Month: October 2020

3616-56-6, 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. 3616-56-6, name is 2,2-Diethoxy-N,N-dimethylethanamine, A new synthetic method of this compound is introduced below.

5.0 g (20.0 mmol) of the intermediate (A-11), 4.8 g (30.0 mmol) of (dimethylamino)acetaldehyde diethylacetal, and 78 ml of acetic acid were loaded and the mixture was stirred for 96 hr while being heated at 140¡ãC. The reaction solution was cooled to room temperature and then the solvent was removed by evaporation under reduced pressure. The resultant residue was purified by silica gel column chromatography to give 2.3 g (8.4 mmol, yield: 42 molpercent) of an intermediate (A-12). FD-MS, m/z 274 [M]

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; Nippon Steel & Sumikin Chemical Co., Ltd.; ISHIYAMA, Takaya; HAYASHIDA, Hiroyuki; SAKAI, Mitsuru; NIINA, Masashi; SHIRAISHI, Kazuto; YOSHIMURA, Kazuaki; EP2687530; (2014); A1;,
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20469-65-2, 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 20469-65-2 as follows.

1-iodo-3,5-dimethoxybenzene:A dried round bottom flaks was charged with 1-bromo-3,5-dimethoxy- benzene (15.0 g, 69.1 mmol) and dry tetrahydrofuran (275 cm3). The resulting solution was cooled down to -78 0C, then n-butyllithium (2.5 M in hexanes, 29.0 cm3, 72.6 mmol) was added dropwise over 10 minutes. The mixture was stirred at -78 0C for 1 hour, then 1,2-iodoethane (20.5 g, 72.6 mmol) in dry tetrahydrofuran (75 cm3) was added rapidly to the solution. After an additional 1 hour at -78 0C, the resulting mixture was warmed to room temperature and stirred overnight. The mixture was poured into saturated sodium thiosulfate solution (200 cm3), extracted with diethyl ether four times and dried over magnesium sulfate. The solvent was removed under reduced pressure, and the residue was recrystallized from methanol to obtain the title product as a white crystalline solid(13.0 g, yield 71 %). NMR (1H, 300 MHz1 CDCI3) : delta 6.85 (d, J = 2.3 Hz, 2H); 6.40 (t, J = 2.3 Hz, 1 H); 3.76 (s, 6H).

According to the analysis of related databases, 1-Bromo-3,5-dimethoxybenzene, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK PATENT GMBH; BLOUIN, Nicolas; MITCHELL, William; WANG, Changsheng; TIERNEY, Steven; WO2011/18144; (2011); A2;,
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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. 2752-17-2, name is 2,2′-Oxydiethanamine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. 2752-17-2

General procedure: The parent compound 9 (0.36g, 1mmol) was dissolved in CH2Cl2 (6mL), then oxalyl chloride (4mmol) was added dropwise. The mixture was stirred for 4h at the room temperature. The solvent and excess oxalyl chloride was evaporated to obtain the crude farnesylthiosalicyl chloride. Then to a mixture of different diamines (1.5mmol) and TEA (0.45mmol) in 10mL CH2Cl2 was added dropwise the CH2Cl2 solution (5mL) of farnesylthiosalicyl chloride (1.12g, 0.3mmol) at 0C over 1h. After stirring for another 0.5h the reaction was quenched by adding 20mL water. The mixture was extracted with CH2Cl2 (20mL¡Á3) and the organic layer was combined, washed with brine, dried with anhydrous Na2SO4 and concentrated in vacuo. The crude product was separated by silica gel chromatography (petroleum ether/ethyl acetate=1:1 v/v; then CH2Cl2-MeOH=4:1 as the eluent) to afford compound 10a-g and 11a-g as yellowish oil.

The synthetic route of 2752-17-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Ling, Yong; Wang, Zhiqiang; Zhu, Hongyan; Wang, Xuemin; Zhang, Wei; Wang, Xinyang; Chen, Li; Huang, Zhangjian; Zhang, Yihua; Bioorganic and Medicinal Chemistry; vol. 22; 1; (2014); p. 374 – 380;,
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Some common heterocyclic compound, 54149-17-6, name is 1-Bromo-2-(2-methoxyethoxy)ethane, molecular formula is C5H11BrO2, 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. 54149-17-6

Example 20 Synthesis and Utility of 2,7-dibromo-9,9-bis(3,6-dioxaheptyl)-fluorene Benzyltriethylammonium chloride (3.19 g, 14 mmole, 0.077 eq) and 2,7-dibromofluorene (59 g, 182 mmole, 1 equiv.) were suspended in 178 mL DMSO. 50% aqeous NaOH 80 mL was added. 1-Bromo-2-(2-methoxyethoxy)ethane (80 g, 437 mmole, 2.4 equiv.) was then added in small portions. The reaction was stirred at room temperature for 2 hours before it was stopped and the aqueous layer was extracted with ether. The combined ether layers were washed with water five times and dried over Na2SO4. The organic layer was filtered, evaporated to dryness and the residual was flash chromatographed on a silica-gel column to give the pure compound (73 g), in a yield of 86%. This compound can be used for example to modify the solubility parameter of the compound of Example 16. To do this 2,7-dibromo-9,9-bis(3,6-dioxaheptyl)-fluorene is used in place of 2,7-dibromo-9,9-dioctyl fluorene in Example 16.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 54149-17-6, its application will become more common.

Reference:
Patent; 3M Innovative Properties Company; US7271406; (2007); B2;,
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A common compound: 702-24-9, name is 4-Methoxy-N-methylbenzylamine, belongs to ethers-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 702-24-9

A mixture of ethyl 6-bromopyrazolo[1,5-a]pyrimidine-3-carboxylate (1.5 g, 5.55 mmol), N-(4- methoxybenzyl)-N-methylamine (1.67 g, 11.04 mmol) and N,N-diisopropylethylamine (2.75 ml, 16.63 mmol) in ethanol (25ml) was stirred at 85 ¡ãC for 96h. The mixture was concentracted to dryness and the residue was purified by column chromatography (eluent 50percent ethyl acetate: petroleum ether) to afford ethyl 6-[(4-methoxyphenyl)methyl-methyl-amino]pyrazolo[1,5- a]pyrimidine-3-carboxylate (1120 mg, 57.5percent yield) as a yellow solid. (ESI): m/z = 341.2 [M+1]+.

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, 702-24-9, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; BRYAN, Marian, C.; GOBBI, Alberto; KIEFER, James, Richard, Jr.; KOLESNIKOV, Aleksandr; OLIVERO, Alan, G.; DROBNICK, Joy; LIANG, Jun; RAJAPAKSA, Naomi; (846 pag.)WO2017/108723; (2017); A2;,
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2930-05-4, 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. 2930-05-4, name is 2-((Benzyloxy)methyl)oxirane belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route 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.

The synthetic route of 2930-05-4 has been constantly updated, and we look forward to future research findings.

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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The chemical industry reduces the impact on the environment during synthesis 1535-75-7, name is 2-(Trifluoromethoxy)aniline, I believe this compound will play a more active role in future production and life. 1535-75-7

2-Trifluoromethoxyaniline (0.8Og, 5.0mmol) and sodium hydride (60% dispersion in mineral oil, 1.7eq) were stirred in dry DMF at room temperature for 2 hours, and 5-bromo- 2-chloropyridine (1.0Og, 5.0mmol) was added and the mixture stirred at room temperature overnight. Iced water was added slowly to the mixture, and the mixture was extracted with DCM (3x). The DCM was washed with 2M HCl solution (2x), dried (MgSO4), and concentrated. The residue was purified by column chromatography eluting using a gradient (EtOAc/hexanes 1 :9 v/v).

The chemical industry reduces the impact on the environment during synthesis 1535-75-7. I believe this compound will play a more active role in future production and life.

Reference:
Patent; BioMarin IGA, Ltd.; WREN, Stephen Paul; WYNNE, Graham Michael; LECCI, Cristina; WILSON, Francis Xavier; DAVIS, Paul James; WO2010/57833; (2010); A1;,
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22236-10-8, A common heterocyclic compound, 22236-10-8, name is 4-(Difluoromethoxy)aniline, molecular formula is C7H7F2NO, 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: N-formylation of amines by CO2 and DMAB in the presence of UiO-66 as a catalyst was carried out in autoclave. The synthesis of formamides is as follows, Amines (5.0 mmol), UiO-66 (10 mg), DMAB (1.5 equiv.), DMF (7 mL) were added in the reactor at room temperature, reactor was closed, flushed two to three times by CO2 and 1 MPa CO2 pressure was introduced into reactor, then the reactor was heated to required temperature with continuous stirring. After the reaction was complete, the reactor was cooled, and the CO2 pressure was carefully discharged from the autoclave. The UiO-66 MOF was separated by centrifugation. The resultant mixture was concentrated by rotary evaporator and subjected to the column chromatography with ethyl acetate-petroleum ether used as an eluent to obtain the product. All the products are confirmed by GCMS.

The synthetic route of 22236-10-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Phatake, Vishal V.; Mishra, Ashish A.; Bhanage, Bhalchandra M.; Inorganica Chimica Acta; vol. 501; (2020);,
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The chemical industry reduces the impact on the environment during synthesis 2252-44-0, name is 3-(Trifluoromethoxy)bromobenzene, I believe this compound will play a more active role in future production and life. 2252-44-0

EXAMPLE 92 (RR,SS)-3-(2-methoxyphenyl)-2-methyl-3-(1-naphthyl)-2-({4-[3-(trifluoromethoxy)phenyl]piperazin-1-yl}carbonyl)propanenitrile (RR,SS)-3-(2-methoxyphenyl)-2-methyl-3-(1-naphthyl)-2-(piperazin-1-ylcarbonyl)propanenitrile (377 mg, 0.913 mmol), meta-trifluoromethoxy bromobenzene (200 mg, 0.830 mmol), sodium tert-butoxide (111 mg, 1.16 mmol), tris(dibenzylideneacetone) dipalladium (0) (22.8 mg, 0.025 mmol), racemic BINAP (31 mg, 0.05 mmol), and toluene (3 mL) were combined in a Carius tube, vacuum degassed, placed under an argon atmosphere, sealed and heated to 80 C. overnight. The reaction was cooled, taken up in diethyl ether, filtered, washed with water, saturated aqueous sodium bicarbonate, brine, dried over MgSO4, filtered, evaporated, and purified on slica gel (10% hexanes/CH2Cl2) to yield 255 mg of the title compound as a white powder. 1H NMR 500 MHz (DMSO-D6): delta 7.97 (d, 1H, J=7.18 Hz), 7.88 (m, 1H), 7.84 (m, 1H), 7.78 (d, 1H, J=8.25 Hz), 7.52 (t, 1H, J=7.48 Hz), 7.41 (m, 2H), 7.30 (t, 1H, J=8.25 Hz), 7.23 (td, 1H, J=7.79 Hz, 1.68 Hz), 7.12 (m, 2H), 6.91 (dd, 1H, J=8.40 Hz, 1.68 Hz), 6.79 (m, 2H), 6.72 (d, 1H, J=8.09 Hz), 6.01 (s, 1H), 4.01 (s, 3H), 3.68 (bs, 4H0, 3.16 (bs, 4H) 1.63 (s, 3H) MS (ESI) m/z 574 ([M+H]+); Anal. calcd for C33H30F3N3O3. 0.35 C6H14: C, 69.82; H, 5.83; N, 6.96. Found: C, 69.81 H, 5.91; N, 6.74.

The chemical industry reduces the impact on the environment during synthesis 2252-44-0. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Wyeth; US2005/256132; (2005); A1;,
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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 2-cyanoacetate (0.89 mL, 10.1 mmol) inDMF (20 mL) at rt was added sodium hydride (0.97 g, 24.2 mmol),and the reaction mixture was stirred at rt for 15 min. Tetrabutylammoniumiodide (0.37 g, 1.0 mmol) and ((2-bromoethoxy)methyl)benzene (3.35 mL, 21.19 mmol) were added, and the reactionmixture was stirred at 90 C for 3 h. Water was added and theaqueous layer was extracted with ether (3). The combinedorganic layers were washed with brine, dried over anhydroussodium sulfate, and filtered, and the filtrate was concentrated togive the crude product. The crude product was purified by silicagel chromatography eluting with 0?30percent EtOAc/hexanes to give14 (2.4 g, 65percent yield) as a colorless oil. 1H NMR (500 MHz, CDCl3)d 7.41?7.27 (m, 10H), 4.49 (s, 4H), 3.78?3.69 (m, 5H), 3.45 (s,3H), 2.49?2.40 (m, 2H), 2.06 (dt, J = 14.2, 4.7 Hz, 2H). LC/MS m/z:(M+H)+ calcd for C22H26NO4, 368.19; found 368.3.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1462-37-9, its application will become more common.

Reference:
Article; Wu, Yong-Jin; Guernon, Jason; McClure, Andrea; Luo, Guanglin; Rajamani, Ramkumar; Ng, Alicia; Easton, Amy; Newton, Amy; Bourin, Clotilde; Parker, Dawn; Mosure, Kathleen; Barnaby, Omar; Soars, Matthew G.; Knox, Ronald J.; Matchett, Michele; Pieschl, Rick; Herrington, James; Chen, Ping; Sivarao; Bristow, Linda J.; Meanwell, Nicholas A.; Bronson, Joanne; Olson, Richard; Thompson, Lorin A.; Dzierba, Carolyn; Bioorganic and Medicinal Chemistry; vol. 25; 20; (2017); p. 5490 – 5505;,
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