Author: Jessica.F

Synthetic Route of 13985-15-4, 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. 13985-15-4, name is 2,3,6,7-Tetramethoxy-9,10-dimethylanthracene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A solution of 2,3,6,7-tetrakis(methoxy)-9, 10-dim-ethylanthracene (10.0 g) obtained from the step 2A-1,sodium dichromate (50 g) and acetic acid (500 ml) wasrefluxed for 60 minutes to obtain 2,3,6,7-tetrakis(methoxy)anthracene-9, 10-dione (2).10336] 2,3,6,7-tetrakis(methoxy) anthracene-9, 1 0-dione:?H NMR (600 MHz, CDC13) oe 7.32 (s, 4H), 4.06 (t, 8H),1.76 (m, 8H), 1.57 (m, 8H), 1.43-1.26 (m, 72H), 0.88 (t,1 2H)

The synthetic route of 2,3,6,7-Tetramethoxy-9,10-dimethylanthracene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; INDUSTRY-UNIVERSITY COOPERATION FOUNDATION HANYANG UNIVERSITY; SUH, Donghack; CHOI, Kyounghwan; (106 pag.)US2019/31586; (2019); A1;,
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Synthetic Route of 439814-87-6, A common heterocyclic compound, 439814-87-6, name is 4-Bromo-1-(dimethoxymethyl)-2-fluorobenzene, molecular formula is C9H10BrFO2, 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 2 4-(4-Acetylpiperazin-l-yl)-2-fluorobenzaldehyde Palladium(II) acetate (111 mg, 0.49 mmol), 2-dicyclohexylphosphino-2′,6′-di-i-propoxy- Iota,Gamma-biphenyl (469 mg, 0.98 mmol) and sodium teri-butoxide (4.88 g, 49.2 mmol) were combined and the flask was purged with nitrogen. A solution of 1-piperazin-l-ylethanone (4.1 g, 32 mmol) and 4-bromo-l-(dimethoxymethyl)-2-fluoro-benzene (6.13 g, 24.6 mmol) in 1,4-dioxane (82 mL) was then added and the reaction was stirred at 100 C for 16 hours. The reaction was then filtered through diatomaceous earth and concentrated. The resulting residue was dissolved in 50 mL of THF and 50 mL of 1 N aqueous HC1 was added and the reaction was stirred at ambient temperature for 16 hours. The reaction was then neutralized with saturated aqueous Na2C03 and extracted with dichloromethane (x3), dried with MgSC>4, concentrated and purified by silica gel column chromatography (0-10% methanol in dichloromethane) to give 4-(4-acetylpiperazin-l-yl)-2-fluoro- benzaldehyde (3.68 g, 60% yield). LCMS (m/z) ES+251 [M+l]+.

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; F. HOFFMANN-LA ROCHE AG; FAUBER, Benjamin; RENE, Olivier; WO2013/92941; (2013); 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 1187160-18-4 as follows. name: 7-Methoxy-2,3-dihydro-1H-inden-1-amine hydrochloride

To a stirred solution of ethyl 4-chloro-2-methyIthiopyrimidine-5-carboxylate (2.24 g, 9.62 mmol) in 35 mL of anhydrous tetrahydrofuran was added triethylamine (4.00 mL, 2.90 g, 28.72 mmol). The solution was cooled to 0-5 0C and 7-methoxy-l -aminoindane hydrochloride (2.00 g, 10.01 mmol) was added. The reaction mixture was allowed to warm to room temperature and stirred 48 h. The precipitate was filtered off, washed with ethyl acetate (1 x 25 mL), and the combined filtrates were evaporated to dryness. The residue was dissolved in dichloromethane (35 mL) washed with saturated sodium bicarbonate solution (1 x 17 mL), dried over magnesium sulfate, filtered and concentrated to give 4-(7-methoxy- 2,3-dihydro-l H-inden-l -ylamino)-2-(methylthio)pyrimidine-5-carboxylate as an oil (3.31 g, 9.21 mmol, 95%). ESMS m/z 360 (M+H)+; 1H NMR (400 MHz, CDCl3) delta ppm 8.63 (s, I H), 8.43 (d, J = 6.5 Hz, I H), 7.21 – 7.26 (m, I H), 6.88 (d, J= 7.5 Hz, I H), 6.72 (d, J= 8.3 Hz, I H), 5.69 – 5.78 (m, IH), 4.26 (q, J= 7.2 Hz, 2H), 3.78 (s, 3H), 3.01 – 3.13 (m, I H), 2.82 – 2.94 (m, I H), 2.59 – 2.67 (m, I H), 2.56 (s, 3H), 2.04 – 2.14 (m, IH), 1.33 (t, J= 7.2 Hz, 3H).

According to the analysis of related databases, 1187160-18-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; AFRAXIS, INC.; CAMPBELL, David; DURON, Sergio G.; VOLLRATH, Benedikt; WADE, Warren; WO2010/71846; (2010); A2;,
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Adding a certain compound to certain chemical reactions, such as: 33839-11-1, name is 4-Bromo-2-ethyl-1-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 33839-11-1, Quality Control of 4-Bromo-2-ethyl-1-methoxybenzene

178.1 A solution of 4-bromo-2-ethyl-1-methoxybenzene (J. Chem. Soc., Perkin Trans. 1, 1987, 1423; 2.13 g, 9.9 mmol) in THF (30 ml) was cooled to -78 C. A 1.6M solution of n-BuLi in hexane (7.42 ml, 11.9 mmol) was added slowly and the mixture was stirred for 1.5 h. at -78 C. The mixture was warmed slowly to -10 C. and subsequently again cooled to -78 C. DMF (2.29 ml, 29.7 mmol) was added slowly and the mixture was stirred for 1 h. at -78 C. and for 1 h. at 0 C. The reaction mixture was poured into ice-cold 3M HCl and extracted with diethyl ether. The organic phase was dried and filtered, and the filtrate was concentrated. The residue was purified by chromatography (SiO2, hexane/EtOAc 8_1=>2:1). There were obtained 690 mg (42%) of 3-ethyl-4-methoxy-benzaldehyde as a yellowish 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; Ackermann, Jean; Alig, Leo; Chucholowski, Alexander; Groebke, Katrin; Hilpert, Kurt; Kuehne, Holger; Obst, Ulrike; Weber, Lutz; Wessel, Hans P.; US2001/1799; (2001); A1;,
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Reference of 131713-50-3, 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. 131713-50-3, name is 2,2-Dimethoxypropan-1-amine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

[(3 S)-(7-BroMo-2-oxo-5-pyridin-2-yl-2, 3 -dihydro- 1H-benzo[e] [1,4] diazepin-3 -yl)-propionic acid Methyl ester (Compound of formula TV, S enantiomer,25.0 gr) and dichloromethane (?IVIDC?, 375 ml) were charged into a clean, dry 4 neck RBF. The reaction mixture was stirred for 5-10 minutes at temperature of 20-25C and a clear solution was obtained. 2-bromo pyridine (29.46 gr) was added to the solution and the obtained reaction mixture was stirred for 5-10 minutes. The obtained reaction mass was cooled down to a temperature of -15 to -20C. Then, Triflic anhydride (26.32 gr) was slowly added, over a period of 30-45 minutes to the cooled reaction mass, at the same temperature of-15 to -20C. After the addition was completed, the obtained reaction mixture was stirred for 30-45 minutes, at the same temperature of -15 to -20C. The reaction progress was monitored by HPLC (monitor intermediate (S)-3 -(2-(methoxycarbonyl)ethyl)-7-bromo-5 – (pyridin-2-yl)-3H-benzo [e] [1,4] diazepin-2-yl trifluoromethanesulfonate formation). Afterwards, 1-amino-2,2-dimethoxypropane (14.81 gr) in dichloromethane (2 vol, 50 mL) solution was slowly added over a period of about 30 minutes to the reaction mixture at temperature of -15 to -20C. After complete addition, Triethylamine (31.44 gr) was slowly added over a period of about 30 minutes at the same temperature of -15 to -20C, and the obtained mixture was stirred at temperature of -15 to -20C for 60-120 minutes. The reaction progress was monitored by HPLC. After the reaction was completed, ammonium chloride solution (20%, 125 ml) was added, and the temperature was raised to 15-20C; the obtained mixture was stirred for 30 minutes. The organic layer was separated, washed with DM water (125 ml) and re-separated. The organic layer was then concentrated to volume of 1-1.5 vol, at a temperature below 45C. Toluene (50m1) was added to the reaction mass, and then stripped out 1 vol under vacuum at a temperature below 60C. Then, Toluene (50m1) was added and the obtained mixture was heated to temperature of 60-65C, and was stirred at this temperature for 30-45 minutes. Heating was discontinued and the reaction mass was slowly cooled to temperature of 0-10C, and was stirred for 3-4 hours – crystallization occurred. The obtained suspension was stirred at temperature of 0-10C for 3 0-45 minutes. The obtained solid was filtered and washed twice with pre-cooled (temperature of about 5-10 C) toluene (12.5 ml X 2 times), and suck-dried for 20-30 minutes. The wet solid was further dried under vacuum at temperature of 40-45C for 6-8 hours. Yield (dry): 26.5 gm (85%)

The synthetic route of 2,2-Dimethoxypropan-1-amine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; WATSON LABORATORIES INC.; BEN-ZION, Dolitzky; MARIOARA, Mendelovici; RAJARAM, Bodkhe Arjun; SHIVAJI, Mane Ganesh; SRIHARI, Samala Rajamouli; VIJAY, Joshi Ashutosh; LUTHRA, Parven Kumar; SINGH, Amit; MUTHUSAMY, Anantha Rajmohan; (62 pag.)WO2018/148361; (2018); A1;,
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Reference of 6850-60-8, 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. 6850-60-8, name is (4-Ethoxyphenyl)methanamine, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: A corresponding primary amine (1.1 equiv.) and an excess of 37% formalinaldehyde free of paraformaldehyde (1.0 mL, 13.5 mmol) were added to a suspension of Guareschi imide triethylammonium salt 1a-c (0.8-0.9 mmol) in EtOH (6-12 mL). The mixture was refluxed for 3-5 min with stirring and allowed to stand for48 h at 20 C (precipitation of the corresponding “bispidinate”5a-m is possible). The mixture was acidified with 10% aqueousHCl to pH 3-4, after 1 day a precipitate formed was collected by filtration, washed with cold EtOH and diethyl ether, and, if necessary, recrystallized from the acetone-EtOH solvent system

The chemical industry reduces the impact on the environment during synthesis (4-Ethoxyphenyl)methanamine. I believe this compound will play a more active role in future production and life.

Reference:
Article; Chigorina; Frolov; Dotsenko; Goloveshkin; Bushmarinov; Krivokolysko; Russian Chemical Bulletin; vol. 65; 9; (2016); p. 2260 – 2269; Izv. Akad. Nauk, Ser. Khim.; 9; (2016); p. 2260 – 2269,10;,
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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. 104566-41-8, name is (3-(Benzyloxy)phenyl)methanamine hydrochloride, This compound has unique chemical properties. The synthetic route is as follows., category: ethers-buliding-blocks

EXAMPLE 1A 4-Chloro-5-(3-benzyloxybenzylamino)-2-i-propyl-3-(2H)pyridazinone (Compound No. 95) STR61 A mixture comprising 8.24 g of 3-benzyloxybenzylamine hydrochloride prepared in Reference Example 2A, 3.11 g of 2-i-propyl-4,5-dichloro-3(2H)pyridazinone, 7.26 g of potassium carbonate, 30 ml of 1,4-dioxane and 90 ml of water was refluxed under stirring for 4.5 hours. The majority of 1,4-dioxane was distilled off under reduced pressure, and the residue was extracted with ethyl acetate. The extract was washed with diluted hydrochloric acid, and then treated with cerite to remove the precipitate. The organic layer was separated, and washed with water and a saturated sodium chloride aqueous solution, and then dried over sodium sulfate. Then, the solvent was distilled off. The pale yellow oily substance thereby obtained was crystallized from ether-n-hexane to obtain 2.51 g of the above identified compound having a melting point of from 106 to 108 C. as colorless crystals. NMR(CDCl3)6: 7.48 (1H, s), 7.30 (5H, s), 7.3-6.7 (4H, m), 5.02 (2H, s), 4.49, 4.40 (total 2H, each s), 5.2-4.8 (1H, broad s), 1.30 (6H, d). MS (m/e): 383(M+), 348, 91 (100%).

According to the analysis of related databases, 104566-41-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Nissan Chemical Industries Ltd.; US5098900; (1992); A;,
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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. 887267-47-2, name is 2-Bromo-5-(trifluoromethoxy)aniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Safety of 2-Bromo-5-(trifluoromethoxy)aniline

Reference Example 1-1N-(2-Bromo-5-trifluoromethoxyphenyl)-2,2,2-trifluoroacetamide Under ice-cooling, to a solution of 2-bromo-5-trifluoromethoxyaniline (0.98 g) in tetrahydrofuran (10 mL) were added trifluoroacetic anhydride (0.79 mL) and pyridine (0.61 mL). The solution was stirred at room temperature for 16 hours. The reaction mixture was concentrated under reduced pressure. To the residue was added ethyl acetate, and the organic layer was washed with 10% aqueous citric acid solution, a saturated aqueous sodium hydrogen carbonate solution, and saturated brine successively, and then dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the obtained crude product was purified by silica gel column chromatography (eluting solvent: hexane-ethyl acetate) to obtain the title compound (1.30 g).1H-NMR (CDCl3) delta ppm: 8.60-8.30 (2H, m), 7.65 (1H, d, J=8.9 Hz), 7.10-7.00 (1H, m)

The synthetic route of 887267-47-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KISSEI PHARMACEUTICAL CO., LTD.; US2012/122931; (2012); A1;,
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Related Products of 439814-87-6,Some common heterocyclic compound, 439814-87-6, name is 4-Bromo-1-(dimethoxymethyl)-2-fluorobenzene, molecular formula is C9H10BrFO2, 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.

To a solution of 4-bromo-1-dimethoxymethyl-2-fluorobenzene (4.53 g, 18.2 mmol) in tetrahydrofuran (50 mL) were added n-butyllithium (1.6 mol/L in hexanes; 15 mL) and dimethylformamide (2.1 mL, 27 mmol) sequentially at -78 C. under nitrogen atmosphere, and the mixture was stirred for 15 min. Water was added, and the mixture was extracted twice with ether. The organic layer was combined, washed with brine and dried on anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography (6:1 Hexane/ethyl acetate) to afford 4-dimethoxymethyl-3-fluorobenzaldehyde (2.26 g, 63%). 1H NMR (400 MHz, CDCl3) delta (ppm) 3.36 (s, 6H), 5.61 (s, 1H), 7.53 (dd, J=9.8, 1.6 Hz, 1H), 7.65 (dd, J=7.8, 1.6 Hz, 1H), 7.73 (t, J=7.8 Hz, 1H), 9.95 (d, J=2.0 Hz, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Bromo-1-(dimethoxymethyl)-2-fluorobenzene, its application will become more common.

Reference:
Patent; Akama, Tsutomu; Holcomb, Ryan; Tolman, Richard L.; US2002/120144; (2002); A1;,
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Reference of 17087-50-2, 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 17087-50-2 as follows.

In addition to the foregoing, numerous other chromatographic separations using a column bonded with a CSP including a derivatized cyclofructan residue were carried out. Tables 5-9 list some additional examples of chromatographic separations using a column bonded with a CSP of the present invention. AU examples of chromatographic separations using columns bonded with CSPs of the present invention were carried out using the following experimental conditions and procedures.|0132| The high performance liquid chromatography (HPLC) column packing system was composed of an air driven fluid pump (HASKEL, DSTV- 122), an air compressor, a pressure regulator, a low pressure gauge, two high-pressure gauges (10,000 and 6,000 psi), a slurry chamber, check valves, and tubings. The CSPs were slurry packed into a 25 cm x 0.46 cm (inner diameter, I. D.) stainless steel column.|0133| The HPLC system was an Agilent 1 100 system (Agilent Technologies, Palo Alto,CA), which consisted of a diode array detector, an autosampler, a binary pump, a temperature- controlled column chamber, and Chemstation software. All chiral analytes were dissolved in ethanol, methanol, or other appropriate mobile phases, as indicated. For the LC analysis, the injection volume and flow rate were 5 muL and 1 mL/min, respectively. Separations were carried out at room temperature (~20 0C) if not specified otherwise. The wavelengths of UV detection were 195, 200, 210, and 254 nm. The mobile phase was degassed by ultrasonication under vacuum for 5 min. Each sample was analyzed in duplicate. Three operation modes (the normal phase mode, polar organic mode, and reversed phase mode) were tested, unless indicated otherwise. In the normal phase mode, heptane with ethanol or isopropanol was used as the mobile phase. In some cases, trifluoroacetic acid (TFA) was used as an additive, as indicated. The mobile phase of the polar organic mode was composed of acetonitrile/methanol and small amounts of acetic acid and triethylamine. Water/acetonitrile or acetonitrile/acetate buffer (20 mM, pH = 4.1 ) was used as the mobile phase in the reversed-phase mode.|0134| Two different supercritical fluid chromatographic instruments were used. One was a Berger SFC unit with an FCM 1200 flow control module, a TCM 2100 thermal column module, a dual pump control module, and a column selection valve. The flow rate was 4 mL/min. The cosolvent was composed of methanol/ethanol/isopropanol = 1 : 1 : 1 and 0.2% diethylamine (DEA). The gradient mobile phase composition was 5% cosolvent hold during 0- 0.6 min, 5-60% during 0.6-4.3 min, 60% hold during 4.3-6.3 min, 60%-5% during 6.3-6.9 min, and 5% hold during 6.9-8.0 min. The other SFC system was a Jasco (MD, USA) system comprised of an autosampler unit (AS-2059-SF Plus), a dual pump module (PU-2086 Plus), a column thermostat module (CO-2060 Plus), a UV/Vis detector (UV-2075 Plus), and a back pressure regulator module (SCH-Vch-BP). Unless otherwise specified, the mobile phase was composed of CCVmethanol (0.1 % TFA or 0.1% diethylamine). The flow rate was 3 mL/min.|0135| For the calculations of chromatographic data, the “dead time” to was determined by the peak of the refractive index change due to the sample solvent or determined by injecting l ,3,5-tri-/e/-/-butylbenzene in the normal phase mode.

According to the analysis of related databases, 17087-50-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BOARD OF REGENTS, THE UNIVERSITY OF TEXAS SYSTEM; ARMSTRONG, Daniel, W.; PING, Sun; BREITBACH, Zachary, S.; WANG, Chunlei; WO2010/148191; (2010); A2;,
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