methyl)benzene, molecular formula is C9H11BrO, 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.

Preparation 83-Amino-6-(2-benzyloxy-ethoxy)-indazole-1-carboxylic acid tert-butyl esterScheme 1, Step Hb)A mixture of 3-amino-6-hydroxy-indazole-1-carboxylic acid tert-butyl ester (249 mg, 1 mmol), K2CO3 (152 mg, 1.1 mmol) and benzyl 2-bromoethyl ether (0.179 ml, 1.1 mmol) in dry DMF (5 ml) was stirred at 50°C for 12h. More benzyl 2-bromoethyl ether (30 muIota) was added and the mixture stirred at 50°C for additional 4h. The reaction mixture was poured into water (50 ml) and extracted with EtOAc (50 ml). The organic layer wad dried over sodium sulfate and evaporated to dryness. The crude residue was purified by flash chromatography over silica gel eluting with DCM / EtOAc 7:3 affording 274 mg (yield: 72percent) of the title compound.1H-NMR (400 MHz), delta (ppm, DMSO-cie): 7.71 (d, J=8.66 Hz, 1 H), 7.48 (bs, 1 H), 7.38 – 7.27 (m, 5H), 6.91 (dd, J=2.19, 8.66 Hz, 1 H), 6.19 (bs, 2H), 4.59 (s, 2H), 4.25 – 4.20 (m, 2H), 3.85 – 3.80 (m, 2H), 1.58 (s, 9H) ESI (+) MS m/z 384 (MH+)

The synthetic route of 1462-37-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NERVIANO MEDICAL SCIENCES S.R.L.; LOMBARDI BORGIA, Andrea; CIOMEI, Marina; DONATI, Daniele; NESI, Marcella; WO2012/152763; (2012); A1;,
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These common heterocyclic compound, 33311-29-4, name is 4-(2-Methoxyethoxy)aniline, 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. name: 4-(2-Methoxyethoxy)aniline

To a solution of compound 3 (400 mg, 1.0 mmol) and 4-(2-methoxyethoxy)aniline (0.2 g, 1.2 mmol) in 8 ml dioxane was added 4-methylbenzenesulfonic acid monohydrate (0.15g, 0.8 mmol). The mixture was stirred at 100 0C for two hours. The solvent was evaporated. The residue was dissolved in 30 ml ethyl acetate and washed with NaHCO3 aqueous solution, water and brine. The organic layer was separated and dried over Na2SO4. After removal of solvent, the crude product was subject to chromatography on silica gel (hexane:EtOAc = 1 :1). 0.40 g of the title compound 5 was obtained: MS m/z: 530.1, 532.1(M+H+).

The synthetic route of 4-(2-Methoxyethoxy)aniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AVILA THERAPEUTICS AND USES THEREOF; WO2009/158571; (2009); A1;,
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Reference of 494-99-5, 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. 494-99-5, name is 1,2-Dimethoxy-4-methylbenzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

(a) 80.0 g (0.6 mole) of aluminium chloride are introduced in portions, while stirring, into a solution of 84.1 g (0.5 mole) of 1,2-dimethoxy-4-methylbenzene (homopyrocatechol dimethyl ether or 4-methylveratrole) in 750 ml of 1,2-dichloroethane, during which the temperature is maintained at 20 maximum by cooling with an ice bath. Then, at 15-20, 85.0 g (approximately 73 ml, 0.55 mole) of phenyl acetyl chloride are added dropwise in the course of one hour, during which there is moderate evolution of hydrogen chloride and the aluminium chloride is dissolved. The reaction mixture is then stirred at room temperature for a further 6 hours and subsequently poured into 3000 ml of a mixture of ice and water. The resulting layers are separated and the organic phase is washed in succession with 2N hydrochloric acid, twice with water, then with 1N sodium bicarbonate solution and a further twice with water, dried, filtered and concentrated by evaporation. The partially crystallized residue is caused to crystallise completely from ether/petroleum ether (boiling range 40-65), 1-(4,5-dimethoxy-2-methylphenyl)-2-phenyl-1-ethanone having a melting point of 45-48 being obtained.

The synthetic route of 1,2-Dimethoxy-4-methylbenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Ciba-Geigy Corporation; US4500542; (1985); A;,
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Electric Literature of 41365-75-7,Some common heterocyclic compound, 41365-75-7, name is 1-Amino-3,3-diethoxypropane, molecular formula is C7H17NO2, 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: A mixture of 0.6 mmol of quinomethane 1a-1c and 0.6 mmol of 3,3-diethoxypropan-1-amine (2) or 4,4-diethoxybutan-1-amine (3) in 1 mL of 1,4-dioxane was stirred for 2-3 h at room temperature under argon. When the reaction was complete, the solvent was removed under reduced pressure (water-jet pump), and the residue was washed with hexane and dried in a vacuum (oil pump) until constant weight.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Amino-3,3-diethoxypropane, its application will become more common.

Reference:
Article; Vagapova; Amirova; Burilov; Pudovik; Sinyashin; Russian Journal of Organic Chemistry; vol. 51; 9; (2015); p. 1268 – 1271; Zh. Org. Khim.; vol. 51; 9; (2015); p. 1294 – 1297,4;,
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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 592-55-2 as follows. Quality Control of 1-Bromo-2-ethoxyethane

To a solution of 3-(3-ethylazepan-3-yl)phenol (step a, 0.42 g, 1.92 mmol) in ACN (20 mL), N-ethyldiisipropylamine (0.67 mL, 3.830 mmcl) and 1-bromo-2-ethoxyethane (0.24 mL, 2.11 mmol) were added and the reaction mixture was heated at 65?C overnight. The reaction mixture was cooled and partitioned between 5% aqueous KHCO3 solution and AcOEt. The layers were separated and the organic layer wasdried over anh Na2SO4, filtered and concentrated to dryness. The crude product thus obtained was purified by flash chromatography on silica gel, gradient DCM/MeOH (0 to 10% MeOH) to give the title compound (0.15 g, 28% yield).HPLC-MS (Method A): Ret, 2.12 min; ESI-MS m/z, 292.4 (M+H).

According to the analysis of related databases, 592-55-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; LABORATORIOS DEL DR. ESTEVE, S.A.; MERCE-VIDAL, Ramon; ALMANSA-ROSALES, Carmen; GARCIA-LOPEZ, Monica; (148 pag.)WO2017/121645; (2017); A1;,
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