Tag: M.W=200-300

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. 51388-20-6, name is 4-(Benzyloxy)aniline hydrochloride, A new synthetic method of this compound is introduced below., Application In Synthesis of 4-(Benzyloxy)aniline hydrochloride

A solution of 4-benzyloxyaniline hydrochloride (4.0 g, 17.0 mmol), methanesulfonylacetic acid (2.35 g, 17.0 mmol) and HBTU (6.89 g, 18.2 mmol) in DMF (70 mL) was stirred at ambient temperature one minute. DIEA (6.5 mL, 37.2 mmol) was added all at once, and the resultant solution was stirred at ambient temperature. The solution was poured into water, and the product crystallized. The product, 5.4 g (99%), was collected by filtration and was used without any further purification in the subsequent reaction. MS m/z 320 (MH+). 1H NMR(DMSO-d6) delta 3.17 (s, 3H), 4.25 (s, 2H), 5.07 (s, 2H), 7.00 (d, 2H), 7.32-7.55 (m, 7H) and 10.32 (s, 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; Carson, John R.; McNally, James J.; US2005/182108; (2005); A1;,
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Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 4316-51-2, name is 4-Methoxytriphenylamine, This compound has unique chemical properties. The synthetic route is as follows., Formula: C19H17NO

POCl3 (6 mL, 64.17 mmol) was carefully added to a solution of 4-methoxy-N,N-diphenylaniline (10 g, 36.32 mmol), DMF (5 mL, 64.85 mmol) and 50 mL of 1,2-dichloroethane. The mixture was refluxed for 4 h, then cooled to room temperature (r.t.), and poured into a saturated aqueous sodium acetate solution (100 mL). The product was extracted with dichloromethane. The organic layer was dried over anhydrous MgSO4. The solvent was evaporated by a rotary evaporator. The residue was purified by silica gel column chromatography using ethyl acetate: n-hexane (2:3) to give (1) (7.6 g, Yield: 69%). TOF/MS (ESI): found 326.1 (M+Na+). 1H NMR (300 MHz, CDCl3, delta): 9.79 (s, 1H, ArCHO), 7.68-6.89 (m, 14H, ArH), 3.83 (s, 3H, ArOCH3).

According to the analysis of related databases, 4316-51-2, the application of this compound in the production field has become more and more popular.

Reference:
Article; Giang, Ha Ngoc; Kinashi, Kenji; Sakai, Wataru; Tsutsumi, Naoto; Journal of Photochemistry and Photobiology A: Chemistry; vol. 291; (2014); p. 26 – 33;,
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Synthetic Route of 6358-77-6, A common heterocyclic compound, 6358-77-6, name is 5-Bromo-2-methoxyaniline, molecular formula is C7H8BrNO, 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 (±)-12: A pressure glass tube charged with trifluoroborate (±)-10 (31 mg, 0.10 mmol), Cs2CO3 (98 mg, 0.30 mmol) and PdCl2(dppf)·CH2Cl2 (4 mg, 5 mol %) was alternatively evacuated and sparged with argon three times. A solution of 4-bromoanisol (21 mg, 0.11 mol) in toluene (1.5 mL) previously flushed with argon, then water (0.5 mL) were added by syringes. The reaction mixture was stirred at 100 C for 18 h and then cooled to room temperature. Water (5 mL) was added and the mixture extracted with EtOAc (5 mL × 2). The combined organic layers were washed with water (5 mL × 2), dried (MgSO4) and concentrated in vacuo. The residue was purified by column chromatography (cyclohexane/EtOAc 9:1), affording 12 as a colorless oil (24 mg, 75%).

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; Ty, Nancy; Pontikis, Renee; Chabot, Guy G.; Devillers, Emmanuelle; Quentin, Lionel; Bourg, Stephane; Florent, Jean-Claude; Bioorganic and Medicinal Chemistry; vol. 21; 5; (2013); p. 1357 – 1366;,
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Adding a certain compound to certain chemical reactions, such as: 5414-19-7, name is 1-Bromo-2-(2-bromoethoxy)ethane, 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 5414-19-7, SDS of cas: 5414-19-7

General procedure: 1,3-Dibromopropane (2.2 Kg, 10.9 mol) was slowly added to a stirred suspension of 264 g magnesium turnings (11 mol)In tetrahydrofuran (17.6 L).Control the dropping rate to maintain the reaction temperature at minus 40 ~ 50 degrees Celsius.After the addition is complete, the mixture is precooled to minus 50 degrees Celsius for two hours at minus 40 to 50 degrees Celsius,And the reaction mixture prepared from 2-chloropyridine was added.Control the dropping rate to maintain the reaction temperature at minus 40 ~ 50 degrees Celsius.After the addition was completed, the temperature was slowly raised to 60 C and stirred for 3 hours.The reaction mixture was concentrated under reduced pressure to 20 liters of n-hexane (20 L).The resulting solid was removed by filtration.Concentration of the filtrate followed by pressure distillation gave the desired target intermediate (1.16 Kg, 62%) as a colorless liquid.

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; Zhejiang Xingyue Pharmaceutical Technology Co., Ltd.; Ying Lv; Chen Qingquan; Hu Junbin; (103 pag.)CN104177394; (2017); B;,
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Synthetic Route of 43229-65-8, 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. 43229-65-8, name is N-Benzyl-1-(4-methoxyphenyl)propan-2-amine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

[0140] General procedure for Enantiomeric Separation of 2- benzylaminopropanes [(R)-10-14, (S)-10-14]. The appropriate racemic 2- benzylaminopropane (1 eq) was combined with the appropriate optically active mandelic acid (1 eq) in methanol (c= 0.5 M) and refluxed until the solution homogenized, then cooled to RT. The crystals were filtered, collected, and recrystallized twice from methanol (c = 0.3 M) to afford the optically active 2- benzylaminopropane ? mandelic acid salt. The salts were converted to the free amine for the purpose of collecting NMR and rotation data by partitioning the mandelic acid salt between 10% K2CO3 and CHCl3, drying organic extracts (Na2SO4) and evaporating; [0143] (R)-(-)-l-(4′-Methoxyphenyl)-2-benzylaminopropane [(R)-Il]. A sample of 3.02 g (11.8 mmol) of l-(4′-methoxyphenyl)-2-benzylaminopropane (42) was reacted with 1.8 g (11.8 mmol) f5rJ-(+)-mandelic acid to give 530 mg (35% based on enantiomeric abundance) of the free amine after workup. 1H NMR (CDCl3) delta 1.10 (d, 3H, J = 6.3 Hz), 2.57-2.76 (m, 2H), 2.88-2.94 (m, IH), 3.79 (s, 3H), 3.72-3.88 (m, 2H), 6.82 (d, 2H, J = 8.7 Hz), 7.07 (d, 2H, J= 8.4 Hz), 7.15-7.31 (m, 5H); MS (APCI+) m/z (rel): 256 (100); [alpha]D = -30.4 (c = 1.25 MeOH).

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, N-Benzyl-1-(4-methoxyphenyl)propan-2-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; THE GOVERNMENT OF THE UNITED STATES OF AMERICA AS REPRESENTED BY THE SECRETARY OF THE DEPARTMENT OF HEALTH AND HUMAN SERVICES; WO2008/22038; (2008); 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 5414-19-7 as follows. Safety of 1-Bromo-2-(2-bromoethoxy)ethane

Part F:; To a DMF (9 mL) solution of Part E (1.08 g, 2.71 mmol) was added K2CO3 (1.12 g, 8.16 mmol), 18-crown-6 (0.21 g, 0.80 mmol), and bis (2-bromoethyl) ether (0.37 mL, 2.9 mmol). The slurry was stirred at 60C for 72 hr. Additional bis (2-bromoethyl) ether was added at 24 hr (0.4 mmol) and 48 hr (1.2 mmol). The solvent was stripped in vacuo, and the residue was partitioned between ethyl acetate (50 mL) and water (30 mL). The organic layer was separated, dried over MgS04, and evaporated to an oil. Recrystallization from diethyl ether produced 0. 88 g (69 %) of the desired compound in the form of a white solid. LCMS: itvz = 469.2 (M+H).

According to the analysis of related databases, 5414-19-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PHARMACIA CORPORATION; WO2005/42521; (2005); A2;,
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Adding a certain compound to certain chemical reactions, such as: 116557-46-1, name is 3-Bromo-2-methoxyaniline, 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 116557-46-1, SDS of cas: 116557-46-1

A suspension of 3-bromo-2-methoxyaniline (500 mg, 2.47 mmol), bis(pinacolato)diboron (755 mg, 2.97 mmol) and potassium acetate (729 mg, 7.42 mmol) in 1,4-dioxane (8 mL) was sparged with nitrogen for 5 min. Pd(dppf)Cl2·DCM (173 mg, 0.21 mmol) was added and the mixture was heated under reflux for 2.5 h then cooled to room temperature. The reaction was diluted with DCM (35 mL) and washed with water (35 mL). The organic phase was concentrated under reduced pressure then purified by flash column chromatography, eluting with 0-100% EtOAc in isohexane, to return 49h (358 mg, 58%) an off-white solid. 1H NMR (300 MHz, DMSO-d6) delta 6.72-6.83 (m, 3H), 4.80 (s, 2H), 3.64 (s, 3H), 1.28 (s, 12H).

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:
Article; Newton, Rebecca; Bowler, Katherine A.; Burns, Emily M.; Chapman, Philip J.; Fairweather, Emma E.; Fritzl, Samantha J.R.; Goldberg, Kristin M.; Hamilton, Niall M.; Holt, Sarah V.; Hopkins, Gemma V.; Jones, Stuart D.; Jordan, Allan M.; Lyons, Amanda J.; Nikki March; McDonald, Neil Q.; Maguire, Laura A.; Mould, Daniel P.; Purkiss, Andrew G.; Small, Helen F.; Stowell, Alexandra I.J.; Thomson, Graeme J.; Waddell, Ian D.; Waszkowycz, Bohdan; Watson, Amanda J.; Ogilvie, Donald J.; European Journal of Medicinal Chemistry; vol. 112; (2016); p. 20 – 32;,
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Adding a certain compound to certain chemical reactions, such as: 74137-36-3, name is 1,3-Dibromo-5-methoxybenzene, 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 74137-36-3, Recommanded Product: 74137-36-3

To a solution of 1,3-dibromo-5-methoxybenzene (9.18 mmol, 1 eq) in 2 ml of xylene under a nitrogen atmosphere, acrylic acid (0.63 ml, 9.18 mmol, 1 eq), Pd(OAc)2 (1 mole percent, 20.66 mg), triphenylphosphine (4 mole percent, 69.2 mg) and triethylamine (19.278 ml, 2.7, 2.1 eq) are added. The reaction mixture is stirred at 100° C. for 11 h. Thereafter, 20 ml of water and 2 g of sodium carbonate were added, and the mixture was stirred at 100° C. for some minutes. The aqueous phase was subsequently separated and acidified. The precipitate that formed was dried and purified by means of column chromatography (eluent hexane/ethyl acetate 1/1) to obtain the desired product in a yield of 32percent (751 mg). C10H9Br3O; MW 256/258; 1H-NMR (CD3OD): delta 7.61 (d, J=16.1 Hz, 1H), 7.38-7.37 (m, 1H), 7.17-7.16 (m, 2H), 6.53 (d, J=16.1 Hz, 1H), 3.87 (s, 3H); 13C-NMR (CD3OD): delta 169.8, 162.3, 144.5, 138.9, 124.2, 121.4, 120.0, 113.4, 56.2

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, 1,3-Dibromo-5-methoxybenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Hartmann, Rolf; Frotscher, Martin; Oberwinkler, Sandrine; Ziegler, Erika; Messinger, Josef; Thole, Heinrich-Hubert; US2010/204234; (2010); A1;,
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Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 589-10-6, name is (2-Bromoethoxy)benzene, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C8H9BrO

Same procedure as in lit.32 with modifications: a biphasic solution of 2-bromo-1-phenoxy ethane32b (20.0 g, 0.1 mol), NBu4HSO4 (33 g, 0.1 mol) in Et2O (400 mL) and 50% aqueous NaOH (100 mL) was vigorously stirred at rt for 4 h. The organic phase was washed with H2O (3 × 50 mL), the aqueous phases were extracted with Et2O (2 × 50 mL), the combined organic phases dried (MgSO4) and evaporated. 27b was purified by distillation (7.8 g, 65%) at 70 C, 28 Torr. The reaction in toluene as in lit.32b gave a weaker yield (40%).1H NMR (250 MHz, CDCl3): similar values as in lit.37 S.-R. Sheng, X.-L. Liu, X.-C. Wang, Q. Xin and C.-S. Song, Synthesis (2004), pp. 2833-2836. Full Text via CrossRef | View Record in Scopus | Cited By in Scopus (21)37

According to the analysis of related databases, 589-10-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Chevrier, Carine; Le Nouen, Didier; Defoin, Albert; Tarnus, Celine; Carbohydrate Research; vol. 346; 10; (2011); p. 1202 – 1211;,
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Application of 5467-58-3, A common heterocyclic compound, 5467-58-3, name is 1-Bromo-4-methoxynaphthalene, molecular formula is C11H9BrO, 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.

Under nitrogen conditions,To the magnetic stirrer,thermometer,6.6 g (27.9 mmol) was added to a 250 mL three-necked flask of a condenser.1-bromo-4-methoxynaphthalene,12.0 g (36.3 mmol) of 4-nitrophenyl-2-amino-9,9-dimethylhydrazine,10.6g (167.4mmol) of copper powder,23.1 g (167.4 mmol) of potassium carbonate,7.4 g (27.9 mmol) of 18-crown-6,Then add 57.2 ml of o-dichlorobenzene,Reacting at 170 C for 20 h;The mixture was filtered while hot, and o-dichlorobenzene was distilled off under reduced pressure. The crude product was recrystallized from ethanol and N,N-dimethylacetamide (V:V = 1:2.7) to give 4-nitrophenyl-4. ‘-Methoxynaphthyl-2-amino-9,9-dimethylhydrazine 10.2 g, yield 75%;

The synthetic route of 5467-58-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Jilin University; Chen Chunhai; Su Kaixin; Wang Daming; Sun Ningwei; Zhou Hongwei; Zhao Xiaogang; (24 pag.)CN108929297; (2018); A;,
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