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. 1978-39-8, name is 5-Fluoro-2-methoxyaniline, A new synthetic method of this compound is introduced below., name: 5-Fluoro-2-methoxyaniline

To a THF (20 mL) solution of 5-fluoro-2-methoxyaniline (1.76 g), a THF (30 mL) solution of pyridinium bromide perbromide (4.36 g) was added dropwise under ice-cooling, and the reaction solution was agitated for 30 minutes at room temperature. The solid which deposited from the reaction mixture was separated by filtering and the solid was washed by THF. After the obtained solid was dissolved with water and ethyl acetate, the aqueous layer was neutralized with a saturated sodium bicarbonate water, and the organic layer was partitioned. After the obtained organic layer was washed with a saturated saline solution, it was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography (elution solvent:hexane-ethyl acetate system), and 1.83 mg of the title compound was obtained. 1H-NMR (CDCl3) delta (ppm): 3.82 (s, 3H), 3.91 (brs, 2H), 6.50 (d, J=9.6 Hz, 1H), 6.84 (d, J=6.0 Hz, 1H).

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; Eisai Co., Ltd.; US2006/4013; (2006); A1;,
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Reference of 22483-09-6, 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. 22483-09-6, name is 2,2-Dimethoxyethanamine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a solution of isobenzofuran-i, 3-dione (80.Og, 0.540 mol) in toluene (1000 mL) added2, 2-dimethoxyethanamine (85.10 g, 0.811 mol), followed by N,N-diisopropylethylamine(0.187 mL, 1.080 mol) at room temperature. The reaction mixture was stirred at 120 C with dean stark apparatus for 16 h. After completion of the reaction, the reaction mixture was evaporated under reduced pressure. The residue obtained was diluted with in dichloromethane, filtered through pad of celite and dried over sodium sulfate and concentrated. The crude obtained was washed with petroleum ether to give the titled compound (100 g, 79%) as an off white solid. LCMS: m/z no ionization; ?H NMR (300 MHz, Chloroform-d) 7.89 – 7.81 (m, 2H), 7.76 – 7.68 (m, 2H), 4.77 (td, J = 5.8, 0.8 Hz, 1H), 3.82 (dd, J= 5.8, 0.8 Hz, 2H), 3.38 (d, J= 0.9 Hz, 6H).

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

Reference:
Patent; AURIGENE DISCOVERY TECHNOLOGIES LIMITED; CHIKKANNA, Dinesh; KHAIRNAR, Vinayak; PANIGRAHI, Sunil Kumar; WO2014/111871; (2014); A1;,
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Related Products of 450-91-9, A common heterocyclic compound, 450-91-9, name is 4-Fluoro-2-methoxyaniline, molecular formula is C7H8FNO, 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.

iii: Intermediate 3 (1.0 eq) and cesium carbonate (2.0 eq) and corresponding phenylamine (1.2 eq) were added into a dry reaction flask. Dry DMF was used as reaction solvent, N2 was used to remove water vapor and oxygen. Then catalyst and ligand Pd(AcO)2 (0.1 eq) and Xantphos (0.1 eq) were added. The reaction mixture was transferred to a 60 C oil bath, 6~7 hours. After the reaction completed, the mixture was filtered and evaporated. Intermediate 4 was gained. The yield was 50%.

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; Rong, Juan; Feng, Zhan-Zhan; Shi, Yao-Jie; Ren, Jing; Xu, Ying; Wang, Ning-Yu; Xue, Qiang; Liu, Kun-Lin; Zhou, Shu-Yan; Wei, Wei; Yu, Luo-Ting; Bioorganic and Medicinal Chemistry Letters; vol. 29; 19; (2019);,
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Reference of 64465-53-8, These common heterocyclic compound, 64465-53-8, name is 4-Fluoro-3-methoxyaniline, 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.

4-Fluoro-3-methoxyaniline (Apollo-Chem, 0.0085g) was added to intermediate 30 (0. 021 G) in ethanol (3ML), pyridine hydrochloride 0.012g) was added, and the mixture was heated under reflux for 5h. The solvent was evaporated to give a brown gum (0.033g), which was purified by mass directed preparative HPLC (Method A); 2N hydrochloric acid (1ML) was added to the product fractions, and the solvents evaporated to give the title compound (0.0067g). LC/MS Rt 1. 91min m/z 504 [MH+]

The synthetic route of 64465-53-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; WO2005/30212; (2005); A1;,
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Adding a certain compound to certain chemical reactions, such as: 494-99-5, name is 1,2-Dimethoxy-4-methylbenzene, 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 494-99-5, Recommanded Product: 1,2-Dimethoxy-4-methylbenzene

General procedure: A mixture of 3,4-disubstituetedtoluene (1 mmol), NBS(213 mg, 1.2 mmol) and AIBN(16 mg, 0.1 mmol) in anhydrous CCl4 (15 mL) was refluxed and monitored by TLC. After refluxing for 4 h, the reaction mixturewas filtered. The filtrate was concentrated to crude product, which was used inthe subsequent reaction 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, 1,2-Dimethoxy-4-methylbenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Ge, Bing-Chen; Feng, Hong-Fang; Cheng, Yu-Fang; Wang, Hai-Tao; Xi, Bao-Ming; Yang, Xue-Mei; Xu, Jiang-Ping; Zhou, Zhong-Zhen; European Journal of Medicinal Chemistry; vol. 141; (2017); p. 440 – 445;,
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Some common heterocyclic compound, 107622-80-0, name is (4-Phenoxyphenyl)methanamine, molecular formula is C13H13NO, 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-Phenoxyphenyl)methanamine

General procedure: The appropriate pyrazole (1.0 equiv) was treated with phosgene(20% in toluene) at 0 C. The reaction mixture was stirred at room temperature for 1 h.The solvent was removed under reduced pressure and the crude carbamoyl chloride was redissolved in anhydrous CH2Cl2 (0.5 M). The appropriate amine (1.0 equiv) and Et3N (1.2 equiv) were dissolved in CH2Cl2 and cooled to 0 C. The crude carbamoyl chloride was added dropwise and the reaction mixture was stirred at room temperature for 16 h.The mixture was diluted with EtOAc, washed with saturated aqueous NaCl, and dried over Na2SO4. Evaporation under reduced pressure yielded the crude coupling product that was purified by flash chromatography (SiO2).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 107622-80-0, its application will become more common.

Reference:
Article; Otrubova, Katerina; Srinivasan, Venkat; Boger, Dale L.; Bioorganic and Medicinal Chemistry Letters; vol. 24; 16; (2014); p. 3807 – 3813;,
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Reference of 22236-08-4, 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 22236-08-4 as follows.

Intermediate.11 rac-Allyl [l -{N’-cyano-N-[3-(difluoromethoxy)phenyl]carbamimidoyl} -3-(3,4-dichlorophenyl)-4,5- dihydro- l//-pyrazol-4-yl]carbamate To a stirred solution of m-difluoromethoxy aniline, 8.20 ml. (65.5 mmol) in anhydrous tetrahydrofuran (100 mL) at -78 C was added n -butyl lithium, 33.0 mL (65.5 mmol, 2 M in hexane) dropwise, while maintaining the reaction temperature below -65 C during the addition. The reaction mixture was stirred for 1 hour at -78 C before rac-phenyl 4-{[(ailyioxy)carbonyl]amino}-N-cyano-3-(3,4- dichlorophenyl)-4,5-dihydro- 1 H-pyrazole- 1 -carboximidate (intermediate 9), 10.0 g (21.8 mmol) in anhydrous tetrahydrofuran (600 mL) was added dropwise maintaining the reaction temperature below -65 C. The reaction mixture was stirred for 2 hours at -78 C before slowly pouring over saturated ammonium chloride solution (700 mL). The crude product was extracted into ethyl acetate (700 mL) and the organic layers were combined and washed with brine solution (350 mL). The collected organic phase was dried over magnesium sulfate, filtered and the solvent evaporated to yield an off-white crude solid. The crude solid was precipitated from a minimum volume of ethyl acetate, filtered, and washed with diethyl ether to yield rac-allyl [ 1 – {N’-cyano-N- [3 – (difluoromethoxy)phenyi]carbamimidoyl}-3-(3,4-dichlorophenyl)-4,5-dihydro-lH-pyrazoi-4- yl] carbamate, 7.6 g (67%) as a white solid. NM R (400 MHz, DMSO-d6): delta [ppm] = 4.08 (dd, 1H), 4.36-4.53 (m, 3H), 5.11 (dd, 1H), 5.17 (dd, 1H), 5.50-5.59 (m, 1H), 5.77-5.90 (m, 1H), 6.99 (dd, 1H), 7.16 (t, 1H), 7.21 (t, 1H), 7.23 (dd, 1H), 7.39 (t, 1H), 7.73-7.81 (m, 2H), 8.15 (d, 1H), 8.17 (d, 1H), 9.79 (br s, 1H). I MS (method 3): Rt = 1.78 min MS (ESI): [M + Hf = 523.2

According to the analysis of related databases, 22236-08-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; STELLFELD, Timo; MOWAT, Jeffrey Stuart; STRESEMANN, Carlo; HILLIG, Roman; KOeHR, Silke; STOeCKIGT, Detlef; WEISKE, Joerg; HARTUNG, Ingo; BARAK, Naomi; CHRIST, Clara; TER LAAK, Antonius; BADOCK, Volker; CRAMPTON, Rosemary Helen; STEFANUTI, Ian; (194 pag.)WO2016/166186; (2016); A1;,
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Related Products of 6096-89-5, The chemical industry reduces the impact on the environment during synthesis 6096-89-5, name is 2-(4-Fluorophenoxy)ethylamine, I believe this compound will play a more active role in future production and life.

2-(4-Fluorophenoxy)ethylamine (5A-1) in hydrochloride form is dissolved in wa- ter and basified with 1N sodium hydroxide (NaOH) to basic pH, and then extracted with ether. The free amine is thus obtained (yield = 74%).The malonate monoester (O) (7.5 g), the amine (5A)-1 (4.14 g) in ethanolic solution (30%) and hydroxybenzotriazole (HOBT) (3.97 g) in 70 ml of THF are placed in a 500 ml three-necked flask. After complete dissolution, the whole is cooled to -7C and DCC (5.5 g) diluted in 30 ml of THF is then added dropwise over 30 minutes.The mixture is allowed to warm to room temperature and is then left stirring for 19 hours. At room temperature, the medium becomes cloudy (white precipitate).The precipitate (dicyclohexyl urea) is filtered off and concentrated to dryness. 15.77 g of a beige-coloured solid are obtained.This crude solid is taken up in ethyl acetate (400 ml) and washed with:- HCMN (150 ml)- saturated sodium hydrogen carbonate solution (NaHCO3) (150 ml)- saturated NaCI solution (150 ml) – water (150 ml).After drying over MgSO4 and evaporating off the solvent, 9.34 g of a beige-coloured solid are obtained.YId: 84% m.p. = 1200C 1H NMR (DMSO delta in ppm): 1.08 (s, 3H); 3.41 (t, 2H); 3.93 (t, 2H); 4.07 (q, 2H);6.89 (t, 2H); 7.08 (t, 2H); 7.31 (s, 4H); 7.83 (s, 1H); 8.60 (t, 1H).Purity = 67%MS (APCI) m/z: 419 [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-(4-Fluorophenoxy)ethylamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK PATENT GMBH; WO2008/6432; (2008); A1;,
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Application of 2752-17-2, These common heterocyclic compound, 2752-17-2, name is 2,2′-Oxydiethanamine, 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.

H(5O,2)-CBZ; Several approaches were tried to synthesize the N,N,N’,N’-Tetrakis-(2-amino-ethyl)- 3-oxapentane- l ,5-diamine [H(5O,2)-amine]. It was found that the reaction of 5LIO-amine with CBZ-aziridine provides clean H(5O,2)-CBZ.; 5LIO-amine (0.21 g, 2 mmol) and CbZ-aziridine ( 1.77 g, 10 mmol) were mixed in tert- butanol (30 ml.) at room temperature under N2. The mixture was stirred under a N2 atmosphere at 8O0C for 16 hrs. when TLC showed the completeness of the reaction. The volatile were removed under vacuum and the residue was dissolved in dichloromethane. The appropriate fractions of a gradient flash silica gel column ( 1 -7% methanol in dicholoromethane) were collected and evaporated to dryness to give a pale beige thick oil, yield: 1.28 g, 79%.[0301] ‘ H NMR(300MHz, CDCl3): delta 2.53(s,br, 12H), 3.17(s,br, 4H), 3.83(s, br, 8H), 5.04(s, 8H), 7.29(s,br, 20H). 1 3C NMR (300MHz, CDCI3): delta 38.8, 53.0, 53.6, 69.3, 128.0, 128.1 , 128.4, 136.6, 156.4. MS(FAB+, DTT/DTE): 813.5 (MH+).

The synthetic route of 2752-17-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; WO2008/8797; (2008); A2;,
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Reference of 578-57-4,Some common heterocyclic compound, 578-57-4, name is 1-Bromo-2-methoxybenzene, molecular formula is C7H7BrO, 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: DMF (40 mL), NaI (375 mg, 2.5 mmol), and 1,2-dibromoethane (100muL, 1.16 mmol) were added to an undivided electrochemical cell, fitted with an iron/nickel (64/36) anode, and surrounded by a nickel foam as the cathode (surface: 40 cm2, porosity: 500 mum, Goodfellow).The mixture was electrolyzed under argon at a constant current intensityof 0.2 A at r.t. for 15 min. The current was then stopped, then NiBr2bpy (187 mg, 0.5 mmol) and aryl or heteroaryl halide (5 mmol),were sequentially added. The solution was electrolyzed at 0.2 A untilthe starting aryl or heteroaryl halide had been totally consumed (2-5h). Sat. aq EDTA-Na2 solution (50 mL) was added, and the resultingsolution was extracted either with EtOAc (for aryl halides) or withCH2Cl2 (for heteroaryl halides) (3 × 50 mL). The combined organic layerswere washed with brine (50 mL), dried (MgSO4), filtered, and concentratedunder vacuum. The crude product was purified by flashchromatography (silica gel, 70-200 mum).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Bromo-2-methoxybenzene, its application will become more common.

Reference:
Article; Rahil, Rima; Sengmany, Stephane; Le Gall, Erwan; Leonel, Eric; Synthesis; vol. 50; 1; (2018); p. 146 – 154;,
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