Category: ethers-buliding-blocks

Synthetic Route of 57478-19-0, A common heterocyclic compound, 57478-19-0, name is 4-(4-(Trifluoromethyl)phenoxy)aniline, molecular formula is C13H10F3NO, 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.

5-Nitro-N-para-[4-(trifluoromethyl)phenoxy]phenyl-isothiazole-3-carboxamide (58) To 0.8g (4.6mmol) of 5-nitro-isothiazole-3-carboxylic acid (prepared according to the method described in R. J. A. Walsh, K. R. H. Woolbridge, J. Chem. Soc. Perkin Trans 1, 1972,1247-1249) is added 14 ml of thionyl chloride under nitrogen, and the resulting mixture is stirred at reflux for 3 hours. After cooling, the solvent is evaporated to give a solid. This solid is suspended in a mixture of 20ml of diethyl ether and 20ml of dichloromethane. The suspension is added to a mixture of 2.74g (10.8mmol) of 4-[4-(trifluoromethyl) phenoxy] aniline and 2.5ml (18.3mmol) of triethylamine in 40ml of diethyl ether. The resulting mixture is stirred at room temperature for 4 hours and left to stand at room temperature overnight. The resulting suspension is filtered, the filtrate is washed with a saturated sodium chloride solution, then dried and concentrated to give a brown solid which is chromatographed (ethyl acetate/heptane) to give 1.2g (63%yield) of an orange solid (M+1 =410).

The synthetic route of 57478-19-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bayer CropScience S.A.; EP1275301; (2003); A1;,
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Related Products of 36865-41-5, 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. 36865-41-5 name is 1-Bromo-3-methoxypropane, 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.

A mixture of 5-bromo-2-chloro-phenol (22.0 g, 106 mmol), l-bromo-3-methoxy-propane (19.5 g, 127 mmol) and K2C03 (30 g, 212 mmol) in DMF (50 mL) was heated at 50 C for 3 hrs. Then the mixture was partitioned between ethyl acetate and water. The organic layer was separated, dried over anhydrous Na2S04 and concentrated under reduced pressure to give crude 4-bromo-l-chloro-2-(3-methoxypropoxy)benzene (30.0 g), which was used directly in the next step without further purification

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Bromo-3-methoxypropane, and friends who are interested can also refer to it.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; HAN, Xingchun; JIANG, Min; YANG, Song; (109 pag.)WO2016/128335; (2016); A1;,
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Electric Literature of 583-19-7, 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. 583-19-7, name is 1-Bromo-2-ethoxybenzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

(1) 4-(3-bromo-4-ethoxyphenyl)-4-oxobutanoic acid To a suspension of bromo-2-ethoxybenzene (12.0 g) and succinic anhydride (6.9 g) in dichloromethane (40 mL) was gradually added aluminum chloride (19.0 g) under ice-cooling, and the mixture was heated with stirring at 50C for 0.5 hr. The reaction mixture was cooled, and poured into concentrated hydrochloric acid (100 mL)-ice. The mixture was stirred for 1 hr, and extracted with ethyl acetate. The obtained organic layer was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give 4-(3-bromo-4-ethoxyphenyl)-4-oxobutanoic acid (6.5 g) as crude crystals. 1H-NMR (CDCl3)delta: 1.51(3H, t, J=7.2Hz), 2.74(2H, t, J=6.6Hz), 3.34(2H, t, J=6.6Hz), 4.19(2H, q, J=7.2 Hz), 6.92(1H, d, J=8.7Hz), 7.92(1H, dd, J=8.7Hz, 2.4Hz), 8.19(1H, d, J=2.4Hz)

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-2-ethoxybenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Takeda Pharmaceutical Company Limited; EP1845081; (2007); A1;,
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These common heterocyclic compound, 82830-49-7, name is 2-Fluoro-1,4-dimethoxybenzene, 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. Safety of 2-Fluoro-1,4-dimethoxybenzene

General procedure: Eaton?s reagent was prepared from phosphorus pentoxide (P2O5) and methanesulfonic acid (CH3SO3H) (weight ratio P2O5/CH3SO3H 1:10). The mixture was heated at 40 C under nitrogen atmosphere until complete homogeneity. Benzoic acid (1.15-1.5 equiv) and aromatic derivative (1.0 equiv) were then added to Eaton?s reagent. The mixture was heated at 50 C under inert atmosphere for 3-14 h. After cooling to room temperature, the reaction medium was diluted with dichloromethane and carefully poured into a separatory funnel containing sodium bicarbonate aqueous solution (50% NaHCO3) (neutralization to pH 7). The aqueous solution was extracted with dichloromethane, and the combined organic layers were dried (MgSO4). Solvent was removed under reduced pressure to produce a brownish oil. The crude product was purified by Flash chromatography on RediSep packed columns to provide pure fluorobenzophenones 7a-f.

The synthetic route of 2-Fluoro-1,4-dimethoxybenzene has been constantly updated, and we look forward to future research findings.

Reference:
Article; Ghinet, Alina; Tourteau, Aurelien; Rigo, Benoit; Stocker, Vivien; Leman, Marie; Farce, Amaury; Dubois, Joelle; Gautret, Philippe; Bioorganic and Medicinal Chemistry; vol. 21; 11; (2013); p. 2932 – 2940;,
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Some common heterocyclic compound, 10541-78-3, name is 2-Methoxy-N-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. Computed Properties of C8H11NO

Intermediate 36a (24 mg. 0.092 mmol), 2-methoxy- N-methylaniline (16 mg, 0.11 mmol), HAITI (38 mg, 0.10 mmol), and DIEA (64 sL, 0.37 mmol) were all combined in MeCN (1 mL) and stirred for 24 h at room temperature. The solution was then purified by preparative HPLC with a CIS silica gel stationary phase using a gradient of H20 0.05% TFA : CH3CN 0.05% TFA (70 :30 to 5 : 95) and detection by U V at 254 nm to give the title compound (18 mg, 52%) as a while solid. MS (ES, m/zy. 380 [M+if. 1H-NMR (400 MHz, CDCI3) delta 7.30-7.22 (m, 1H), 7.22-7.13 (m, 2H), 7.09 (d, J = 8.3 Hz, 1H), 6.88 (t, J- 7.5 Hz, I H), 6.68 (Patent; ARDELYX, INC.; LEWIS, Jason, G.; REICH, Nicholas; CHEN, Tao; JACOBS, Jeffrey W.; CHARMOT, Dominique; NAVRE, Marc; FINN, Patricia; CARRERAS, Christopher; SPENCER, Andrew; WO2013/96771; (2013); A1;,
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Application of 5414-19-7, 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. 5414-19-7 name is 1-Bromo-2-(2-bromoethoxy)ethane, 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.

Step 1: Ethyl 4-(4-bromophenyl)tetrahydro-2H-pyran-4-carboxylate 6.0 g (24.7 mmol) of ethyl 4-bromophenylacetate were dissolved in 120 ml of abs. DMF under argon, 1.48 g (37.0 mmol, 60% strength) of sodium hydride were added, while cooling in an ice bath, and the mixture was stirred for 30 min. 5.72 g (24.7 mmol) of bis(2-bromoethyl)ether were then added, while constantly cooling in an ice bath, and the mixture was stirred at approx. 0 C. for 1 h. After renewed addition of 1.48 g of 60% strength sodium hydride, the mixture was stirred again for 1 h, while cooling in an ice bath. Saturated aqueous ammonium chloride was then added and the mixture was extracted with ethyl acetate. The organic phase was washed with water and with saturated sodium chloride solution, dried over magnesium sulfate, filtered and concentrated on a rotary evaporator. The residue was purified by column chromatography over silica gel (mobile phase: cyclohexane/ethyl acetate 10:1). 2.62 g (33% of th.) of the title compound were obtained. 1H-NMR (400 MHz, CDCl3, delta/ppm): 7.47 (d, 2H), 7.25 (d, 2H), 4.14 (q, 2H), 3.93 (dt, 2H), 3.56 (td, 2H), 2.59 (dd, 2H), 1.93 (m, 2H), 1.19 (t, 3H). MS (DCI, NH3): m/z=329 [M+NH4]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Bromo-2-(2-bromoethoxy)ethane, and friends who are interested can also refer to it.

Reference:
Patent; BAYER SCHERING PHARMA AKTIENGESELLSCHAFT; Haerter, Michael; Beck, Hartmut; Ellinghaus, Peter; Berhoerster, Kerstin; Greschat, Susanne; Thierauch, Karl-Heinz; Suessmeier, Frank; US2013/196964; (2013); A1;,
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Synthetic Route of 41864-45-3,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.

Reference Example 76 N-(2-methyl-4,5-dimethoxyphenyl)cinnamamide To a solution of 4,5-dimethoxy-2-methylaniline (40.1 g), pyridine (48.5 ml), and acetone (350 ml), cinnamoyl chloride (44.0 g) was added dropwise at room temperature over 15 minutes. After allowing to react at room temperature for 2 hours, water (15 ml) was added and the mixture was stirred for 20 minutes. The solvent was distilled off under reduced pressure, and the residue was dissolved in chloroform, followed by washing with 1N HCl, 1N caustic soda and water in this order, and drying. Chloroform was evaporated. Precipitated crystals were collected by filtration with ether. 69.8 g of the title compound was obtained as yellow crystals (97.8%). 1 H-NMR(CDCl3)delta: 2.24(3H,s), 3.86(6H,s), 6.60(1H,d,J=15.1 Hz), 6.69(1H,s), 7.20(1H,bs), 7.37(3H,bs), 7.53(3H,bs), 7.75(1H,d,J=15.1 Hz).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4,5-Dimethoxy-2-methylaniline, its application will become more common.

Reference:
Patent; Kowa Co., Ltd.; US5576324; (1996); A;,
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Reference of 22483-09-6, 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. 22483-09-6, name is 2,2-Dimethoxyethanamine, This compound has unique chemical properties. The synthetic route is as follows.

A solution of 2,2-dimethoxyethan-1-amine (1600 g, 15.22 mol) in toluene (8 L), was added a solution of NaOH (858 g, 21.45 mol) in water (4.42 L). This was followed by the addition of CbzCl (2598 g, 15.23 mol) dropwise with stirring at <20 C. The resulting solution was stirred for 4 h at room temperature. The organic layer was separated and washed with 3x5 L of brine. The organic layer was dried over anhydrous sodium sulfate and concentrated under vacuum to afford benzyl N-(2,2-dimethoxyethyl)carbamate as a white solid. The chemical industry reduces the impact on the environment during synthesis 2,2-Dimethoxyethanamine. I believe this compound will play a more active role in future production and life. Reference:
Patent; FORMA THERAPEUTICS, INC.; ZABLOCKI, Mary-Margaret; GUERIN, David J.; NG, Pui Yee; WANG, Zhongguo; SHELEKHIN, Tatiana; CARAVELLA, Justin; LI, Hongbin; IOANNIDIS, Stephanos; (518 pag.)WO2019/32863; (2019); A1;,
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Related Products of 111-95-5, 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. 111-95-5, name is Bis(2-methoxyethyl)amine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To the product from step 46 2 (116 mg, 0.19 mmol) was added 43 bis(2-methoxylethyl)amine (3.0 mL, 2.71 g, 20.3 mmol) and a ?spatula tip? of Pd(PPh3)4. The resulting mixture was heated to 140 C. for 2 h. The reaction was cooled and concentrated. The residue was purified by flash chromatography (SiO2, 10/1 CHCl3-MeOH). The resulting 47 material was purified again by reverse phase medium pressure chromatography (C18, 10-50% manual gradient acetonitrile in 0.1% TFA) to afford 12 mg (10% yield) of Example 4 as an orange-brown film: LCMS (15-95% gradient acetonitrile in 0.1% TFA over 10 min), single peak retention time=3.85 min on 250 mm column, (M+H)+=661. UV/vis (100 ?M in PBS) ?abs=434 nm. Fluorescence ?ex=449 nm, ?em=559 nm.

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, Bis(2-methoxyethyl)amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MediBeacon Inc.; Debreczeny, Martin P.; Rajagopalan, Raghavan; Dorshow, Richard B.; Neumann, William L.; Rogers, Thomas E.; (54 pag.)US2019/125901; (2019); A1;,
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Reference of 458-52-6, 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. 458-52-6, name is 2-Fluoro-4-methoxyaniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A. (Z)-l-(2-Amino-l,2-dicyanovinyl)-3-(2-fluoro-4-methoxyphenyl)urea.; In a 100 mL round-bottomed flask was added 2-fluoro-4-methoxyaniline (0.79 g, 5.60 mmol) and trichloromethyl carbonochloridate (0.68 mL, 5.60 mmol) in toluene (6 mL) to give a purple suspension. The mixture was then stirred at 1 10 ¡ãC for 3 h. Upon heating, the suspension becomes a homogeneous solution. After 3 h, no starting material remained (TLC, 3: 1 hex/EtOAc). The reaction mixture was concentrated to afford 2-fluoro-l- isocyanato-4-methoxybenzene (0.936 g, 5.6 mmol, quant.) as a green oil. The intermediate 2-fluoro-l-isocyanato-4-methoxybenzene (0.936 g, 5.6 mmol) was then dissolved in acetonitrile (20 ml) and reacted with 2,3-diaminomaleonitrile (0.605 g, 5.60 mmol) according to General Procedure A. The product was filtered to give the title compound (1.36 g, 88percent). MS (ESI) m/z 276.3[M+1]+.

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

Reference:
Patent; SIGNAL PHARMACEUTICALS, LLC; WO2008/51494; (2008); A1;,
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