Category: ethers-buliding-blocks

Reference of 93919-56-3, 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. 93919-56-3, name is (4-(Trifluoromethoxy)phenyl)methanamine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

6-Methoxy-5-({[4-(trifluoromethoxy)benzyl]amino}methyl)-2-naphthoic acid methyl ester To a stirred solution of 6-methoxy-5-formyl-2-naphthoic acid methyl ester (1.09 g, 4.46 mmol) in EtOH (40 ML) at room temperature was added 4-trifluoromethoxy-benzyl amine (0.749 ML, 4.91 mmol) followed by HOAc (0.255 ML, 4.46 mmol).After 10 min. at this temperature, sodium cyanoborohydride (0.420 g, 6.69 mmol) was added, and reaction was continued stirring at rt for 4 h.After 1 h at this temperature, the reaction was heated to 45 C. for 2 h.The solution was quenched with sat. aq. NaHCO3 (20 ML) and then extracted with EtOAc (200 ML).The organic layer was washed with brine (20 ML) and dried (MgSO4).After concentration, the residue was purified by flash chromatography (0 to 10% MeOH:CHCl3 gradient) to afford the product (0.780 g, 42%) as a solid; 1H NMR (DMSO-d6) delta3.77 (s, 2H), 3.86 (s, 3H), 3.88 (s, 3H), 4.07 (s, 2H), 7.26 (d, J =8.0 Hz, 2H), 7.44 (d, J=8.6 Hz, 2H), 7.48 (d, J=9.2 Hz, 1H), 7.88 (dd, J=1.9, 8.9 Hz, 1H), 8.06 (d, J=5.2 Hz, 1H), 8.08 (d, J=5.3 Hz, 1H), 8.52 (d, J=1.7 Hz, 1H); mass spectrum [(+) El], m/z 420 (M+H)+.

The synthetic route of (4-(Trifluoromethoxy)phenyl)methanamine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Wyeth; US2004/127570; (2004); A1;,
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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. 54314-84-0, name is ((3-Bromopropoxy)methyl)benzene, This compound has unique chemical properties. The synthetic route is as follows., Formula: C10H13BrO

Magnesium (317.2 mg, 13.05 mmol) was suspended in 5 mL of ether, a solution of 2.30 mL (13.0 mmol) of 3-benzyloxypropyl bromide in 7 mL of ether was dropped into the suspension over 10 minutes, a flake of iodine was added thereto and the mixture was heated to reflux for 1 hour. The reaction mixture was cooled with an ice-methanol bath, a solution of 5.1 mg (0.011 mmol) of N-methoxy-N-methyl-(1-methylindole)-2-carboxamide in tetrahydrofuran was added thereto and the mixture was stirred at 0°C for 2 hours. Ice water was added to the reaction solution and the mixture was acidified with 6 mol/L hydrochloric acid and extracted with ether. The organic layer was washed with water and a saturated aqueous saline solutio dried over anhydrous sodium sulfate and the solvent was evaporated. The residue was purified with a silica gel column chromatography (hexane/ethyl acetate = 8/1) to give 0.79 g (54percent) of 2-(4-benzyloxy-1-oxobutyl)-1-methylindole.1H-NMR(270MHz, DMSO-d6, delta); 2.09(m, 2H), 3.10(t, J=7.3Hz, 2H), 3.58(t, J=6.1Hz, 2H), 4.05(s, 3H), 4.50(s, 2H), 7.15(m, 1H), 7.26-7.39(m, 8H), 7.69(dd, J=1.0Hz, 8.3Hz, 1H). Fab-MS(m/z); 308[M+1]+

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 54314-84-0.

Reference:
Patent; KYOWA HAKKO KOGYO CO., LTD.; EP1464645; (2004); A1;,
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Related Products of 910251-11-5, 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. 910251-11-5, name is Potassium trifluoro(methoxymethyl)borate, This compound has unique chemical properties. The synthetic route is as follows.

Example 33 Synthesis of rac-1-((1R,2R)-2-hydroxy-7-(methoxy methyl)-4,4-dimethyl-1,2,3,4-tetrahydronaphthalen-1-yl)-3-(5-methyl-2-(tetrahydro-2H-pyran-4-yl)pyridin-3-yl)urea A crude product (82 mg) of rac-1-((1R,2R)-7-bromo-2-hydroxy-4,4-dimethyl-1,2,3,4-tetrahydronaphthalen-1-yl)-3-(5-methyl-2-(tetrahydro-2H-pyran-4-yl)pyridin-3-yl)urea was obtained from the compound (63 mg) obtained in (Example 26) and the compound (50 mg) obtained in (Example 32) in the same method as in (Example 2) . Tris(dibenzylideneacetone)dipalladium (0) (34 mg), 2-dicyclohexylphosphino-2′,6′-diisopropoxy-1,1′-biphenyl (35 mg), potassium (methoxymethyl) trifluoroborate (0.14 g), cesium carbonate (0.24 g), 1,4-dioxane (1.0 mL), and water (0.25 mL) were added to this crude product (82 mg), and after purging with nitrogen by degassing under reduced pressure, the mixture was stirred at 110 C. for 15 hours. The reaction solution was filtered, and the filtrate was purified by preparative LC-Mass to obtain the title compound (12 mg).

The chemical industry reduces the impact on the environment during synthesis Potassium trifluoro(methoxymethyl)borate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; MOCHIDA PHARMACEUTICAL CO., LTD.; SAITOH, Fumihiko; NAGASUE, Hiroshi; (124 pag.)US2019/23657; (2019); A1;,
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Application of 109-85-3, 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. 109-85-3, name is 2-Methoxyethylamine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Compound4-amino-N-hydroxy-1,2,5-oxadiazole-3-carbamimidinyl chloride(4.0g, 24.7mmol)Soluble in ethyl acetate (40 ml),2-methoxyethane-1-amine (2.29 ml, 25.9 mmol) was added to the ice bath for 5 minutes.Additional triethylamine (5.16 ml, 37.05 mmol) was added and stirred for two hours until the reaction was complete.Washed with water, washed with saturated brine, dried over anhydrous sodium sulfate,Concentration under reduced pressure in vacuo gave compound 4-amino-N’-hydroxy-N-(2-methoxyethyl)-1,2,5-oxadiazol-3-carboximidamide 1d (4.5 g, 92 %).

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

Reference:
Patent; Jiangsu Hansoh Pharmaceutical Group Co., LTD (CN); Shanghai Hansoh Biomedical Co.,Ltd (CN); WU, SHENG HUA; GUO, FENG YING; LI, KAI LONG; HUANG, ZHI QIANG; BAO, RUDI; (94 pag.)TW2018/23219; (2018); A;,
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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. 2688-84-8, name is 2-Phenoxyaniline, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 2-Phenoxyaniline

Stage 2 (i) 2- amino diphenyl ether from (1.80g, 9.8mmol) and 2-methoxy-3-pyridine carboxaldehyde (2.0g, 14.6mmol) in a mixture 90 under hydrogen with 1h . The reaction mixture was cooled to 0 C., was added MeOH (20mL), then sodium borohydride (1.11g, 29.4mmol) was added over 20 minutes in small portions. The mixture was stirred for 24 h at RT. It was added formic acid (2.4g, 53.0mmol), and the mixture was stirred for 15 minutes. The solvent was removed in vacuo, the residue was quenched with 10% aqueous sodium bicarbonate (100 mL), and extracted with DCM (2 × 30mL), dried over magnesium sulfate, filtered and the solvent in vacuo It was removed. The crude material DCM (A): silica gel chromatography eluting with ethyl acetate (B) was obtained (2% (B), 80g, 2.0CV, 60mL / min) The impure product is purified by. Samples By crystallization from methanol, 2.2 g (73%) of (2-methoxy-pyridin-3-ylmethyl)-(2-phenoxy-phenyl)amine as a white solid

According to the analysis of related databases, 2688-84-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GE HEALTHCARE LIMITED; WADSWORTH, HARRY JOHN; TRIGG, WILLIAM JOHN; (36 pag.)JP5787873; (2015); B2;,
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Related Products of 39538-68-6, The chemical industry reduces the impact on the environment during synthesis 39538-68-6, name is 2-Methoxy-4-methylaniline, I believe this compound will play a more active role in future production and life.

General procedure: To a magnetically stirred ice-bath cooled solution of the selected succinic monoamide derivative (4 mmol) in anhydrous dioxane (20 ml) neat oxalyl chloride was added (8 mmol). After stirring over 30 min the reaction mixture was warmed to room temperature. Two hours later, the reaction mixture was re-cooled to 0 C in ice bath followed by drop wise addition of the particular aromatic amine (4 mmol) in pyridine (10 mL) to the reaction mixture. After stirring over 30 min the reaction mixture was warmed to room temperature and allowed to stir over 24 h. Subsequently, the reaction was carefully quenched with saturated sodium bicarbonate solution (200 mL). Finally, the mixture was filtered to offer the products as whitish to gray solids that were re-crystallized from acetone (see Scheme 2).

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-Methoxy-4-methylaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Habash, Maha; Taha, Mutasem O.; Bioorganic and Medicinal Chemistry; vol. 19; 16; (2011); p. 4746 – 4771;,
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Reference of 645-36-3,Some common heterocyclic compound, 645-36-3, name is 2,2-Diethoxyethanamine, molecular formula is C6H15NO2, 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 an amine of formula g or h (1.1 -1.5 eq) and triethylamine (1.1 eq) in dichloromethane (0.2 M) is added a solution of an acid chloride of formula XI (1 eq) in dichloromethane (0.2 – 1.0 M) at 0-5 C. The cooling bath is removed and the reaction mixture is allowed to warm to room temperature. After 2h the reaction mixture is partitioned between an organic solvent such ethyl acetate or tert-butyl methyl ether and water. The layers are separated. The aqueous layer is extracted with two portions of organic solvent. The combined organic layers are washed with one portion of saturated ammonium chloride solution, dried over anhydrous sodium sulfate and concentrated in vacuo to give an amide intermediate of formula XII or XIII, respectively. The title compound was obtained as white solid in quantitative yield from amino acetaldehyde diethyl acetal and tra/?s-4-chlorocarbonyl-cyclohexanecarboxylic acid methyl ester according to general procedure (III). MS m/e: 302 ([M+H]+)

The synthetic route of 645-36-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; DOLENTE, Cosimo; SCHNIDER, Patrick; WO2011/141396; (2011); A1;,
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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 52189-63-6 as follows. Formula: C8H9FO2

Example 16 Preparation of 5-fluororesorcinol (16) Using general method E, 3,5-dimethoxyfluorobenzene (5.0 g, 32.0 mmol, Aldrich) gives Compound 16 as 3.69 g (92%) of a colorless crystalline solid: m.p. 134-136 C.; 1 H-NMR (d6 -DMSO) 9.60 (s, 2H), 6.05 (s, 1H), 5.97 (d, 2H). 19 F-NMR (d6 -DMSO) 108.26 (t, J=11.1 Hz,). Anal. calc. for C6 H5 FO2: C, 56.26; H, 3.93. Found: C, 56.33; H, 3.98.

According to the analysis of related databases, 52189-63-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Molecular Probes, Inc.; US6162931; (2000); A;,
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These common heterocyclic compound, 102-52-3, name is 1,1,3,3-Tetramethoxypropane, 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. Quality Control of 1,1,3,3-Tetramethoxypropane

82.1 g (0.5 mol) of 1, 1, 3, 3-tetramethoxypropane and 39.7 g (0.45 mol) of 1,3-dimethylurea were dissolved in 400 ml of methanol, 49.0 g (0.5 mol) of concentrated sulfuric acid was added dropwise thereto at room temperature, and the mixture was allowed to undergo the reaction at 50C for 30 minutes. After completion of the reaction, this was cooled to room temperature, and the precipitated crystals were collected by filtration to obtain 59.7 g (yield 69%) of the title compound (purity 99.8%, melting point 203 – 205C).

The synthetic route of 1,1,3,3-Tetramethoxypropane has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sankio Chemical Co., Ltd.; EP1559711; (2005); A1;,
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Synthetic Route of 37466-89-0, The chemical industry reduces the impact on the environment during synthesis 37466-89-0, name is 3-Methoxybenzene-1,2-diamine, I believe this compound will play a more active role in future production and life.

General procedure: A dispersion of the according 1,2-phenylenediamine or aniline (1 eq) in butyric anhydride (3 eq) was treated with a few drops of concentrated hydrochloric acid and stirred at room temperature or heated at 40-120 C for 1.5-4 h. The reaction mixture was cooled to room temperature and the formed precipitate was either sucked off and washed with 1 N sodium hydroxide solution or the solution was further diluted with water and basified with 6 N sodium hydroxide solution to be extracted with DCM (2×). The combined organic phases were washed with brine, dried over anhydrous sodium sulfate, filtered and DCM was removed under reduced pressure. The mono- and bis-butyric anilide intermediates were refluxed with 4-6 N hydrochloric acid (~5-6 times of the weight) at 100 C for 2-14 h to obtain the corresponding benzimidazoles. The reaction mixture was then diluted with water and basified with 6N sodium hydroxide solution. After extraction with DCM (3×) the organic phases were collected, washed with brine, dried over anhydrous sodium sulfate and filtered. DCM was removed under reduced pressure. The products were purified by column chromatography (DCM/MeOH, 95:5 or EA/MeOH, 8:2).

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:
Article; Schoepf, Anna M.; Salcher, Stefan; Obexer, Petra; Gust, Ronald; European Journal of Medicinal Chemistry; vol. 185; (2020);,
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