Tag: M.W=100-200

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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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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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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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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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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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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Adding a certain compound to certain chemical reactions, such as: 1535-73-5, name is 3-Trifluoromethoxyaniline, 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 1535-73-5, Safety of 3-Trifluoromethoxyaniline

(a) Synthesis of 4-bromo-3-(trifluoromethoxy)aniline A solution of N-bromosuccinimide (3.78 g, 21.2 mmol) in N,N-dimethylformamide (11 ml) was added dropwise to a solution of 3-trifluoromethoxyaniline (3.84 g, 21.2 mmol) in N,N-dimethylformamide (11 ml) at room temperature over a period of 40 minutes. After completion of the dropwise addition, the resulting mixture was stirred overnight. After completion of the reaction, the reaction mixture was poured into water and extracted with ethyl acetate, and the organic layer was dried over magnesium sulfate and filtered. The filtrate was concentrated and the crude product thus obtained was purified by a silica gel column chromatography (hexane/chloroform = 6/4) to obtain 4-bromo-3-(trifluoromethoxy)aniline (4.96 g, 91percent).

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

Reference:
Patent; Sumitomo Pharmaceuticals Company, Limited; EP1500643; (2005); A1;,
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Adding a certain compound to certain chemical reactions, such as: 74654-07-2, name is 2-(2-(2-Methoxyethoxy)ethoxy)ethanamine, 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 74654-07-2, Quality Control of 2-(2-(2-Methoxyethoxy)ethoxy)ethanamine

Example 56A tert-Butyl [(trans-4-{[(2S)-3-[5′-({2-[2-(2-methoxyethoxy)ethoxy]ethyl}carbamoyl)-2′-methylbiphenyl-3-yl]-1-oxo-1-{[4-(1H-tetrazol-5-yl)phenyl]amino}propan-2-yl]carbamoyl}cyclohexyl)methyl]carbamate 3′-[(2S)-2-{[(trans-4-{[(tert-Butoxycarbonyl)amino]methyl}cyclohexyl)carbonyl]amino}-3-oxo-3-{[4-(1H-tetrazol-5-yl)phenyl]amino}propyl]-6-methylbiphenyl-3-carboxylic acid (100 mg, 0.15 mmol) and 2-[2-(2-methoxyethoxy)ethoxy]ethanamine (29 mg, 0.17 mmol) were dissolved in tetrahydrofuran (4 ml), N-[(dimethylamino)(3H-[1,2,3]triazolo[4,5-b]pyridin-3-yloxy)methylidene]-N-methylmethanaminium hexafluorophosphate (67 mg, 0.17 mmol) and N,N-diisopropylethylamine (23 mg, 0.17 mmol) were added and the mixture was stirred at RT overnight. Subsequently, the mixture was concentrated and the residue was purified chromatographically by HPLC (Method 10). This gave 45 mg (37% of theory) of the title compound. LC-MS (Method 4): Rt=1.20 min; MS (ESIpos): m/z=827.6 [M+H]+.

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, 2-(2-(2-Methoxyethoxy)ethoxy)ethanamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Bayer Pharma Aktiengesellschaft; ROeHN, Ulrike; ELLERMANN, Manuel; STRASSBURGER, Julia; WENDT, Astrid; ROeHRIG, Susanne; WEBSTER, Robert Alan; SCHMIDT, Martina Victoria; TERSTEEGEN, Adrian; BEYER, Kristin; SCHAeFER, Martina; BUCHMUeLLER, Anja; GERDES, Christoph; SPERZEL, Michael; SANDMANN, Steffen; HEITMEIER, Stefan; HILLISCH, Alexander; ACKERSTAFF, Jens; TERJUNG, Carsten; (163 pag.)US2016/244437; (2016); A1;,
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Adding a certain compound to certain chemical reactions, such as: 41789-95-1, name is 1-(3-Methoxyphenyl)-N-methylmethanamine, 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 41789-95-1, Formula: C9H13NO

Example 11 2-((3-methoxy-N-methybenzylamino)methyl)-1H-anthra[1,2-d]imidazole-6,11-dione (CL09) Compound CL01 (1.18 g, 4 mmole) and DIPEA (1.4 mL, 8 mmole) were stirred in 30 mL anhydrous tetrahydrofuran (THF) for 10 minutes. Then, 3-methoxy-N-methybenzylamine (1.19 mL, 8 mmole) was added thereto. The mixed solution was reacted by heating under reflux for 6 hours. After completion of reaction, the mixed solution was concentrated under reduced pressure (by reduced pressure concentrator such as Vacuum Evaporator). Then the concentrated mixture was extracted with ethyl acetate/H2O. The extract was dried by MgSO4 and concentrated under reduced pressure to obtain a crude product. The crude product was recrystallized in ethyl acetate/n-hexane, the mixture was filtered to collect the crystal which was rinsed with acetone to obtain a yellowish brown compound. Mol. Wt.: 411.4525 (C25H21N3O3); Yield: 39%; Mp: 150-151 C.; Rf: 0.79 (ethyl acetate:dichloromethane:methanol=2:2:1); HRMS (ESI) m/z calcd for C25H21N3O3+[M]+: 411.1583. Found: [M+H]+=412.1701, [M+Na]+=434.1519. 1H-NMR (300 MHz, CDCl3) delta (ppm): 2.44 (s, 3H, -N-CH3), 3.74 (s, 2H, -CH2-), 3.86 (s, 3H, -O-CH3), 4.01 (s, 2H, -CH2-), 6.83 (d, J=7.8 Hz, 1H, Ar’-H), 7.03-7.00 (m, 2H, Ar’-H), 7.27 (t, J=6.9 Hz, 1H, Ar’-H), 7.77-7.80 (m, 2H, Ar-H8,9), 7.99 (d, J=8.4 Hz, 1H, Ar-H4), 8.17 (d, J=8.1 Hz, 1H, Ar-H5), 8.23-8.32 (m, 2H, Ar-H7,10); 13C-NMR (75 MHz, CDCl3) delta (ppm): 29.15, 42.87, 54.97, 55.27, 62.17, 113.85, 114.55, 118.40, 121.54, 121.64, 125.53, 126.63, 127.62, 128.82, 129.74, 130.13, 132.61, 133.53, 133.82, 134.13, 134.33, 149.00, 160.23, 182.99, 184.88.

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

Reference:
Patent; HUANG, Hsu-Shan; US2011/207719; (2011); A1;,
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Adding a certain compound to certain chemical reactions, such as: 4179-19-5, name is 3,5-Dimethoxytoluene, 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 4179-19-5, HPLC of Formula: C9H12O2

1,3-dimethoxy-5-methylbenzene (30 g, 0.20 mol) and dichloromethane (900 mL) were added to a dry round bottom flask (1 L) and cooled to the above solution in an ice bath. Disulfone chloride (52.5 g, 0.40 mol) was added dropwise, and the mixture was added dropwise and stirred at room temperature overnight. After the reaction was completed, an aqueous solution of sodium hydrogencarbonate was added dropwise to adjust pH = 8, and dichloromethane was extracted with dilute hydrochloric acid, respectively.Washed with distilled water,Drying and concentration under reduced pressure gave compound 2,4-dichloro-1,5-dimethoxy-3-methylbenzene (31 g, white solid).

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, 3,5-Dimethoxytoluene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Rudong Lingda Bio-pharmaceutical Technology Co., Ltd.; Wang Hui; (35 pag.)CN109721599; (2019); A;,
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