Tag: M.W=100-200

859855-53-1, name is 3-Amino-4-fluorobenzonitrile, belongs to nitriles-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: 3-Amino-4-fluorobenzonitrile

3-amino-4-fluorobenzonitrie (9.82 g, 72.1 mmol) was dissolved in acetonitrie to give a pale yellow solution. NBS (13.5g, 75.7 mmol) was added in portions; the reaction mixture tumed brown-blackish but remained a soution. After the completion of the reaction was confirmed by TLC and HPLC, silica gel was added to the reaction mixture and the solvent was evaporated under reduced pressure. The crude product was leaded on a CombiFlash column (330 g) and the product was eluted with hexanes/ethyl acetate (0 – 15% gradient). The clean fractions were combined to give 9.63 g (62%) of a yellowish off-white solid. More product was found in mixed fractions which were discarded. 1H NMR (300 MHz, dmso) 3 7.57 (d, J = 10.9 Hz. 1H). 7.17 (d. J= 8.7 Hz. 1H). 5.85 (s br. 2H); MS (ES) 213/215 (M-H).

The synthetic route of 859855-53-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; RIGEL PHARMACEUTICALS, INC.; MCMURTRIE, Darren; KOLLURI, Rao; MASUDA, Esteban; TSO, Kin; ALVAREZ, Salvador; HECKRODT, Thilo; HOLLAND, Sacha; KELLEY, Ryan; DUNCTON, Matthew; SINGH, Rajinder; WO2014/89112; (2014); A1;,
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Adding a certain compound to certain chemical reactions, such as: 51762-67-5, name is 3-Nitrophthalonitrile, 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 51762-67-5, Application In Synthesis of 3-Nitrophthalonitrile

General procedure: 2.60g (15.00mmol) 3-nitrophthalonitrile or 4-nitrophthalonitrile and 2.39g (15.50mmol) 2,6-dimethoxyphenol were dissolved in 30mL anhydrous dimethylsulfoxide (DMSO). After stirring for 15min, finely ground 5.39g (39mmol) anhydrous K2CO3 was added to this solution. The reaction mixture was stirred at 25C for 72h under nitrogen atmosphere. Then the mixture was poured into ice-water. The precipitated white product was filtered off, washed with water, and then dried in vacuum at 50C. The crude product was purified by column chromatography using silica gel eluting with chloroform (CHCl3).

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

Reference:
Article; Pi?kin, Mehmet; Polyhedron; vol. 104; (2016); p. 17 – 24;,
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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. 327056-73-5, name is 3-Chloro-5-fluorobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 3-Chloro-5-fluorobenzonitrile

Step 3: 3-Chloro-5-{[5-chloro-l-(4-methoxybenzyl)-lH-l,2,3-benzotriazol-4- yl]oxy}benzonitrile; A stirred suspension of 5 -chloro-l-(4-methoxybenzy I)- IH- 1,2, 3 -benzotriazol-4-ol (0.050 g, 0.173 mmol), 3-fluoro-5-chloro-benzonitrile (0.081 g, 0.518 mmol) and cesium carbonate (0.068 g, 0.207 mmol) in NMP (1.5 mL) was heated at 1400C for 72 hours. The reaction mixture was then quenched with aqueous ammonium chloride (25 mL) and extracted with dichloromethane (2 x 100 mL). The combined extracts were concentrated under reduced pressure. The resulting residue was subjected to reverse phase chromatography (5-95% MeCN/H2theta, 0.1% TFA). The product fractions were combined and extracted with dichloromethane (2 x 100 mL). The combined extracts were dried over MgSO4, filtered and concentrated under reduced pressure to yield the title product. lH NMR (DMSO dbeta) delta 7.90- 7.88(m, IH), 7.80(s, IH), 7.79-7.75(m, IH), 7.60-7.55(m, 2H), 7.40-7.35(d, J-6.9Hz, 2H), 6.95- 6.88 (m, 2H), 5.80(s, 2H), 3.71(s, 3H).

According to the analysis of related databases, 327056-73-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK & CO., INC.; WO2008/76223; (2008); 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. 89001-53-6, name is 2-Methyl-4-nitrobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C8H6N2O2

(b) Synthesis of 4-amino-2-methylbenzonitrile Tin chloride dihydrate (18.5 g, 82.0 mmol) was added to a solution of 2-methyl-4-nitrobenzonitrile (3.80 g, 23.4 mmol) in ethanol (140 ml), and the resulting mixture was stirred for 3 hours under refluxing conditions. After completion of the reaction, the solvent was distilled off and the resulting residue was diluted with ethyl acetate and washed with a saturated aqueous sodium hydrogencarbonate solution. After the precipitate obtained during the washing was filtered by the use of Celite, the filtrate was extracted with ethyl acetate and the extract solution was dried over magnesium sulfate and filtered. The filtrate was concentrated to obtain 4-amino-2-methylbenzonitrile (2.89 g, 94%).

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 89001-53-6.

Reference:
Patent; Sumitomo Pharmaceuticals Company, Limited; EP1500643; (2005); A1;,
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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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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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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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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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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;,
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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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