Author: Jessica.F

Some common heterocyclic compound, 126829-31-0, name is 2-Ethynyl-1,3-dimethoxybenzene, molecular formula is C10H10O2, 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. Formula: C10H10O2

General procedure: 1 ethynyl 2-methoxybenzene (2a) (265 mg, 2 mmol) and phenylazide (238 mg, 2 mmol) were added in 8 mL of a water and tertbutanol(1:1) mixture. Then 200 mL of freshly prepared 1 M aq.solution of sodium ascorbate (0.2 mmol) was added, following theaddition of 65 mL of aq. CuSO4*5H20 (5 mg, 0.02 mmol) solution. Thereaction mixture was stirred for approximately 14 h at room temperatureand reaction progress was monitored by TLC until its reactantswere completely consumed. Then 30 mL of ice cold waterwas poured into the reaction mixture and flask put in ice bath for15 min following the filtration to get white precipitate that werethoroughly rinsed with cold water (2 x 15 mL). The collected solidwas dried under vacuum to get pure product [23,24].

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 126829-31-0, its application will become more common.

Reference:
Article; Jabeen, Sobia; Khera, Rasheed Ahmad; Iqbal, Javed; Asgher, Muhammad; Journal of Molecular Structure; vol. 1206; (2020);,
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Adding a certain compound to certain chemical reactions, such as: 6358-77-6, name is 5-Bromo-2-methoxyaniline, 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 6358-77-6, name: 5-Bromo-2-methoxyaniline

N, N-DIISOPROPYLETHYLAMINE (13.49 ml, 77.4 mmol) and methyl bromoacetate (0.95 eq, 49.0 mmol) were added to a solution of 5-bromo-2-methoxyaniline (1 eq, 51.6 mmol) in anhydrous DMF (100 ml) under nitrogen. The solution was heated for 16 hours at 60 C before cooling to ambient temperature. DMF was removed under reduced pressure. The residue was dissolved in 500 ml of DCM, washed with 2 x 200 ml of water, was dried over sodium sulfate and was filtered and concentrated under reduced pressure. The title compound was precipitated from DCM/hexanes as an off-white, brownish solid (10.34 G)

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; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2004/41799; (2004); A1;,
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Reference of 74654-07-2, These common heterocyclic compound, 74654-07-2, name is 2-(2-(2-Methoxyethoxy)ethoxy)ethanamine, 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.

2-(3,4-Dichlorophenyl)-N-{(l S)-2-((3S)-3-hydroxypyrrolidin-l -yl)-l – phenylethyl}-N-methylacetamide (3) (0.030 g, 0.074 mmol) and 4-nitrophenyl carbonochloride (0.017 g, 0.081 mmol) were dissolved in 3 mL of dichloromethane. N,N- diisopropylethylamine (0.018 g, 0.15 mmol) was added under stirring. The reaction mixture was stirred at room temperature for two hours. 2-(2-(2-methoxyethoxy)ethoxy)ethanamine (0.033 g, 0.20 mmol) was added. The reaction mixture was stirred at room temperature for 6 hours. 100 mL of dichloromethane was added into the reaction mixture. The resultant solution was washed with saturated sodium chloride (60 mL chi 3) and was dried over sodium sulfate. Evaporation of the solvent and purification of the residue by flash chromatography yielded (35)-l -[(21S)-2-{[(3,4-Dichlorophenyl)acetyl](methyl)amino}-2- phenylethyl]pyrrolidin-3-yl {2-[2-(2-methoxyethoxy)ethoxy]ethyl} carbamate (0.023 g, 58% yield). NMR (500 MHz, CDC13): delta 7.45-7.26 (m, 7H), 7.16 (m, 1 H), 6.10 (m, 0.85H), 5.20 (m, 2H), 5.05 (m, 0.15H), 3.85-3.62 (m, 10H), 3.57 (m, 4H), 3.38 (s, 3H), 3.15 (t, 1 H), 2.98 (m, 2H), 2.75 (m, 4H), 2.40 (m, 1H), 2.20 (m, 1 H), 1.82 (m, 2H); MS (EI) for C29H39C12N306: 596 (MH+).

Statistics shows that 2-(2-(2-Methoxyethoxy)ethoxy)ethanamine is playing an increasingly important role. we look forward to future research findings about 74654-07-2.

Reference:
Patent; NEKTAR THERAPEUTICS; ANAND, Neel, K.; DUARTE, Franco, J.; ZHANG, Wen; REN, Zhongxu; WO2014/210436; (2014); A2;,
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Some common heterocyclic compound, 50742-37-5, name is (3-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: (3-Phenoxyphenyl)methanamine

Example 17 – 3-[(Z)-2-Chloro-3,3,3-trifluoro-prop-1-enyl]-2,2-dimethyl-N-[(3-phenoxyphenyl) methyl]cyclopropanecarboxamide 55 A solution of 3-[(Z)-2-chloro-3,3,3-trifluoro-prop-1-enyl]-2,2-dimethyl-cyclopropanecarbonyl chloride (100mg, 1.1 eq) in toluene (6ml_) was added dropwise to a solution of (3- phenoxyphenyl)methanamine (170mg, 1 eq) and pyridine (68muIota_, 1 eq) in toluene (6ml_). The reaction mixture was stirred overnight at room temperature after which time TLC analysis showed the reaction had gone to completion. The reaction mixture was diluted with ethyl acetate (15ml_) and washed with water (2 x 10ml_) and brine (10ml_) before being dried over MgS04 and the solvent removed in vacuo. The residue was purified by flash chromatography (solvent 9: 1 hexane/ethyl acetate) to afford the product as a clear oil (86mg, 24 %). 1 H NMR deltaEta (CDCIs, 300 MHz): 7.22 (m, 3H), 7.04 (m, 2H), 6.94 (m, 3H), 6.84 (m, 2H), 5.78 (s, 1 H), 4.33 (ddd, J= 20.7, 15.0, 5.7 Hz, 2 H), 1.99 (m, 2 H), 1.21 (s, 3H), 1.19 (s, 3H); ESI-MS 424.2 [MH]+..

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 50742-37-5, its application will become more common.

Reference:
Patent; REDX PHARMA LIMITED; THOMPSON, William; JACKSON, Peter; LINDSAY, Derek; SCREEN, Thomas; MOLTON, Benjamin; URCH, Christopher; WO2013/136073; (2013); A1;,
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Synthetic Route of 92248-06-1,Some common heterocyclic compound, 92248-06-1, name is Bis(3-methoxyphenyl)amine, molecular formula is C14H15NO2, 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.

Under a nitrogen atmosphere,Adding 2,2′-dibromo-9,9′-spirobifluorene (0.7 g, 1.48 mmol),Bis (3-methoxyphenyl) amine (1.01 g, 4.44 mmol),Palladium acetate (18mg, 0.082mmol),Cesium carbonate (1.74g, 5.33mmol)And tri-tert-butylphosphine (0.038mL, 0.15mmol) in toluene(10mL) mixed well in the solution,Heat and stir at 110 C for 20 hours.After cooling to room temperature,The reaction was quenched with a saturated ammonium chloride solution.The aqueous layer was extracted three times with ethyl acetate,Use up the combined organic phasesAnd washed with aqueous sodium chloride.After the organic phase was dried over anhydrous sodium sulfate,The solvent was evaporated to dryness under reduced pressure,The obtained product was further purified by silica gel column chromatography,Petroleum ether / ethyl acetate (10: 1, v / v) was used as the eluent.Get pure product,As a white solid.Yield: 95% (1.08 g).

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

Reference:
Patent; Nanjing Tech University; Hang Xiaochun; Qian Chunyue; Huang Wei; Shen Kang; Qin Tianshi; (57 pag.)CN110790629; (2020); A;,
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19500-02-8, name is 3-Methoxy-2-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. Application In Synthesis of 3-Methoxy-2-methylaniline

General procedure: Ammonium thiocyanate was added to a solution of aniline in 1.0 N HCl(aq). The reaction was stirred at 100 C for 16 h-20 h,cooled to room temperature over 1 h, diluted with cold water(30 mL), and then neutralized with saturated NH4OH(aq) (pH > 7).The precipitatewas collected by vacuum filtration andwashed withwater and diethyl ether: n-hexanes (1: 3) to give the desiredproduct. The product was purified by Isco Combi-Flash Companioncolumn chromatography.

The synthetic route of 19500-02-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Lin, Shu-Yu; Kuo, Yu-Hsien; Tien, Ya-Wen; Ke, Yi-Yu; Chang, Wan-Ting; Chang, Hsiao-Fu; Ou, Li-Chin; Law, Ping-Yee; Xi, Jing-Hua; Tao, Pao-Luh; Loh, Horace H.; Chao, Yu-Sheng; Shih, Chuan; Chen, Chiung-Tong; Yeh, Shiu-Hwa; Ueng, Shau-Hua; European Journal of Medicinal Chemistry; vol. 167; (2019); p. 312 – 323;,
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Synthetic Route of 2930-05-4, 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. 2930-05-4 name is 2-((Benzyloxy)methyl)oxirane, 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.

General procedure: In a typical procedure, an admixture comprising of a solid cata-lyst (20 mg), an aryloxy epoxide (1 mmol) and an amine (1 mmol)were taken in a 5 mL screw capped vial and stirred vigorously fora given time period (monitored by TLC) under solvent free con-dition. At the end of the reaction, products amino alcohols wereobtained as viscous liquids or solids. Therefore, the reaction mix-ture was repeatedly washed with methanol (3 mL) and centrifuged.Methanol from the combined organic layer was evaporated underreduced pressure to get crude amino alcohol. A small sample of thecrude product was subjected to HPLC to find out regioselectivity,while rest of the reaction mixture was subjected to flash columnchromatography (hexane/ethyl acetate, 90:10) to get the majorregioisomer in pure form. The purified product was characterizedby1H and13C NMR, FTIR, Microanalysis and characterization datafor all the ring opening products are given in supporting informa-tion. The residue obtained from centrifugation was dried in air (1 h)and then in oven at 100C for 3 h to get back the catalyst (>97%recovery) for further use.

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

Reference:
Article; Shah, Arpan K.; Prathap, K. Jeya; Kumar, Manish; Abdi, Sayed H.R.; Kureshy, Rukhsana I.; Khan, Noor-ul H.; Bajaj, Hari C.; Applied Catalysis A: General; vol. 469; (2014); p. 442 – 450;,
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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. 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. Recommanded Product: 1-Fluoro-2-methoxybenzene

Step 1. Preparation of 3′-fluoro-4′-methoxyacetophenone Aluminum chloride (80.0 g, 0.6 mol) and chloroform (750 mL) were placed in a 2 L three-necked round bottom flask fitted with a mechanical stirrer and cooled by means of an ice bath. To the stirred solution was added acetyl chloride (51.0 g, 0.65 mol) dropwise, maintaining the temperature between 5-10 C. The mixture was allowed to stir for 10 minutes at 5 C. before the dropwise addition at 5-10 C. of 2-fluoroanisole (63.06 g, 0.5 mol. The mixture was stirred at 0-10 C. for 1 hour and poured into ice (1 L). The resultant layers were separated and the aqueous layer was extracted with methylene chloride (2*250 mL). The combined organic layers were washed with water (2*150 mL), dried over magnesium sulfate, and concentrated to 300 mL. Hexanes crystallized from the mixture: mp 92-94 C.; 1 H NMR (d6 -DMSO) 7.8 (m, 2H), 7.3 (t, J=8.7Hz, 1H), 3.9 (s, 3H), 2.5 (s, 3H).

The synthetic route of 321-28-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; G.D. Searle & Co.; US5760068; (1998); A;,
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Reference of 38336-04-8, 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. 38336-04-8, name is 2-(Benzyloxy)-1-ethanamine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

N-(2-benzyloxyethyl)-2,6-dichloro-3-nitrobenzenesulfonamide Following the general procedure for sulfonamide formation outlined in example 15, 2,6-dichloro-3-nitrobenzenesulfonyl chloride (2.0 g, 6.88 mmol), 2-benzyloxyethyl amine(1.04 g, 6.88 mmol) and triethylamine(1.92mL, 13.76 mmol) were reacted to form the desired product (2.31 g, 83%). 1H NMR (MeOD-d4): delta 7.69 (d, 1H), 7.53 (d, 1H), 7.25 (m, 3H), 7.14 (d, 2H), 4.26 (s, 2H), 3.45 (t, 2H), 3.36 (t, 2H).

The synthetic route of 2-(Benzyloxy)-1-ethanamine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SmithKline Beecham Corporation; US6500863; (2002); B1;,
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Application of 1462-37-9,Some common heterocyclic compound, 1462-37-9, name is ((2-Bromoethoxy)methyl)benzene, molecular formula is C9H11BrO, 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 methyl 3-hydroxy-5-methoxybenzoate (Chakraporty, T. K. and Reddy, G. V. J. Org. Chem, 57, 1992, 5462.) (3.3 g, 18.1 mmol) in dry DMF (30 mL) was added K2CO3 (6.3 g, 45.3 mmol) at room temperature. The reaction was stirred at room temperature for 10 minutes then ((2-bromoethoxy)methyl)benzene (3.4 mL, 21.7 mmol) was added and the mixture stirred at 160 C. for 2 hrs. The reaction was cooled down to room temperature and diluted with EtOAc, washed with water and brine, and dried over MgSO4, filtered and concentrated to give the crude product (90%) which was used in the next step without further purification.

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

Reference:
Patent; SENOMYX, INC.; Tachdjian, Catherine; Karanewsky, Donald; Tang, Xiao Qing; Liu, Hanghui; US2015/245642; (2015); A1;,
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