Category: ethers-buliding-blocks

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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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 2062-98-8 as follows. Computed Properties of C6F12O2

General procedure: To a magnetic stirred solution of 15.6 g triethylamine (0.15 mol) and 10.10 g allyl alcohol (0.17 mol) in anhydrous chloroform (150 mL) in a dry three-neck flask, 74.90 g perfluoro-2,5-dimethyl-3,6-dioxa-nonanoyl fluoride (0.15 mol) were added dropwise over a period of 3 h under agitation at 0 C. The reaction mixture was stirred for a further 12 h, with the temperature of reaction mass being maintained at room temperature. Distilled water was added to extract the triethylammonium fluoride and the unreacted allyl alcohol at the end of the reaction. The chloroform layer was dried over anhydrous sodium sulfate, and the major portion of the chloroform was distilled off in the vacuum of a water-jet pump over water. Additionally, the crude product was obtained and distilled under reduced pressure to give the pure product.

According to the analysis of related databases, 2062-98-8, the application of this compound in the production field has become more and more popular.

Reference:
Article; Shi, Xiang; Shi, Hongxin; Wu, Hongke; Shen, HaiMin; Research on Chemical Intermediates; vol. 44; 9; (2018); p. 5091 – 5105;,
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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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1462-37-9, name is ((2-Bromoethoxy)methyl)benzene, belongs to ethers-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. Product Details of 1462-37-9

Step-1: 1-(2-(benzyloxy)ethyl)-4-iodo-lH-pyrazoleTo a stirred solution 4-iodo-lH-pyrazole (2.0 g, 10.3 mmol) in DMF (20 ml) was addedpotassium carbonate (3.5 g, 25 mmol) followed by drop wise addition of ((2-bromoethoxy)methyl)benzene (2.43 g, 11 mmol) and stirred the reaction at RT for 15 h. Thereaction was monitored by TLC (50percent ethyl acetate in hexane). The reaction mixture was dilutedwith ice water (150 ml) and extracted with ethyl acetate (2×50 ml). The organic layer was driedover Na2S04, and concentrated under reduced pressure to afford 3.1 g (91.7percent yield) of 1-(2-fluorobenzyl )-4-iodo-1 H-pyrazole.1H NMR (DMSO-d6, 300MHz): 8 7.29 (s, lH), 7.55 (s, lH), 7.37-7.22 (m, SH), 4.45 (s, 2H),4.34-4.30 (t, 2H), 3.77-3.74 (t, 2H); LCMS: rn/z = 329.1 (M+l).

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

Reference:
Patent; AURIGENE DISCOVERY TECHNOLOGIES LIMITED; UM PHARMAUJI SDN. BHD; GUMMADI, Venkateshwar Rao; HOSAHALLI, Subramanya; NANDURI, Srinivas; AGGUNDA RENUKAPPA, Girish; WO2014/24077; (2014); A1;,
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Synthetic Route of 59557-91-4, The chemical industry reduces the impact on the environment during synthesis 59557-91-4, name is 4-Bromo-2-methoxyaniline, I believe this compound will play a more active role in future production and life.

4-(Dipropylphosphoryl)-2-methoxyaniline To a solution of 4-bromo-2-methoxyaniline (0.100 g, 0.495 mmol) in 2 mL DMF was added dipropylphosphine oxide (0.0730 g, 0.544 mmol), palladium acetate (5.6 mg, 0.025 mmol), XANTPHOS (17.2 mg, 0.030 mmol), and potassium phosphate (0.116 g, 0.544 mmol). The mixture was purged with nitrogen, and subjected to microwaves at 150 C. for 20 minutes. The reaction mixture was concentrated and purified by silica gel chromatography (0-12% 7N ammonia in methanol:dichloromethane) and the fractions were concentrated. The residue was acidified with 2.5 M HCl in ethanol and the solution was concentrated to provide 4-(dipropylphosphoryl)-2-methoxyaniline as the hydrochloride salt (0.132 g, 91% yield).

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, 4-Bromo-2-methoxyaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ARIAD PHARMACEUTICALS, INC.; Wang, Yihan; Huang, Wei-Sheng; Liu, Shuangying; Shakespeare, William C.; Thomas, Ranny M.; Qi, Jiwei; Li, Feng; Zhu, Xiaotian; Kohlmann, Anna; Dalgarno, David C.; Romero, Jan Antoinette C.; Zou, Dong; US2015/225436; (2015); 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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Electric Literature of 157869-15-3,Some common heterocyclic compound, 157869-15-3, name is 2-((4-Methoxyphenyl)ethynyl)aniline, molecular formula is C15H13NO, 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 sealed tube was charged with the mixture of 2-alkynylaniline 1 (1 mmol), carbon disulfide (1.5 mmol), then stirred in a solution of DBUH+ in CH3CN (1.5 mL) at room temperature under nitrogen atmosphere for indicated time. After completion, then H2O (5 mL) was added and the mixture was extracted with EtOAc (5 mL x 3), dried by anhydrous Na2SO4. Evaporation of the solvent followed by purification on silica gel (petroleum ether/ethylacetate = 4/1) provided the corresponding product 2.

The synthetic route of 157869-15-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhao, Peng; Liao, Qian; Gao, Hongxin; Xi, Chanjuan; Tetrahedron Letters; vol. 54; 19; (2013); p. 2357 – 2361;,
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