Month: September 2021

Reference of 886762-08-9, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 886762-08-9 name is 5-Bromo-2-(trifluoromethoxy)aniline, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

General procedure: To a solution of 76 (120 mg, 0.37 mmol) in dry pyridine (12 mL) under N2 at RT, was added 2,4-difluorobenzenesulphonyl chloride (159 mg, 0.74 mmol) in CH2Cl2 (1.5 mL) dropwise over 5 min. The mixture was stirred at 45 C under N2 for 16 , and the solvent then removed under reduced pressure. The reaction was quenched with a little water and the resulting solid collected by filtration and washed with water and Et2O. Purification was carried out by trituration with hot CH2Cl2/MeOH solution to give 4 as a pale brown solid (65%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Bromo-2-(trifluoromethoxy)aniline, and friends who are interested can also refer to it.

Reference:
Article; Spicer, Julie A.; Miller, Christian K.; O’Connor, Patrick D.; Jose, Jiney; Huttunen, Kristiina M.; Jaiswal, Jagdish K.; Denny, William A.; Akhlaghi, Hedieh; Browne, Kylie A.; Trapani, Joseph A.; European Journal of Medicinal Chemistry; vol. 137; (2017); p. 139 – 155;,
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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. 1579-40-4, name is Di-p-tolyl Ether, A new synthetic method of this compound is introduced below., HPLC of Formula: C14H14O

In einem mit Argon begasten 100 ML Reaktor werden 2 g 4, 4′-OXYBIS (toluen) (CAS Reg. Nr. 1579-40-4) [10 mmol] in 39.2 ml Acetonitril unter Zusatz von 0.8 ML Dimethylsulfoxid [11. 2 mmol] bei 75 C geloest. Zur Loesung werden 60 mg Cu (OAc) 2, 30 mg FES04-7 H20 und 10 ml Wasser beigefuegt. 10.8 g NA2S208 geloest in 30 ML Wasser werden anschliessend unter heftigem Ruehren zugetropft. Nach 45 Minuten ist die Reaktion beendet. Die organische Phase wird mit Ethylacetat erschoepfend extra- hiert. Die gebildeten Produkte werden mit Hilfe der HPLC untersucht. Die Ausbeute des Dialdehyds 4, 4′-OXYBIS (benzaldehyd) (CAS Reg. Nr. 2215-76-1) betraegt 87 mol%. Damit liegt diese Ausbeute gegenueber den Ausbeuten mit bisher bekannten Oxidationsverfahren von 30-40% wesentlich hoeher, wodurch sich die Selektivitaet des erfindungsgemaessen Verfahrens auszeichnet.

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; TEX-A-TEC AG; WO2004/43891; (2004); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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.

B. 3-Benzyloxyphenyl isocyante. To a stirred solution of 3-benzyloxyaniline (507 mg, 2.54 mmol) in toluene (5 mL) containing TEA (740 muL, 5.34 mmol) was added 20percent phosgene in toluene (1.5 mL, 2.83 mmol). The reaction was stirred for 20 h at rt. The organic layer was washed with H2O (20 mL), dried (MgSO4) and concentrated to give a clear brown oil (497 mg, 87percent). The material was used in subsequent steps without charaterization.

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

Reference:
Patent; Butler, Christopher R.; Edwards, James P.; Fourie, Anne M.; Grice, Cheryl A.; Karlsson, Lars; Savall, Brad M.; Tays, Kevin L.; Wei, Jianmei; US2006/223792; (2006); A1;,
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These common heterocyclic compound, 36805-97-7, name is 1,1-Di-tert-butoxy-N,N-dimethylmethanamine, 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. Formula: C11H25NO2

Hexadecandioic acid (40.0 g, 140 mmol) was suspended in toluene (250 ml) and the mixture was heated toreflux. N,N-Dimethylformamide di-tert-butyl acetal (76.3 g, 375 mmol) was added drop-wise over 4 hours. The mixturewas refluxed overnight. The solvent was removed in vacuo at 50 C, and the crude material was suspended in dichloromethane/ethyl acetate (500 ml, 1:1) and stirred for 15 mins. The solids were collected by filtration and triturated withdichloromethane (200 ml). The filtrated were evaporated in vacuo to give crude mono-tert-butyl hexadecandioate, 30grams. This material was suspended in dichloromethane (50 ml), cooled with ice for 10 mins, and filtered. The solventwas removed in vacuo to leave 25 gram crude mono-tert-butyl hexadecandioate, which was recrystallized from heptane(200 ml) to give mono-tert-butyl hexadecandioate, 15.9 g (33 %). Alternatively to recrystallization, the mono-ester canbe purified by silica chromatography with ethyl acetate/heptane. 1H-NMR (CDCl3) delta: 2.35 (t, 2H), 2.20 (t, 2H), 1.65-1.55(m, 4H), 1.44 (s, 9H), 1.34-1.20 (m, 20 H).

The synthetic route of 1,1-Di-tert-butoxy-N,N-dimethylmethanamine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Novo Nordisk A/S; HOEG-JENSEN, Thomas; JAKOBSEN, Palle; SENSFUSS, Ulrich; FLEDELIUS, Christian; RIBEL-MADSEN, Ulla; (32 pag.)EP2448962; (2016); B1;,
Ether – Wikipedia,
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54149-17-6, name is 1-Bromo-2-(2-methoxyethoxy)ethane, 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. Recommanded Product: 1-Bromo-2-(2-methoxyethoxy)ethane

Hydrazinemonohydrate and ethanol were put into a reaction container under a nitrogen atmosphere. A compound represented by Formula 1-122-1) was added, rollowed by heating and stirring The resultant product was concentrated to obtain a mixture containing a compound represented ny Formula (i-±2/–L)

The synthetic route of 54149-17-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DIC CORPORATION; TENG, Yan; HORIGUCHI, Masahiro; KADOMOTO, Yutaka; KOISO, Akihiro; HAYASHI, Masanao; SAITOU, Yoshitaka; LI, Zhimin; (201 pag.)WO2017/79867; (2017); A1;,
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Adding some certain compound to certain chemical reactions, such as: 1535-73-5, name is 3-Trifluoromethoxyaniline, 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 1535-73-5. 1535-73-5

General procedure: To a stirred solution of 11 (13.14 mmol) in 1,2-dichloroethane (240 mL) were added appropriate substituted anilines (19.71 mmol) and AcOH (13.14 mmol), and the mixture was heated to reflux for 2 h under nitrogen atmosphere. The reaction mixture was cooled to 0 °C, and MeOH (60 mL) and THF (20 mL) were added. To it, (AcO)3BHNa (26.20 mmol) or NaBH4 (52.56 mmol) was added portionwise, and then the reaction mixture was allowed to warm to room temperature and stirred for an additional 3 h. The pH of the reaction mixture was adjusted to 7?8 at 0 °C with 1 NHCl, and then the organic layer was separated. The aqueous layer was extracted with CH2Cl2 (2× 300 mL). The combined organic layers was washed with brine (300 mL) and dried over anhydrous Na2SO4, filtered, and evaporated to dryness under reduced pressure. The residue was purified by MPLC on silica gel to afford the titled compounds as a solid.

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 3-Trifluoromethoxyaniline.

Reference:
Article; Jin, Cheng Hua; Krishnaiah, Maddeboina; Sreenu, Domalapally; Subrahmanyam, Vura Bala; Park, Hyun-Ju; Park, So-Jung; Sheen, Yhun Yhong; Kim, Dae-Kee; Bioorganic and Medicinal Chemistry; vol. 22; 9; (2014); p. 2724 – 2732;,
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Ether | (C2H5)2O – PubChem

Reference of 20781-20-8, 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. 20781-20-8, name is (2,4-Dimethoxyphenyl)methanamine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

According to Scheme 35, a 10 mL micro wavable vial was charged with compound 10 (250 mg, 0.73 mmol), 2,4-dimethoxybenzylamine (Aldrich, 0.54 mL, 3.63 mmol), Pd2(dba)3 (21 mg, 0.036 mmol), NaOBu-t (140 mg, 1.46 mmol), BINAP (45 mg, 0.07 mmol) and dioxane/DMF (3 mL/1 mL). The mixture was purge with argon and then stirred at 160C under microwave for 20 min. The reaction mixture was cooled to room temperature and diluted with EtOAc. The EtOAc was isolated and dried over MgS04. The EtOAc was evaporated and the residue was subjected to flash column chromatography (hexanes/EtOAc) to give compound 11 as white solid (yield 55%) (m/z + H) 474.

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, (2,4-Dimethoxyphenyl)methanamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PURDUE PHARMA L.P.; NI, Chiyou; SHAO, Bin; TAFESSE, Laykea; YAO, Jiangchao; YU, Jianming; ZHOU, Xiaoming; WO2012/35421; (2012); A2;,
Ether – Wikipedia,
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Synthetic Route of 36865-41-5, The chemical industry reduces the impact on the environment during synthesis 36865-41-5, name is 1-Bromo-3-methoxypropane, I believe this compound will play a more active role in future production and life.

To a solution of the compound of Reference Example 76-1 (94.0 mg, 0.21 mmol) in DMF (5 mL), potassium carbonate (87.0 mg, 0.63 mmol) and 1-bromo-3-methoxypropane (48.0 mg, 0.31 mmol) were added, and the mixture was stirred at room temperature overnight. A saturated aqueous solution of ammonium chloride was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with a saturated aqueous solution of ammonium chloride twice and with a saturated saline solution once, then dried over sodium sulfate and filtered, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain the title compound (105.0 mg, 96%). MS (ESI+) 522 (M+1, 100%)

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-Bromo-3-methoxypropane, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Sumitomo Dainippon Pharma Co., Ltd.; IKUMA Yohei; FUKUDA Nobuhisa; IWATA Masato; KIMURA Hidenori; SUZUKI Kuniko; EP2876105; (2015); 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. 7252-83-7, name is 2-Bromo-1,1-dimethoxyethane, A new synthetic method of this compound is introduced below., category: ethers-buliding-blocks

[000398] A mixture of Compound 24A (10 g, 89 mmol), 2-bromo-l,l- dimethoxyethane(15 g, 89 mmol), K2C03 (18.4 g, 134 mmol), KI (100 mg) in DMF (100 mL) was stirred at reflux for 3 h, then cooled to rt, and filtered. The filtrate was added water (200 mL), extracted with ethyl acetate (100 mL x 2), washed with water (100 mL x 3), brine (100 mL x 1), dried over Na2S04, concentrated, and purified by silica gel column chromatography (ethyl acetate in petroleum ether, 10% v/v) to render Compound 24B (15 g, yield 85%>) as a colorless liquid. 1H-NMR (CDC13, 400 MHz) major characteristic peaks: delta (ppm) 3.46 (s, 6H), 3.96 (d, J= 5.2 Hz, 2H), 4.71 (t, J= 5.6 Hz, 1H), 6.90 (m, 2H), 7.26 (m, 2H).

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; BIOMARIN PHARMACEUTICAL INC.; WANG, Bing; CHU, Daniel; BRIDGES, Alexander, James; WO2015/42397; (2015); 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. 437-83-2, name is 3-Fluoro-2-methoxyaniline, A new synthetic method of this compound is introduced below., Application In Synthesis of 3-Fluoro-2-methoxyaniline

General procedure: NaNO2 (12.0 g, 173 mmol, in 40 mL of water) solution was addeddropwise to the mixture of 3-fluoro-2-methoxyaniline (20.0 g, 158 mmol) in 200 mL of hydrobromic acid (47 %) and100 mL of water at -5 ~ 0 C and stirred for 1 hour. This solution was then added slowly to the suspension of CuBr(45.2 g, 315 mmol) in 50 mL of hydrobromic acid (47 %) at 0 C. The resulting mixture was stirred at 0 C for 1 hourthen warmed to 50 C and stirred for 1 hour. The reaction mixture was poured into ice water and extracted withether (2 X 500 mL). The combined organic layer was washed with brine, dried over anhydrous Na2SO4 and concentratedto give 1-bromo-3-fluoro-2-methoxybenzene.

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; Merck Sharp & Dohme Corp.; PASTERNAK, Alexander; BLIZZARD, Timothy; CHOBANIAN, Harry; DE JESUS, Reynalda; DING, Fa-Xiang; DONG, Shuzhi; GUDE, Candido; KIM, Dooseop; TANG, Haifeng; WALSH, Shawn; PIO, Barbara; JIANG, Jinlong; (128 pag.)EP2744499; (2016); B1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem