Ethers-buliding-blocks

Adding a certain compound to certain chemical reactions, such as: 111-95-5, name is Bis(2-methoxyethyl)amine, 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 111-95-5, Formula: C6H15NO2

EXAMPLE 61 Bis-(2-methoxy-ethyl)-prop-2-ynyl-amine Propargyl bromide (17.8 g, 150 mmol) was added dropwise to a mixture of bis(2-methoxy-ethyl)amine (20 g, 150 mmol) and cesium carbonate (49 g, 150 mmol) in 350 mL of acetone. The mixture was stirred overnight under nitrogen at room temperature. The inorganic salts were then filtered off, and the solvent was removed. The residue was dissolved in saturated sodium bicarbonate solution and extracted with ethyl acetate. The organic extracts were then evaporated to give 20 g of bis-(2-methoxy-ethyl)-prop-2-ynyl-amine: mass spectrum (m/e): M+H 172.

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; American Cyanamid Company; US6297258; (2001); B1;,
Ether – Wikipedia,
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Related Products of 588-63-6,Some common heterocyclic compound, 588-63-6, name is (3-Bromopropoxy)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.

General procedure: 3,5-dimethyl-1-(3-phenoxypropyl)-1H-pyrazole (L1): A solution of 3,5-dimethyl-1H-pyrazole (0.30 g, 3.2 mmol) in DMF/THF (v/v = 1:1, 12 mL) was added to a suspension of NaH (0.15 g, 6.4 mmol) in DMF/THF (v/v = 2:1, 15 mL) and stirred at 60 ¡ãC for 2 h. Then, the resulting solution was added under stirring to a solution of 3-bromopropyl phenyl ether (0.70 g, 3.2 mmol) in DMF (7 mL). The mixture was allowed to stir for 24 h at 60 ¡ãC, cooled, and treated cautiously with H2O (5 mL) to decompose excess NaH. The solvents were then evaporated under reduced pressure. The residue was extracted with ethyl acetate (3 * 15 mL), washed with H2O (2 * 15 mL). The organic phase was dried over MgSO4 and filtered, before the solvent was evaporated under reduced pressure. After workup and purification by chromatographic column on silica gel (hexane/ethyl acetate, 90:10), L1 was obtained as a colorless oil (0.47 g, 64percent).

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

Reference:
Article; Ulbrich, Ana H.D.P.S.; Campedelli, Roberta R.; Milani, Jorge L. Sonego; Santos, Joao H.Z. Dos; Casagrande, Osvaldo De L.; Applied Catalysis A: General; vol. 453; (2013); p. 280 – 286;,
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Electric Literature of 767-91-9, A common heterocyclic compound, 767-91-9, name is 2′-Methoxyphenyl acetylene, molecular formula is C9H8O, 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: A mixture of aryl iodide (2 mmol), aryl alkyne (2.4 mmol), Ni(OAc) 2 (10 mol %), Et3N (6 mmol) and 1,4-dioxane (15 mL) were charged into the reactor (steel bomb). The reactor was closed and pressurized to ~2bar CO and then stirred at 100 C for 4 h. The reaction Progress was monitored by TLC. The reaction mixture was cooled to room temperature, before being filtered through a pad of Celite. The filtrate was concentrated and purified by silica gel with a mixture of hexane and ethyl acetate to give the pure product. For all examples, reactions were performed on 100 mg scale of corresponding aryl iodides.

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:
Article; Charugandla, Renuka; Vangala, Markandeya Sarma; Chidara, Sridhar; Korupolu, Raghu Babu; Tetrahedron Letters; vol. 59; 34; (2018); p. 3283 – 3287;,
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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 5414-19-7 as follows. Product Details of 5414-19-7

Part F:; To a DMF (9 mL) solution of Part E (1.08 g, 2.71 mmol) was added K2CO3 (1.12 g, 8.16 mmol), 18-crown-6 (0.21 g, 0.80 mmol), and bis (2-bromoethyl) ether (0.37 mL, 2.9 mmol). The slurry was stirred at 60C for 72 hr. Additional bis (2-bromoethyl) ether was added at 24 hr (0.4 mmol) and 48 hr (1.2 mmol). The solvent was stripped in vacuo, and the residue was partitioned between ethyl acetate (50 mL) and water (30 mL). The organic layer was separated, dried over MgS04, and evaporated to an oil. Recrystallization from diethyl ether produced 0. 88 g (69 %) of the desired compound in the form of a white solid. LCMS: itvz = 469.2 (M+H).

According to the analysis of related databases, 5414-19-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PHARMACIA CORPORATION; WO2005/42521; (2005); A2;,
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Ether | (C2H5)2O – PubChem

Electric Literature of 1484-26-0, A common heterocyclic compound, 1484-26-0, name is 3-Benzyloxyaniline, molecular formula is C13H13NO, 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.

Synthesis of Compound 113To a stirred solution of compound 1703 (200 mg, 1.26 mmol) in DCM (10 rnL) was added N-methylmorpholine (0.41 rnL, 3.79 mmol) and 3-benzyloxy-phenylamine (251 mg, 1.26 mmol) at 00C. The reaction mixture was stirred at room temperature overnight. The progress of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was concentrated under vacuum to remove DCM. The residue was dissolved in water and extracted with ethyl acetate (2 x 50 mL), and the organic layer was washed with brine and dried over anhydrous sodium sulfate to afford coupled product 113 (120 mg, 28percent) with HPLC purity of 91.4percent. Mass: 340 [M+H]; 1H NMR (500 MHz, CDCl3): delta 1.35 (m, 5H), 1.6-1.85 (m, 6H), 4.1 (d, IH), 5.1 (s, 2H), 6.78 (m, IH), 7.08 (m, IH), 7.2-7.6 (m, 7H), 8.38 (s, IH).

The synthetic route of 1484-26-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ARETE THERAPEUTICS, INC.; WO2008/73623; (2008); A2;,
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148583-65-7, name is 4-Fluoro-2-isopropoxyaniline, 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. Computed Properties of C9H12FNO

Intermediate 29 Ethyl 7-chloro-4-{[4-fluoro-2-(propan-2-yloxy)phenyl]amino}-5-methyl^ d]pyrimidine-6-carboxyla te A mixture of Intermediate 28 (320 mg, 1.17mmol), 4-fluoro-2-isopropoxyaniline (179 muIota, 1.17 mmol) and PTSA (22 mg, 0.117 mmol) in IPA (15 ml) was stirred and heated at 60″C for 3 hours. The reaction was allowed to cool to rt and then concentrated to dryness. The residue was diluted with DCM and washed with sat. NaHCOs (aq). The aqueous phase was re-extracted with DCM. The combined organic phases were dried and concentrated. The crude product was pre-absorbed on to silica gel prior to purification by flash chromatography on silica gel eluting with 40:1 DCM: IPA to give a pale beige coloured solid (395 mg, 83 %). 1H NMR (400 MHz, DMSO-d6) delta ppm 1 ,27 (d, J=5.95 Hz, 6 H), 1.38 (t, J=7.10 Hz, 3 H), 4.31 (s, 3 H), 4.37 – 4.47 (m, 2 H), 4.73 (dt, J=12.02, 6.13 Hz, 1 H), 6,77 – 6.86 (m, 1 H), 7.07 (dd, J=10.99, 2.75 Hz, 1 H), 8.27 (dd, J=8.70, 6.41 Hz, 1 H), 8.38 (s, 1 H), 8.43 (s, 1 H)

The synthetic route of 148583-65-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MEDICAL RESEARCH COUNCIL TECHNOLOGY; WINTER-HOLT, Jon James; MCIVER, Edward Giles; LEWIS, Stephen; OSBORNE, Joanne; (106 pag.)WO2017/85483; (2017); A1;,
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Reference 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 phthalic anhydride (10.00 g), aminoacetaldehyde (7.81 g) and N,N-diisopropylethylamine (13.09 g) in toluene under an atmosphere of nitrogen was heated at 120 C for 16 h and then quenched with NH4C1(aq) (100 mL, 2 M). The aqueous phase was extracted with ethyl acetate (3×50 mL). The combined organic extracts were washed with water and brine, dried over anhydrous sodium sulfate, filtered. The filtrate was concentrated to get the crude residue S-I-I (15.49 g, y: 98%).

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; NATIONAL HEALTH RESEARCH INSTITUTES; SHIH, Chuan; SHIA, Kak-Shan; WU, Chien-Huang; CHOI, Ming-Chen; SONG, Jen-Shin; WANG, Yun; (84 pag.)WO2018/132326; (2018); 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. 1758-46-9, name is 2-Phenoxyethylamine, A new synthetic method of this compound is introduced below., HPLC of Formula: C8H11NO

[0070] [6-CHLORO-N- (2-METHOXYBENZYL)-NAPOS;- (2-PHENOXYETHYL)- [1,] 3, 5] triazine- 2, 4-diamine (3). Procedure 1 : 1.00 eq. of 2 in [CH2C12] is cooled to ODC under nitrogen and Et3N or Hunig’s base (3.00 eq. ) is added. To the stirring solution, 1.00 eq. [OF 2-PHENOXY-ETHYLAMINE] is added dropwise. The temperature rises several degrees upon completion of addition ; warming is then allowed to continue until the reaction reaches room temperature. The reaction is allowed to stir at room temperature for 12 hours and then the mixture is partitioned between [CHUCK] and 1.0 N [HC1.] The acid layer is extracted once with [CH2C12] and then the pooled [CH2C12] layers washed several times with H20 and once with brine. The [CH2CI2] extract is dried over [NA2S04,] and the solvent removed under reduced pressure to provide crude 3, which is purified by flash chromatography using 1: 4 ethyl acetate (EtOAc)/hexanes as eluent. [0071] Procedure 2: 1.00 eq. of 2 in CH2C12 is cooled to [OOG] under nitrogen and Et3N or Hunig’s base (3.00 eq. ) is added. To the stirring solution, 1.00 eq. of 2- [PHENOXY-ETHYLAMINE] is added dropwise. The temperature rises several degrees upon completion of addition; warming is then allowed to continue until the reaction reaches room temperature. The resulting mixture is heated to [100¡ãC] for 30 minutes, cooled to room temperature, and partitioned between [H20/CH2C12.] The aqueous layer is extracted with [CH2C12] and combined organic extracts were dried over [NA2S04.] The solvent is removed under reduced pressure and the resulting residue is purified by flash chromatography [(1] : 4 EtOAc/hexanes) to yield 3.

The synthetic route of 1758-46-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CELLULAR GENOMICS, INC.; WO2004/820; (2003); A2;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Adding a certain compound to certain chemical reactions, such as: 168971-68-4, name is 1-Bromo-2-fluoro-4-(trifluoromethoxy)benzene, 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 168971-68-4, Formula: C7H3BrF4O

Example 106Preparation of Compound 416CF3Step A – synthesis of compound 206BCompound 206A (2.14 g, 8.3 mmol) was combined with PdCl2(dppf) (0.20 g, 0.25 mmol), bis(pinicolato)diboron (2.52 g, 9.9 mmol), and KOAc (2.43 g, 24 mmol) in DMSO (10 mL). The mixture was put under N2 atmosphere, heated to 1000C and allowed to stir at this temperature for 4 hours, then partitioned with water and 1 : 1 EtOAc/hexane. The organic phase was dried (MgSO4) and concentrated in vacuo, and the resulting residue was purified using flash column chromatography on silica (10% EtOAc/hexane) to provide compound 206B as a white solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Bromo-2-fluoro-4-(trifluoromethoxy)benzene, and friends who are interested can also refer to it.

Reference:
Patent; SCHERING CORPORATION; WO2008/130581; (2008); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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. 102-52-3, name is 1,1,3,3-Tetramethoxypropane, A new synthetic method of this compound is introduced below., Product Details of 102-52-3

100 g of Compound 1 was added to 96 ml of water, and 5.4 ml of hydrochloric acid and 105.6 g of liquid bromine were slowly added dropwise at 0 C, and stirred at room temperature overnight.The water was spun off at 45 C, filtered, and the solid was washed several times with PE: EA and dried to give 50 g of Intermediate 3.

The synthetic route of 102-52-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Yaoya Science And Technology (Shanghai) Co., Ltd.; Zeng Zhaosen; Liang Yonghong; (6 pag.)CN109824586; (2019); A;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem