Author: Jessica.F

Application of 707-07-3, The chemical industry reduces the impact on the environment during synthesis 707-07-3, name is (Trimethoxymethyl)benzene, I believe this compound will play a more active role in future production and life.

General procedure: N -(2-aminobenzoyl)benzotriazoles (0.25 mmol) 1 previously synthesized by our group were reacted with orthoester (0.50 mmol) 2 and ammonium acetate (1.0 mmol) in dioxane for 6-10 h. After completion of the reaction, the solvent was evaporated under reduced pressure. The reaction mixture was purified by column chromatography over silica gel with a EtOAc/n-hexane mixture (from 1:2 or 1:1) to obtain white crystals (62%-95%).

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, (Trimethoxymethyl)benzene, other downstream synthetic routes, hurry up and to see.

Reference:
Article; ?enol, ?lbilge Merve; Celik, ?lhami; Avan, ?lker; Turkish Journal of Chemistry; vol. 43; 6; (2019); p. 1580 – 1596;,
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These common heterocyclic compound, 1535-75-7, name is 2-(Trifluoromethoxy)aniline, 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. COA of Formula: C7H6F3NO

General procedure: Commercially available substituted aniline (63.4mmol) was portionwise added to a solution of concentrated HCl (13mL), ethanol (20mL) and water (7mL). To the above mixture was added dropwise a solution of NaNO2 (4.69g, 69.7mmol) in water (15mL) at 0-5C. After the completion of addition, the reaction mixture was stirred at this temperature for 30min, and then added into a mixture of ethyl 2-chloroacetoacetate (10.88g, 63.4mmol), anhydrous sodium acetate (15.60g, 190.10mmol), and water (90mL) at 0C. The reaction mixture was stirred at 0C for 10min and then at room temperature for 4h. The solid which precipitated was collected by filtration and recrystallized from ethanol to afford light yellow solids (21a-21m) in 75.2-90% yields. 6.3.8 Ethyl 2-chloro-2-(2-(2-(trifluoromethoxy)phenyl)hydrazono)acetate (21h) Light yellow solid; Yield: 90%; M.p.: 93-94 C; MS (ESI) m/z(%): 333.1 [M+Na]+.

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

Reference:
Article; Liu, Ju; Nie, Minhua; Wang, Yanjing; Hu, Jinxing; Zhang, Feng; Gao, Yanlin; Liu, Yajing; Gong, Ping; European Journal of Medicinal Chemistry; vol. 123; (2016); p. 431 – 446;,
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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. 126-38-5, name is 1-Bromo-2,2-dimethoxypropane, A new synthetic method of this compound is introduced below., name: 1-Bromo-2,2-dimethoxypropane

The thioamide from above (0.36 g, 1.63 mmol, 1.0 eq) was suspended in EtOH (10 mL, absolute) under argon at rt. 1-Bromo-2,2-dimethoxypropane (0.22 mL, 1.63 mmol, 1.0 eq) was added via syringe and stirring continued for 72 h at rt. The mixture was then heated to 70 C. for 16 h and concentrated in vacuo. Mass spectrometric analysis of the crude residue was consistent with a corresponding thiazole structure, and no further manipulation was performed before removal of the Boc protecting group in the next step. ESI-MS (m/z) 257 [M+H]+, 201 [M-tBu]+, 157 [M-Boc]+.

The synthetic route of 126-38-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Erickson, Shawn David; Baldwin, John J.; Dolle III, Roland Ellwood; Inglese, James; Ohlmeyer, Michael H.J.; Ho, Koc-Kan; Bohnstedt, Adolph C.; Kultgen, Steven G.; Conti, Paolo Giovanni Martino; Leysen, Dirk; van der Louw, Jaap; US2004/87601; (2004); A1;,
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Adding a certain compound to certain chemical reactions, such as: 24599-58-4, name is 2,5-Dimethoxytoluene, 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 24599-58-4, Computed Properties of C9H12O2

Preparation of 2,5-dimethoxy-4-methylacetophenone. 1 mol (152 g) of 2,5-dimethoxytoluene is introduced, whilst stirring, into 230 ml of acetyl chloride at -10 C. 160 g of aluminium chloride are then added in the course of 3 hours, whilst stirring and keeping the temperature of the reaction medium at between -10 and 0 C. When the addition has ended, the mixture is stirred for a further 3 hours at between -10 and 0 C. The reaction medium is then poured onto 1 kg of crushed ice to which 110 ml of hydrochloric acid (d=1.19) have been added. After a few hours, the reaction product which has precipitated is filtered off. After washing with water, a 2 N solution of sodium hydroxide and then again with water, the 2,5-dimethoxy-4-methylacetophenone is recrystallized from ethanol. After drying in vacuo, it melts at 75 C.

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; Bugaut; Andree; Grollier; Jean-Francois; Vandenboosche; Jean-Jacques; US4185958; (1980); A;,
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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. 54314-84-0, name is ((3-Bromopropoxy)methyl)benzene, A new synthetic method of this compound is introduced below., category: ethers-buliding-blocks

To a mixture of 1-(2-hydroxyethyl)-4-[2-(4-hydroxyphenyl)ethyl]-3-(2,3,4,6-tetra-O-pivaloyl-beta-D-glucopyranosyloxy)-1H-indazole (2 g), cesium carbonate (1.64 g) and sodium iodide (0.38g) in N,N-dimethylformamide (10 mL) was added benzyl 3-bromopropyl ether (0.86 g), and the mixture was stirred at room temperature overnight. The reaction mixture was poured into water, and the resulting mixture was extracted with diethyl ether. The extract was washed with water and brine, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the residue was dissolved in dichloromethane (15 mL). To the solution were added triethylamine (1.22 mL) and pivaloyl chloride (0.93 mL), and the mixture was stirred at room temperature overnight. The reaction mixture was poured into 0.5 mol/L hydrochloric acid, and the resulting mixture was extracted with diethyl ether. The extract was washed with water, a saturated aqueous sodium hydrogen carbonate solution and brine, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate = 3/1) to give 4-{2-[4-(3-benzyloxypropoxy)phenyl]ethyl}-3-(2,3,4,6-tetra-O-pivaloyl-beta-D-glucopyranosyloxy)-1-(2-pivaloyloxyethyl)-1H-indazole (2.11 g). This material was dissolved in ethyl acetate (20 mL). To the solution was added 10percent palladium-carbon powder (0.5 g), and the mixture was stirred at room temperature under a hydrogen atmosphere for 2 hours. The insoluble material was removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate = 2/1 – 1/1) to give the title compound (1.59 g). 1H-NMR (CDCl3) delta ppm: 1.02 (9H, s), 1.03 (9H, s), 1.13 (9H, s), 1.15 (9H, s), 1.17 (9H, s), 2.0-2.1 (2H, m), 2.8-2.9 (1H, m), 2.9-3.0 (1H, m), 3.0-3.15 (1H, m), 3.2-3.3 (1H, m), 3.8-3.9 (2H, m), 3.9-4.0 (1H, m), 4.05-4.2 (3H, m), 4.21 (1H, dd, J=12.4Hz, 1.6Hz), 4. 3-4. 5 (4H, m), 5.2-5.3 (1H, m), 5.35-5.55 (2H, m), 6.05 (1H, d, J=7.8Hz), 6.64 (1H, d, J=6.9Hz), 6.75-6.85 (2H, m), 7.0-7.1 (3H, m), 7.15-7.2 (1H, m)

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; Kissei Pharmaceutical Co., Ltd.; EP1724278; (2006); A1;,
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Electric Literature of 175278-17-8,Some common heterocyclic compound, 175278-17-8, name is 2-Bromo-4-(trifluoromethoxy)aniline, molecular formula is C7H5BrF3NO, 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.

A mixture of 2-bromo-4-(trifluoromethoxy)aniline 17 (Maybridge, 2.048 g, 8.00 mmol), methyl acrylate (1.80 mL, 20.0 mmol), Pd(OAc)2 (215.5 mg, 0.960 mmol), tri-o-tolylphosphine (1.169 g, 3.84 mmol), and dry Et3N (4.30 mL, 30.9 mmol) in dry CH3CN (16.0 mL) was stirred under reflux conditions under N2 for 4 h, then concentrated in vacuo. The residue was partitioned between H2O (30 mL) and AcOEt (30 mL). The organic layer was separated and the aqueous layer was extracted with AcOEt (30 mL × 2). The organic layers were combined, dried over anhydrous MgSO4, filtered, and concentrated in vacuo to afford 3.630 g of the title product 21 (crude). This compound was used for the next step without further purification. 1H NMR (270 MHz, CDCl3) delta 7.74 (1H, d, J = 15.8 Hz), 7.23-7.02 (2H, m), 6.68 (1H, d, J = 8.72 Hz), 6.36 (1H, d, J = 15.8 Hz), 4.00 (2H, br s), 3.81 (3H, s).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Bromo-4-(trifluoromethoxy)aniline, its application will become more common.

Reference:
Article; Hayashi, Shigeo; Ueno, Naomi; Murase, Akio; Nakagawa, Yoko; Takada, Junji; European Journal of Medicinal Chemistry; vol. 50; (2012); p. 179 – 195;,
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38336-04-8, name is 2-(Benzyloxy)-1-ethanamine, 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: C9H13NO

A mixture of e-1 (0.0037 mol) and e-2 (0.0151 mol) was stirred at 60C for 2 hours, then purified by column chromatography over silica gel (eluent: CH2CyCH3OH (98/2); 15mum). The pure fractions were collected and the solvent was evaporated. Yield: 1 g of intermediate e-3 (100%).

The synthetic route of 38336-04-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TIBOTEC PHARMACEUTICALS LTD; WO2006/136561; (2006); A1;,
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Application of 3616-56-6, A common heterocyclic compound, 3616-56-6, name is 2,2-Diethoxy-N,N-dimethylethanamine, molecular formula is C8H19NO2, 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.

EXAMPLE 43 N,N-Diethyl-5-[[2-(dimethylamino)ethyl]amino]-2H-[1]benzothiopyrano[4,3,2-cd]indazole-2-ethanamine A mixture of 5.0 g (0.015 mol) of 5-amino-N,N-diethyl-2H[1]benzothiopyrano[4,3,2-cd]indazole-2-ethanamine, 2.4 g (0.015 mol) of 2,2-diethoxy-N,N-dimethyl ethanamine, and 0.001 g of p-toluenesulfonic acid in 100 ml of 2-propanol was heated under reflux for four hours, allowed to cool to room temperature, and treated portionwise with 1.0 g (0.026 mol) of NaBH4 over a two hour period. The mixture was stirred at room temperature for 16 hours and poured into 1 l of H2 O. The precipitate that formed was collected, washed with H2 O, dried, and recrystallized to give the product. An example of another 5-(monoalkylated or acylated)-2-(substituted)benzothiopyrano[4,3,2-cd]-indazole, prepared in the manner of Examples 5-11, is as follows: N-[2-[2-(diethylamino)ethyl]-2H[1]benzothiopyrano[4,3,2-cd]indazol-5-yl]-1,3-propanediamine, hydrochloride salt, mp 222° C. dec.

The synthetic route of 3616-56-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Warner-Lambert Company; US4604390; (1986); A;,
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Some common heterocyclic compound, 658-89-9, name is 4-(Trifluoromethoxy)benzene-1,2-diamine, molecular formula is C7H7F3N2O, 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: C7H7F3N2O

2-Hydroxymethyl- and 2-ethyl-5-trifluoromethoxybenzimidazole. The procedure of Philips, M. A. was used. A mixture of 2-amino-4-trifluoromethoxyaniline (0.7 g, 0.0036 Mol) and corresponding carboxylic acid (0.00546 Mol) in HCl (3.5 ml, 4N) was refluxed for 6 h. Water (5 mL), and 0.5 g of charcoal were added, and the mixture was refluxed 10-15 min. After cooling, the mixture was filtered and resulted clear filtrate was washed with ether (2×10 mL). The water layer was neutralized with excess of diluted NH4OH, the precipitate was filtered, washed with water, and dried.2-Hydroxymethyl-5-trifluoromethoxybenzimidazole. Glycolic acid was used, R(HO)CH2. Yield 0.65 g (75 wt. %). M.p. 192-194 C. 1H NMR (DMSO-d6): 4.68 (d, 5.5 Hz, 2H), 5.67 (t, 5.5 Hz, 2H), 7.05 (d, J=8.0 Hz, 1H), 7.38 (s, 1H), 7.49 (br s, 1H), 12.48 (br s, 1H). 13C NMR (DMSO-d6): 57.62, 104.44, 110.79, 111.98, 114.70, 118.20, 120.08 (q, J=254.8 Hz), 143.21, 157.22. 19F NMR (DMSO-d6): -57.76. [M+1]+ 233.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 658-89-9, its application will become more common.

Reference:
Patent; The United States of America as represented by the United States Department of Energy; US8242284; (2012); B1;,
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Application of 36449-75-9, 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. 36449-75-9, name is 1-(2-Bromoethyl)-2-methoxybenzene, This compound has unique chemical properties. The synthetic route is as follows.

Example 76 3-(1-((3,5-Dimethylisoxazol-4-yl)methyl)-1H-pyrazol-4-yl)-1-(2-methoxyphenethyl)imidazolidine-2,4-dione Prepared as in example 52 from 3-(1-((3,5-dimethylisoxazol-4-yl)methyl)-1H-pyrazol-4-yl)imidazolidine-2,4-dione (example 1) and 2-methoxyphenethyl bromide. Yield: 52%. 1H NMR (DMSO-d6, 400 MHz): delta2.11 (s, 3H), 2.38 (s, 3H), 2.80 (t, J=7.2 Hz, 2H), 3.51 (t, J=7.2 Hz, 2H), 3.75 (s, 3H), 4.03 (s, 2H), 5.17 (s, 2H), 6.85 (t, J=7.2 Hz, 1H), 6.95 (d, J=8.4 Hz, 1H), 7.16-7.21 (m, 2H), 7.73 (s, 1H), 8.13 (s, 1H). MS M+H calculated 410.2. found 410.1. Melting point: 97-98 C. The title compound was shown to inhibit hT2R08 bitter receptor and had an IC50 of 0.14 muM. Example 52 3-(1-((3,5-Dimethylisoxazol-4-yl)methyl)-1H-pyrazol-4-yl)-1,5,5-trimethylimidazolidine-2,4-dione 3-(1-((3,5-Dimethylisoxazol-4-yl)methyl)-1H-pyrazol-4-yl)-5-methylimidazolidine-2,4-dione (example 41) (50 mg, 0.173 mmol) and 60% NaH (8 mg, 0.190 mmol) were mixed in DMF (1 mL) for 30 minutes. MeI (0.04 mL, 0.190 mmol) was added and the reaction was stirred an additional 4 hours. The reaction was acidified with 1N HCl and diluted with ethyl acetate (2 mL). The organic phase was dried, filtered and solvent was removed under a stream of nitrogen. The crude product was re-suspended in MeOH (1 mL) and purified by reversed phase HPLC (5 to 95% acetonitrile in H2O: 16 minutes gradient). The pure fractions were combined and solvent removed under vacuum to afford 3-(1-((3,5-dimethylisoxazol-4-yl)methyl)-1H-pyrazol-4-yl)-1,5,5-trimethylimidazolidine-2,4-dione as a white solid (25 mg, 50%). 1H NMR (CDCl3, (CDCl3, 400 MHz): delta 1.45 (s, 6H), 2.19 (s, 3H), 2.42 (s, 3H), 2.94 (s, 3H), 5.05 (s, 2H), 7.92 (s, 1H), 8.08 (s, 1H). The title compound was shown to inhibit hT2R08 bitter receptor and had an IC50 of 0.80 muM.

The chemical industry reduces the impact on the environment during synthesis 1-(2-Bromoethyl)-2-methoxybenzene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; SENOMYX, INC.; PATRON, Andrew; TACHDJIAN, Catherine; SERVANT, Guy; DITSCHUN, Tanya; (257 pag.)US2016/376263; (2016); A1;,
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