Tag: M.W=100-200

Electric Literature of 1535-73-5,Some common heterocyclic compound, 1535-73-5, name is 3-Trifluoromethoxyaniline, molecular formula is C7H6F3NO, 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) [3-(trifluoromethoxy)phenyl]hydrazine hydrochloride 3-(Trifluoromethoxy)aniline (3.68 ml) was dissolved in 6 M hydrochloric acid (71 ml), and an aqueous solution (4.7 ml) of sodium nitrite (2.08 g) was added dropwise over 20 min at -5° C. Tin (II) chloride (1.954 ml) was dissolved in 6 M hydrochloric acid (25 ml), and the solution was cooled to -5° C., and added quickly to the above-mentioned reaction mixture at -5° C. The mixture was stirred at -5° C. for 2 hr, and the precipitated solid was collected by filtration, washed with 0.1M hydrochloric acid, and dried under reduced pressure to give the title compound (2.72 g). 1H NMR (300 MHz, CDCl3) delta 6.81-7.03 (3H, m), 7.41 (1H, t, J=8.3 Hz), 8.64 (1H, br. s.), 10.35 (2H, br. s.)

The synthetic route of 1535-73-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Yoshikawa, Masato; Suzuki, Shinkichi; Hasui, Tomoaki; Fushimi, Makoto; Kunitomo, Jun; Kamisaki, Haruhi; Taniguchi, Takahiko; US2013/150344; (2013); 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. 54149-17-6, name is 1-Bromo-2-(2-methoxyethoxy)ethane, This compound has unique chemical properties. The synthetic route is as follows., Formula: C5H11BrO2

Example 7 (+-)-3-{1-[2-(2-Methoxyethoxy)ethyl]-trans-3,4-dimethylpiperidinyl}phenol To a solution of (+-)-3-(trans-3,4-dimethylpiperidinyl)phenol (60 mg, 0.29 mmol) in N,N-dimethylformamide (5.0 mL) at room temperature was added sodium hydrogencarbonate (27 mg, 0.32 mmol), and 1-bromo-2-(2-methoxyethoxy)ethane (59 mg, 0.32 mmol). The solution was heated at 120 C. for 1 hour, cooled and then water (10 mL) was added. The aqueous layer was extracted with ethyl acetate and the combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo to give a crude oil. This was purified by preparative HPLC on a Dynamax column, 42*250 mm; flow 8.0 mL min-1; employing U.V. detection at 275 nm; eluant gradient of acetonitrile:0.05 M aqueous ammonium acetate solution (90:10 to 10:90) to afford the title compound (71 mg, 80%) as its acetate salt. 1H-NMR (data for the acetate salt): 0.82 (d, 3H), 1.35 (s, 3H), 1.72 (m, 1H), 2.03-2.10 (m, 4H), 2.38 (m, 1H), 2.81-3.13 (m, 6H), 3.40 (s, 3H), 3.50-3.63 (m, 4H), 3.70-3.78 (m, 2H), 6.68 (m, 1H), 6.81-6.82 (m, 2H), 7.18 (t, 1H). MS (TSI+): m/z [MH+] 308.3; C18H29NO3+H requires 308.2.

According to the analysis of related databases, 54149-17-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Pfizer Inc.; US6518282; (2003); B1;,
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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. 171290-52-1, name is 3,5-Dimethoxyphenylacetylene, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 3,5-Dimethoxyphenylacetylene

Compound 3-iodo-1-((2- (trimethylsilyl) ethoxy) methyl) -1H-pyrazole 4-formamidine 2c (2.7 g, 7.3 mmol), 1-ethynyl-3,5-dimethoxybenzene (1.78 g, 11 mmol), triethylamine (2.2 g, 21.9 mmol), bis (triphenylphosphonium) palladium chloride (512 mg, 0.73 mmol) and anhydrous tetrahydrofuran (70 mL) were mixed, deoxygenated, and stirred at room temperature under an argon atmosphere for 15 hours.The solvent was removed under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate / petroleum ether = 10/1 to 2/1) to give the target product 3-((3,5-dimethoxyphenyl) acetylene Yl) -1-((2- (trimethylsilyl) ethoxy) methyl) -1H-pyrazole-4-carboxamide 2d (1.5 g, yellow solid), yield: 51%.

According to the analysis of related databases, 171290-52-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BEIJING TIANCHENG PHARMA CO., LTD.; CHEN, XIANGYANG; GAO, YINGXIANG; KONG, NORMAN XIANGLONG; (118 pag.)TW2019/38538; (2019); A;,
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Electric Literature of 6851-80-5,Some common heterocyclic compound, 6851-80-5, name is 1-(2-Methoxyphenyl)-N-methylmethanamine, 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: To a mixture of the corresponding R1R2NH (3.0 mmol), anhydrous K2CO3 (449 mg, 3.25 mmol) and KI (20.75 mg, 0.125 mmol) in CH3CN (12 ml) were added the appropriate intermediates 6-9 (2.5mmol). The reaction mixture was warmed to 60-65 C and stirred for 6-8 h under an argon atmosphere. After complete reaction, the solvent was evaporated under reduced pressure. Then water (25 mL) was added to the residue and the mixture was extracted with dichloromethane (25 mL×3). The combined organic phases were washed with saturated aqueous sodium chloride (30 mL), dried over sodium sulfate, and filtered. The solvent was evaporated to dryness under reduced pressure. The residue was purified on a silica gel chromatography using mixtures of petroleum ether/EtOAc as eluent, obtaining the corresponding intermediates 10-13a-d.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-(2-Methoxyphenyl)-N-methylmethanamine, its application will become more common.

Reference:
Article; Li, Yuxing; Qiang, Xiaoming; Li, Yan; Yang, Xia; Luo, Li; Xiao, Ganyuan; Cao, Zhongcheng; Tan, Zhenghuai; Deng, Yong; Bioorganic and Medicinal Chemistry Letters; vol. 26; 8; (2016); p. 2035 – 2039;,
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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. 707-07-3, name is (Trimethoxymethyl)benzene, This compound has unique chemical properties. The synthetic route is as follows., Safety of (Trimethoxymethyl)benzene

General procedure: To a solution of 2′-hydroxy-2-nitroacetophenone (13.3 g, 0.074 mol) in trimethyl orthoformate (66.4 mL) was added concentrated sulfuric acid (0.36 g). The reaction mixture was then refluxed for 6 h and distilled to a dry residue. The solid that formed was washed with water and recrystallized from methanol to give a brown solid in 84% yield (11.7 g).

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 707-07-3.

Reference:
Article; Iaroshenko, Viktor O.; Mkrtchyan, Satenik; Gevorgyan, Ashot; Vilches-Herrera, Marcelo; Sevenard, Dmitri V.; Villinger, Alexander; Ghochikyan, Tariel V.; Saghiyan, Ashot; Sosnovskikh, Vyacheslav Ya.; Langer, Peter; Tetrahedron; vol. 68; 11; (2012); p. 2532 – 2543;,
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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. 82830-49-7, name is 2-Fluoro-1,4-dimethoxybenzene, A new synthetic method of this compound is introduced below., Computed Properties of C8H9FO2

A 3-neck 1-liter flask equipped with a low temperature thermometer, N2 line, and dropping funnel was charged with 1,4-dimethoxy-2-fluorobenzene (20.42 g, 131 mmol). The solid was dissolved in distilled THF (450 mL) and cooled to an internal temperature of -74 C. A 2.5 M solution of n-BuLi in hexane (63 mL, 157 mmol) was subsequently added over 25 min. under N2 via a dropping funnel. The reaction was maintained at -75 C. for 30 min., before adding solid sulfur (5.01 g, 157 mmol) in one portion. Nitrogen sparging of the reaction mixture was begun at this time and continued throughout the reaction. The internal temperature rose to -65 C. but quickly recorded to -75 C. The reaction temperature was maintained at -75 C. for 30 min. At this time, the excess dry ice in the dry ice/acetone bath was removed and the reaction was allowed to slowly warm to -20 C. over 1.5 h. The reaction was quenched with 2 N HCl with vigorous N2 bubbling until the color of the reaction turned pale yellow. The internal temperature of the reaction rose to 10 C. The reaction was extracted with EtOAc. The organic layer was collected, washed with brine, dried over MgSO4, filtered, and concentrated in vacuo. The yellow residue was purified by silica gel chromatography with 20% EtOAc/hexane as the eluant to give the desired product as a light yellow solid. 1H 600 MHz NMR(CDCl3) ppm(delta): 3.84 (s, 3H), 3.86 (s, 3H), 6.56 (dd, J=1.8 Hz, J=8.9 Hz, 1H), 6.70 (t, 1H).

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; DiNinno, Frank P.; Hammond, Milton Lloyd; US2003/225132; (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. 41365-75-7, name is 1-Amino-3,3-diethoxypropane, A new synthetic method of this compound is introduced below., Recommanded Product: 1-Amino-3,3-diethoxypropane

General procedure: 3.2. Reaction of Wang Resin 1 with Trichloroacetonitrile and Fmoc-amino Alcohol (Resin 2)Wang resin 1 (1 mmol/g loading, 1 g) was suspended in 10 mL of anhydrous DCM, then 1.5 mL oftrichloroacetonitrile was added, and the resin was left in a freezer for 30 min. Next, a solution of 100 Lof DBU in 2 mL of anhydrous DCM was added, and the slurry was shaken for 1 h. The resin waswashed with anhydrous DCM (3) and anhydrous THF (3). The solution of Fmoc-amino alcohol(3 mmol) in 10 mL of anhydrous THF was added to the resin, followed by the dropwise addition of63 L of a solution of BF3Et2O, and the slurry was shaken for 30 min. Resin 2 was washed THF (3),MeOH (3), and DCM (5). A sample of the resin was washed with MeOH (3) and dried, and10 mg was cleaved with 50% TFA for 30 min, and the product quantified (Fmoc absorbance at 300 nm).Typical loading was between 0.35-0.50 mmol/g.3.3. Acylation with a-Bromocarboxylic Acids (Resins 3 And 13)Resin 2 (1 g) was washed with DCM and DMF, Fmoc was deprotected with 50% piperidine inDMF for 15 min, and the resin was washed with DMF (3) and DCM (5). Reaction of the resinwith a solution of -bromocarboxylic acid (5 mmol) in 10 mL of DCM was carried out in a syringewith a frit, and DIC (2.5 mmol, 386 L) was added. After 5 min, DIU was filtered, and the solutionwas transferred to the syringe with resin 1 and shaken for 1 h. When bromoacetic acid was used,DIEA (2.5 mmol, 436 L) was also added. Then, the resin was washed with DCM (3)._ 3.4. Reaction with Amino-aldehyde Dialkyl Acetal and N-Derivatization (Resin 4)Resin 3 (1 g) was washed with DMF (3), a solution of amino-aldehyde dialkyl acetal (10 mmol)and DIEA (10 mmol, 1.74 mL) in 10 mL of DMF was added, and the slurry was shaken for 2 h.An analytical sample was taken for analysis, reacted with 0.5 M Fmoc-OSu in DCM for 1 h and cleavedwith 50% TFA for 30 min.Resin from the previous step was split into four 250 mg portions, which were washedwith reaction solvent: DCM for sulfonamides (Ns-Cl, Tos-Cl) (1 mmol) and DMSO for 4-fluoro-3-nitrobenzotrifluoride (1 mmol). Then, 3 mL of the reaction solvent and DIEA (1.8 mmol, 174 L) wasadded, and the slurry was shaken for 2 h (in the case of sulfonamides) or overnight (in the case of4-trifluoromethyl-2-nitroaryl). Resin 4 was washed with the reaction solvent (3) and then DCM (3).A sample for analysis was reacted with 0.5 M Fmoc-OSu in DCM for 1 h and cleaved with 50% TFA for30 min.

The synthetic route of 41365-75-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Gimenez-Navarro, Vanesa; Krch?ak, Viktor; Molecules; vol. 23; 5; (2018);,
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Application of 10541-78-3, The chemical industry reduces the impact on the environment during synthesis 10541-78-3, name is 2-Methoxy-N-methylaniline, I believe this compound will play a more active role in future production and life.

EXAMPLE 3 STR52 (Process (a)) 5.69 g (0.02 mol) of 2-chlorosulphonylaminocarbonyl-4-ethyl-5-methoxy-2,4-dihydro-3H-1,2,4-triazol-3-one are introduced into 150 ml of methylene chloride, and a solution of 2.74 g (0.02 mol) of 2-methoxy-N-methylaniline and 2.02 g (0.02 mol) of triethylamine in 20 ml of methylene chloride is added to this mixture at 20 C. The reaction mixture is stirred for 60 minutes at 20 C. It is then washed three times using 150 ml of water in each case, dried using sodium sulphate and filtered. The filtrate is concentrated under a water pump vacuum and the residue is recrystallized from isopropanol. 3.2 g (40% of theory) of 2-(2-methoxy-N-methyl-phenylamino)-sulphonylaminocarbonyl-4-ethyl-5-methoxy-2,4-dihydro-3H-1,2,4-triazol-3-one of melting point 134 C. are obtained.

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

Reference:
Patent; Bayer Aktiengesellschaft; US5654438; (1997); A;,
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Synthetic Route of 768-70-7, 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. 768-70-7, name is 3-Ethynylanisole belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: To a mixture of alpha-azidoamide 16aa (34 mg, 0.20 mmol) and phenylacetylene (9a; 24 L,0.20 mmol) in t-BuOH/H2O (2 mL, 1:1) were added 0.5 M CuSO4 (0.020 mL, 0.010 mmol) and 1.0 M sodium ascorbate (0.020 mL, 0.020 mmol). The reaction mixture was stirred at room temperature for 1 day, and then the resulting reaction mixture was filtered. The separated solid was washed with H2O and hexanes, and triturated with hexane/EtOAc (10:1) to give the 1-morpholino-2-(4-phenyl-1H-1,2,3-triazol-1-yl)ethanone (2aaa; 52 mg, 96%) as a white solid

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

Reference:
Article; Lee, Doohyun; Kim, Daehun; Lee, Seungyeon; Kim, Taegeum; Kim, Joobin; Kim, Sohee; Liu, Kwang-Hyeon; Lee, Sangkyu; Bae, Jong-Sup; Song, Kyung-Sik; Cho, Chang-Woo; Son, Youn Kyung; Baek, Dong Jae; Lee, Taeho; Molecules; vol. 20; 11; (2015); p. 19984 – 20013;,
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Synthetic Route of 24332-20-5, 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 24332-20-5 as follows.

To a solution of 1,1,2-trimethoxy-ethane (25.0 g, 208.07 mmol) in methanol (125 mL) was added NH2OH.HCl (14.45 g, 208.07 mmol) at 0 C. The mixture was stirred for 16 h at room temperature. The mixture was cooled to 10 C. and aqueous NaOH solution (8.32 g, 208 mmol in 65 mL water) was added. The mixture was then stirred for 4 h at room temperature. The mixture was concentrated in vacuo and the remanence extracted with EtOAc (2×100 mL). The combined organic layers were dried over Na2SO4 and evaporated to dryness to give the crude oxime as a pale yellow liquid (12.0 g, 62%).

According to the analysis of related databases, 24332-20-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; H. Lundbeck A/S; US2012/252853; (2012); A1;,
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