Author: Jessica.F

Adding a certain compound to certain chemical reactions, such as: 6621-59-6, name is 6-Bromohexanenitrile, belongs to nitriles-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 6621-59-6, Recommanded Product: 6-Bromohexanenitrile

General procedure: TBAF in 1M THF was added to a starting solution of alkyl-substituted triazole (8a-c) or non-substituted triazole (7a) in dried THF. The mixture was stirred for 24-48 h at 60 C, and the solution was cooled to room temperature. The mixture was poured into ethyl acetate and water and extracted twice with ethyl acetate. The combined organic layers were dried with Na2SO4, filtered and concentrated. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to yield the desired compound.

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, 6-Bromohexanenitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Lee, Sun-Mi; Yoon, Kyoung Bin; Lee, Hyo Jeong; Kim, Jiwon; Chung, You Kyoung; Cho, Won-Jea; Mukai, Chisato; Choi, Sun; Kang, Keon Wook; Han, Sun-Young; Ko, Hyojin; Kim, Yong-Chul; Bioorganic and Medicinal Chemistry; vol. 24; 21; (2016); p. 5036 – 5046;,
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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. 16588-02-6, name is 2-Chloro-5-nitrobenzonitrile, A new synthetic method of this compound is introduced below., Application In Synthesis of 2-Chloro-5-nitrobenzonitrile

2-chloro-5-nitro-benzonitrile (1.83 g, 10.0 mmol) was added to a 100 mL round bottom flask and dissolved in acetonitrile (20 mL).K2CO3 (2.76 g, 20.0 mmol) and di-n-hexylamine (1.85 g, 9.98 mmol) were added with stirring, and the reaction system was heated to 80[deg.] C. for 40 h.After the reaction was completed, the mixture was cooled to room temperature, poured into dichloromethane (100 mL), washed with water (100 mL × 3) and saturated brine (100 mL), and dried over anhydrous sodium sulfate.The solvent was evaporated under reduced pressure and the crude product was purified by column chromatography (petroleum ether/ethyl acetate (V/V) = 125/2) to give a yellow oil (2.89 g, 87%).

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; SUNSHINE LAKE PHARMA CO., LTD.; ZHANG, YINGJUN; ZHANG, JIANCUN; WANG, XIAOJUN; LIN, RUNFENG; CAO, SHENGTIAN; WANG, ZHAOHE; LI, JING; (226 pag.)TWI607995; (2017); B;,
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Synthetic Route of 151-18-8, A common heterocyclic compound, 151-18-8, name is 3-Aminopropanenitrile, molecular formula is C3H6N2, 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.

Add 284 g of ethyl formate to a 500 mL three-neck bottle.At a certain temperature (see Table 1 for specific temperature selection), slowly add 35g of solid sodium ethoxide at a rate of 1.2g/min and raise the temperature to 10 C.Then add 30 g of beta-aminopropionitrile at a rate of 1.0 g/min.The above reaction solution was poured into a 500 mL autoclave, and stirring was started.Heating to raise the temperature to 65-70 C,The pressure range is 5.0-6.0MPa, and it will naturally drop to 20C after 10h of heat preservation.After suction filtration, the filter cake was washed twice with 25 g of ethyl formate, and the filter cake was dried at 50 C.getAlpha-formyl-beta-formylaminopropionitrileYellowish solid sodium salt 65.8g,The content is 90.4%,The yield was 93.8%.

The synthetic route of 151-18-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Northeast Pharmaceutical Group Co., Ltd.; Yang Huifen; Zhang Li; Qu Zhuangzhi; (6 pag.)CN108484439; (2018); A;,
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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. 67515-59-7, name is 4-Fluoro-3-(trifluoromethyl)benzonitrile, A new synthetic method of this compound is introduced below., name: 4-Fluoro-3-(trifluoromethyl)benzonitrile

Preparation of 4-(4,4-difiuoropiperidin-l-yl)-3-(trifiuoromethyl)benzonitrile (compound- 4):; A solution stirred solution of compound 1 (5.0 g, 0.026 mmol) and 4,4- difluoropiperidine HCl (4.58 g, 0.029 mmol) in DMSO (50 mL), K2C03 (9.12 g, 0.066 mmol) was added at RT. The reaction mixture was heated at about 100 C for about 12 h. Upon complete consumption of starting material, the reaction mixture was cooled to RT and poured into crushed ice. The aqueous layer was extracted with EtOAc (2 x 100 mL), washed with water (60 mL), brine (60 mL), dried over sodium sulfate and concentrated under reduced pressure to get crude compound which was purified by column chromatography using 2 % EtOAc /Hexane to get compound 4 as white solid (3.2 g, 42 %). .H NMR (200 MHz, CDC13): delta 2.06-2.25 (m, 4H), 3.13 (t, J = 5.4 Hz, 4H), 7.36 (d, J = 8.4 Hz, 1H), 7.78 (dd, J = 8.4, 2.2 Hz, 1H), 7.92 (d, J= 2.2 Hz, 1H). MS (ESI): 290 (M++H).

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; ABBOTT LABORATORIES; CUSACK, Kevin, P.; BREINLINGER, Eric, C.; FIX-STENZEL, Shannon, R.; STOFFEL, Robert, H.; WOLLER, Kevin, R.; WO2011/71570; (2011); 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. 1835-65-0, name is 3,4,5,6-Tetrafluorophthalonitrile, This compound has unique chemical properties. The synthetic route is as follows., Safety of 3,4,5,6-Tetrafluorophthalonitrile

Referential Example 3; Synthesis of 4,5-bis(2-chloro phenylthio)-3-fluoro-6-(2,6-dimethylphenoxy)phthalocyanine; Into a four-neck flask of glass provided with a stirrer, a thermometer, a water separation tube, and a cooling tube and having an inner volume of 100 ml, 30 gr of 2-butanone, 10 gr (0.05 mol) of tetrafluorophthalonitrile, and 7.26 gr (0.125 mol) of potassium fluoride were placed and the flask was dipped in a water bath. 15.2 g (0.105 mol) of 2-chlorobenzene thiol was added to the reaction mixture with stirred at room temperature over about 40 minutes. The reaction temperature rose to the maximum of about 35° C. When the reaction was continued for additional one hour after the completion of this addition, the conversion of tetrafluorophthalonitrile reached 99.2percent. The content of the bisthiol moiety, 4,5-bis(2-chloro phenylthio)-3,6-difluorophthalonitrile, a determined by liquid chromatography, was 92.5percent. Then, 7.33 gr (0.06 mol) of 2,6-xylenol, 4.35 gr (0.075 mol) of potassium fluoride and and 6 gr of 2-butanone were added to the reaction mixture in the reaction vessel and the resultant mixture was heated to a temperature in the range of 83-86° C., and then left reacting under reflux for 30 hours. The conversion of 4,5-bis(2-chloro phenylthio)-3,6-difluorophthalonitrile after the completion of the reaction was determined by liquid chromatography, to find to be 99.8percent and the content of the target product, 4,5-bis(2-chloro phenylthio)-3-fluoro-6-(2,6-dimethylphenoxy)phthalonitrile, as determined by liquid chromatography, was 70percent. The reaction slurry was cooled to room temperature and filtered to separate a solid component. The filtrate consequently formed was separated. The resultant cake was washed with about 200 ml of chloroform. By evaporating the washing under a reduced pressure at 50° C., 18.0 g (0.0326 mol, yield: 65.2 mol percent based on tetrafluoronitrile) of 4,5-bis(2-chloro phenylthio)-3-(2,6-dimethylphenoxy)-6-fluorophthalonitrile was obtained.

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 1835-65-0.

Reference:
Patent; Hirota, Kouichi; Hashimoto, Yukihide; Masuda, Kiyoshi; Kitao, Masunori; US2005/203293; (2005); A1;,
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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 114344-60-4 as follows. Recommanded Product: 114344-60-4

A solution of 0.37g sodiumnitrite in 3ml of water is added at -5C to a solution of 1 g of 2-amino-3-bromo-benzonitrile (Synthetic Communications (1989), 19(13-14), 2255-63) in 8ml of concentrated hydrochloric acid. The mixture is stirred at -5C for 90min.In a separate flask a solution of 0.22 g of copper(ll) chloride dihydrate in 14 ml of glacial acetic acid is saturated with sulfur dioxide and then cooled to -8C. Then the mixture of with the diazonium salt is added dropwise at -8C to -3C and stirred for 2 hours.The reaction mixture is poured into ice cooled water. The aqueous layer is extracted three times with dichloromethane. The combined organic layers are dried over magnesium sulfate, filtered and concentrated in vacuo. The resulting residue is suspended in cyclohexane and filtered. The resulting residue is washed with cyclohexane and dried to afford 1.2 g of 2-bromo-6-cyano- benzenesulfonyl chloride.1H-NMR (CDCI3, 400 MHz): 8.15 (d, 1 H), 7.96 (d, 1 H), 7.67 (t, 1 H) ppm.

According to the analysis of related databases, 114344-60-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; WO2009/141305; (2009); A1;,
Nitrile – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 3939-09-1, name is 2,4-Difluorobenzonitrile, belongs to nitriles-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 3939-09-1, name: 2,4-Difluorobenzonitrile

Example 8a Preparation of 4-Fluoro-2-(tetrahydro-pyran-4-ylamino)-benzonitrile A mixture of 2,4-difluorobenzonitrile (0.420 g, 3.0 mmol), 4-aminotetrahydropyran (0.306 g, 3.0 mmol) and DIPEA (0.523 mL, 3.0 mmol) in DMSO (5.0 mL) is stirred at 150 C. (preheated oil-bath) for 20 min. After cooling to room temperature, the resulting mixture is poured into saturated aqueous NH4Cl solution and extracted with ethyl acetate (3*20 mL). The combined organic layer is washed with brine (3*15 mL) and dried over Na2SO4, filtered and concentrated at reduced pressure to dryness. The residue obtained is purified by column chromatography (silica gel, 40:60 ethyl acetate/hexane) to afford 4-Fluoro-2-(tetrahydro-pyran-4-ylamino)-benzonitrile (0.214 g, 32%) as a pale yellow solid: ESI MS m/z 221 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2,4-Difluorobenzonitrile, and friends who are interested can also refer to it.

Reference:
Patent; SERENEX, INC.; US2008/119457; (2008); A1;,
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Reference of 766-84-7,Some common heterocyclic compound, 766-84-7, name is 3-Chlorobenzonitrile, molecular formula is C7H4ClN, 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 400 L glass lined vessel was charged 1,3-dibromo-5,5-dimethyl-hydantoin (DBH) (10.88 kg, 38.6 mol), followed by methane sulfonic acid (111.4 kg). The resulting slurry was warmed to 35 C. to form a DBH solution. [0306] To a separate 400 L vessel was charged 3-chlorobenzonitrile 1-1 (8.050 kg, 58.5 mol, Acros, Lancaster) melt and cyclohexane (1.8 L total), followed by methanesulfonic acid (47.6 kg) to form a benzonitrile solution, which was warmed to 25-30 C. to dissolve any solids. The DBH solution was added to the benzonitrile solution over a period of about 30 minutes with fast agitation while maintaining a batch temperature of <30 C. The empty DBH solution containing vessel was rinsed with methane sulfonic acid (5.0 kg) and the rinse was added to the reaction mixture. The reaction was aged at 30 C. for 1 to 2 hours to affect reaction conversion >95 area % (tracked via HPLC assay). The reaction was then cooled to about 14 C. and slowly quenched with water (80.5 L) to maintain a temperature of <30 C. The reaction was then re-cooled to 20 C. and MTBE was added (208.5 kg) at <30 C. under agitation. The mixture was allowed to settle, the layers were separated and the aqueous layer was extracted with 101 kg of MTBE at 30 C., followed by 30 kg of MTBE. The organic layers were combined and washed with 50 kg 1.6 N NaOH, and 54 kg water, and then concentrated to 48 L, cooled and seeded (10 g of seed). Once a slurry formed, the concentration was resumed until a batch volume of 40 L was achieved. The resulting slurry was aged at 20 C. for 1.5 hours and then filtered. The cake was washed with 12 kg of 1:1 MTBE:cyclohexane (in 2 drops). The wet solids were dried in a filter dryer to give 1-2. 1H NMR (CDCl3, 400 MHz) delta 7.39 (d, J=2.2 Hz, 1H), 7.22 (dd, J=2.3, 8.4 Hz, 1H), 7.16 (d, J=8.5 Hz, 1H) The synthetic route of 766-84-7 has been constantly updated, and we look forward to future research findings. Reference:
Patent; Boice, Genevieve N.; Conrad, Karen M.; Corley, Edward G.; Matty JR., Louis; Murry, Jerry A.; Savarin, Cecile G.; US2004/181070; (2004); A1;,
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Application of 6136-93-2, These common heterocyclic compound, 6136-93-2, name is 2,2-Diethoxyacetonitrile, 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.

Diethoxyacetamidine hydrochloride was synthesized according to the literature method.3 To a solution of sodium methoxide (0.09 g, 1.6 mmol) in methanol (8.4 mL) was added diethoxyacetonitrile (2.00 g, 15.5 mmol) and the reaction mixture was stirred for 4 hours at room temperature. Solid carbon dioxide (0.5 g) was added and most of the methanol was evaporated. Diethyl ether was added and the sodium carbonate was removed by filtration.The filtrate was concentrated to afford methyl diethoxyacetimidate as a colorless oil (2.47 g, 99 % yield) which was used in the next step without further purification. The oil was dissolved in methanol (4mL), ammonium chloride (0.82 g, 15.3 mmol) was added, and the resultant mixture was stirred overnight at room temperature. The mixture was filtered and the methanol was removed in vacuo. The resulting oil was cooled to -78 C to form a solid and washed by diethyl ether (3 mL). The solid was filtered, warmed to ambient temperature and dried in vacuo to givedi ethoxyacetamidine hydrochloride (1.64 g, 58 %, 2 steps) as a white solid. 1H NMR (400 MHz, DMSO-d6): 9.15(br, 4 H), 5.29 (s, 1H), 3.61 (q, 4 H, J = 6.8 Hz), 1.18 (t, 6 H, J = 6.8 Hz).

The synthetic route of 6136-93-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Hattori, Yohei; Nishikawa, Michihiro; Kusamoto, Tetsuro; Kume, Shoko; Nishihara, Hiroshi; Chemistry Letters; vol. 43; 7; (2014); p. 1037 – 1039;,
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Related Products of 21803-75-8, 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. 21803-75-8, name is 4-Amino-3-chlorobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows.

i. 3-Chloro-4-dibenzylamino-benzonitrile, 2 To a solution of 4-amino-3-chlorobenzonitrile (1.0 g, 6.56 mmol, 1 eq) and benzyl bromide (3.12 mL, 26.2 mmol, 4.0 eq) in dry DMF (10 mL) was added at rt NaH (1.31 g, 32.8 mmol, 5 eq) portionwise under Ar (g). The reaction mixture was stirred at rt overnight, and was subsequently partitioned with H2O (30 mL) and extracted with EtOAc (5*20 mL) and CH2Cl2 (20 mL). The combined organic extracts were dried over MgSO4 and the solvent was removed in vacuo. The residue was further purified by silica gel column chromatography with hexane/EtOAc (1:0-9:1) to furnish 2 as a white solid (2.09 g, 96%). 1H NMR (400 MHz, CDCl3) deltaH: 7.68 (d, J=2.0 Hz, 1H), 7.28-7.37 (m, 6H), 7.26 (d, J=2.5 Hz, 5H), 6.92 (d, J=8.5 Hz, 1H), 4.34 (s, 4H). MS (ES+) 355.1 (100%, [M+Na]+).

The chemical industry reduces the impact on the environment during synthesis 4-Amino-3-chlorobenzonitrile. I believe this compound will play a more active role in future production and life.

Reference:
Patent; KARUS THERAPEUTICS LIMITED; Shuttleworth, Stephen Joseph; Silva, Franck Alexandre; US2013/109688; (2013); A1;,
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