Tag: M.W=100-200

Application of 7664-66-6, A common heterocyclic compound, 7664-66-6, name is 4-Isopropoxyaniline, molecular formula is C9H13NO, 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.

To a mixture of 1-(4-chlorobenzyl)-3-(ethoxycarbonylmethyl)-6-iodoquinazoline-2,4-dion (200 mg, 0.4 mmol), palladium acetate (13.5 mg, 0.06 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (52.2 mg, 0.09 mmol), cesium carbonate (261 mg, 0.8 mmol) and dioxane (4 mL) was added 4-isopropoxyaniline (0.071 mL, 0.48 mmol) under nitrogen atmosphere, and the resulting mixture was heated at reflux for 2 hours. The reaction mixture was poured into a mixture of water (100 mL) and 5% aqueous citric acid (10 mL), and the resulting mixture was extracted with ethyl acetate (100 mL). The extract was washed by water (100 mL), dried over anhydrous sodium sulphate, and concentrated in vacuo. The resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane), and the residue was precipitated by hexane to give 1-(4-chlorobenzyl)-3-(ethoxycarbonylmethyl)-6-(4-isopropoxyphenylamino)-quinazolin e-2,4-dion (7.7 mg, Yield: 3.7%) as yellow solid. 1H-NMR (delta ppm TMS/CDCl3): 1.28 (3H, t, J=7.2 Hz), 1.33 (6H, d, J=6.0 Hz), 4.24 (2H, q, J=7.2 Hz), 4.74 (1H, m), 4.88 (2H, s), 5.29 (2H, s), 5.61 (1H, s), 6.84 (2H, d, J=8.7 Hz), 6.91 (1H, d, J=9.0 Hz), 7.01 (2H, d, J=8.7 Hz), 7.11 (1H, dd, J=3.0, 9.0 Hz), 7.19 (2H, d, J=8.7 Hz), 7.30 (2H, d, J=8.7 Hz), 7.68 (1H, d, J=2.7 Hz).

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; Shionogi & Co., Ltd.; KAI, Hiroyuki; ENDOH, Takeshi; JIKIHARA, Sae; ASAHI, Kentaro; HORIGUCHI, Tohru; EP2604260; (2013); A1;,
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Synthetic Route of 2339-58-4, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 2339-58-4 name is 3-Fluoro-5-methoxyaniline, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

2-Fluoronicotinic acid methyl ester (0.4 g, 2.58 mmol) and 3-fluoro-5-methoxyaniline(0.354 ml, 3.09 mmol) were heated by microwave irradiation at 120 C for 50 mm. 0.1 ml(0.873 mmol) of 3-fluoro-5-methoxyaniline was added and the mixture was irradiated for 30mm at 120 C. Some DCM was added and the mixture was washed twice with H20. Organicphase was dried over Na2SO4, filtered and evaporated. Crude product was purified bytrituration with diethyl ether. 0.293 g of the title compound was obtained.?H NMR (400 MHz, DMSO-d6) 6 ppm 3.78 (s, 3 H) 3.91 (s, 3 H) 6.48 (dt, 1 H) 6.96 (dd, 1H) 7.03 – 7.11 (m, 1 H) 7.42 (dt, 1 H) 8.29 (dd, 1 H) 8.48 (dd, 1 H) 10.20 (s, 1 H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Fluoro-5-methoxyaniline, and friends who are interested can also refer to it.

Reference:
Patent; ORION CORPORATION; ARVELA, Riina; HOLM, Patrik; VESALAINEN, Anniina; WO2015/144976; (2015); A1;,
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24599-58-4, name is 2,5-Dimethoxytoluene, belongs to ethers-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. SDS of cas: 24599-58-4

2-Methyl-1,4-bis(methyloxy)benzene (6.12 g, 40 mmol) was dissolved in acetic acid (20 mL) and heated at 40 C. A solution of nitric acid (4.32 g) in acetic acid (10 mL) was added to above solution drop wise over 5 minutes. The reaction mixture was stirred at 40 C. for 30 min (yellow precipitates formed), then room temperature for 30 min and then diluted with water (300 mL). The precipitate was collected by filtration, washed with water, and dried in the air for 16 h to afford the title compound (7.56 g, 96%) as a yellow solid. MS (ES) m/e 198 [M+H]+.

The synthetic route of 24599-58-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Goodman, Krista B.; Neeb, Michael J.; Sehon, Clark A.; Viet, Andrew Q.; Wang, Gren Z.; US2008/21023; (2008); A1;,
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Related Products of 50868-73-0,Some common heterocyclic compound, 50868-73-0, name is 2-Methoxy-6-methylaniline, molecular formula is C8H11NO, 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.

[1893] A solution of 2-methoxy-6-methylaniline (4 equivalents) in dichloromethane (0.2 M) was treated with pyridine (8 equivalents) followed by bromoacetyl chloride (1 equivalent). After 3 hours at room temperature, the mixture was treated with sodium carbonate (12 equivalents) and the product from Example 119A (3 equivalents) in dioxane:water (2:1). The heterogeneous mixture was heated to 40 C. overnight. The reaction mixture was cooled to room temperature, concentrated under reduced pressure and the residue triturated with 5% methanol:dichloromethane. The solid inorganic material was filtered and the filtrated concentrated and purified by HPLC. Isolated as an acetate salt. (45 mg, 44%). 1H NMR (300 MHz, DMSO-d6) delta1.71 (m, 2H), 1.99 (m, 4H), 2.15 (m, 3H), 2.30 (m, 2H), 3.10 (m, 1H), 3.15 (s, 2H), 3.75 (s, 3H), 6.86 (dd, J=9, 1.5 Hz, 2H), 7.16 (t, J=9 Hz, 1H), 7.30 (m, 2H), 7.45 (m, 1H), 8.26 (dd, J=4.5, 1.5 Hz, 1H), 8.95 (s, 1H); MS (DCI/NH3) m/e 340 (M+H-16)+; 356 (M+H)+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Methoxy-6-methylaniline, its application will become more common.

Reference:
Patent; Bhatia, Pramila A.; Daanen, Jerome F.; Hakeem, Ahmed A.; Kolasa, Teodozyj; Matulenko, Mark A.; Mortell, Kathleen H.; Patel, Meena V.; Stewart, Andrew O.; Wang, Xueqing; Xia, Zhiren; Zhang, Henry Q.; US2003/229094; (2003); 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. 37466-89-0, name is 3-Methoxybenzene-1,2-diamine, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C7H10N2O

To a 40% aqueous sodium hydrogen sulfite solution (10 mL) was added 4-fluorobenzaldehyde (1.45 mL), and the mixture was stirred at room temperature for 1 hour. To the reaction solution was added a solution of 3-methoxybenzene-1,2-diamine (1.7 g) in EtOH (45 mL), and the mixture was stirred for 2 hours under heating to reflux. Water was added to the reaction solution, and the mixture was stirred at room temperature for 10 minutes. Then, the precipitate was filtered and the resulted solid was washed with Et2O to give 2-(4-fluorophenyl)-4-methoxy-1H-benzimidazole (2.38 g).

According to the analysis of related databases, 37466-89-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; OTSUKA PHARMACEUTICAL CO., LTD.; KAWANO, Yoshikazu; SHIMIZU, Hiroshi; ISHIKAWA, Shunpei; TAKEMURA, Isso; HARIGUCHI, Norimitsu; MATSUBA, Miki; MATSUMOTO, Makoto; (92 pag.)US2019/40039; (2019); A1;,
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Electric Literature of 67191-35-9,Some common heterocyclic compound, 67191-35-9, name is 1-Isopropoxy-2-vinylbenzene, molecular formula is C11H14O, 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 1 Metathesis by Ethenolysis of Methyl Oleate Catalyzed by a Type 3 Complex (FIG. 1) in an Ionic Liquid; 1 ml of 3-butyl-1,2-dimethylimidazolium bis-triflylamide with formula [BMMI]+[N(CF3SO2)2]- pre-dried overnight at 80 C., 148 mg of methyl oleate (source: Fluka, with a purity higher than 98%) and 15 mg of the complex with formula Cl2Ru(CH-o-O-iPrC6H4)PCy3 (synthesized by reacting the 1st generation Grubbs complex with formula Cl2Ru(CHC6H5)(PCy3)2 with 1-isopropoxy-2-vinylbenzene in the presence of CuCl), this corresponding to 5% molar of catalyst with respect to methyl oleate, were introduced, in an inert atmosphere of argon, into an autoclave reactor provided with an agitation system and a pressure sensor. The autoclave was then placed under vacuum and pressurized to obtain a pressure of 10 bars (1 MPa) of ethylene (origin: Alphagas, quality N25). The temperature was kept constant at 20 C. The medium was stirred at ambient temperature for 2 hours, then the excess ethylene was slowly purged by returning to atmosphere pressure at a temperature not exceeding 20 C. and the autoclave was again placed under an atmosphere of argon. The products were separated from the ionic liquid by adding 2 to 3 ml of heptane distilled over CaH2 and degassed. An aliquot (100 mul) of the extracted solution was passed through a short silica column (2 cm) eluted with diethyl ether. It was analyzed by gas phase chromatography (ZB-1 column, 100% dimethylpolysiloxane, 30 metres, helium vector gas 2 ml/min, temperature programming: 60 C. then 5 C./min to 220 C.) coupled to a mass spectrometer. The methyl oleate conversion was 95%. It was calculated using decane as an internal reference. The reaction products were composed of 1-decene (fraction A) and methyl decenoate (fraction B). The presence of 1-decene isomers was not detected. Homo-metathesis products were present in trace amounts and could not be quantified.

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

Reference:
Patent; Olivier-Bourbigou, Helene; Vallee, Christophe; Hillion, Gerard; US2007/179307; (2007); A1;,
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Some common heterocyclic compound, 41864-45-3, name is 4,5-Dimethoxy-2-methylaniline, molecular formula is C9H13NO2, 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. category: ethers-buliding-blocks

The synthetic procedure used in this preparation is outlined in Scheme M. 4-(4-Fluoro-phenyl)-1-(2-hydroxy-ethyl)-2-oxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxylic acid (180 mg), 4,5-dimethoxy-2-methyl-phenylamine (86 mg) and benzotriazol-1-yl-oxytripyrrolidinophosphonium hexafluorophosphate (PyBOP, 265 mg) were dissolved in 10 mL DMF, followed by 0.2 mL di-iso-propylethyl amine. The mixture was heated at 50 for 72 hours, then cooled, diluted with aqueous pH 2 buffer and ethyl acetate, and the layers separated. The organic layer was washed with saturated sodium bicarbonate and brine, then dried over Na2SO4, filtered and the solvent removed in vacuo. The residue was chromatographed in 3% MeOH/DCM. The fraction containing the product was washed with 10% aqueous HCl, and concentrated in vacuo to yield 52 mg of 4-(4-fluoro-phenyl)-1-(2-hydroxy-ethyl)-2-oxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxylic acid (4,5-dimethoxy-2-methyl-phenyl)-amide, MS (M+H)=430.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 41864-45-3, its application will become more common.

Reference:
Patent; Brotherton-Pleiss, Christine E.; Caroon, Joan Marie; Lopez-Tapia, Francisco Javier; Walker, Keith Adrian Murray; US2011/28502; (2011); A1;,
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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. 101-84-8, name is Diphenyl oxide, A new synthetic method of this compound is introduced below., name: Diphenyl oxide

EXAMPLE 1; Catalyzed Bromination [0047] A reactor was configured from a 1 -liter Morton flask with a mechanical stirrer, thermometer, 60 mL addition funnel, and fractionation column (10″ x 1″ (ca. 25.4 cm x 2.54 cm) with 5 mm x 5 mm Raschig rings) topped by a O0C reflux condenser. The outlet of the condenser was connected to a H2O trap. A small N2 purge was added to the line from the condenser to the H2O trap. The reactor was charged with 3.5 g OfAlCl3 and 1577g of bromine (containing 11 ppm H2O). The addition funnel was charged with 47.04 g of diphenyl oxide.The reactor was heated to 550C and the diphenyl oxide was added drop-wise supersurface. The time for the initiation of the diphenyl oxide addition was noted. The reactor was heated by a mantle. Twenty-seven minutes into the diphenyl oxide feed, half of the diphenyl oxide had been added and the reaction mass temperature was 560C. One and a quarter hours after the diphenyl oxide feed was initiated, all of the diphenyl oxide had been added and the reaction mass temperature was 570C. The compressor on the refrigeration system was shut off to allow slow warm-up of the condenser. The reaction mass was refluxed through the fractionation column. At one hour and 18 minutes after feed initiation, the reaction mass temperature was 590C. Two hours and three minutes after diphenyl oxide feed initiation the condenser water was at 2O0C and the reaction temperature was at 610C. At two hours and seven minutes after feed initiation, the condenser water was at 3O0C. Thirty two minutes later the addition funnel was replaced with a N2 inlet. A slow N2 purge of the reactor was started. The reaction mass temperature was 610C. The N2 purge was at 100 mL/min into the vapor space of the reactor. Four hours and fifty minutes after the initiation of the diphenyl oxide feed, the reaction mass temperature was 610C and the condenser water was at 370C. At six hours and 15 minutes after the initiation of the diphenyl oxide feed the reaction mass was cooled to 550C, 350 mL deionized H2O was added, the fractionation column was removed, and the reactor was set for distillation. Br2 was distilled off. When most of the Br2 was gone 150 mL more deionized water was added. The remaining Br2 was distilled off to 1000C. The remaining mixture was cooled to 6O0C, and 30 mL of 25% NaOH was added to pH 13-14. The resultant mix was filtered and washed well with deionized water. A sample was subjected to GC analysis. The GC trace showed the product to contain 0.21% of the first nonabromodiphenyl oxide peak (deemed to be meta- and para-hydrogen isomers), 0.24% of the second nonabromodiphenyl oxide peak (deemed to be the ortho-hydrogen isomer) and 99.54% of decabromodiphenyl oxide. The sample was oven dried.

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; ALBEMARLE CORPORATION; WO2008/27776; (2008); A2;,
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Application of 1535-75-7, The chemical industry reduces the impact on the environment during synthesis 1535-75-7, name is 2-(Trifluoromethoxy)aniline, I believe this compound will play a more active role in future production and life.

General procedure: Acetamides (1a-1x, 1ab, 1ac and 1ba-1bc). To a solution of 2-phenylacetic acid (7.0mmol), 2-(trifluoromethoxy)aniline (7.7mmol) in anhydrous CH2Cl2 (25mL) were added EDCI (1.745g, 9.1mmol) and DMAP (256.6mg, 2.1mmol). The reaction mixture was stirred at room temperature overnight, diluted with HCl (1M) aqueous solution, and extracted with CH2Cl2 (3×25mL). The combined organic phase was washed with saturated NaHCO3 aqueous solution and brine, dried over anhydrous Na2SO4, and concentrated under vacuum. Purification by flash chromatography (Silica gel, petroleum ether: ethyl acetate=50: 1 as eluent) gave the corresponding 2-phenyl-N-[2-(trifluoromethoxy)phenyl]acetamide compound.

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-(Trifluoromethoxy)aniline, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Zhao, Xiao-Jing; Zhao, Jie; Sun, Xin; Liu, Ji-Kai; Wu, Bin; Tetrahedron; vol. 73; 25; (2017); p. 3463 – 3477;,
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39538-68-6, name is 2-Methoxy-4-methylaniline, belongs to ethers-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. HPLC of Formula: C8H11NO

General procedure: To a magnetically stirred solution of the selected aromatic amine (0.01 mol) in anhydrous dioxane (30 ml), succinic anhydride (0.01 mol) was added and the resulting suspension was refluxed for 24 h. Subsequently, the reaction mixture was cooled to room temperature. Subsequently, petroleum ether (200 mL) was added to the reaction mixture to yield the succinic monoamide derivatives (112-119, see Scheme 2) as white to grey solids. Using the same general procedure, the following compounds were synthesized.

The synthetic route of 39538-68-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Habash, Maha; Taha, Mutasem O.; Bioorganic and Medicinal Chemistry; vol. 19; 16; (2011); p. 4746 – 4771;,
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