Tag: M.W=100-200

321-28-8,Some common heterocyclic compound, 321-28-8, name is 1-Fluoro-2-methoxybenzene, molecular formula is C7H7FO, 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.

Step 1: Preparation of 3′-fluoro-4′-methoxy-acetophenone Aluminum chloride, (80.0 g, 0.6 mol) and chloroform (750 mL) were placed in a 2 L three-necked round bottom flask fitted with a mechanical stirrer and cooled by means of an ice bath. To the stirred solution acetyl chloride (51.0 g, 0.65 mol) was added dropwise, maintaining the temperature between 5-10 C. The mixture was stirred for 10 minutes at 5 C. before the dropwise addition at 5-10 C. of 2-fluoroanisole (62.6 g, 0.5 mol). The mixture was stirred at 0-10 C. for 1 hour and poured into ice (1 L). The resultant layers were separated and the aqueous layer was extracted with dichloromethane (2*250 mL). The combined organic layers were washed with water (2*150 mL), dried over anhydrous MgSO4, filtered and concentrated in vacuo to a volume of 300 mL. Hexanes were added and a white solid formed which was isolated by filtration and air dried. This material was recrystallized from a mixture of dichloromethane and hexanes to afford (77.2 g, 92%) of material suitable for use in the next step: mp 92-94 C.; 1 H NMR (DMSO-d6) 7.8 (m, 2H), 7.3 (t, 1H), 3.9 (s, 3H), 2.5 (s, 3H).

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

Reference:
Patent; G.D. Searle & Co.; US5760068; (1998); A;,
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6346-09-4, 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. 6346-09-4, name is 4,4-Diethoxybutan-1-amine, A new synthetic method of this compound is introduced below.

General procedure: To the cooled solution (5-8) of appropriate sulfonyl chloride (20 mmol) and triethylamine (3.5 ml) in dichloromethane (100 ml) 4,4-diethoxybutane-1-amine (3.4 g, 20 mmol) was added. Reaction mixture was stirred at room temperature for 12 h, washed with saturated NaHCO3 solution in water (100 ml). Organic layer was separated, dried over MgSO4 and evaporated to give target compounds 1.

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:
Article; Gazizov, Almir S.; Smolobochkin, Andrey V.; Anikina, Ekaterina A.; Voronina, Julia K.; Burilov, Alexander R.; Pudovik, Michail A.; Synthetic Communications; vol. 47; 1; (2017); p. 44 – 52;,
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54149-17-6, Adding some certain compound to certain chemical reactions, such as: 54149-17-6, name is 1-Bromo-2-(2-methoxyethoxy)ethane, 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 54149-17-6.

General procedure: DBU (4.5mmol) and 1-bromo-2-methoxyethane or 1-(2?-methoxyethoxy)-2-bromoethane were added to a solution of a triterpenic acid 1, 2, 3, 4 (2.2mmol) in the mixture of CH2Cl2 (6mL) and MeCN (2mL). The reaction mixture was stirred for 2 days at room temperature. The work-up (A), column chromatography on silica gel, and crystallization afforded final products 1a – 3a and 1b – 3b.

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 54149-17-6.

Reference:
Article; Eignerova, Barbara; Tichy, Michal; Krasulova, Jana; Kvasnica, Miroslav; Rarova, Lucie; Christova, Romana; Urban, Milan; Bednarczyk-Cwynar, Barbara; Hajduch, Marian; Sarek, Jan; European Journal of Medicinal Chemistry; vol. 140; (2017); p. 403 – 420;,
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60792-79-2, 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 60792-79-2 as follows.

Intermediate 20 6-(2-(2-Amino-ethoxyl-ethylamino(at)7-chloro-1-cyclopropyl-4-oxo-1,4-dihydro- quinoline-3-carboxylic acid (A) and 7-f 2-(2-Amino-ethoxy)-ethylaminol-1-cyclouropyl-6-flnoro-4-oxo-1,4-dihydro (at)uinoIine- 3-carboxylic acid (B) To a solution of 7-chloro-l-eyelopropyl-6-fluoro-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid (0.55g, 1.95 mmol) in 1-methyl-2-pyrrolidone (40 mL) bis-(2-aminoethyl)-ether dihydrochloride (2.1g, 11.9 mmol, 6eq. ) and DBU (3.49 mL, 23.4 mmol, 12 eq. ) added and the reaction mixture was stirred at 110 C for 18 hours. The reaction mixture was then diluted with water (70 mL), pH was adjusted to 11 and extracted with CH2Cl2 (9×40 mL). Water layer was then acified with H2S04 to pH 6.8, extracted with 50 mL of CH2C12 and then evaporated in vacuum. Crude product was diluted in 2-propanol (60 mL), stirred at 82 C for 20 minutes and filtrated. Precipitate was pure salt (Na2S04). 2-Propanol was evaporated in vacuum and product was purified by column chromatography (fraction, eluent: CH2C12- MeOH-NH3-CH3CN=4:4:2:1) yielding 0.5g of title compounds as a mixture of chloro and fluoro derivatives in ratio 3:1 MS (ES+) m/z : [MH] + = 365.8 (A) (75 %) MS (ES+) m/z : [MH] (at) = 349.4 (B) (25 %)

According to the analysis of related databases, 2,2′-Oxybis(ethylamine) dihydrochloride, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PLIVA-ISTRAZIVACKI INSTITUT D.O.O.; WO2005/108413; (2005); A1;,
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461-82-5, The chemical industry reduces the impact on the environment during synthesis 461-82-5, name is 4-(Trifluoromethoxy)aniline, I believe this compound will play a more active role in future production and life.

A method for preparing 2,6-dibromo-4- (trifluoromethoxy) aniline,Including the following steps:The sodium sulfate was filtered off embodiment Example 4 156g crystallization mother liquor into 250mL 4-neck flask,Start stirring dropping 17.5 (0.175mol) sulfuric acid,Then, 36.5 g of sodium bromide (0.354 moL) was added and then 30 g (99percent, 0.168 mol) of 4-trifluoromethoxyaniline was added.Adjust the temperature to above 30 ,Start dropping 35percent hydrogen peroxide 38g,When dropping temperature rise,When the temperature rose to 50 ,By controlling the cooling liquid dripping temperature control between 50 ~ 55 ,Keep the temperature drops off,Drip finished insulation 3 hours,Cooling to about 30 ,filter,Filter cake drying,White crystals of 2,6-dibromo-4-trifluoromethoxyaniline 55.8 g, purity99.6percent (HPLC), yield 99.2percent.

The chemical industry reduces the impact on the environment during synthesis 4-(Trifluoromethoxy)aniline. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Yancheng Limin Agrochemical Co., Ltd.; Huang Haijun; Zhu Mingliang; (7 pag.)CN106631839; (2017); A;,
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Adding a certain compound to certain chemical reactions, such as: 1579-40-4, name is Di-p-tolyl Ether, 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 1579-40-4, 1579-40-4

Representative Experimental Protocol: 2,7-Dimethyl-9-(4-nitro)phenyl xanthen-9-ol (R = NO2: 3e): Di-p-tolyl ether (1, 5 g, 25.5 mmol), 4-nitro benzoic acid (5.13 g, 30.7 mmol) and ZnCl2 (10 g, 73.4 mmol) are taken into a 100 ml double neck RB flask and charged with POCl3 (7.5 mL) and heated to 95 C for 4 h. The reaction mixture turned into a brown viscous mass that was difficult to stir. The reaction mixture was then cooled to room temperature and crushed ice was added slowly while keeping the low temperature. To the above mixture was added H2O (75 mL) and stirred for 12 h. The above reaction mixture was filtered and the residue was washed with H2O (20 mL) and hexane (20 mL) to afford 4-nitro-DMPx 3e as white powder. The crude product was dissolved in EtOAc and washed with NaHCO3 to remove the excess of 4-nitro benzoic acid. The EtOAc layer was evaporated under reduced pressure to furnish the desired product as fine powder 7.5 g (86%).

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, Di-p-tolyl Ether, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Banerjee, Shyamapada; Srishylam; Rajendra Prasad; Migawa, Michael T.; Swayze, Eric E.; Sanghvi, Yogesh S.; Tetrahedron Letters; vol. 53; 35; (2012); p. 4669 – 4672;,
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A common heterocyclic compound, 321-28-8, name is 1-Fluoro-2-methoxybenzene, molecular formula is C7H7FO, 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. 321-28-8.

The mixture of 2-chloro-5-nitrobenzoyl chloride (4.0 g, 18.18 mmol), 2-fluoroanisole (5.0 mL) and AlCl3 (3.63 g, 27.27 mmol) was stirred at room temperature for 24 h. The reaction mixture was poured into 10% HCl aqueous solution cooled in ice bath, which was extracted with EtOAc (100 mL ¡Á 3). The combined organic layer was washed with brine (100 mL ¡Á 1) and dried over anhydrous Na2SO4. The crude product was provided after evaporation and recrystalized with EtOAc to give compound 2b as white solid (5.40 g, 96%); mp 113-115 C; 1H NMR (DMSO-d6) delta (ppm): 8.41 (dd, J1 = 8.7 Hz, J2 = 2.4 Hz, 1H, ArH), 8.35 (d, J = 2.4 Hz, 1H, ArH), 7.88 (d, J = 8.7 Hz, 1H, ArH), 7.60-7.67 (m, 2H, ArH), 7.28 (t, J = 8.4 Hz, 1H, ArH), 4.01 (s, 3H, OCH3); HRMS (ESI): m/z, Calcd for C14H10ClFNO4 [M+H+]: 310.0277, Found 310.0297.

The synthetic route of 1-Fluoro-2-methoxybenzene has been constantly updated, and we look forward to future research findings.

Reference:
Article; Liu, Chang; Jin, Jing; Chen, Liang; Zhou, Jie; Chen, Xiaoguang; Fu, Decai; Song, Hongrui; Xu, Bailing; Bioorganic and Medicinal Chemistry; vol. 20; 9; (2012); p. 2992 – 2999;,
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A common heterocyclic compound, 4179-19-5, name is 3,5-Dimethoxytoluene, molecular formula is C9H12O2, 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. 4179-19-5.

To a 3-necked, round-bottomed flask was added 3,5-dimethoxytoluene (6.088 g, 40 mmol) and cyclohexane (28 mL) under nitrogen. Dimethyl carbonate (30.3 g, 336 mmol) was added and the reaction mixture was heated at 60 C. Excess chlorosulfonic acid was added over a period of 15 min. The liberated HCl gas was removed by inserting a tube into solid sodium hydroxide. On completion of the addition, the reaction mixture was heated to 70-72 C. for 1 h and then cooled to room temperature. The solid was filtered off and washed with dimethyl carbonate/cyclohexane (1:1, 20 mL). The solid was dried in vacuo to obtain pure material (6.13 g, 66%). To a mixture of the sulfonic acid (product from above, 4.65 g, 20 mmol) and triethyl amine (2.03 g, 2.79 mL) in acetone (40 mL) was added 2,4,6-trichloro-1,3,5-triazine (cyanuric chloride, 3.69 g, 20 mmol). The reaction mixture was heated under reflux for 20 h before being cooled to room temperature. The solution was passed through a Celite pad and evaporated in vacuo to leave a solid, which was filtered off and washed with hexane. The mixture of product and salt of cyanuric hydroxide and triethyl amine (7.58 g) was used for the next step without further purification.To a 3-necked, round-bottomed flask, equipped with a condenser (acetone-dry ice cooling), was added the mixture from the step above (7.58 g) and acetone (100 mL). The reaction mixture was cooled to -78 C. and ammonia gas was bubbled through the solution for 0.5 h. The reaction mixture was kept standing overnight, allowing slow evaporation of ammonia gas, followed by the evaporation of solvent. Water was added and the product was extracted with DCM. The solvent was dried and evaporated to leave a mixture of solid and a dense liquid. The solid was filtered off and washed with hexane to leave pure sulfonamide (3.23 g, 70%).To a round-bottomed flask was added 3,5-dimethyl-4-hydroxybenzoic acid (2.99 g, 18 mmol). Anhydrous DMF (20 mL) was added, followed by sodium hydride (1.8 g, 45 mmol). The reaction mixture was stirred at room temperature for 1 h. p-Methoxybenzyl chloride (6.20 g, 39.6 mmol) was added and the mixture was stirred at room temperature overnight (20 h). The reaction mixture was poured into water, acidified with 1 N HCl and stirred for 1 h. The precipitated solid was filtered off, washed with water and hexane to obtain pure B-ring building block (6.93 g, 95%).The B-ring building block (6.93 g, 17.1 mmol) was dissolved in a mixture of methanol (50 mL) and tetrahydrofuran (50 mL). Potassium hydroxide (1.25 g, 22.2 mmol) in water (20 mL) was added. The reaction mixture was refluxed at 70 C. for 24 h. The solvent was evaporated in vacuo. Water was added and the reaction mixture was acidified with 1 N HCl (pH 4-5). The solid was filtered off, washed with water and hexane. The yield was 4.61 g (94%). The product (1.932 g, 6.75 mmol) and the sulfonamide from above (1.04 g, 4.5 mmol) were taken in a 3-necked, round-bottomed flask under nitrogen. Dichloromethane (100 mL) was added with stirring. To this stirred mixture was added N-(3-dimethylaminopropyl)-N’-ethylcarbodiimide hydrochloride (EDCl. HCl, 1.36 g, 7.09 mmol), followed by N,N-dimethylaminopyridine (2.06 g, 16.9 mmol). The reaction mixture was stirred at room temperature for 24 h before being washed with 1 N HCl, 2.5% NaOH and saturated sodium bicarbonate solutions. The organic layers were dried and evaporated in vacuo to leave a residue, which was purified by silica gel (100 g) column chromatography, employing 20-50% ethyl acetate in hexane and 5% methanol in dichloromethane as eluents. Fractions 30-66 were combined to obtain pure materials (1.35 g, 60%). The compound from the step above (0.105 g, 0.21 mmol) was dissolved in tetrahydrofuran under nitrogen and cooled to -78 C. n-Butyllithium was added and the reaction mixture was allowed to warm to room temperature slowly and stirred overnight (14 h). TLC showed incomplete conversion. The reaction mixture was quenched with saturated ammonium chloride solution and extracted with ethyl acetate. The solvent was evaporated in vacuo to leave a residue that was purified by silica gel (15 g) column chromatography, employing 20-50% ethyl acetate in hexane as eluents. The product was not pure enough, so another column was used, employing 0.5% methanol in hexane as eluent, and finally preparative TLC was employed to purify the material. The compound from the step above (0.277 g) was dissolved in trifluoroacetic acid (10 mL) under nitrogen and the reaction mixture was refluxed (bath temperature 80 C.) for 4 d. The solvent was evaporated in vacuo and the residue was dissolved in 0.25 N NaOH (20 mL), and acidified with acetic acid. The solid had precipitated out at this point. The solid was filtered off and washed with water, hexane and dried. From one batch, 0.005 g of pure material was isolated. From another batch, 0.060 g compound was isolated, which was not pure enough. This compound was further purified by preparat…

The synthetic route of 3,5-Dimethoxytoluene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Wong, Norman C.W.; Tucker, Joseph E.L.; Hansen, Henrik C.; Chiacchia, Fabrizio S.; McCaffrey, David; US2008/188467; (2008); A1;,
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22236-08-4, name is 3-(Difluoromethoxy)aniline, 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. 22236-08-4

General procedure: Step-1:4-amino-2,6-dichloro pyrimidine: 2,4,6-trichloro pyrimidine (1.0 mmol) in ethanol (5 mL) was treated with an aromatic amine (1.1 mmol) in the presence of Na2CO3 (1.1 mmol) at rt. The mixture was stirred at reflux for 2-4 h until completion of the reaction. The reaction progress was followed by TLC. After completion of the reaction, an equal volume of water was added with cooling. The resulting white precipitate was filtered, washed with water, and dried in vacuum over night to yield 4-substituted 2,6-dichloro pyrimidine. In case of no precipitation, ethanol was removed by rota vap., and the residue was dissolved in CH2Cl2. The organic layer was washed twice with water, brine, dried (Na2SO4), filtered, and concentrated. The resulting crude was purified by column chromatography to afford the 4-amino-2,6-dichloro pyrimidines in 85-95% yield. Step-2: 2,4-diamino-6-chloropyrimidine: 4-amino-2,6-dichloro pyrimidine (1.0 mmol) prepared from the above procedure was treated with another aliphatic amine or aromatic amine (2.0 mmol) in the presence of DIEPA (5.0 mmol) in n-BuOH (5 mL) at rt. For an aliphatic amine the reaction mixture was stirred at rt for overnight. For an aromatic amine the reaction mixture was refluxed for 24-72 h or placed in microwave (150 C, 2-7 h) until completion of the reaction. The reaction progress was followed by TLC. After completion of the reaction, solvents were removed by rota vap., and the residue was dissolved in CH2Cl2. The organic layer was washed twice with water, brine, dried (Na2SO4), filtered, and concentrated. The resulting crude was purified by column chromatography (EtOAc/hexane) to afford the 2,4-diammino-6-chloropyrimidines in 85-90% yield. Step-3: 2,4,6-triaminopyrimidine: 2,4-diamino-6-chloropyrimidine (1.0 mmol) prepared from the above procedure was treated with another suitable aliphatic amine or aromatic amine (3.0 mmol). For an aliphatic amine, 2,4-diamino-6-chloropyrimidine (1.0 mmol) was treated with aliphatic amine (3.0 mmol) and DIPEA (5.0 mmol) in n-BuOH (5 mL) and placed in microwave (150 C) for 3-7 h. After the completion of the reaction (monitored by TLC), solvents were removed and the residue was dissolved in EtOAc. The organic layer was washed twice with water, brine, dried (Na2SO4), filtered, and concentrated. The resulting crude was purified by column chromatography to afford the 2,4,6-triaminopyrimidines 90-95% yield. For aromatic amine; 2,4-diamino-6-chloropyrimidine (1.0 equiv) was dissolved in dioxane under argon and to that were added Pd2(dba)3 (10 mol %), Xantphos (10 mol %), aromatic amine (1.2 mmol), t-BuOK (1.2 mmol). The resulting solution was degassed with argon for 5 min and heated to 85 C for overnight. The reaction mixture was filtered through a pad of celite, washed with CH2Cl2 (2 ¡Á 10 mL) and the resulting filtrate was concentrated. The resulting crude was purified by flash column chromatography to yield 2,4,6-triaminopyrimidines in 90-95% yield.

Statistics shows that 22236-08-4 is playing an increasingly important role. we look forward to future research findings about 3-(Difluoromethoxy)aniline.

Reference:
Article; Sagi, Vasudeva Naidu; Liu, Tianyu; Lu, Xiaoying; Bartfai, Tamas; Roberts, Edward; Bioorganic and Medicinal Chemistry Letters; vol. 21; 23; (2011); p. 7210 – 7215;,
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These common heterocyclic compound, 702-24-9, name is 4-Methoxy-N-methylbenzylamine, 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. 702-24-9

N-methyl-4-methoxybenzylamine (30.2 mg, 0.2 mmol), molybdenum disulfide (4 mg, 0.025 mmol), and oneThe pellet was placed in a reaction tube, and after replacing the inert gas, 1 ml of DMF was added to seal the reaction tube. The reaction tube was placed in a 150 ¡ã C oil bath reaction pot, and the reaction was stirred for 18 hours; after cooling to room temperature, the catalyst was removed by filtration, the filtrate was diluted with 15 mL of water, and extracted with ethyl acetate three times, each time 15 mL; The organic layer was dried over anhydrous sodium sulfate and filtered, and the filtrate was concentrated under reduced pressure. The crude product was purified by column chromatography with ethyl acetate: petroleum ether = 1:2 (1percent triethylamine). Yellow oil in 96percent yield.

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 702-24-9.

Reference:
Patent; Xiangtan University; Gong Xing; Xie Guilin; Cai Changqun; Ma Juan; (19 pag.)CN107827817; (2018); A;,
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