Tag: M.W=100-200

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., Application In Synthesis of 4-Methoxy-N,N-dimethylaniline

General procedure: Under an atmosphere of N2, KOt-Bu (2.2 mmol), dioxane (0.9 mL), DMSO (1.65 mmol), tertiary amine 1 (0.55 mmol), and aryl halide 2(1.65 mmol) were successively added to a Schlenk reaction tube. The mixture was stirred vigorously at 80-120 C for 12 h. Then the mixture was diluted with EtOAc, washed with sat. brine, and dried (anhyd Na2SO4). Then the solvent was removed under reduced pressure and the residue was purified by flash column chromatography (petroleum ether and petroleum ether-EtOAc, 100:1 for the methoxy group derived products) to give pure products 3.

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; Huang, Pei; He, Bang-Yue; Wang, Hui-Min; Lu, Jian-Mei; Synthesis; vol. 47; 2; (2015); p. 221 – 227;,
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Reference of 6738-23-4, These common heterocyclic compound, 6738-23-4, name is 2,4-Dimethylanisole, 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.

Reference Example 32 2-Methoxy-3,5-dimethylbenzaldehyde To a solution of 1-methoxy-2,4-dimethylbenzene (8.00 g, 58.7 mmol) and 1,1-dichloromethyl methyl ether (7.40 g, 64.7 mmol) in methylene chloride (30 mL) was added titanium tetrachloride (20.0 g, 105 mmol) at 0 C. and the mixture was stirred at that temperature for 20 minutes. This reaction mixture was poured into iced water and the organic layer was taken, washed with saturated aqueous sodium hydrogen carbonate solution, dried over MgSO4, and filtered. The filtrate was concentrated under reduced pressure to provide 9.40 g of the title compound. Yield 98%. Oil. 1H-NMR (CDCl3) delta: 2.306 (3H, s), 2.312 (3H, s), 3.85 (3H, s), 7.25-7.27 (1H, m), 7.48 (1H, d, J=1.8 Hz), 10.3 (1H, s).

Statistics shows that 2,4-Dimethylanisole is playing an increasingly important role. we look forward to future research findings about 6738-23-4.

Reference:
Patent; Takeda Chemical Industries, Ltd.; US6248766; (2001); B1;,
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Adding a certain compound to certain chemical reactions, such as: 19500-02-8, name is 3-Methoxy-2-methylaniline, 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 19500-02-8, Recommanded Product: 19500-02-8

Reference Production Example 4 (0558) A mixture of 15.0 g of 3-amino-1-methoxy-2-methylbenzene, 48.7 g of triphosgene, and 350 ml of toluene was stirred with heating under reflux for 3 hours. The reaction mixture allowed to cool was concentrated under reduced pressure to obtain 17.0 g of 1-methoxy-3-isocyanato-2-methylbenzene. 1-Methoxy-3-isocyanato-2-methylbenzene (0559) (0560) 1H-NMR (CDCl3) delta (ppm): 7.09 (1H, t, J=8.2 Hz), 6.72 (1H, dd, J=0.5, 8.0 Hz), 6.69 (1H, d, J=8.2 Hz), 3.82 (3H, s), 2.19 (3H, 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; SUMITOMO CHEMICAL COMPANY, LIMITED; HOU, Zengye; TAKAHASHI, Teruki; (156 pag.)US2016/174558; (2016); A1;,
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Electric Literature 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.

Under an argon atmosphere, sodium hydride (2.41g, 100 mmol) was suspended in THF (20 mL). Pyrrolidine (3.50 g, 50 mmol) dissolved in 30 mL of THF was added dropwise to the solution. The mixture was stirred at 25C for 15 h, then 1-bromo-2-(2-methoxyethoxy)ethane (9.15 g, 50 mmol) was added to the solution. After stirring at 70C for 15 h, the resulting suspension was filtered to remove the white precipitate. The solvent was removed from the filtrate by rotary evaporation to give the yellow crude product. The crude product was purified by distillation under reduced pressure. The fraction collected at 120C under a reduced pressure of 1 mm Hg afforded the pyrrolidine derivative 1-(2-(2-methoxyethoxy)ethyl)pyrrolidine (OE2py) as a colorless oil (yield=6.16 g, 72%). 1H NMR (CDCl3 relative to tetramethylsilane (TMS), 300 MHz): delta (ppm)=3.41 (m, 6H), 3.38 (s, 3H), 2.69 (t, J=5.2Hz, 2H), 2.55 (t, J=5.1Hz, 4H), 1.76 (m, 4H). MS (FAB+): m/z=174.2.

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:
Article; Horiuchi, Shunsuke; Zhu, Haijin; Forsyth, Maria; Takeoka, Yuko; Rikukawa, Masahiro; Yoshizawa-Fujita, Masahiro; Electrochimica Acta; vol. 241; (2017); p. 272 – 280;,
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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. 103-50-4, name is Benzyl ether belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. category: ethers-buliding-blocks

General procedure: A mixture of azobenzene 1 (0.25 mmol), dibenzyl ether 2 (0.75 mmol), TBHP (1.5 mmol), and DCE (1 mL) was charged into a sealed tube. After stirring vigorously at 120 C for 24 h, the mixture was evaporated under vacuum. The corresponding product 7 was isolated by silica gel column chromatography with a PE/EtOAc mixture as eluent.

The synthetic route of 103-50-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Hong, Gang; Aruma, Alfred Njasotapher; Zhu, Xiaoyan; Wu, Shengying; Wang, Limin; Synthesis; vol. 48; 8; (2016); p. 1147 – 1158;,
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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. 1836-62-0, name is 2-(2-Methoxyphenoxy)ethylamine, A new synthetic method of this compound is introduced below., Formula: C9H13NO2

(f) A mixture comprising 2-(2-methoxyphenoxy)ethylamine (10 g, 59.9 mmol), diisopropylethylamine (13.9 mL, 81.6 mmol) and dichloromethane (80 mL) was cooled to 0 C. and then a solution of 3-methoxy-4-nitrobenzoyl chloride (11.76 g, 54.4 mmol) in dichloromethane (50 mL) was added dropwise. The mixture was allowed to warm to 23 C. over two hours, quenched with aqueous hydrochloric acid (3M, 20 mL), washed with water (3*20 mL), dried (Na2SO4) and concentrated in vacuo to provide N-[2-(2-methoxyphenoxy)ethyl]-3-methoxy-4-nitrobenzamide (14 g, 74% yield) an off white solid; MS (PB-PCI) C17H18N2O6 m/e calc 346.34; found 347 (MH+).

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:
Patent; Church, Timothy J.; Cutshall, Neil Scott; Gangloff, Anthony R.; Jenkins, Thomas E.; Linsell, Martin S.; Litvak, Joane; Rice, Kenneth D.; Spencer, Jeffrey R.; Wang, Vivian R.; US2001/53779; (2001); A1;,
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Application of 16452-01-0, The chemical industry reduces the impact on the environment during synthesis 16452-01-0, name is 3-Methoxy-4-methylaniline, I believe this compound will play a more active role in future production and life.

g. 2-bromo-5-methoxy-4-methyl-aniline. To a solution of 3-methoxy-4-methyl-aniline (8.19 g, 59.71 mmol) in dichloromethane (200 mL), was added tetrabutylammonium tribromide (28.79 g, 59.71 mmol) and the reaction mixture was stirred at room temperature for 2.5 hrs. Aqueous NaHCO3 was added and the layers separated. The aqueous layer was further extracted with dichloromethane and the combined organics washed successively with water and brine, dried over MgSO4, filtered and evaporated. The residue was chromatographed on silica gel (20% ethyl acetate in hexane) to give 11.05 g of 2-bromo-5-methoxy-4-methyl-aniline (85% yield). 1H NMR (300 MHz; CDCl3): 2.09 (s, 3 H), 3.75 (s, 3 H), 3.95 (br s, 1 H), 6.27 (s, 1 H), 7.13 (s, 1 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, 3-Methoxy-4-methylaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Pfahl, Magnus; Tachdjian, Catherine; Spruce, Lyle W.; Al-Shamma, Hussien A.; Boudjelal, Mohamed; Fanjul, Andrea N.; Wiemann, Torsten R.; Pleynet, David P.M.; US2003/144329; (2003); A1;,
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Reference of 7664-66-6, 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. 7664-66-6 name is 4-Isopropoxyaniline, 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.

To a mixture of 3-chloro-6-methyl-4-(4-methylbenzyl)pyridazine (200 mg, 0.859 mmol), 4-isopropoxyaniline (169 mg, 1.12 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (112 mg, 0.193 mmol), cesium carbonate (560 mg, 1.72 mmol) and dioxane (4 mL) was added palladium acetate (28.9 mg, 0.129 mmol) under nitrogen atmosphere, and the resulting mixture was heated at reflux for 1 hour. To the reaction mixture were added water (200 mL) and saturated aqueous ammonium chloride (5 mL). The resulting mixture was extracted with ethyl acetate (200 mL). The extract was washed by brine (200 mL), dried over anhydrous magnesium sulfate, and concentrated in vacuo. The resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give 3-(4-isopropoxyphenylamino)-6-methyl-4-(4-methylbenzyl)pyridazine (187 mg, Yield: 62.7%) as yellow amorphous. 1H-NMR (delta ppm TMS/CDCl3): 1.31 (6H, d, J=6.1 Hz), 2.37 (3H, s), 2.56 (3H, s), 3.84 (2H, s), 4.46 (1H, sep, J=6.1 Hz), 5.96 (1H, s), 6.80 (2H, d, J=8.3 Hz), 7.08 (2H, d, J=7.9 Hz), 7.18 (2H, d, J=7.9 Hz), 7.34 (2H, d, J=8.3 Hz).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Isopropoxyaniline, and friends who are interested can also refer to it.

Reference:
Patent; Shionogi & Co., Ltd.; KAI, Hiroyuki; ENDOH, Takeshi; JIKIHARA, Sae; ASAHI, Kentaro; HORIGUCHI, Tohru; EP2604260; (2013); A1;,
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Related Products 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.

a-5-1) 1-tert-Butoxycarbonylamino-3,3-diethoxypropane A mixture of di-tert-butyl dicarbonate (9 g, 40 mmol.) in dioxane (40 ml) is added drop by drop, with stirring and at 0 C., to a solution of 1-amino-3,3-diethoxypropane (5.52 g, 37 mmol) and Et3N (4.04 g, 40 mmol) in 5 ml dioxane. After 2 hrs, the mixture is stirred at ambient temperature for 12 hrs then the solvent is evaporated. The residual oil is taken up in 10 ml of water, acidified with 30 ml HCl (1%), then extracted with ethyl acetate (60 ml*3). The organic phases are dried (MgSO4) and evaporated to give 8.89 g of 1-tert-butoxycarbonylamino-3,3-diethoxypropane (90%). 1H NMR (CDCl3): 1.20 (t, 6H, J=8.8 Hz, CH3), 1.40 (s, 9H, C(CH3)3), 1.60-2.00 (m, 2H, CH2C), 3.00-3.80 (m, 6H, OCH2+NHCH2), 4.50 (t, 1H, J=6.4 Hz, CH), 5.05-5.10 (br, 1H, NH).

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:
Patent; Baudy Floc’h, Michele; Busnel, Olivier; Muller, Sylviane; US2011/44974; (2011); A1;,
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These common heterocyclic compound, 658-89-9, name is 4-(Trifluoromethoxy)benzene-1,2-diamine, 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-(Trifluoromethoxy)benzene-1,2-diamine

[0227] Quinoline-7-carboxylic acid (34.6 mg, 0.2 mmol, 1.0 equiv) and 4- trifluoromethoxy-l,2-diaminobenzene (40.3 mg, 0.21 mmol, 1.05 equiv) were suspended in dry Nu,Nu-dimethyl formamide (0.17 M) under argon atmosphere followed by the addition of triethylamine (1.2 equiv). Then HATU (N-[(Dimethylamino)-lH-l,2,3-triazolo-[4,5-b]pyridin-l- ylmethylene]-N-methylmethanaminium hexafluorophosphate N-oxide) (1.2 equiv) was added and the reaction mixture was stirred for 16 hours at room temperature. After dilution with water, the mixture was extracted with dichloromethane (3 x 20 mL). Combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The crude product was purified on C18-silica gel (water/acetonitrile + 0.1% trifluoroacetic acid). Fractions containing the desired product were combined and solvent was removed in vacuo. Solid product was dissolved in glacial acetic acid (0.2 M) and the resulting solution was heated in a sealed vial at 140 C for 2 hours. After cooling down to room temperature, acetic acid was removed in vacuo and the crude product was purified on C18-silica gel (water/acetonitrile + 0.1% trifluoroacetic acid). Fractions containing the desired product were combined and treated with saturated sodium bicarbonate solution. This mixture was extracted with dichloromethane (3 x 20 mL). Combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to give 47.5 mg of the desired product 74 as an off-white solid (38% yield) in >95% purity as determined by HPLC. 1H NMR (500 MHz; CD30D): delta 8.95 (dd, J = 4.3, 1.5 Hz, 1H), 8.71 (s, 1H), 8.43 (d, J = 8.2 Hz, 1H), 8.35 (dd, J = 8.6, 1.7 Hz, 1H), 8.13 (d, J = 8.6 Hz, 1H), 7.71 (d, J = 8.9 Hz, 1H), 7.61 (dd, J (0637) (s, 1H), 7.24 (d, J= 8.8 Hz, 1H); LC/MS [m/z]: 330 [M+H]+.

The synthetic route of 4-(Trifluoromethoxy)benzene-1,2-diamine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ACTAVALON, INC.; DNEPROVSKAIA, Elena, V.; HOLZWARTH, Michael, S.; RYCHNOVSKY, Scott, D.; (184 pag.)WO2018/85348; (2018); A1;,
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