Tag: M.W=100-200

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. 4457-67-4, name is 1-Bromo-4-methoxybutane, A new synthetic method of this compound is introduced below., Formula: C5H11BrO

EXAMPLE 10 10-Hydroxy-10-(4-methoxybutyl)-2,3,4,10-tetrahydropyrimido[1,2-a]indole Ether (60 ml) and 4-bromo-1-methoxy-butane (10.2 g) were added to magnesium turnings (1.46 g). After formation of the Grignard reagent, the mixture was cooled to 0¡ã and 3,4-dihydropyrimido[1,2-a]indol-10(2H)-one (3.72 g) in dry 1,2-dichloroethane (20 ml) added dropwise over 20 minutes. The solution was stirred under argon at 0¡ã C. for 1 hour, poured onto a swirling mixture of ice (100 ml) and saturated aqueous ammonium chloride (60 ml) and the mixture was stirred for a further 20 minutes. The mixture was concentrated in vacuo and the aqueous residue extracted with chloroform (3*100 ml). The extracts were dried (Na2 SO4) and concentrated in vacuo. Ether (20 ml) was added and the product was filtered and recrystallized from ethyl acetate to give the title compound or the free base (3.55 g), m.p. 128¡ã-139¡ã C. The free base was acidified with ethereal HCl to give the title compound as the hydrochloride, m.p. 178¡ã-179¡ã C. Found: C, 61.55; H, 7.55; N, 8.80percent C16 H22 N2 O2.HCl requires: C, 61.85; H, 7.45; N, 9.0percent.

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; John Wyeth & Brother Ltd.; US4784996; (1988); A;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Synthetic Route of 2186-92-7,Some common heterocyclic compound, 2186-92-7, name is P-anisaldehyde dimethyl acetal, molecular formula is C10H14O3, 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: Under an atmosphere of argon, to a mixture of benzaldehyde dimethyl acetal (0.152 g, 1.0 mmol) and Al-MCM-41 (30 mg, Si/Al=48, dried prior to use at 120 C for 1 h under vacuum) in dichloromethane (1.5 mL), allyltrimethylsilane (0.172 g, 1.5 mmol) in dichloromethane (0.5 mL) was added through a syringe at 30 C. The reaction mixture was stirred at 30 C for 45 min. The catalyst was removed by filtration and washed with dichloromethane (40 mL). After the filtrate was concentrated under reduced pressure, almost pure homoallyl methyl ether was obtained. Further purification by silica-gel column chromatography (hexane to hexane/Et2O=10:1) afforded 4-methoxy-4-phenylbut-1-ene[27] and 27(a) as a colorless oil (0.151 g, 93%).

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

Reference:
Article; Ito, Suguru; Hayashi, Akira; Komai, Hirotomo; Yamaguchi, Hitoshi; Kubota, Yoshihiro; Asami, Masatoshi; Tetrahedron; vol. 67; 11; (2011); p. 2081 – 2089;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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. 126940-10-1, name is 1-Fluoro-3-(methoxymethoxy)benzene, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 126940-10-1

To a solution of 1 -fluoro-3-(methoxymethoxy)benzene (25 g, 130.2 mmol, 1 .0 eq) in dry THF (250 mL) and dry cyclohexane (40 mL) was added sec-BuLi (121.82 mL, 195.3 mmol, 1.5 eq) dropwise at -78 C under argon, the resulting mixture stirred for 2 h at the same temperature, then 1 ,1 ,2- trichloro-1 ,2,2-trifluoroethane (62 ml_, 520.3 mmol, 4.0 eq) was added and the mixture stirred for 10 mins at the same temperature. TLC analysis indicated formation of a polar spot then the reaction mass was quenched with saturated NH4CI solution, and the reaction mixture was dissolved in ether (2×500 ml_) and washed with brine (2×200 ml_) and water (2×200 ml_). The separated organic layer was dried over Na2S04 and concentrated under reduced pressure to afford crude product which was purified by column chromatography (silica gel, 100-200 mesh) using 1 % EtOAc in petroleum ether as an eluent to afford 2- chloro-1 -fluoro-3-(methoxymethoxy)benzene (20 g, 45.1 %) as a pale yellow colored liquid.

According to the analysis of related databases, 126940-10-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ONTARIO INSTITUTE FOR CANCER RESEARCH (OICR); AL-AWAR, Rima; ISAAC, Methvin; CHAU, Anh My; MAMAI, Ahmed; WATSON, Iain; PODA, Gennady; SUBRAMANIAN, Pandiaraju; WILSON, Brian; UEHLING, David; (191 pag.)WO2019/119145; (2019); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Electric Literature of 2338-54-7, A common heterocyclic compound, 2338-54-7, name is 4-Fluoro-3-methylanisole, molecular formula is C8H9FO, 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.

1-Fluoro-4-methoxy-2-methylbenzene a11 (0.0140 g, 0.10 mmol), acridine photosensitizer (A) (0.0029 g, 0.005 mmol) and L-guanidine were added sequentially under argon atmosphere. Ethyl acetate b1 (0.0218 g, 0.15 mmol), 1,2-dichloroethane (DCE) 2.0 mL.The reaction was irradiated for 48 hours under a 6W blue light at room temperature.After completion of the reaction, the solvent was evaporated under reduced pressure and purified by column chromatography, eluting solvent: (V) petroleum ether / (V) ethyl acetate = 20/1.A yellow liquid (28) (0.0140 g, 83%) was obtained.

The synthetic route of 2338-54-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Central China Normal University; Zhou Shaolin; Shi Weimin; (27 pag.)CN110294685; (2019); A;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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 127657-97-0 as follows. Formula: C11H16O3

D-tryptophan methyl ester hydrochloride (4.07 g, 16 mmol) and Intermediate 14 (3.75 g, 19 mmol) were combined with stirring in a solution of IPA (80 mL) and water (20 mL). To the resulting mixture was added 2N HCl (2 mL) and the resulting mixture heated at 70 C. for 18 hours. The mixture was neutralized with saturated aqueous NaHCO3, then extracted with methylene chloride (2¡Á400 mL). The combined organic extracts were dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by flash column chromatography, eluting with methylene chloride/acetone (98:2), to provide the cis-carboline Intermediate 15 as an orange oil (1.5 g, 27%): TLC Rf (6:1 methylene chloride/ethyl acetate)=0.49; 1H NMR (300 MHz, CDCl3): delta: 8.46 (s, 1H), 7.50.(d, J=0.7 Hz, 1H), 7.47-7.25 (m, 6H), 7.18-7.06 (m, 2H), 4.65 (s, 2H), 4.44-4.39 (m, 2H), 3.88-3.82 (m, 1H), 3.81 (s, 3H), 3.66 (t, J=8.7 Hz, 1H), 3.18-3.11 (m, 1H), 2.88-2.78 (m, 1H), 1.87 (bs, 1H).

According to the analysis of related databases, 127657-97-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Orme, Mark W.; Schultze, Lisa M.; Sawyer, Jason Scott; Daugan, Alain Claude-Marie; Brown, Raymond; US2003/236263; (2003); 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. 4457-67-4, name is 1-Bromo-4-methoxybutane, A new synthetic method of this compound is introduced below., Quality Control of 1-Bromo-4-methoxybutane

Step A: N-(1,1-Dimethylethyl)-3,4-dihydro-4-hydroxy-2-(4-methoxybutyl)-2H-thieno[3,2-e]-1,2-thiazine-6-sulfonamide 1,1-dioxide The product from Example 3, Step A (8.75 g, 0.26 mol) was dissolved in DMF (25 mL) and the solution was cooled to -0¡ã C. Sodium hydride (1.56 g of an oil dispersion, 0.03 mol) was added, stirred for 30 min, and then 4-methoxybutyl bromide (8.6 g,0.052 mol) in DMF (15 mL) was added; this mixture was warmed to room temperature and stirred for 15 hr. A saturated aqueous solution of ammonium chloride (20 mL) was added and the mixture was extracted with ethyl acetate (5*50 mL). The combined extracts were washed with brine (10 mL), dried (MgSO4) and evaporated to an oil which was purified by column chromatography (silica, gradient: 50percent to 60percent ethyl acetate/hexane) to give the desired product (9.5 g, 86percent) as a yellow oil.

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; Alcon Laboratories, Inc.; US5378703; (1995); A;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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 2106-18-5 as follows. Quality Control of 2-(Trifluoromethoxy)fluorobenzene

To a solution of 1-fluoro-2-(trifluoromethoxy)benzene [2106-18-5] (20.0 g, 111 mmol) in dry THF (200 mL), cooled to -78C, was added dropwise n-BuLi (2.5 M solution in n-hexane; 65 mL, 160 mmol) and subsequently TMEDA (60 mL). The reaction mixture was stirred for additional 60 min at -78C, followed by addition of a solution of iodine (30.2 g, 120 mmol) in dry THF (50 mL). The resulting mixture was stirred for 1 h and then quenched by addition of a saturated aqueous NH4CI solution (20 mL). The organic layer was washed with 1 N HCI, water and brine, and dried over MgS04. Volatiles were removed in vacuo to afford the title compound as yellow oil. The product was used in the next reaction step without further purification. MS (LC/MS): 306.0 [M+H]+.

According to the analysis of related databases, 2106-18-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NOVARTIS AG; ALTMANN, Eva; HOMMEL, Ulrich; LORTHIOIS, Edwige Liliane Jeanne; MAIBAUM, Juergen Klaus; OSTERMANN, Nils; QUANCARD, Jean; RANDL, Stefan Andreas; SIMIC, Oliver; VULPETTI, Anna; ROGEL, Olivier; WO2012/93101; (2012); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Some common heterocyclic compound, 93489-14-6, name is (4-Ethoxy-3-methoxyphenyl)methanamine, molecular formula is C10H15NO2, 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. name: (4-Ethoxy-3-methoxyphenyl)methanamine

Ethyl 2- (4 , 5-dibromo-6-oxopyridazin-l (6H) -yl) acetate (500 mg, 1.47 mmol) and 3-ethoxy-4-methoxybenzylamine(960 mg, 4.41 mmol) in 1, 4-dioxane-water (1:1, 5 mL) were stirred with triethylamine (0.615 mL) at 100C for 2.5 hours. After cooling, ethyl acetate was added, and the organic layer was washed with saturated aqueous ammonium chloride and saturated aqueous sodium chloride and dried over anhydrous magnesium sulfate, and the solvent was removed by distillation. The resulting residue was purified by silica gel chromatography (chloroform/2- propanol = 20/1) to give the desired product (640 mg, 98% yield) .Morphology: pale yellow solid LC/MS: Condition 3, retention time 3.70 min LC/MS (ESI+) :440, 442 [MH-I] + LC/MS(ESI-) :438, 440 [M-I]-

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 93489-14-6, its application will become more common.

Reference:
Patent; NISSAN CHEMICAL INDUSTRIES, LTD.; WO2009/57827; (2009); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Reference of 14093-86-8, 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. 14093-86-8, name is 1-Methoxy-2-methylnaphthalene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

EXAMPLE 1 STR1 In a four-necked, round-bottomed flask fitted with a stirrer, a thermometer, a cooler and a dropping funnel, were placed 0.5 g of potassium ferricyanide, 17.2 g of 1-methoxy-2-methylnaphthalene (90% content), 10 ml of water and 100 ml of glacial acetic acid. The mixture was heated with stirring, and dropping of 35% hydrogen peroxide was started when the internal temperature reached 55 C., with the total amount (33 g) being added over a period of one hour. Stirring was further continued for four hours while maintaining the internal temperature within the range of 50 to 60 C. High-performance liquid chromatography (HPLC) was used to confirm the consumption of 1-methoxy-2-methylnaphthalene. At the end of reaction, 200 ml of hot water (about 50 C.) was added and the resulting mixture was extracted twice with 200 ml each isopropylether. To the combined extracts were added 200 ml of n-hexane and 5 g of activated charcoal, the mixture was stirred at 50 C. for 30 minutes, and the insoluble matters and activated charcoal were filtered off. The filtrate was dried over anhydrous magnesium sulfate and concentrated, giving 9.5 g (61.0%) of 2-methyl-1,4-naphthoquinone as yellow crystals. The purity was 98.8% when measured by HPLC (relative peak-area method; UV detection at 254 nm).

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-Methoxy-2-methylnaphthalene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Eisai Chemical Co., Ltd.; US4906411; (1990); A;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Electric Literature of 15799-79-8, A common heterocyclic compound, 15799-79-8, name is 3-Methoxy-N,N-dimethylaniline, molecular formula is C9H13NO, 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: A round-bottom flask was chargedwith N,N-dialkyl aniline dissolved in toluene solution, under N2 condition. TBHP was added drop wise and reaction was stirred for 2 min. Triethylamine was added thereafter, and then the contents of the reaction were stirred for 3 h at 110 C under inert N2 condition. The reaction mixture was washed 2-3 times with H2O and ethyl acetate. The upper organic layer was separated and dried over sodium sulphate and then subjected to rotavapour. The crude mixture was purified by column chromatography on silica gel (60-120).

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

Reference:
Article; Botla, Vinayak; Barreddi, Chiranjeevi; Daggupati, Ramana V; Malapaka, Chandrasekharam; Journal of Chemical Sciences; vol. 128; 9; (2016); p. 1469 – 1473;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem