Tag: M.W=100-200

Adding a certain compound to certain chemical reactions, such as: 6298-96-0, name is 1-(4-Methoxyphenyl)ethylamine, 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 6298-96-0, COA of Formula: C9H13NO

a) 10.0 g (66.1 mmol) (S)-4-methoxy-alpha-methylbenzylamine are added to 30 mL HBr (30% in AcOH) and stirred at 100 C. for 4 h. The reaction mixture is cooled to r.t. and the solvent is removed in vacuo. The crude product is used without further purification.

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-(4-Methoxyphenyl)ethylamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; FLECK, Martin; HEINE, Niklas; NOSSE, Bernd; ROTH, Gerald Juergen; US2014/213568; (2014); A1;,
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Reference of 446-61-7, 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. 446-61-7, name is 2-Fluoro-6-methoxyaniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

(E)-3-Ethoxy-N-(3-fluoro-2-methoxyphenyl)acrylamide (3a) A mixture of 6-fluoro-o-anisidine (2a) (5.08 g, 36 mmol), DMAP (0.44 g, 3.6 mmol) and pyridine (25 mL) was stirred in an ice bath for one hour. After concentrating, water (50 mL) and AcOEt (100 mL) were added. Concentrated HCl was added to pH 1. Extraction was performed with AcOEt as the organic layer was washed with was washed successively with: 25 mL saturated NaCl containing 2 mL 1 M HCl, 25 mL saturated NaCl containing 5mL NaHCO3, and finally with 25 mL saturated NaCl. The organic layer was dried with MgSO4 and purified by passing through a column of silica gel using a solvent system of 1:1 followed by 2:1 hexanes-AcOEt. The product was further purified by column chromatography using a solvent system combination of 10:1 4:1 2:1. The product was recrystallized from cold 10:1 hexanes-AcOEt to give (3.16 g, 37% yield) as off white crystals. 1H NMR (400 MHz, CDCl3) 8.19 (d, J=8.4 Hz, 1H), 7.64 (d, J=11.2 Hz, 1H), 7.56 (bs, 1H), 7.01-6.94 (m, 1H), 6.81-6.74 (m, 1H), 5.36 (d, J=12 Hz, 1H), 3.98 (d, J=1.6 Hz, 3H), 3.96 (q, J=7.2 Hz, 2H), 1.36 (t, J=7.2 Hz, 3H). 19F NMR (376 MHz, CHCl3) -131.37.

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-Fluoro-6-methoxyaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Horwitz, Jerome P.; Polin, Lisa; Hazeldine, Stuart T.; Corbett, Thomas H.; US2007/54938; (2007); A1;,
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Synthetic Route of 1535-75-7, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 1535-75-7 name is 2-(Trifluoromethoxy)aniline, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

General procedure: Acetamides (1a-1x, 1ab, 1ac and 1ba-1bc). To a solution of 2-phenylacetic acid (7.0mmol), 2-(trifluoromethoxy)aniline (7.7mmol) in anhydrous CH2Cl2 (25mL) were added EDCI (1.745g, 9.1mmol) and DMAP (256.6mg, 2.1mmol). The reaction mixture was stirred at room temperature overnight, diluted with HCl (1M) aqueous solution, and extracted with CH2Cl2 (3×25mL). The combined organic phase was washed with saturated NaHCO3 aqueous solution and brine, dried over anhydrous Na2SO4, and concentrated under vacuum. Purification by flash chromatography (Silica gel, petroleum ether: ethyl acetate=50: 1 as eluent) gave the corresponding 2-phenyl-N-[2-(trifluoromethoxy)phenyl]acetamide compound.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-(Trifluoromethoxy)aniline, and friends who are interested can also refer to it.

Reference:
Article; Zhao, Xiao-Jing; Zhao, Jie; Sun, Xin; Liu, Ji-Kai; Wu, Bin; Tetrahedron; vol. 73; 25; (2017); p. 3463 – 3477;,
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Electric Literature of 7252-83-7, These common heterocyclic compound, 7252-83-7, name is 2-Bromo-1,1-dimethoxyethane, 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.

Example 31 [000431] A mixture of Compound 31A (3.00 g, 14.93 mmol), 2-bromo-l,l- dimethoxyethane (2.77 g, 16.42 mmol) and K2C03 (4.12 g, 29.86 mmol) in DMF (26 mL) was stirred at 150 C for 2 h. It was evaporated to remove DMF. The residue was diluted with ethyl acetate (200 mL), washed with water and brine, dried with anhydrous Na2S04, and evaporated to render Compound 31B (3.80 g, yield 88%) as a white solid. 1H-NMR (CDC13, 400 MHz) major characteristic peaks: delta (ppm) 4.10 (d, J= 5.2 Hz, 2H), 4.75 (t, J= 5.2 Hz, 1H), 6.89 (d, J= 9.2 Hz, 1H), 7.61-7.64 (m, 1H), 7.93 (s, 1H), 10.42 (s, 1H).

The synthetic route of 7252-83-7 has been constantly updated, and we look forward to future research findings.

Reference:
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 41365-75-7 as follows. Application In Synthesis of 1-Amino-3,3-diethoxypropane

To a solution of 0.98 g (11.3 mmol) of morpholine in 11mL of CH2Cl2 2.0 g (12.3 mmol) of 1,1′-carbonyldiimidazole was added. The reaction mixture was stirred for 48 hours at room temperature. Then, 1.65 g (11.3 mmol) of 3,3-diethoxypropan-1-amine 3 was added and mixed for 48 hours at room temperature. The reaction mixture was extracted with water (310 mL), the organic layer was collected and dried over anhydrous Na2SO4. The solvent was evaporated to give carboxamide 4d as a yellow oil, which was used without further purification.

According to the analysis of related databases, 41365-75-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Smolobochkin, Andrey V.; Gazizov, Almir S.; Burilov, Alexander R.; Pudovik, Michail A.; Synthetic Communications; vol. 48; 19; (2018); p. 2545 – 2552;,
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Application of 22236-10-8, 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. 22236-10-8, name is 4-(Difluoromethoxy)aniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example 6 N-(4-(difluoromethoxy)phenyl)-2-(imidazo[1,2-a]pyridin-5-yl)acetamide (0278) To a mixture of 2-(imidazo[1,2-a]pyridin-5-yl)acetic acid (50 mg) and anhydrous DMF (1.9 mL) were added 4-(difluoromethoxy)aniline (54 mg), HATU (160 mg) and DIPEA (0.059 mL) at room temperature, and the mixture was stirred at room temperature for 17 hr. To the reaction mixture were added water, saturated brine and saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The obtained organic layer was dried over anhydrous magnesium sulfate and the solvent was evaporated under reduced pressure. The obtained residue was purified by NH silica gel column chromatography (NH, ethyl acetate/methanol) and recrystallized from ethanol-hexane to give the title compound (31 mg). 1H NMR (300 MHz, DMSO-d6) delta4.14 (2H, s), 6.84-7.41 (5H, m), 7.54 (1H, d, J = 9.0 Hz), 7.58-7.66 (3H, m), 7.87 (1H, s), 10.50 (1H, s).

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

Reference:
Patent; Takeda Pharmaceutical Company Limited; KIMURA, Eiji; MIYANOHANA, Yuhei; OGINO, Masaki; TANAKA, Yuta; FUSHIMI, Makoto; OKAWA, Tomohiro; HANYA, Yuki; KOIKE, Tatsuki; (67 pag.)EP3239150; (2017); A1;,
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Some common heterocyclic compound, 651734-54-2, name is 2,6-Difluoro-3,5-dimethoxyaniline, molecular formula is C8H9F2NO2, 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: C8H9F2NO2

To a stirred solution of 2,6-difluoro-3,5-dimethoxyaniline (9.03 g, 47.7 mmol), sodium triacetoxyborohydride (38.0 g, 180 mmol) in methylene chloride (60 mL) / trifluoroacetic acid (30 mL), 4,6-dichloronicotinaldehyde (8.00 g, 45.5 mmol) was added in small portions at room temperature. After 1 hour, the volatiles were removed in vacuo and saturated aqueous NaHCC (200 mL) was added. The resulting mixture was extracted with DCM (3 x 150 mL). The organic layers were combined, dried over Na2S04, and concentrated. The residue was purified on silica gel (eluting with 0 to 0-40% EtOAc in hexanes) to afford the desired product (15.0 g). LC-MS calculated for C14H13CI2F2N2O2 [M+H]+ m/z: 349.0; found 349.1.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 651734-54-2, its application will become more common.

Reference:
Patent; INCYTE CORPORATION; LU, Liang; WU, Liangxing; QIAN, Ding-Quan; YAO, Wenqing; (102 pag.)WO2016/134314; (2016); A1;,
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Related Products of 592-55-2, These common heterocyclic compound, 592-55-2, name is 1-Bromo-2-ethoxyethane, 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.

To a solution of methyl 3-hydroxy-2-methylbenzoate (0.83 g, 5.00 mmol) in DMF (10 ml) was added potassium carbonate (1.38 g, 10.0 mmol) and potassium iodide (0.83 g, 5.00 mmol) followed by 2- bromoethyl ethyl ether (0.7 ml, 6.00 mmol). The reaction mixture was heated at 100 C with stirring. After 30 minutes, more 2-bromoethyl ethyl ether (0.5 ml, 4.3 mmol) was added and the heating continued for another 45 minutes. After cooling to room temperature, the mixture was poured into water and extracted with EtOAc (x3). The combined organic extract was washed with brine, dried (Na2S04), filtered and concentrated. Dry column vacuum chromatography (heptane : EtOAc 95 : 5 – 90 : 10 – 80 : 20) afforded 0.85 g (71% yield) of methyl 3-(2-ethoxyethoxy)-2-methylbenzoate as a solid. 1H NMR (400 MHz, CDC13) d 7.38 (d, 1H), 7.14 (t, 1H), 6.96 (d, 1H), 4.09 (m, 2H), 3.85 (s, 3H), 3.78 (m, 2H), 3.59 (q, 2H), 2.42 (s, 3H), 1.21 (t, 3H). MS (ESI, positive mode) m/z 261.1 [M+Na]+.

Statistics shows that 1-Bromo-2-ethoxyethane is playing an increasingly important role. we look forward to future research findings about 592-55-2.

Reference:
Patent; BASF AS; SKJAeRET, Tore; FRASER, David Alan; STEINEGER, Hilde Hermansen; (179 pag.)WO2020/74964; (2020); A1;,
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Adding a certain compound to certain chemical reactions, such as: 7252-83-7, name is 2-Bromo-1,1-dimethoxyethane, 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 7252-83-7, category: ethers-buliding-blocks

i. Preparation of compound 311. 1-(2-Amino-3-chloro-4-hydroxy-phenyl)-ethanone 310 (40 g, 215 mmol) was dissolved in DMF (360 ml). Cesium carbonate (140 g, 430 mmol) was added, followed by bromoacetaldehyde dimethyl acetal (54.5 g, 323 mmol). The mixture was then vigorously stirred at 65 C for 24 hours. Upon cooling to room temperature, EtOAc (1 L) and H20 (1 L) were added to the mixture. The organic layer was extracted with EtOAc (1 x 400 ml). The combined organic layer was washed with aqueous 3% LiCI solution (2 x 1 L), brine, dried (Na2S04) and concentrated in vacuo. The residue was purified by silica gel chromatography to give compound 311 as a white solid (39 g, 67%).

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; GILEAD SCIENCES, INC.; RAY, Adrian S.; WATKINS, William J.; LINK, John O.; OLDACH, David W.; DELANEY, IV, William E.; WO2013/40492; (2013); A2;,
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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. 701-56-4, name is 4-Methoxy-N,N-dimethylaniline, A new synthetic method of this compound is introduced below., Recommanded Product: 4-Methoxy-N,N-dimethylaniline

General procedure: N,N-dimethylaniline (0.4 mmol, 1.0 equiv.) and diphenyliodonium salts (0.8 mmol, 2.0 equiv.) were added to a dried Schlenk tube. The tube was degassed with Nitrogen for three times. Then Toluene (3.0 mL) were added via a syringe, finally add 0.8 mL LiHMDS (0.8 mmol, 2.0 equiv.) 1 mol/L solution in THF under ice bath conditions. The mixture was stirred at 110 oC for 16 h, and then cooled down to room temperature. The crude products were directly purified using flash column chromatography on silica gel (petroleum ether/ethyl acetate 100:1 as eluants) to afford the desired product.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Article; Zhang, Zhiang; Wu, Xunshen; Han, Jianwei; Wu, Wenjun; Wang, Limin; Tetrahedron Letters; vol. 59; 18; (2018); p. 1737 – 1741;,
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