Month: July 2021

Application of 261762-35-0,Some common heterocyclic compound, 261762-35-0, name is 5-Bromo-1,2-difluoro-3-methoxybenzene, molecular formula is C7H5BrF2O, 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.

3,4-Difluoro-5-methoxybenzoic acid (72a) (0327) The title compound was prepared by reaction of 5-bromo-1,2-difluoro-3-methoxybenzene (1.03 g, 4.62 mmol, 1.0 equiv) and magnesium (112 mg, 4.61 mmol, 1.0 equiv) and iodine (2 mg) in 13 ml diethylether under reflux for 2 h. Carbon dioxide was bubbled through the solution at 10 C. until all solvent (13 ml) was evaporated two times. The crude product was dissolved in 10 mL THF and carbon dioxide was bubbled through the solution for additional 1 h. The reaction was quenched with 1 M HCl, extracted with ethyl acetate, dried with magnesium sulfate and concentrated under reduced pressure to afford the crude product, which was purified by flash chromatography; yield: 31% (265 mg). 1H NMR (300 MHz, MeOH-d4) delta 7.65-7.45 (m, 2H), 3.99 (s, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Bromo-1,2-difluoro-3-methoxybenzene, its application will become more common.

Reference:
Patent; ELEXOPHARM GMBH; Hartmann, Rolf; Frotscher, Martin; Ahmed, Ahmed Saad Abdelsamie; Bey, Emmanuel; van Koppen, Chris J.; Oberwinkler-Marchais, Sandrine; Boerger, Carsten; Siebenbuerger, Lorenz; Hernandez Olmos, Victor; (72 pag.)US2016/318895; (2016); A1;,
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Application of 37466-89-0, 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. 37466-89-0, name is 3-Methoxybenzene-1,2-diamine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

4-Methoxy-2-trifluoromethyl-1H-benzimidazole The compound of Example 11 (6.49 g) was dissolved in trifluoroacetic acid (75.0 mL) under ice cooling, followed by stirring for 5 hours under the condition of heating under reflux. After evaporating the solvent under reduced pressure, the residue was dissolved in ethyl acetate and poured into a saturated aqueous sodium hydrogen carbonate solution. The organic layer was separated out, washed with saturated brine, and then dried over anhydrous sodium sulfate. After evaporating the solvent under reduced pressure, the resulting solid was suspended in hexane and collected by filtration to obtain the desired product (8.69 g) as a yellowish brown powder. 1H-NMR (CDOl3, 400 MHz): delta 4.01 (3H, s), 6.89 (1H, d, J=8.0 Hz), 7.24 (1H, d, J=8.0 Hz), 7.32 (1H, t, J=8.0 Hz).

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, 3-Methoxybenzene-1,2-diamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Kyorin Pharmaceutical Co., Ltd.; EP2168960; (2010); A1;,
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Related Products of 41365-75-7, 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 41365-75-7 as follows.

1.1 N-(3,3-Diethoxy-propyl)-3-methoxy-2-methoxymethyl-2-methyl-propionamide5 g of 3-methoxy-2-methoxymethyl-2-methyl-propionic acid (prepared as described in EP609058) were dissolved in 49 mL of DCM and 12 mL of THF. 11.4 mL of DIPEA, 5.84 g of HOBt, 7.07 g of EDC and 5.45 g of 3,3-diethoxy-propylamine were added sequentially. The mixture was stirred for 23 h at rt, diluted with DCM and washed with sat. NaHCO3. The organic phase was dried over anh. Na2SO4 and concentrated in vacuo. The resulting crude material was purified by CC using Hept/EtOAc from 3/1 to 0/1 as eluant to yield 7.25 g of N-(3,3-diethoxy-propyl)-3-methoxy-2-methoxymethyl-2-methyl-propionamide as a yellowish oil.1H-NMR (CDCl3): 7.04 (s, 1H), 4.51 (t, 1H), 3.45-3.7 (m, 4H), 3.43 (s, 4H), 3.32 (s, 6H), 3.30 (dd, 2H), 1.79 (dd, 2H), 1.19 (t, 6H), 1.12 (s, 3H).

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; Hilpert, Kurt; Hubler, Francis; Renneberg, Dorte; US2011/207815; (2011); A1;,
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Reference of 578-57-4, A common heterocyclic compound, 578-57-4, name is 1-Bromo-2-methoxybenzene, molecular formula is C7H7BrO, 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.

The 186 mg (1mmol) 2 – bromoanisole, 186 mg (2mmol) aniline, 9.05 mg (0.05mmol) Cu (OAc)2, 36.1 mg (0.1mmol) ligand L3, 489mg (1.5mmol) Cs2CO3, 2 ml MeOH, adding 10 ml reaction tube, sealing, 60 C reaction under the condition of 3h. After the stop of the reaction, water, extracted with ethyl acetate, washing, saturated salt water washing, after drying with anhydrous sodium sulfate, filtered, the filtrate is distilled under reduced pressure, purification by silica gel chromatography separation column column, shall be 2 – methoxy – N – phenylaniline 175 mg, yield 88%.

The synthetic route of 578-57-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sun Yat-sen University; Wan Yiqian; Ding Xiaomei; Huang Manna; Zhu Xinhai; Yi Zhou; CN106883132; (2017); A;,
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Reference of 321-28-8, 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. 321-28-8, name is 1-Fluoro-2-methoxybenzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

5-Bromo-2-chlorobenzoyl chloride 9b (124 g, 0.49 mol)Was dissolved in dichloromethane (600 mL)Cooled to -5 C,2-fluoroanisole (61.8 g, 0.49 mol) was added,Anhydrous aluminum chloride (133 g, 1.0 mol) was added in portions,The resulting mixture was stirred at room temperature for 4 hours.The reaction solution is poured into crushed ice,Extracted with dichloromethane (400 mL x 2)The combined organic phases were washed successively with saturated sodium bicarbonate solution (300 mL)And saturated brine (300 mL)Dried over anhydrous sodium sulfate,Concentrated under reduced pressure,To the residue was added anhydrous ethanol (500 mL) and stirred at 0 C for 30 minutes. The solid was collected by suction filtration,The title compound 9c was obtained as a white solid (129 g, 77%).

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

Reference:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Gu Zheng; Wu Wuyong; Qu Tong; Tan Haoxiong; Kang Panpan; Deng Bingchu; (48 pag.)CN106892948; (2017); A;,
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Reference of 578-57-4,Some common heterocyclic compound, 578-57-4, name is 1-Bromo-2-methoxybenzene, molecular formula is C7H7BrO, 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: DMF (40 mL), NaI (375 mg, 2.5 mmol), and 1,2-dibromoethane (100muL, 1.16 mmol) were added to an undivided electrochemical cell, fitted with an iron/nickel (64/36) anode, and surrounded by a nickel foam as the cathode (surface: 40 cm2, porosity: 500 mum, Goodfellow).The mixture was electrolyzed under argon at a constant current intensityof 0.2 A at r.t. for 15 min. The current was then stopped, then NiBr2bpy (187 mg, 0.5 mmol) and aryl or heteroaryl halide (5 mmol),were sequentially added. The solution was electrolyzed at 0.2 A untilthe starting aryl or heteroaryl halide had been totally consumed (2-5h). Sat. aq EDTA-Na2 solution (50 mL) was added, and the resultingsolution was extracted either with EtOAc (for aryl halides) or withCH2Cl2 (for heteroaryl halides) (3 × 50 mL). The combined organic layerswere washed with brine (50 mL), dried (MgSO4), filtered, and concentratedunder vacuum. The crude product was purified by flashchromatography (silica gel, 70-200 mum).

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

Reference:
Article; Rahil, Rima; Sengmany, Stephane; Le Gall, Erwan; Leonel, Eric; Synthesis; vol. 50; 1; (2018); p. 146 – 154;,
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Application 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.

H(5O,2)-CBZ; Several approaches were tried to synthesize the N,N,N’,N’-Tetrakis-(2-amino-ethyl)- 3-oxapentane- l ,5-diamine [H(5O,2)-amine]. It was found that the reaction of 5LIO-amine with CBZ-aziridine provides clean H(5O,2)-CBZ.; 5LIO-amine (0.21 g, 2 mmol) and CbZ-aziridine ( 1.77 g, 10 mmol) were mixed in tert- butanol (30 ml.) at room temperature under N2. The mixture was stirred under a N2 atmosphere at 8O0C for 16 hrs. when TLC showed the completeness of the reaction. The volatile were removed under vacuum and the residue was dissolved in dichloromethane. The appropriate fractions of a gradient flash silica gel column ( 1 -7% methanol in dicholoromethane) were collected and evaporated to dryness to give a pale beige thick oil, yield: 1.28 g, 79%.[0301] ‘ H NMR(300MHz, CDCl3): delta 2.53(s,br, 12H), 3.17(s,br, 4H), 3.83(s, br, 8H), 5.04(s, 8H), 7.29(s,br, 20H). 1 3C NMR (300MHz, CDCI3): delta 38.8, 53.0, 53.6, 69.3, 128.0, 128.1 , 128.4, 136.6, 156.4. MS(FAB+, DTT/DTE): 813.5 (MH+).

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

Reference:
Patent; THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; WO2008/8797; (2008); A2;,
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Ether | (C2H5)2O – PubChem

Related Products of 6096-89-5, The chemical industry reduces the impact on the environment during synthesis 6096-89-5, name is 2-(4-Fluorophenoxy)ethylamine, I believe this compound will play a more active role in future production and life.

2-(4-Fluorophenoxy)ethylamine (5A-1) in hydrochloride form is dissolved in wa- ter and basified with 1N sodium hydroxide (NaOH) to basic pH, and then extracted with ether. The free amine is thus obtained (yield = 74%).The malonate monoester (O) (7.5 g), the amine (5A)-1 (4.14 g) in ethanolic solution (30%) and hydroxybenzotriazole (HOBT) (3.97 g) in 70 ml of THF are placed in a 500 ml three-necked flask. After complete dissolution, the whole is cooled to -7C and DCC (5.5 g) diluted in 30 ml of THF is then added dropwise over 30 minutes.The mixture is allowed to warm to room temperature and is then left stirring for 19 hours. At room temperature, the medium becomes cloudy (white precipitate).The precipitate (dicyclohexyl urea) is filtered off and concentrated to dryness. 15.77 g of a beige-coloured solid are obtained.This crude solid is taken up in ethyl acetate (400 ml) and washed with:- HCMN (150 ml)- saturated sodium hydrogen carbonate solution (NaHCO3) (150 ml)- saturated NaCI solution (150 ml) – water (150 ml).After drying over MgSO4 and evaporating off the solvent, 9.34 g of a beige-coloured solid are obtained.YId: 84% m.p. = 1200C 1H NMR (DMSO delta in ppm): 1.08 (s, 3H); 3.41 (t, 2H); 3.93 (t, 2H); 4.07 (q, 2H);6.89 (t, 2H); 7.08 (t, 2H); 7.31 (s, 4H); 7.83 (s, 1H); 8.60 (t, 1H).Purity = 67%MS (APCI) m/z: 419 [M+H]+

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-(4-Fluorophenoxy)ethylamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK PATENT GMBH; WO2008/6432; (2008); A1;,
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Reference of 22236-08-4, 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 22236-08-4 as follows.

Intermediate.11 rac-Allyl [l -{N’-cyano-N-[3-(difluoromethoxy)phenyl]carbamimidoyl} -3-(3,4-dichlorophenyl)-4,5- dihydro- l//-pyrazol-4-yl]carbamate To a stirred solution of m-difluoromethoxy aniline, 8.20 ml. (65.5 mmol) in anhydrous tetrahydrofuran (100 mL) at -78 C was added n -butyl lithium, 33.0 mL (65.5 mmol, 2 M in hexane) dropwise, while maintaining the reaction temperature below -65 C during the addition. The reaction mixture was stirred for 1 hour at -78 C before rac-phenyl 4-{[(ailyioxy)carbonyl]amino}-N-cyano-3-(3,4- dichlorophenyl)-4,5-dihydro- 1 H-pyrazole- 1 -carboximidate (intermediate 9), 10.0 g (21.8 mmol) in anhydrous tetrahydrofuran (600 mL) was added dropwise maintaining the reaction temperature below -65 C. The reaction mixture was stirred for 2 hours at -78 C before slowly pouring over saturated ammonium chloride solution (700 mL). The crude product was extracted into ethyl acetate (700 mL) and the organic layers were combined and washed with brine solution (350 mL). The collected organic phase was dried over magnesium sulfate, filtered and the solvent evaporated to yield an off-white crude solid. The crude solid was precipitated from a minimum volume of ethyl acetate, filtered, and washed with diethyl ether to yield rac-allyl [ 1 – {N’-cyano-N- [3 – (difluoromethoxy)phenyi]carbamimidoyl}-3-(3,4-dichlorophenyl)-4,5-dihydro-lH-pyrazoi-4- yl] carbamate, 7.6 g (67%) as a white solid. NM R (400 MHz, DMSO-d6): delta [ppm] = 4.08 (dd, 1H), 4.36-4.53 (m, 3H), 5.11 (dd, 1H), 5.17 (dd, 1H), 5.50-5.59 (m, 1H), 5.77-5.90 (m, 1H), 6.99 (dd, 1H), 7.16 (t, 1H), 7.21 (t, 1H), 7.23 (dd, 1H), 7.39 (t, 1H), 7.73-7.81 (m, 2H), 8.15 (d, 1H), 8.17 (d, 1H), 9.79 (br s, 1H). I MS (method 3): Rt = 1.78 min MS (ESI): [M + Hf = 523.2

According to the analysis of related databases, 22236-08-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; STELLFELD, Timo; MOWAT, Jeffrey Stuart; STRESEMANN, Carlo; HILLIG, Roman; KOeHR, Silke; STOeCKIGT, Detlef; WEISKE, Joerg; HARTUNG, Ingo; BARAK, Naomi; CHRIST, Clara; TER LAAK, Antonius; BADOCK, Volker; CRAMPTON, Rosemary Helen; STEFANUTI, Ian; (194 pag.)WO2016/166186; (2016); A1;,
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Some common heterocyclic compound, 107622-80-0, name is (4-Phenoxyphenyl)methanamine, molecular formula is C13H13NO, 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. name: (4-Phenoxyphenyl)methanamine

General procedure: The appropriate pyrazole (1.0 equiv) was treated with phosgene(20% in toluene) at 0 C. The reaction mixture was stirred at room temperature for 1 h.The solvent was removed under reduced pressure and the crude carbamoyl chloride was redissolved in anhydrous CH2Cl2 (0.5 M). The appropriate amine (1.0 equiv) and Et3N (1.2 equiv) were dissolved in CH2Cl2 and cooled to 0 C. The crude carbamoyl chloride was added dropwise and the reaction mixture was stirred at room temperature for 16 h.The mixture was diluted with EtOAc, washed with saturated aqueous NaCl, and dried over Na2SO4. Evaporation under reduced pressure yielded the crude coupling product that was purified by flash chromatography (SiO2).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 107622-80-0, its application will become more common.

Reference:
Article; Otrubova, Katerina; Srinivasan, Venkat; Boger, Dale L.; Bioorganic and Medicinal Chemistry Letters; vol. 24; 16; (2014); p. 3807 – 3813;,
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