Month: July 2021

Synthetic Route of 36805-97-7, A common heterocyclic compound, 36805-97-7, name is 1,1-Di-tert-butoxy-N,N-dimethylmethanamine, molecular formula is C11H25NO2, 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: A suspension of 6-chloro-4-(isopropylamino)nicotinic acid (240 g, 1118 mmol) in toluene (1800 mL) in a 1 L round bottom flask was heated to 90 C. N,N-dimethylformamide di-tert-butyl acetal (1609 mL, 6709 mmol) in toluene (1800 mL) was added slowly over 8-9 hrs. The reaction mixture was heated at 90 C. for 12 hrs. After completion of 12 hrs, the reaction mixture was cooled and concentrated under reduced pressure to remove excess of solvent and obtain the crude material. The crude material was purified by flash column chromatography using silica gel as stationary phase and EtOAc: pet ether (2:8) as eluent to afford the title compound, tert-butyl 6-chloro-4-(isopropylamino)nicotinate (275 g, 91% yield). LC/MS 271.0 (M+H). 1H NMR (400 MHz, CDCl3) delta=8.59 (s, 1H), 8.14-8.08 (m, 1H), 6.51 (s, 1H), 3.71-3.61 (m, 1H), 1.57 (s, 9H), 1.28 (d, J=6.5 Hz, 6H).

The synthetic route of 36805-97-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Santella, Joseph B.; Kumar, Sreekantha Ratna; Duncia, John V.; Gardner, Daniel S.; Paidi, Venkatram Reddy; Nair, Satheesh Kesavan; Hynes, John; Wu, Hong; Murugesan, Natesan; Sarkunam, Kandhasamy; Arunachalam, Piramanayagam; US2015/191464; (2015); A1;,
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Adding a certain compound to certain chemical reactions, such as: 2674-34-2, name is 1,4-Dibromo-2,5-dimethoxybenzene, 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 2674-34-2, SDS of cas: 2674-34-2

General procedure: To an N-heterocycle was added a solution of i-PrMgCl*LiCl (1.33 M, 1.8 eq. with respect to N-heterocycle, in THF) and (i-Pr)2NH (0.1 with respect to N-heterocycle). The mixture was stirred at room temperature under an argon atmosphere for 18 hours. An electrophile was added and the mixture was stirred at room temperature for 20 minutes. The reaction was quenched by addition of saturated aqueous NH4Cl (20 mL), and a saturated Na2S2O3 solution (20 mL) in the case of I2 as an electrophile. The mixture was extracted three times with EtOAc, the organic layer was dried over MgSO4, filtered and the solvent was removed under reduced pressure.

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; Nxumalo; Dinsmore; Synthetic Communications; vol. 45; 21; (2015); p. 2478 – 2484;,
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Electric Literature of 20781-20-8, 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. 20781-20-8, name is (2,4-Dimethoxyphenyl)methanamine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 2,4-dimethoxybenzylamine (6.6 mL, 43.5 mmol) in DCM (85 mL) was added saturated aqueous sodium bicarbonate solution (85 mL) and the mixture was stirred vigorously at RT for 15 min. Stirring was stopped then thiophosgene (6.6 mL, 87 mmol) was added via syringe to the bottom layer. The mixture was stirred at RT for 90 min then the aqueous layer was separated and the organic layer was washed with brine, dried over Na2SC>4 and concentrated in vacuo twice from DCM to give 9.1 g of l-(isothiocyanatomethyl)-2,4-dimethoxybenzene as yellow oil.

The synthetic route of (2,4-Dimethoxyphenyl)methanamine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MCKITTRICK, Brian; CALDWELL, John, P.; MCCAULEY, John, A.; VACCARO, Henry; CHAN, Tin-Yau; KIM, Hyunjin; SMITH, Elizabeth; HONG, Liwu; KHAN, Tanweer; YING, Shihong; WANG, Hongwu; (66 pag.)WO2018/118827; (2018); A1;,
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Reference of 929-75-9, A common heterocyclic compound, 929-75-9, name is 1,11-Diamino-3,6,9-trioxaundecane, molecular formula is C8H20N2O3, 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: All macrocyclic compounds were obtained as previously described. 20,21 The corresponding diester (1-3) (10 mmol) and diamine (4-8) (10 mmol) were dissolved in MeOH (100 ml). The reaction mixture was stirred for 7 d at rt. After completion of the reaction (monitored by TLC), the solvent was evaporated and the residue was puriofied by chromatography on a silica gel column using 0-5% solutions of MeOH/CH2Cl2. Analytical and spectroscopic data are collected in the Supplementary Materials.

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; Pikus, Grzegorz; Pa?niczek, Ewa; Jurczak, Janusz; Arkivoc; vol. 2017; 2; (2017); p. 534 – 545;,
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Adding a certain compound to certain chemical reactions, such as: 2062-98-8, name is Perfluoro(2-methyl-3-oxahexanoyl) fluoride, 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 2062-98-8, COA of Formula: C6F12O2

While the solution containing compound (c1-1) was stirred at 0C, 1.7 g of triethylamine was added. Then, 4.4g of 2-(heptafluoropropoxy)-2,3,3,3-tetrafluoropropionic acid fluoride (compound d1-1) was dropwise added. After completionof dropwise addition, the solution was stirred at room temperature for 1 hour to obtain a solution containingcompound (m1-1). The solution containing compound (m1-1) was poured into ice water, followed by extraction three times withethyl acetate. Then, the resulting organic layer was dried over magnesium sulfate to remove the solvent, and the residuewas purified by silica gel column chromatography (eluent: ethyl acetate/hexane=1/2 (volume ratio)) to obtain 2.0 g ofcompound (m1-1). Compound (m1-1) was identified by 1H-NMR and 19F-NMR. NMR spectra of compound (m1-1): 1H-NMR (300.4MHz, solvent:CDCl3, standard:TMS) delta (ppm): 1.85(s, 6H), 4.27(t, J=4.8, 2H), 4.52(t, J=4.8, 2H),5.87(dd, J=10.5, 10.8, 1 H), 6.16(dd, J=10.5, 17.1, 1H), 6.45(dd, J=17.1, 17.4, 1H), 6.92(d, J=9.0, 2H), 7.90(d,J=9.0, 2H). 19F-NMR(282.7MHz, solvent:CDCl3, standard:CFCl3)delta5(ppm):-132.0(m, 1F), – 129.6(m, 2F), -85.4(m, 1F), -81.2(m, 6F), -79.5(m, 1F).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Perfluoro(2-methyl-3-oxahexanoyl) fluoride, and friends who are interested can also refer to it.

Reference:
Patent; Asahi Glass Company, Limited; ITO, Masahiro; TSURUOKA, Kaori; EP2792665; (2014); A1;,
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Synthetic Route 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.

Example 2: 4- {3-Hydroxy-3- [4- (2-ethoxyethoxy)-5, 5, 8, 8- tetramethyl-5,6, 7, 8-tetrahydronaphth-2-yl] prop-1-ynyl}- benzoic acid; a. 5,5, 8, 8-Tetramethyl-4- (2-ethoxyethoxy)- 5,6, 7,8-tetrahydronaphthalene-2-carbaldehyde 36 g (156 mmol) of 4-hydroxy-5,5, 8,8-tetra- methyl-5,6, 7, 8-tetrahydronaphthalene-2-carbaldehyde are dissolved in 400 mL of anhydrous DMF. 6.5 g (163 mmol) of 60% sodium hydride are added portionwise and the reaction medium is stirred for 1 hour. 25 g (163 mmol) of 2-ethoxyethyl bromide are added portionwise and the medium is stirred at room temperature for 2 hours and then hydrolysed and extracted with ethyl ether. The organic phase is washed with 1N sodium hydroxide solution, and then three times with water. The residue obtained is purified by chromatography (eluent: heptane). A yellow oil is obtained (m = 40.7 g; yield = 86%).

The synthetic route of 592-55-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GALDERMA RESEARCH & DEVELOPMENT, S.N.C.; WO2005/56510; (2005); 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. 7025-06-1, name is 1-Bromo-2-phenoxybenzene, A new synthetic method of this compound is introduced below., Formula: C12H9BrO

The THF solution (50 mL) of the compound 3 (g [ 7.5 ], 40mmol) was dropped at the roomtemperature at metal magnesium (1 g, 40mmol), 1,2dibromoethane (0.2 mL), and themixture of THF (50 mL), and was stirred into them for 3 hours. The THF solution (20 mL) ofthe phosphorus trichloride (2.6 mL, 30mmol) was dropped here at 78 degree C, and it stirredat the room temperature for 1 hour. It removed under decompression of a solvent and anexcessive phosphorus trichloride, THF (50 mL) was newly added, and the solution of thecompound 4 was obtained. The solution of the compound 2 of the preceding paragraph wasdropped here at 78 degree C, and it stirred at the room temperature for 2 hours to make the solution of the compound 5.

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; JAPAN POLYETHYLENE CORPORATION; JAPAN POLYPROPYLENE CORPORATION; XIN, SHIXUAN; SHIMIZU, FUMIHIKO; SATO, NAOMASA; TANNA, AKIO; (45 pag.)JP5812764; (2015); B2;,
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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. 1663-61-2, name is (Triethoxymethyl)benzene, A new synthetic method of this compound is introduced below., Recommanded Product: (Triethoxymethyl)benzene

1,1,1-Trimethoxyethane (35 mg, 0.291 mmol) and 3 mgcamphorsulfonic acid (0.012 mmol) were added to asolution of 113 mg heptoside 1 (0.242 mmol) in 1 cm3dry CH2Cl2 and stirred for 1 h at rt when TLC showed fullconversion of 1 into intermediate 11 (Rf = 0.33, hexane/EtOAc = 2/1).

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; Walter, Martin; Kohout, Claudia; Blaukopf, Markus; Kosma, Paul; Monatshefte fur Chemie; vol. 148; 1; (2017); p. 111 – 119;,
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Related Products of 112970-44-2, 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 112970-44-2 as follows.

Step 2. Synthesis of N-(2-bromo-3-methoxyphenyl)-2,2,2-trifluoroacetamide (C24) Trifluoroacetic anhydride (3.0 mL, 22 mmol) was added to a solution of 2-bromo-3-methoxyaniline (C23) (2.57 g, 10.77 mmol) and triethylamine (4.51 mL, 32.3 mmol) in dichloromethane (30 mL) at -78 C. The reaction was allowed to warm to room temperature and stirring was continued for 18 hours, whereupon the mixture was poured into water (40 mL) and extracted with dichloromethane (2*20 mL). The combined organic layers were dried over sodium sulfate and concentrated in vacuo. Purification via silica gel chromatography (Gradient: 0% to 30% methyl tert-butyl ether in hexanes) afforded the title compound as a colorless solid. Yield: 2.97 g, 9.96 mmol, 92%. GCMS m/z 297, 299 (M+). 1H NMR (400 MHz, CDCl3) delta 3.94 (s, 3H), 6.81 (dd, J=8.4, 1.2 Hz, 1H), 7.35 (dd, J=8.4, 8.3 Hz, 1H), 7.97 (dd, J=8.3, 1.3 Hz, 1H), 8.59 (br s, 1H).

According to the analysis of related databases, 112970-44-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Pettersson, Martin Youngjin; Johnson, Douglas Scott; Subramanyam, Chakrapani; O’Donnell, Christopher John; Ende, Christopher William Am; Fish, Benjamin Adam; Green, Michael Eric; Mullins, Patrick Bradley; Stiff, Cory Michael; Tran, Tuan Phong; Navaratnam, Thayalan; US2012/252758; (2012); A1;,
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Synthetic Route of 175278-09-8,Some common heterocyclic compound, 175278-09-8, name is 4-Bromo-2-(trifluoromethoxy)aniline, molecular formula is C7H5BrF3NO, 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: Triphosgene (0.14 g, 0.48 mmol) was dissolved in anhydrous CH2Cl2 (15 mL) and the mixture was stirred on the ice-bath for 15 min. 3-Bromo-5-(trifluoromethyl)aniline (0.3 g, 1.2 mmol) in anhydrous CH2Cl2 (10 mL) was added dropwise to the above mixture and stirring continued for 20 min. Et3N (0.2 mL, 1.44 mmol) diluted with CH2Cl2 (5 mL) was then added into the mixture. Stirring was continued for 20 min and a solution of Et3N (0.2 mL, 1.44 mmol), 4-pyridin-3-ylaniline (5) (0.2 g, 1.2 mmol) in anhydrous CH2Cl2 (20 mL) was added. After completion of the action, the reaction was quenched with dilute Na2CO3. The organic layer was washed with water and brine, and dried over Na2SO4. After filtration and concentration in vacuo, the residues was purified by silica gel flash chromatography (PE/AcOEt = 6:1) yielding (L1). yield 73%

The synthetic route of 175278-09-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Su, Ping; Wang, Jinfeng; Shi, Yaling; Pan, Xiaoyan; Shao, Ruili; Zhang, Jie; Bioorganic and Medicinal Chemistry; vol. 23; 13; (2015); p. 3228 – 3236;,
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