Tag: M.W=100-200

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 159847-81-1 as follows. Product Details of 159847-81-1

2-amino-5-cyanobenzoic acid. To a solution of methyl 2-amino-5- cyanobenzoate (0.120 g, 0.68 mmol) in THF (3.5 ml), was added a solution of lithium hydroxide (0.033 g, 1.36 mol, 2.0 eq) in H20 (3.5 ml). After stirring at rt for 3h, the reaction mixture was concentrated. The residue was diluted with H20 (5 ml) and acidified to pH~3 using 1M HCl. The precipitate was collected by filtration, washed with H20 and dried under air. 2-amino-5-cyanobenzoic acid (0.11 g, 95%) was obtained as a white solid. 1H NMR (400 MHz, DMSO-de) delta 8.04 (d, J= 2.1 Hz, 1H), 7.70-7.33 (m, 3H), 6.86 (d, J= 8.8 Hz, 1H).

According to the analysis of related databases, 159847-81-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; UNIVERSITY OF KANSAS; UNIVERSITY OF LOUISVILLE RESEARCH FOUNDATION, INC.; SOUTHERN RESEARCH INSTITUTE; GOLDEN, Jennifer; AUBE, Jeffrey; CHUNG, Donghoon; SCHROEDER, Chad; YAO, Tuanli; WHITE, E. Lucile; TOWER, Nichole A.; WO2014/93869; (2014); 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. 6609-57-0, name is 2-Ethoxybenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., category: nitriles-buliding-blocks

Preparation 7 2-ethoxy-5-(4-ethyl-1-piperazinylsulfonyl)benzonitrile Commercially available 2-ethoxybenzonitrile (25 g, 0.17 Mol) was added dropwise to an ice cooled mixture of chlorosulfonic acid (50.8 mL, 0.765 Mol) and thionyl chloride (12.4 mL, 0.17 Mol) so as to keep the temperature below 10 C. The reaction was then stirred at ambient temperature for 18 h before being poured onto ice/water. This mixture was stirred 1 hr before the precipitated material was filtered off. The resultant solid was dissolved in acetone (300 mL) and triethylamine (25 mL, 0.179 Mol) was added followed by a slow addition of N-ethylpiperazine (25 mL, 0.198 Mol).

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 6609-57-0.

Reference:
Patent; Dunn, Peter James; Dunne, Catherine; US2002/13464; (2002); A1;,
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Electric Literature of 60702-69-4, 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. 60702-69-4, name is 2-Chloro-4-fluorobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows.

1. Synthesis of tert-butyl N-[(1r,3r)-3-(3-chloro-4-cyanophenoxy)-2,2,4,4-tetramethylcyclobutyl]carbamate Into a 100-mL 3-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed a solution of tert-butyl N-[(1r,3r)-3-hydroxy-2,2,4,4-tetramethylcyclobutyl]carbamate (600.0 mg, 2.47 mmol, 1.00 equiv) in N,N-dimethylformamide (10.0 mL). This was followed by the addition of sodium hydride (198.0 mg, 8.25 mmol, 2.00 equiv), in portions at 0 C. After 30 minutes, to this was added 2-chloro-4-fluorobenzonitrile (459.0 mg, 2.95 mmol, 1.20 equiv). The resulting solution was stirred for 1 hour at 70 C. The reaction mixture was cooled to room temperature with a water bath. The reaction was then quenched by the addition of water (20 mL). The resulting solution was extracted with ethyl acetate (20 mL*3) and the organic layers combined. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1/5). This resulted in 100.0 mg (11%) of tert-butyl N-[(1r,3r)-3-(3-chloro-4-cyanophenoxy)-2,2,4,4-tetramethylcyclobutyl]carbamate as colorless oil. LC-MS (ES+): m/z 279.10 [MH-100]+, tR=1.20 min (2.5 minute run).

The chemical industry reduces the impact on the environment during synthesis 2-Chloro-4-fluorobenzonitrile. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Arvinas, Inc.; Crew, Andrew P.; Hornberger, Keith R.; Snyder, Lawrence B.; Zimmermann, Kurt; Wang, Jing; Berlin, Michael; Crews, Craig M.; Dong, Hanqing; (605 pag.)US2018/99940; (2018); A1;,
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Electric Literature of 21803-75-8, 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. 21803-75-8, name is 4-Amino-3-chlorobenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To 4-amino-3-chlorobenzonitrile (52 mg, 0.34 mmol), CS2CO3 (130 mg, 0.4 mmol) were added to tert-butyl 5-chloro-3-formyl-6-methylpyrazolo[l,5-a]pyrimidin-7- yl(cyclopropyl)carbamate (100 mg, 0.29 mmol) dissolved in 1,4-dioxane (1.1 mL). Racemic BINAP (11 mg, 0.017 mmol) and palladium(II) acetate (8 mg, 0.011 mmol) were then added. The mixture was sealed and irradiated at 110 C for 60 min in the microwave. Et20 (3 mL) was added and the solution was filtered. The filtrate was concentrated in vacuo. The crude residue was dissolved in dichloromethane (1.5 mL) and trifluoroacetic acid (1.5 mL). After stirring at room temperature for 1 hour, the solution was concentrated under a stream of air. The crude material was purified by silica gel chromatography (3% acetone/dichloromethane) to yield the product, 3-chloro-4-(7-(cyclopropylamino)-3-formyl-6-methylpyrazolo[l,5- a]pyrimidin-5-ylamino)benzonitrile (34 mg, 33% yield). LCMS (M+l=367)

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, 4-Amino-3-chlorobenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; CYLENE PHARMACEUTICALS INC.; HADDACH, Mustapha; RYCKMAN, David; RAFFAELE, Nicholas; WO2011/31979; (2011); A1;,
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Some common heterocyclic compound, 63069-50-1, name is 4-Amino-3-fluorobenzonitrile, molecular formula is C7H5FN2, 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. category: nitriles-buliding-blocks

Add in a 100mL two-necked flask4-chloro-7-benzyl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine (1.5 g, 5.8 mmol),2-Fluoro-4-cyanoaniline (0.86 g, 6.3 mmol) and 20 mL of tetrahydrofuran, protected with nitrogen,The reaction flask was cooled to 0 C and 60% sodium hydride (0.46 g, 11.5 mmol) was slowly added.The reaction was then warmed to 65 C and stirred overnight.The reaction solution was extracted twice with ethyl acetate and twice with saturated sodium chloride.Dry over anhydrous sodium sulfate and evaporated to dryness under reduced vacuo.Purified by silica gel column chromatography(petroleum ether (PE): ethyl acetate (EA) = 1:1)0.7 g of a yellow solid was obtained in a yield of 35%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 63069-50-1, its application will become more common.

Reference:
Patent; Jiangxi University of Traditional Chinese Medicine; Yang Zunhua; Fang Yuanying; Jin Yi; Wang Qi; Ouyang Hui; Feng Yulin; (33 pag.)CN110256420; (2019); A;,
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Application of 874-89-5, The chemical industry reduces the impact on the environment during synthesis 874-89-5, name is 4-(Hydroxymethyl)benzonitrile, I believe this compound will play a more active role in future production and life.

General procedure: To a mixture of alcohol (1 mmol) and KBr (1.5 mmol, 0.18 g) in acetonitrile (5 mL), P2O5 (1.5 mmol, 0.23 g) was added and the reaction was stirred at room temperature for the time specified in Table 3. After reaction completion (TLC or GC), the reaction mixture was filtered and the residue washed with ethyl acetate (3 × 8 mL). The combined organic layers were washed with water (10 mL) and dried over Na2SO4. The solvent was removed under reduced pressure to afford the corresponding product. If necessary, further purification was performed by column chromatography.

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, 4-(Hydroxymethyl)benzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Khazdooz, Leila; Zarei, Amin; Aghaei, Hamidreza; Azizi, Ghobad; Gheisari, Mohammad Mehdi; Tetrahedron Letters; vol. 57; 2; (2016); p. 168 – 171;,
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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. 17626-40-3, name is 3,4-Diaminobenzonitrile, A new synthetic method of this compound is introduced below., name: 3,4-Diaminobenzonitrile

In a round bottom flask (250ml) 3,4-dichloro-1-(hexadecan-6-yl)-1H-pyrrole-2,5-dione (10g, 25.6 mmol) wasdissolved under argon in 150ml of absolute ethanol. Sodium acetate (2.5g, 30.7mmol) and 3,4-diaminobenzonitrile (3.4g,25.6 mmol) were added. The mixture was stirred overnight at room temperature. Ethanol was removed by distillationunder vacuum at 40C and the crude product was purified by flash chromatography onto silica gel using hexane/methylene-chloride/ethylacetate 60/35/5 as the eluent. 2.5g of pure product were obtained as yellow wax with a yield of 21%. When conditions were made harsher by heating to reflux the final product (5) was obtained (yield 40%).

The synthetic route of 17626-40-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Solvay SA; Caille, Jean-Raphael; Dabeux, Francois; Bolsee, Jean-Christophe; Fenoll, Mathieu; EP2808327; (2014); A1;,
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Electric Literature of 2042-37-7, A common heterocyclic compound, 2042-37-7, name is 2-Bromobenzonitrile, molecular formula is C7H4BrN, 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: K3PO4 (5.62 mmol) in DMSO (4 mL), were added Cu(OAc)2 (0.28 mmol). The flask was evacuatedand backfilled with argon for three times. The resulting suspension was heated in a 80 C oil bathwith stirring for the indicated time. The reactor was cooled to r.t., the flask was opened to air and thereaction mixture was poured into water (20 mL), extracted with ethyl acetate (20 mL × 3), andorganic layer was washed with water (20 mL × 2) and once with brine (25 mL), dried overmagnesium sulfate and concentrated in vacuo. The product was purified by column chromatographyon silica gel using petroleum ether and ethyl acetate as eluent.1-(2-Methoxyphenyl)-1H-pyrrole (3a) [30]: colorless oil (0.43 g, 88%). 1H-NMR (400 MHz, CDCl3) delta (ppm):7.30-7.23 (2H, m), 7.03-6.98 (4H, m), 6.30 (2H,

The synthetic route of 2042-37-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Yuan, Chunling; Zhang, Lei; Zhao, Yingdai; Molecules; vol. 24; 22; (2019);,
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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. 159847-81-1, name is Methyl 2-amino-5-cyanobenzoate, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C9H8N2O2

To a suspension of 3- (chlorosulfonyl) benzoic acid (10.8 g, 49.0 mmol) in CH2Cl2 (105 mL) and three drops [OF DMF] was added oxalyl chloride (12.5 mL) and the reaction was stirred at rt overnight. The solution was concentrated in vacuo, diluted with [CH2C12] (100 mL), and the solution was divided into two reactions. A 50 mL (24.5 mmol) aliquot of the acid chloride was added to a solution of PHA-522499 (4.49 g, 25.5 mmol) dissolved in [CH2C12] (50 mL) and pyridine (3.0 [ML)] and stirred at rt overnight. The solution was diluted with MTBE, washed with 2 N HC1 and brine, concentrated, [TRITURATED WITH MTBE] to afford 7.91 g [(85%)] of methyl [2-{[3-] (chlorosulfonyl) benzoyl] [AMINO}-5-CYANOBENZOATE] as a tan [SOLID. 1H NMR (400 MHZ,] [DMSO-D6)] [8] 11.73 (s, 1 H), 8.67 (d, [J=] 9 Hz, [1] H), 8.37 (d, [J=] 2 Hz, 1 H), 8.25 (s, 1 H), 8.12 (dd, J= 9,2 Hz, 1 H), 7.92 (d, J= 8 Hz, [1] H), 7. [88] (d, J= 8 Hz, 1 H), 7.60 (t, [J= 8 HZ, 1 H),] 3.93 (s, 3H).

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 159847-81-1.

Reference:
Patent; PHARMACIA & UPJOHN COMPANY; WO2004/18414; (2004); A2;,
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Electric Literature of 447-60-9, 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 447-60-9 as follows.

To a solution of 2,2,6,6-tetramethylpiperidine (0.99 g, 7.02 mmol) in THF (25 ml) was added n-BuLi (2.80 ml, 2.5 M hexane solution, 7.02 mmol) at -10 C. After stirring for 10 min, this solution was cooled to -78 C., tris(1-methylethyl)borate (1.58 g, 8.4 mmol) was added, and the mixture was stirred for 5 min. To this solution was added a solution of 2-(trifluoromethyl)benzonitrile (1.00 g, 5.85 mmol) in THF (10 ml), and the mixture was stirred at -78 C. for 2 hr. The reaction solution was allowed to warm to room temperature, the reaction was quenched with acetic acid, and the solvent was evaporated under reduced pressure. Ethyl acetate was added to the residue, the precipitated solid was filtered off, and the filtrate was concentrated to give the title compound (3.14 g) as a mixture. This was used for the next reaction without performing further purification and identification.

According to the analysis of related databases, 447-60-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Kasai, Shizuo; Kamaura, Masahiro; Cho, Nobuo; US2011/251187; (2011); A1;,
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