Category: ethers-buliding-blocks

Synthetic Route of 239122-51-1,Some common heterocyclic compound, 239122-51-1, name is 5-Bromo-3-fluoro-2-methoxyaniline, molecular formula is C7H7BrFNO, 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) N- (5-Bromo-3-fluoro-2-methoxy-phenyl)-2- [(E)-hydroxyiminol -acetamideIn a 500 ml three-necked flask, 2,2,2-trichloroethane-1,1-diol (8.68 g, 52.5 mmol) and sodium sulfate (47.4 g, 334 mmol) were combined with water (122 ml) to give a colorless solution. The reaction mixture was heated to 50 C and a mixture of 5-bromo-3-fluoro-2-methoxyaniline (CAS239122-51-1, 10.50 g, 47.7 mmol) in water (60 ml), dioxane (60 ml) and aqueous hydrochloricacid (7.84 ml, 95.4 mmol) were added. Then hydroxylamine hydrochloride (9.95 g, 143 mmol)in water (60 ml) was added. The reaction mixture was heated to 70 C and stilTed for 15 hoursand then cooled to room temperature. The precipitate was filtered off and washed with water (50ml) and dried in vacuo to yield the title compound as brown solid (13.4 g, 96 %). MS: mle =289.1, 291.3 [M-H].

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-3-fluoro-2-methoxyaniline, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; BISSANTZ, Caterina; BONNAFOUS, Rene; BUETTELMANN, Bernd; JAKOB-ROETNE, Roland; LERNER, Christian; RUDOLPH, Markus; WO2014/102233; (2014); 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. 15799-79-8, name is 3-Methoxy-N,N-dimethylaniline, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 3-Methoxy-N,N-dimethylaniline

[0092] (R)-3-(4-Dimethylamino-2-methoxy-phenyl)-pentanal (Table 1, entry 3): To a 2-dram vial equipped with a magnetic stir bar was added (2S,5S)-5-benzyl-2-tert-butyl-3-methylimidazolidin-4-one (24.6 mg, 0.100 mmol, 0.200 equiv), CH2Cl2 (0.50 ml), HCl (as a 4N solution in 1,4-dioxane, 25.0 uL, 0.100 mmol, 0.200 equiv), and N,N-dimethyl-m-anisidine (73.3 uL, 0.500 mmol, 1.00 equiv). The solution was cooled to -50o C. before pentenal (98.0 uL, 1.00 mmol, 2.00 equiv) was added. After 62 h, the reaction mixture was subjected directly to silica gel chromatography. Elution with 20% EtOAc in hexanes followed by concentration and removal of residual pentenal under vacuum afforded the product as a colorless oil in 68% yield (79.5 mg, 0.338 mmol); 88% ee. IR (film) 2959, 2926, 2871, 2839, 2800, 2721, 1718, 1616, 1569, 1517, 1351, 1237, 1136, 1034, 979.5, 812.9 cm-1;1H NMR (300 MHz, CDCl3) ?9.63 (t, J=2.8 Hz, 1H, CHO), 6.97 (d, J=8.2 Hz, 1H, ArH), 6.30 (dd, J=2.5, 8.3 Hz, 1H, ArH), 6.26 (d, J=2.5 Hz, 1H, ArH), 3.81 (s, 3H, OCH3), 3.40 (dt, J=7.3, 7.4 Hz, 1H, ArCH), 2.94 (s, 6H, N(CH3)2), 2.66 (dd, J=2.7, 7.4 Hz, 2H, CH2CO), 1.72-1.61 (m, 2H, CH2CH3), 0.83 (t, J=7.4 Hz, 3H, CH2CH3); 13C NMR (75 MHz, CDCl3) 203.8, 158.2, 150.6, 128.4, 119.8, 105.0, 96.5, 55.5, 49.7, 1.1, 34.9, 28.4, 12.4. HRMS (CI) exact mass calcd for (C14H21NO2) requires m/z 236.1650 for [M+H]+, found m/z 236.1649. [?]D=-18.9 (c=0.970, CHCl3). The enantiomeric ratio of the product was determined by HPLC analysis of the corresponding alcohol (obtained by NaBH4 reduction) using a Chiracel AD and AD guard column (3.0% ethanol/hexanes, 1 mL/min); S isomer tr=11.5 min, R isomer tr=12.4 min.

According to the analysis of related databases, 15799-79-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MacMillan, David W.C.; Paras, Nick A.; US2003/236438; (2003); 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. 15799-79-8, name is 3-Methoxy-N,N-dimethylaniline, A new synthetic method of this compound is introduced below., category: ethers-buliding-blocks

[0095] (S)-4-Benzoyloxy-3-(4-dimethylamino-2-methoxy-phenyl)-butyraldehyde (Table 1, entry 4): To a 2-dram vial equipped with a magnetic stir bar was added (2S,5S)-5-benzyl-2-tertbutyl-3-methylimidazolidin-4-one (24.6 mg, 0.100 mmol, 0.100 equiv), N,N-dimethyl-anisidine hydrochloride (18.8 mg, 0.100 mmol., 0.100 equiv), CHCl3 (1.00 ml), and N,N-dimethyl-m-anisidine (132 uL, 0.900 mmol, 0.900 equiv). The solution was cooled to -20o C. before 4-benzoyloxy-crotonaldehyde (0.380, 2.00 mmol, 2.00 equiv) was added as a solid. After 24 h, the reaction mixture was subjected directly to silica gel chromatography. Gradient elution with 10-25% EtOAc in hexanes followed by concentration and removal of residual pentenal under vacuum afforded the product as a colorless oil in 89% yield (304 mg, 0.889 mmol); 92% ee. IR (film) 2940, 2892, 2836, 2724, 1719, 1615, 1518, 1273, 1240, 1117, 712.5 cm-1; 1H NMR (300 MHz, CDCl3) ?9.74 (t, J=2.1 Hz, 1H, CHO), 8.01 (ddd, J=0.6, 1.1, 6.3 Hz., 2H, ArH), 7.58-7.40 (m, 3H, ArH), 7.08 (d, J=8.2 Hz, 1H, ArH), 6.30 (dd, J=2.5, 8.5 Hz, 1H, ArH), 6.25 (d, J=2.4 Hz, 1H, ArH), 4.51 (dd, J=5.5, 10.7 Hz, 1H, CH2O), 4.42 (dd, J=8.2, 10.7 Hz, 1H, CH2O), 4.08-3.98 (m, 1H, ArCH), 3.83 (s, 3H, OCH3), 2.98-2.80 (m, 2H, CH2CO), 2.95 (s, 6H, N(CH3); 13C NMR (75 MHz, CDCl3) 202.2, 166.6, 158.2, 151.3, 133.1, 130.3, 129.8, 129.0, 128.6, 115.6, 104.9, 96.3, 67.9, 55.4, 46.3, 50.0, 33.5. HRMS (CI) exact mass calcd for (C20H23NO4) requires m/z 342.1705 for [M+H]+, found m/z 342.1705. [?]D =-16.9 (c=0.751, CHCl3). The enantiomeric ratio of the product was determined by HPLC analysis of the corresponding alcohol (obtained by NaBH4 reduction) using a Chiracel AD and AD guard column (10% ethanol/hexanes, 1 mL/min); R isomer tr=15.2 min, S isomer tr=24.0 min.

The synthetic route of 15799-79-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MacMillan, David W.C.; Paras, Nick A.; US2003/236438; (2003); A1;,
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Some common heterocyclic compound, 578-58-5, name is 2-Methylanisole, molecular formula is C8H10O, 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. Recommanded Product: 2-Methylanisole

a) A solution of 24 g of 2-methylanisole, 35 g of N-bromosuccinimide and 1.24 g of dibenzoyl peroxide in 150 ml of carbon tetrachloride was heated to boiling under reflux for 12 hours. After cooling the solution was filtered and the filtrate is evaporated. The residue was recrystallized from hexane. There were obtained 18.6 g (47%) of 4-bromo-2-methylanisole as a colorless solid; m.p. 66-68.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 578-58-5, its application will become more common.

Reference:
Patent; Hoffmann-La Roche Inc.; US5214046; (1993); A;,
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456-55-3, name is (Trifluoromethoxy)benzene, 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. Quality Control of (Trifluoromethoxy)benzene

Example 1 4-Bromomethyl-1-trifluoromethoxybenzene 300 g of trifluoromethoxybenzene, 111 g of paraformaldehyde, 456 g of sodium bromide, and 900 ml of glacial acetic acid were initially charged and heated at 90 C. To release hydrogen bromide, a mixture of 450 ml of glacial acetic acid and 678 g of concentrated sulfuric acid was then added dropwise. After the addition had ended, the reaction mixture was stirred at 90 C. for 20 hours. The reaction mixture was then poured onto 1,000 g of ice and extracted twice with in each case 300 ml of methyl tert-butyl ether. The combined organic extracts were washed with 100 ml of water and concentrated. The residue was distilled at 20 hPa in a spinning band column. This gave 324.3 g of 4-bromomethyl-1-trifluoromethoxybenzene as a colorless liquid (60% of theory) of b.p. 82-83 C.

The synthetic route of 456-55-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Marhold, Albrecht; Muller, Peter; US2002/82454; (2002); A1;,
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Adding a certain compound to certain chemical reactions, such as: 151414-47-0, name is 2,6-Difluoro-4-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 151414-47-0, Recommanded Product: 151414-47-0

c) N-(2,6-difluoro-4-methoxyphenyl)-2-ri-(4-fluorophenyl)-3-r2-(4- methoxyphenyl)ethyll-5-oxo-2-sulfanylideneimidazolidin-4-yllacetamide (example 97) Oxalyl chloride (65 mu; 0.74 mmol; 2 eq) and dimethylformamide (1 drop) were added to a solution of 2-[l-(4-fluorophenyl)-3-[2-(4-methoxyphenyl)ethyl]-5-oxo-2- sulfanylideneimidazolidin-4-yl]acetic acid (1-21) (150 mg; 0.37 mmol; 1 eq) in dichloromethane (6 mL). The reaction mixture was stirred at room temperature for 2 hours. Then, 2,6-difluoro-4-methoxyaniline (T61) (89 mg; 0.56 mmol; 1.5 eq) and pyridine (90 mu; 1.11 mmol; 3 eq) were added. The reaction mixture was stirred at room temperature for 4 hours. Water (20 mL) was added and the aqueous layer was extracted with ethyl acetate (3 x 35 mL). The combined organic layers were washed with saturated sodium chloride (20 mL), dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude was purified on silica gel using dichloromethane/ethyl acetate (95/5) as an eluent. After trituration in diethyl ether/ethanol the title compound N-(2,6-difluoro-4-methoxyphenyl)-2-[l-(4- fluorophenyl)-3-[2-(4-methoxyphenyl)ethyl]-5-oxo-2-sulfanylideneimidazolidin-4- yl]acetamide was obtained in 10% yield (20 mg) as a white powder. 1H-NMR (DMSO-d6): delta (ppm) 2.92 (m, 2H), 3.14 (m, 1H), 3.41 (m, 1H), 3.76 (m, 7H), 4.1 (m, 1H), 4.73 (s, 1H), 6.85 (m, 4H), 7.3 (m, 6H), 9.8 (s, 1H); MS (ESI+): m/z = 544.2 [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, 2,6-Difluoro-4-methoxyaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; VIVALIS; GUEDAT, Philippe; BERECIBAR, Amaya; CIAPETTI, Paola; VENKATA PITHANI, Subhash; TROUCHE, Nathalie; WO2013/171281; (2013); A1;,
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Adding a certain compound to certain chemical reactions, such as: 10075-63-5, name is 1,5-Dimethoxynaphthalene, 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 10075-63-5, Application In Synthesis of 1,5-Dimethoxynaphthalene

To a suspensionof 1,5-dimethoxy-naphthalene (3.76 g, 20 mmol)in acetonitrile (50 mL) was added NBS (3.9 g,22 mmol) at room temperature. Upon stirring for 2 h,the precipitate was filtered off and washed with acetonitrile thus giving the crude product which wasrecrystallized from methanol and dried. Cyan-bluesolid, yield 88%. 1H NMR spectrum, delta, ppm: 3.85 s(3H), 3.90 s (3H), 6.74-7.13 m (2H), 7.29-7.48 m(1H), 7.54-7.87 m (2H). 13C NMR spectrum, delta, ppm:55.51, 55.72, 105.05, 107.99, 108.26, 114.92, 125.94,128.76, 132.23, 133.67, 154.69, 155.48.

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, 1,5-Dimethoxynaphthalene, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Dong; Zhang; Huang; Meng; Li; Russian Journal of General Chemistry; vol. 87; 4; (2017); p. 837 – 841; Zh. Obshch. Khim.; vol. 87; 4; (2017); p. 837 – 841,5;,
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Related Products of 6850-60-8,Some common heterocyclic compound, 6850-60-8, name is (4-Ethoxyphenyl)methanamine, molecular formula is C9H13NO, 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 solution of carboxylic acid (0.5 mmol) and HATU (0.55 mmol)in anhydrous DMF (2 mL) was stirred at ambient temperature for10 min. To this solution, DIPEA (0.6 mmol) and correspondingamine (0.54 mmol) were added successively and the mixture wasstirred for 18 h. After concentration under reduced pressure, thereaction mixture was treated with water (5 mL) and extracted withDCM (2 5 mL). After evaporation of the solvent, the residue wascrystallized from an appropriate solvent or subjected to columnchromatography on silica gel (DCM/MeOH) or preparative HPLC

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

Reference:
Article; Krasavin, Mikhail; Gureyev, Maxim A.; Dar’in, Dmitry; Bakulina, Olga; Chizhova, Maria; Lepikhina, Anastasia; Novikova, Daria; Grigoreva, Tatyana; Ivanov, Gleb; Zhumagalieva, Aisulu; Garabadzhiu, Alexander V.; Tribulovich, Vyacheslav G.; Bioorganic and Medicinal Chemistry; vol. 26; 9; (2018); p. 2651 – 2673;,
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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. 92028-21-2, name is 6-Methoxy-[1,1′-biphenyl]-3-amine hydrochloride, A new synthetic method of this compound is introduced below., COA of Formula: C13H14ClNO

Under nitrogen, compound X (from Example 38 part a) (5.0 g, 16.7 mmol) was mixed with toluene (80 mL) and 4-methoxy-3-phenylaniline hydrochloride (4.3 g, 18.3 mmol) was added to form a slurry. 2,2′-Bis(diphenylphosphino)-1,1′-binaphthyl (1.6 g, 2.5 mmol) was added, followed by tris(dibenzylideneacetone)dipalladium(0) (760 mg, 0.83 mmol) and finally sodium tert-butoxide (5.3 g, 55 mmol). The mixture was heated at 90 C. for 150 min and then cooled to room temperature. Water (150 mL) was added followed by ethyl acetate (150 mL) and the phases partitioned. The aqueous layer was extracted with ethyl acetate (150 mL) and the combined organics washed three times with 0.5 M sodium bisulfate (200 mL), once with saturated sodium bicarbonate (150 mL) and twice with saturated sodium chloride (150 mL). The organics were dried over magnesium sulfate (50 g) and the volatiles removed under vacuum to give N-tert-butoxycarbonyl-2-[4-(3-[phenyl-4-methoxyphenyl)aminophenyl]ethylamine (LL) (8.4 g) which was used without further purification.

The synthetic route of 92028-21-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Moran, Edmund J.; Jacobsen, John R.; Leadbetter, Michael R.; Nodwell, Matthew B.; Trapp, Sean G.; Aggen, James; Church, Timothy J.; US2003/229058; (2003); A1;,
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Adding a certain compound to certain chemical reactions, such as: 239122-51-1, name is 5-Bromo-3-fluoro-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 239122-51-1, Product Details of 239122-51-1

A solution of 2 (1 eq) and sodium carbonate (1.5 eq) in acetone was stirred in an ice bath under an atmosphere of nitrogen. Thiophosgene (1.5 eq) was added drop wise over 30 minutes. The reaction was stirred for another 30 minutes in the ice bath before being removed and allowed to warm to RT. The reaction was stirred at RT for 1.5 h before the reaction solution was concentrated under vacuum. Toluene was added to the crude product and removed under vacuum to azetrope off any residual thiophosgene and afford the product 3. MS: MH+=262

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; Amiri, Payman; Fantl, Wendy; Levine, Barry Haskell; Poon, Daniel J.; Ramurthy, Savithri; Renhowe, Paul A.; Subramanian, Sharadha; Sung, Leonard; US2004/122237; (2004); A1;,
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