Tag: M.W=100-200

91-16-7, name is 1,2-Dimethoxybenzene, 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. Quality Control of 1,2-Dimethoxybenzene

Preparation A 1,2-dibromo-4,5-dimethoxybenzene 16.16 g of 1,2-dimethoxybenzene (117 mmol) are stirred at 0 C. in CCl4 (120 mL). 13.2 mL of dibromine (2.2 eq; 257.4 mmol; 41.13 g) dissolved in CCl4 (25 mL) are added dropwise (30 min) whilst monitoring the temperature (0-5 C.) [Fit an outlet which bubbles into a solution of Na2CO3 in order to neutralise the hydrobromic acid which forms]. After stirring for 2 hours at 0 C., the reaction mixture is then poured onto a mixture of water+ice, and the organic phase is washed with aqueous 10% NaHSO3 solution and then with aqueous 10% NaOH solution. After evaporation and drying, 33.42 g of a white solid corresponding to the title product are obtained. Yield=97% m.p. 92-93 C. 1H NMR (CDCl3): delta=7.06 (s; 2H); 3.86 (s; 6H). 13C NMR (CDCl3): delta=148.8; 115.9; 114.7; 56.2.

The synthetic route of 91-16-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Les Laboratoires Servier; Vaysse-Ludot, Lucile; Le Flohic, Alexandre; Vaultier, Michel; Pucheault, Mathieu; Kaminski, Thomas; US8859763; (2014); B1;,
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Reference of 6096-89-5, 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 6096-89-5 as follows.

Example 167. N-(3-(3,4-dichlorophenyl)propyl)-l-(2-(4-fluorophenoxy)ethyl)-4- h drox -5 -oxo-2,5 -dihydro- 1 H-pyrrole-3 -carboxamide[00219] To a solution of 2-(4-fluorophenoxy)ethanamine (0.022 g, 0.14 mmol) in MeOH (3 mL) was added DIPEA (0.024 mL, 0.14 mmol). The mixture was stirred for 5 min at rt, then paraformaldehyde (4.19 mg, 0.140 mmol) was added. The mixture heated at 60 C for 10 min using microwave irradiation. The reaction was cooled to rt, then Intermediate 5 (50 mg, 0.140 mmol) was added in a single portion. The reaction mixture was heated at 100 C for 15 min using microwave irradiation, then stirred at rt for 16 h. The reaction mixture was diluted with MeOHiH^O (9: 1) containing 0.1 % TFA, then purified by RP preparative HPLC (Method C) to obtain 9.2 mg (14% yield) of Example 167. HPLC/MS (Method C) RT = 3.35 min, [M+H]+ 468; .H NMR (500 MHz, methanol-^) (delta ppm): 1.83-1.95 (m, 2 H), 2.66 (t, J=7.70 Hz, 2 H), 3.36 (t, J=6.87 Hz, 2 H), 3.85 (t, J=5.22 Hz, 2 H), 4.11-4.20 (m, 4 H), 6.91 (d, J=4.40 Hz, 1 H), 6.93 (d, J=3.85 Hz, 1 H), 6.99 (t, J=8.80 Hz, 2 H), 7.14 (dd, J=8.25, 2.20 Hz, 1 H), 7.35-7.41 (m, 2 H).

According to the analysis of related databases, 6096-89-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; ABELL, Lynn; ADAM, Leonard; CAVALLARO, Cullen L.; FINLAY, Heather; FRIENDS, Todd J.; HANGELAND, Jon J.; JIANG, Ji; LAWRENCE, R. Michael; LLOYD, John; PI, Zulan; TORA, George O.; QIAO, Jennifer X.; HU, Carol Hui; WANG, Tammy C.; WO2013/48982; (2013); A1;,
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Reference of 768-70-7, A common heterocyclic compound, 768-70-7, name is 3-Ethynylanisole, molecular formula is C9H8O, 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.

General procedure: Preparation of Copper Acetylides; Procedure 1To a solution of CuI (3.8 g, 20.0 mmol) in a mixture of NH4OH(28% NH3 solution, 50 mL) and EtOH (30 mL) was added the alkyne1 (10.0 mmol) dropwise. The deep blue reaction mixture wasstirred overnight at r.t. under argon and the yellow precipitate wascollected by filtration and successively washed with NH4OH (10%NH3 solution, 3 × 50 mL), H2O (3 × 50 mL), EtOH (3 × 50 mL), andEt2O (3 × 50 mL). The bright yellow solid was then dried under highvacuum overnight to afford the desired polymeric copper acetylide2, which was used without further purification.

The synthetic route of 768-70-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Theunissen, Cedric; Lecomte, Morgan; Jouvin, Kevin; Laouiti, Anouar; Guissart, Celine; Heimburger, Jeremy; Loire, Estelle; Evano, Gwilherm; Synthesis; vol. 46; 9; (2014); p. 1157 – 1166;,
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Electric Literature of 2734-70-5, The chemical industry reduces the impact on the environment during synthesis 2734-70-5, name is 2,6-Dimethoxyaniline, I believe this compound will play a more active role in future production and life.

A slurry of 398.1 (5.31 g, 28.7 mmol) and potassium hydroxide (3.06 g, 54.5 mmol) in water (20.5 mL) was heated at reflux for 1.25 h. The reaction was allowed to cool to RT and then 3 N HCl was added until the pH was 2. The mixture was extracted with EtOAc (4X). The combined organic layers were dried over anhydrous sodium sulfate and concentrated to afford 398.2 (3.76 g, 83percent yield) as a light yellow oil. Note that 398.2 contains 35percent of the corresponding decarboxylation byproduct 4-ethylthiazole. Yhis mixture was used in the subsequent step. An ice-cooled solution of 398.2 (3.70 g, 65percent pure, 15.3 mmol) in DMF (55 mL) was treated with TEA (5.95 mL, 42.8 mmol) followed by HATU (7.0 g, 18.4 mmol) directly. After 5 min, 2,6-dimethoxyaniline (Amfinecom Inc., 2.3 g, 15.3 mmol) was added. The resulting brown solution was warmed to RT and stirred for 1.75 h. The reaction was then partitioned between water (275 mL) and EtOAc (2X). The combined organic layers were washed with water (1X) and brine (1X), dried over anhydrous sodium sulfate, and concentrated in vacuo. The residue was purified by silica gelchromatography (eluent: 10-100percent EtOAc in hexanes) to provide Example 398.3 (2.54 g, 57percent yield) as a light yellow solid. LCMS-ESI (pos.) m/z: 293.0 (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, 2,6-Dimethoxyaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; AMGEN INC.; CHEN, Ning; CHEN, Xiaoqi; CHEN, Yinhong; CHENG, Alan C.; CONNORS, Richard V.; DEIGNAN, Jeffrey; DRANSFIELD, Paul John; DU, Xiaohui; FU, Zice; HARVEY, James S.; HEATH, Julie Anne; HEUMANN, Lars V.; HORNE, Daniel B.; HOUZE, Jonathan; KALLER, Matthew R.; KAYSER, Frank; KHAKOO, Aarif Yusuf; KOPECKY, David J.; LAI, Su-Jen; MA, Zhihua; MEDINA, Julio C.; MIHALIC, Jeffrey T.; NISHIMURA, Nobuko; OLSON, Steven H.; PATTAROPONG, Vatee; SWAMINATH, Gayathri; WANG, Xiaodong; WANSKA, Malgorzata; YANG, Kevin; YEH, Wen-Chen; (700 pag.)WO2018/97945; (2018); 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. 707-07-3, name is (Trimethoxymethyl)benzene, A new synthetic method of this compound is introduced below., Product Details of 707-07-3

To toluene (200 mL), 5-bromo-2-amino-benzylamine (9.5 g, 47.2 mmol) and trimethyl- benzoic orthoester (8.2 g, 47.2 mmol) were added, followed by p-toulensulfonic acid (1.35 g, 7.1 mmol). The resulting suspension was stirred at reflux for 50 hours. The reaction mixture was cooled at r.t., diluted with AcOEt (150 mL), washed with saturated sodium bicarbonate, then with water. The organic layer was dried and concentrated to provide the intermediate dihydroquinazoline as a light brown solid (8.5 g; 63%). This intermediate is dissolved in DCM (20 mL) at r.t., then MnO2 (5.1 g ) was added. The resulting mixture was stirred at r.t. for 48 hrs, then filtered on celite. The filtrate was concentrated to provide the title product as white solid ( 8.1 g, 95%). Cj4H9BrN2; MW: 285.15; MS m/z: 286 (M+ 1). 1H-NMR (300 MHz, d6-DMSO) ppm: 7.58-7.61 (m, 3H), 8.02 (d, IH), 8.17 (dd, IH), 8.49-8.56(m, 3H), 9.70(s, IH).

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; ROTTAPHARM S.P.A.; WO2009/152868; (2009); A1;,
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41365-75-7, name is 1-Amino-3,3-diethoxypropane, 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 41365-75-7

Part A A solution of 1-amino-3,3-diethoxypropane (5.00 ML, 30.9 mmol) in 5 ML of tetrahydrofuran (THF) was treated with triethylamine (4.51 ML, 34.0 mmol) under an atmosphere of nitrogen and cooled to 0 C. The reaction mixture was then treated dropwise with a solution of di-tert-butyl dicarbonate (7.42 g, 34.0 mmol) in 25 ML of THF. The reaction mixture was stirred for 2 h at 0 C. and then allowed to come to room temperature.After 15 h, the reaction mixture was concentrated under reduced pressure, dissolved in ethyl acetate, washed with water (2*) and brine, dried over Na2SO4, filtered and concentrated under reduced pressure to yield tert-butyl (3,3-diethoxypropyl)carbamate (8.40 g) as a clear, faintly yellow oil.

The synthetic route of 41365-75-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; 3M Innovative Properties Company; US2004/176367; (2004); A1;,
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Application of 4342-46-5, 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. 4342-46-5, name is 4-Methoxycyclohexanamine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Ethylcyclohexane (1200 mL) was added to the autoclave, stirring was started, and 220 g (2 mol) of formamide was added to the solution at a concentration of 40%. After stirring for 10 minutes, 1-amino-4-methoxycyclohexane (130 g, 1 mol) was added. ,Into the reaction kettle to pass CO, so that the pressure in the kettle reaches 0.2MPa, heated to 130 C, heat 20h, in the control of raw materials <2%, the reaction is over, cooled to 25 ~ 30 C, dilute hydrochloric acid was added dropwise to the reaction solution , Adjust the pH to 5-6, there is a solid precipitation, filter out the product, filter cake shampoo once,cis-8-Methoxy-1,3-diazaspiro[4,5]-nonane-2,4-dione, 184 g, yield 92%. The synthetic route of 4-Methoxycyclohexanamine has been constantly updated, and we look forward to future research findings. Reference:
Patent; Henan Zi Wei Xing Chemical Co., Ltd.; Wu Doucan; Mao Longfei; Li Wei; Lu Zhiguo; Wang Zhenggang; Lu Biao; Jia Shuhong; Yuan Zhiguo; (10 pag.)CN107827881; (2018); A;,
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Electric Literature of 67191-35-9, 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. 67191-35-9 name is 1-Isopropoxy-2-vinylbenzene, 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.

Under anhydrous and anaerobic conditions,Grubbs first generation catalyst 1a (1.22mmol)Add to a 100mL Schlenk bottle,Compound IIIba (2863 mg, 2.43 mmol) andPotassium tert-butoxide (477 mg, 4.25 mmol)It was added to the reaction flask, and 50 mL of n-hexane was added.After reacting for 5 hours at 60 C with stirring, the reaction was monitored by TLC.After the reaction was completed, n-hexane was removed under reduced pressure.The intermediate obtained in the previous step was dissolved in 40 mL of dichloromethane.Add cuprous chloride (300 mg, 1.42 mmol) and stir for 5 min.Compound 2a1 (296 mg, 1.82 mmol)It was added to the reaction flask, and the temperature was raised to 40 C, and the reaction was monitored by TLC.After completion of the reaction, column chromatography gave 568 mg of pale green solid powder IIba1, yield: 32.0%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Isopropoxy-2-vinylbenzene, and friends who are interested can also refer to it.

Reference:
Patent; Chengdu Kaimeisi Business Wu Information Advisory Center (Limited Partner); Chen Jianxin; (28 pag.)CN110041262; (2019); A;,
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Synthetic Route of 1535-73-5, 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. 1535-73-5, name is 3-Trifluoromethoxyaniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

3-(trifluoromethoxy)phenylamine (50 mg, 0.28 mmol) was dissolved in dry DCM (5 mL) , triethylamine (56 mg, 0.52 mmol) and triphosgene (27 mg, 0.094 mmol) were added to the reaction mixture and stirred at room temperature for three hours. In the reaction solution N-(6-(3-amino-4-fluorophenoxy)benzo[d]thiazol-2-yl)cyclopropanecarboxamide (96 mg, 0.28 mmol) was added thereto, and after reacting for 2 h, the reaction mixture was evaporated to dryness.The residue was directly purified by column chromatography (eluent: dichloromethane / methanol = 100:3). Finally, 32 mg of a white solid was obtained in a yield of 20percent.

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-Trifluoromethoxyaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Second Military Medical University; Zhuang Chunlin; Miao Zhenyuan; Zhang Hao; Chen Xiaofei; Cai Zhenyu; Zhang Wannian; Xu Lijuan; (36 pag.)CN109053630; (2018); A;,
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Application of 39538-68-6, A common heterocyclic compound, 39538-68-6, name is 2-Methoxy-4-methylaniline, molecular formula is C8H11NO, 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.

(Step 1)Synthesis of 2-methoxy-4-methylphenyl isothiocyanate (compound represented by formula (b)) N 1,1′-thiocarbonyldiimidazole (6.10 g), N-dimethylformamide (80 ml) solution, at room temperature, 2-methoxy-4-N methyl aniline (3.43 g), N-dimethylformamide solution (40 ml) was added and stirred for 1 hour. Then water was added at 0 , and extracted with ethyl acetate. The organic layer was washed with water, then washed with saturated brine. Then, the organic layer was dried over anhydrous magnesium sulfate, filtered, then concentrated in vacuo. The resulting crude product was purified by silica gel column chromatography, to obtain the desired product (4.53g).

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; NIPPONSODA COMPANY LIMITED; SHIMIZU, KAZUYA; SAKAMOTO, RIE; TAKAHASHI, JUN; KANAZAWA, JYUN; (37 pag.)JP2016/29022; (2016); A;,
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