Tag: M.W=100-200

Electric Literature of 7664-66-6, 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. 7664-66-6, name is 4-Isopropoxyaniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

EXAMPLE 19 Preparation of 4-(4-chlorobenzyl)-2-dimethyl-amino-5-(4-isopropoxyphenylamino)pyrimidine (I-181) To a mixture of 5-bromo-2-(methylthio)pyrimidine (600 mg, 2.92 mmol), tris(dibenzylideneacetone)(0)-chloroform (303 mg, 0.293 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (169 mg, 0.293 mmol), cesium carbonate (1.91 g, 5.85 mmol) and dioxane (13 mL) was added 4-isopropoxyaniline (531 mg, 3.51 mmol) under nitrogen atmosphere, and the resulting mixture was stirred at 90 C. for 18 hours. The reaction mixture was poured into water (200 mL), and the mixture was extracted with ethyl acetate (100 mL*3). The extract was washed by brine (100 mL), dried over anhydrous magnesium sulfate, and concentrated in vacuo. The resulting residue was purified by silica gel column chromatography (methanol/dichloromethane and ethyl acetate/hexane). The resulting residue was precipitated by dichloromethane and hexane to give 5-(4-isopropoxyphenylamino)-2-(methylthio)pyrimidine (5.24 g, Yield: 65%) as yellow powder. 1H-NMR (DMSO-d6): 1.24 (6H, d, Hz), 2.46 (3H, s), 4.49 (1H, sept, J=6.0 Hz), 6.85 (2H, d, J=9.0 Hz), 7.02 (2H, d, J=9.0 Hz), 8.06 (1H, s), 8.34 (2H, s).

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

Reference:
Patent; SHIONOGI & CO., LTD.; Kai, Hiroyuki; Endoh, Takeshi; Jikihara, Sae; Horiguchi, Tohru; US9212130; (2015); B2;,
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Related Products of 1484-26-0, 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. 1484-26-0, name is 3-Benzyloxyaniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Methyl 4-bromobenzoate (49 mg, 0.23 mmol) and 3 -benzyloxy aniline (50 mg, 0.25 mmol) are dissolved in dry dioxane (1 mL). Pd2(dba)3 (21 mg, 0.023 mmol), (^Bu)3PHBF4 (13 mg, 0.046 mmol) and cesium carbonate (149 mg, 0.46 mmol) are added and the mixture is degassed with bubbling Ar for 15 min. The vessel is sealed and heated at 120°C for 72 h. LiOH (IN, 0.5 mL) is added and heated at 90°C for 1 h, then is cooled, quenched with IN HCl (5 mL) and extracted into EtOAc (10 mL). The organic layer is dried (MgSO4), filtered, concentrated and purified on reverse phase HPLC (H2O/MeCN gradient) to afford the title compound 4-(3-(benzyloxy)phenylamino)benzoic acid (Hl). 1H-NMR (400 MHz, CDC13) delta = 7.96 (d, J = 8.8 Hz, 2H), 7.40 (m, 5H), 7.25 (t, J = 8.0 Hz, IH), 6.97 (d, J = 8.8 Hz, 2H), 6.81 (t, J = 2.4 Hz, IH), 6.76 (ddd, J = 1.2, 2.4, 8.0 Hz, IH), 6.71 (dd, J = 1.8 Hz, 8.0 Hz, IH), 5.07 (s, 2H). MS calcd. for C20H18NO3 (M+H+) 320.1, found 320.2.

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

Reference:
Patent; IRM LLC; WO2008/121570; (2008); A1;,
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Electric Literature 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.

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

Reference:
Article; Pikus, Grzegorz; Pa?niczek, Ewa; Jurczak, Janusz; Arkivoc; vol. 2017; 2; (2017); p. 534 – 545;,
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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. 39021-83-5, name is 1,4-Dimethoxy-2,3-dimethylbenzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. COA of Formula: C10H14O2

5.2. Formylation of Dimethoxybenzenes by Means of the Duff Reaction1 equivalent of dimethoxybenzene was dissolved in 20 ml of TFA and 1.05 equivalents or urotropin were added to the resulting solution. The reaction mixture was brought to reflux for 2 hours under anhydrous conditions. The TFA was evaporated off under reduced pressure, the residue was dissolved in 100 ml of ether and the organic solution was washed with water (3 times 50 ml) and then dried over MgSO4. The solvent was evaporated off and the residue was subjected to column chromatography, elution being carried out with an 80:20 mixture of light mineral spirit (60-80 C.):diethyl ether.5.2.1. 2,5-Dimethoxy-3,4-dimethylbenzaldehydeThe process was carried out as described in point 5.2 above, using 2.270 g (0.01366 mol) of 1,4-dimethoxy-2,3-dimethylbenzene. The title product was isolated in the form of a white solid (1.18 g, 44%).

The synthetic route of 39021-83-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; bioMerieux; US7626018; (2009); B2;,
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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. 22236-08-4, name is 3-(Difluoromethoxy)aniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. name: 3-(Difluoromethoxy)aniline

General procedure: Step-1:4-amino-2,6-dichloro pyrimidine: 2,4,6-trichloro pyrimidine (1.0 mmol) in ethanol (5 mL) was treated with an aromatic amine (1.1 mmol) in the presence of Na2CO3 (1.1 mmol) at rt. The mixture was stirred at reflux for 2-4 h until completion of the reaction. The reaction progress was followed by TLC. After completion of the reaction, an equal volume of water was added with cooling. The resulting white precipitate was filtered, washed with water, and dried in vacuum over night to yield 4-substituted 2,6-dichloro pyrimidine. In case of no precipitation, ethanol was removed by rota vap., and the residue was dissolved in CH2Cl2. The organic layer was washed twice with water, brine, dried (Na2SO4), filtered, and concentrated. The resulting crude was purified by column chromatography to afford the 4-amino-2,6-dichloro pyrimidines in 85-95% yield. Step-2: 2,4-diamino-6-chloropyrimidine: 4-amino-2,6-dichloro pyrimidine (1.0 mmol) prepared from the above procedure was treated with another aliphatic amine or aromatic amine (2.0 mmol) in the presence of DIEPA (5.0 mmol) in n-BuOH (5 mL) at rt. For an aliphatic amine the reaction mixture was stirred at rt for overnight. For an aromatic amine the reaction mixture was refluxed for 24-72 h or placed in microwave (150 C, 2-7 h) until completion of the reaction. The reaction progress was followed by TLC. After completion of the reaction, solvents were removed by rota vap., and the residue was dissolved in CH2Cl2. The organic layer was washed twice with water, brine, dried (Na2SO4), filtered, and concentrated. The resulting crude was purified by column chromatography (EtOAc/hexane) to afford the 2,4-diammino-6-chloropyrimidines in 85-90% yield. Step-3: 2,4,6-triaminopyrimidine: 2,4-diamino-6-chloropyrimidine (1.0 mmol) prepared from the above procedure was treated with another suitable aliphatic amine or aromatic amine (3.0 mmol). For an aliphatic amine, 2,4-diamino-6-chloropyrimidine (1.0 mmol) was treated with aliphatic amine (3.0 mmol) and DIPEA (5.0 mmol) in n-BuOH (5 mL) and placed in microwave (150 C) for 3-7 h. After the completion of the reaction (monitored by TLC), solvents were removed and the residue was dissolved in EtOAc. The organic layer was washed twice with water, brine, dried (Na2SO4), filtered, and concentrated. The resulting crude was purified by column chromatography to afford the 2,4,6-triaminopyrimidines 90-95% yield. For aromatic amine; 2,4-diamino-6-chloropyrimidine (1.0 equiv) was dissolved in dioxane under argon and to that were added Pd2(dba)3 (10 mol %), Xantphos (10 mol %), aromatic amine (1.2 mmol), t-BuOK (1.2 mmol). The resulting solution was degassed with argon for 5 min and heated to 85 C for overnight. The reaction mixture was filtered through a pad of celite, washed with CH2Cl2 (2 × 10 mL) and the resulting filtrate was concentrated. The resulting crude was purified by flash column chromatography to yield 2,4,6-triaminopyrimidines in 90-95% yield.

The synthetic route of 22236-08-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Sagi, Vasudeva Naidu; Liu, Tianyu; Lu, Xiaoying; Bartfai, Tamas; Roberts, Edward; Bioorganic and Medicinal Chemistry Letters; vol. 21; 23; (2011); p. 7210 – 7215;,
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Application of 24599-58-4,Some common heterocyclic compound, 24599-58-4, name is 2,5-Dimethoxytoluene, molecular formula is C9H12O2, 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.

2-Bromo-5-methylcyclohexa-2,5-diene-1,4-dione (23). To a solution of toluquinol (1) (2.5 g, 20.14mmol,1.0 equiv.) in acetone (15 mL) was added K2CO3 (14 g, 100.70 mmol, 5.0 equiv.) and Me2SO4 (5.7 mL,60.41 mmol, 3.0 equiv.) and the reaction mixture was stirred for 3 h. After this time, the reactionmixture was diluted with water and the aqueous phase was extracted with Et2O. The organic phasewas washed with brine, dried over MgSO4, filtered, and the solvent removed under reduced pressureto obtain the corresponding dimethoxy derivative (~20 mmol), which was used in the next stepswithout purification. To a solution of the dimethoxy derivative obtained above (~20 mmol) and NaOAc(3.3 g, 40.28 mmol, 2.0 equiv.) in AcOH (20 mL) was added bromine (1.2 mL, 2.15 mmol, 1.1 equiv.)over 25 min and, after the addition, the reaction mixture was stirred for 1 h. Then, the reaction mixturewas quenched by a slow addition of a saturated aqueous NaHCO3 solution at 0 C. The aqueousphase was then extracted with EtOAc and the organic phase washed with brine, dried over MgSO4,ltered, and the solvent removed under reduced pressure to obtain the corresponding bromo derivative(~20 mmol), which was used in the next step without purication. The bromo derivative obtainedabove (~20 mmol) was dissolved in CH3CN (35 mL). Then, CAN (28 g, 50.34mmol, 2.5 equiv.) and H2O(20 mL) were added and the reaction mixture was stirred for 1 h at 25 C. After this time, the reactionmixture was diluted with water and the aqueous phase was extracted with Et2O twice. The combinedorganic phases were washed with brine, dried over MgSO4, filtered, and the solvent removed underreduced pressure. The residue was purified by flash column chromatography (silica gel, 1% EtOAc inhexanes) to obtain compound 23 (1.5 g, 37% over 3 steps) as an orange solid [13]: Rf = 0.45 (silica gel,20% EtOAc in hexanes); 1H NMR (400 MHz, CDCl3) delta 7.29 (s, 1 H), 7.26 (s, 2 H), 2.08 (d, J = 1.6 Hz,3 H); 13C NMR (100 MHz, CDCl3) delta 185.1, 179.5, 146.5, 138.1, 137.5, 132.6, 15.7.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2,5-Dimethoxytoluene, its application will become more common.

Reference:
Article; Cheng-Sanchez, Ivan; Torres-Vargas, Jose A.; Martinez-Poveda, Beatriz; Guerrero-Vasquez, Guillermo A.; Medina, Miguel Angel; Sarabia, Francisco; Quesada, Ana R.; Marine Drugs; vol. 17; 9; (2019);,
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Related Products of 2398-37-0, The chemical industry reduces the impact on the environment during synthesis 2398-37-0, name is 1-Bromo-3-methoxybenzene, I believe this compound will play a more active role in future production and life.

General procedure: Under an argon atmosphere a solution of the appropriate bromobenzene (1 equivalent) dissolved in anhydrous THF (approximately 30 mL per mmol bromobenzene) is cooled to -78 C using a nitrogen-ethanol-bath. A solution of 2.3 equivalents of n-butyllithium in hexane is added drop wise keeping the temperature below -78 C. After completion the mixture is stirred for one hour at this temperature. Then 1.5 equivalents of trimethyl borate are added slowly and the reaction mixture is stirred at -78 C for another hour. The cooling bath is then removed, the reaction mixture is stirred until room temperature is reached and quenched with a saturated solution of ammonium chloride. THF and the major part of the water is removed under reduced pressure, the residue is laced with 3M hydrochloric acid until a pH of 3 is reached. After extraction with DCM (3 x) the organic phases are collected, washed with brine, dried over sodium sulphate and filtered. DCM is removed under reduced pressure, the resulting solid is washed first with ice cold water and then with PE and dried.

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-Bromo-3-methoxybenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Obermoser, Victoria; Mauersberger, Robert; Schuster, Daniela; Czifersky, Monika; Lipova, Marina; Siegl, Monika; Kintscher, Ulrich; Gust, Ronald; European Journal of Medicinal Chemistry; vol. 126; (2017); p. 590 – 603;,
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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. 41365-75-7, name is 1-Amino-3,3-diethoxypropane, This compound has unique chemical properties. The synthetic route is as follows., Safety of 1-Amino-3,3-diethoxypropane

[0080] To a stirred solution of intermediate (9) (287 mmol) in CHCl3 (2000 ml) was added 3,3-diethoxy-1-propanamine (474 mmol) at 0 C. in portions. After the addition, the reaction mixture was stirred at 0 C. for 1 hour and then at 15 C. for 2 hours. Thin Layer Chromatography (petroleum ether/ethyl acetate=5/1) showed that the reaction was completed. The reaction mixture was washed by saturated Na2SO3 aqueous (four times with 600 ml) and then saturated NaHCO3 aqueous was added until pH=7. The aqueous layer was extracted by CH2Cl2 (500 ml). The combined organic phases were washed with brine (800 ml), dried over Na2SO4 and concentrated to give the crude product. The crude product was washed by tert-butyl methylether (three times 500 ml) to give 87 g of intermediate (10) (mp. 100.8-103.8 C.).

According to the analysis of related databases, 41365-75-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ELANCO ANIMAL HEALTH IRELAND LIMITED; Guillemont, Jerome Emile Georges; Raboisson, Pierre Jean-Marie Bernard; Lounis, Nacer; US2013/109694; (2013); A1;,
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Synthetic Route of 6346-09-4, A common heterocyclic compound, 6346-09-4, name is 4,4-Diethoxybutan-1-amine, molecular formula is C8H19NO2, 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.

Step1 To the stirred solution of 1,3-dioxo-1,3-dihydro-isoindole-2-carboxylic acid ethyl ester (10 g, 62 mmol, 1 eq) in dry THF (200 mL) were added 4,4-diethoxy-butylamine (13.6 g, 62 mmol, 1 eq) and TEA (8.6 mL, 62 mmol, 1 eq) under ice cooled condition and stirred at RT for 16 h. After completion of the reaction, it was concentrated under reduced pressure to obtain crude product which was purified by silica gel (100-200 mesh) column chromatography (5% EA/Hexane) to afford 2-(4,4-diethoxy-butyl)-isoindole-1,3-dione (17 g, 94% yield) as light yellowish liquid.

The synthetic route of 6346-09-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GRUeNENTHAL GMBH; JAKOB, FLORIAN; NORDHOFF, SONJA; RIDER, DAVID; WAGENER, MARKUS; BAHRENBERG, GREGOR; DUNKERN, TORSTEN; (70 pag.)US2018/78541; (2018); A1;,
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Synthetic Route of 22483-09-6, 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 22483-09-6 as follows.

A solution of aminoacetaldehyde dimethyl acetal (25 mL, 229 mmol) in toluene (120 mL) is treated at 0 C with a 4.85 M sodium hydroxide solution (70.8 mL, 343.5 mmol). The mixture is stirred at 0 C for 10 minutes and benzyl chloroformate (33.8 mL, 229 mmol) is added keeping the internal temperature below 20 C during the addition. The mixture is warmed to room temperature over 4 hours. The organic layer is separated, washed with brine, dried over sodium sulfate, and concentrated to dryness to give the title compound (54 g, 98 %). ES/MS (m/e): 240 (M+H).

According to the analysis of related databases, 22483-09-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ELI LILLY AND COMPANY; GREEN, Steven James; MERGOTT, Dustin James; WATSON, Brian Morgan; WINNEROSKI JR., Leonard Larry; WO2014/143579; (2014); A1;,
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