Month: March 2021

Synthetic Route of 6011-14-9, 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 6011-14-9 as follows.

4-Acetylbenzoic acid (10 g, 0.061 mol) was added to a 500 mL eggplant-shaped bottle. Add N,N-dimethylformamide (150 mL), triethylamine (18 mL, 13.5 g), HOBt (9.7 g, 0.071 mol), and stirred at room temperature for 10 min. After the solid was substantially dissolved, EDCI (13.8 g, 0.071 mol) was added and stirring was continued for 1 h. Aminoacetonitrile hydrochloride (6.16 g, 0.067 mol) was added to react at room temperature, and the reaction was followed by thin layer chromatography (TLC). After 4 h, TLC showed the reaction was completed. A large amount of solid is formed, and the reaction solution is poured into dilute hydrochloric acid (concentration: 12 to 18% by weight), stirred for 30 minutes, and the solid is precipitated, suction filtered, washed with water, and dried to obtain 4-acetyl-N-(cyanomethyl)benzoamide 11.7 g, yield 95%.

According to the analysis of related databases, 6011-14-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Fushun Daheng Chemical Co., Ltd.; Shenyang Jinjiuqi Technology Co., Ltd.; Yu Kai; Zhao Zhiwei; Qu Yuanyuan; Wang Wei; Wang Han; (25 pag.)CN108707119; (2018); A;,
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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. 26830-96-6, name is 2-Amino-4-methylbenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Product Details of 26830-96-6

Combine [L-FLUORO-2-NITRO-BENZENE] (5.34 g, 37.83 mmol), 2-amino-4-methyl- benzonitrile (5.00 g, [37.] 83 [MMOL),] lithium hydroxide monohydrate (3.17 g, 75.66 mmol) and DMSO (70.0 ml) and stir at [55 C. AFER] 16 hours, cool to ambient temperature, pour the mixture onto ice chips and stir. After 1 hour, remove the resulting yellow precipitate by vacuum filtration. Dry the precipitate under vacuum, recrystallize in ethanol to give 5.15 g (54%) of fine, amber colored needles: mp 162-164 C ; mass spectrum (ion spray): m/z = 254.0 (M+1).

The synthetic route of 26830-96-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ELI LILLY AND COMPANY; WO2004/14895; (2004); A1;,
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Adding a certain compound to certain chemical reactions, such as: 53312-77-9, name is 2-Amino-3-chlorobenzonitrile, 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 53312-77-9, Product Details of 53312-77-9

BH3THF complex (1M in THF, 26 mL, 26.2 mmol) was added ina dropwise manner at 0 C (ice-bath) to 2-amino-3-chlorobenzonitrile (7) (1.00 g, 6.6 mmol) under an N2 atmosphere.The stirred reaction mixture was heated at reflux overnight,allowed to cool to room temperature, quenched by addition of HCl(6 N, to pH 2), and heated at reflux for 30 min. The reaction mixturewas allowed to cool to room temperature and then cooled to 0 C(ice-bath) and basified with NaOH (3 M, to pH 12) and extractedwith CH2Cl2 (2 40 mL). The combined organic portion waswashed with H2O (100 mL), dried (MgSO4) and evaporated underreduced pressure to afford 0.93 g (90%) of 8 as a sticky solid. IRspectroscopy indicated the absence of a characteristic cyano band

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Article; Abdelkhalek, Ahmed S.; Musayev, Faik N.; Iyer, Kavita A.; Hemanth, Prithvi; Safo, Martin K.; Dukat, Ma?gorzata; Journal of Molecular Structure; vol. 1202; (2020);,
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Reference of 1092460-79-1, A common heterocyclic compound, 1092460-79-1, name is 3-Chloro-4-(trifluoromethyl)benzonitrile, molecular formula is C8H3ClF3N, 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.

A solution of 3-chloro-4-(trifluoromethyl)-benzonitrile (2 g; 98%; 9.53 mmol) in CHCI3 (16 ml) and MeOH (4 ml) was cooled to 0C. Then HCl-gas was bubbled through this solution for 45min. The flask was closed and stored overnight in the fridge. Then argon was bubbled through to remove excess of HCl-gas and all solvents were evaporated. NH3 (2M solution in MeOH; 24 ml; 47.7 mmol) was added and the solution was stirred at RT for 2 h. The reaction mixture was concentrated to dryness. Then again NH3 (2M solution MeOH; 24 ml; 47.7 mmol) was added and the reaction mixture was stirred at RT overnight. The solvents were removed and the remaining white foamy solid (2.56 g) was used without purification for the next step. MS (ESI): 223.1 (M+H)+.

The synthetic route of 1092460-79-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; HAAP, Wolfgang; KUEHNE, Holger; MAUSER, Harald; (95 pag.)WO2016/87352; (2016); A1;,
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Reference of 5414-21-1, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 5414-21-1 name is 5-Bromovaleronitrile, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Sodium hydride paste (6.16 g. of 61% w/w suspension in liquid paraffin) was added portionwise over 30 minutes to a solution of 3-nitropyrazole (17.4 g.) in dry DMF (150 ml.) with external ice cooling to maintain the temperature at 20-30. The mixture was stirred for 45 minutes and to the almost clear solution was added 5-bromovaleronitrile (25 g.) over 30 minutes, at 25-30, and the mixture was stirred for 4 hours. Water (450 ml.) and EtOAc (450 ml.) were added and the upper layer was separated, dried (MgSO4) and evaporated in vacuo to an oil which was a mixture of 5-(3-nitropyrazol-1-yl)valeronitrile and 5-(5-nitropyrazol-1-yl)valeronitrile. The oil was divided into two 15 g. portions which were fractionated on a silica column (3.5 cm diameter*100 cm long) eluted at 2 atmospheres by EtOAc/60-80 petroleum ether (3:7 v/v). The 1,5 isomer was eluted first followed by the 1,3 isomer. The 5-(3-nitropyrazol-1-yl)valeronitrile had m.p. 32-33. To a solution of 5-(3-nitropyrazol-1-yl)valeronitrile (9.16 g.) in dry THF (200 ml.) was added 5% w/w palladium on carbon (1.8 g.). The mixture was stirred at 20 under an atmosphere of hydrogen. 3.2 Liters of hydrogen were absorbed over 4 hours. The catalyst was filtered off and the filtrate was evaporated in vacuo to give 5-(3-aminopyrazol-1-yl)valeronitrile as an oil.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Bromovaleronitrile, and friends who are interested can also refer to it.

Reference:
Patent; ICI Americas Inc.; Imperial Chemical Industries PLC; US4496564; (1985); A;,
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Related Products of 403-54-3, The chemical industry reduces the impact on the environment during synthesis 403-54-3, name is 3-Fluorobenzonitrile, I believe this compound will play a more active role in future production and life.

A solution of 3-F-benzonitrile (8.2 g, 68 mmol) and N-methylpiperazine (41.5 mL, 374 mmol) in anhydrous DMSO (60 mL) was warmed at 100 C. with stirring for 28 h. After cooling the reaction mixture was poured into water (600 mL) and was extracted with diethylether (3¡Á500 mL). The organic phase was washed with brine, dried over sodium sulfate and concentrated to give 3-(4-methylpiperazin-1-yl)benzonitrile as an oil (10.3 g, 51.2 mmol, 75%).

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

Reference:
Patent; Pharmacia Italia S.p.A.; US2007/112020; (2007); A1;,
Nitrile – Wikipedia,
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96784-54-2, name is 3-Methyl-4-nitrobenzonitrile, 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. Computed Properties of C8H6N2O2

4-Cyano-2-methylaniline was synthesized as previously described (J. Med. Chem. (1991), 34, 3295): To a solution of 3-methyl-4-nitrobenzonitrile (2.0 g, 12.34 mmol) in acetic acid (20 L) was added dropwise a solution of SnCl2 (9.6 g, 49.38 mmol) in conc. HCl (20 mL). After stirring for 3 h, the mixture was added carefully to a saturated NH4OH solution (120 mL) at 0 C. The resulting mixture was extracted with EtOAc (4¡Á30 mL). The combined organic layers were sequentially washed with H2O (30 mL) and a saturated NaCl solution (30 mL), dried (Na2SO4), and concentrated under reduced pressure. The residue was purified by flash chromatography (10% EtOAc/hex) to give 4-cyano-2-methylaniline as a white solid (1.48 g, 92%): TLC (30% EtOAc in hexane) Rf0.23. This material was used without further purification

The synthetic route of 96784-54-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bayer Corporation; US6353006; (2002); B1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 5922-60-1, 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. 5922-60-1, name is 2-Amino-5-chlorobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows.

Step 1 To a solution of (4-fluorophenyl)magnesium bromide (30 mL, 30 mmol) in anhydrous THF (15 mL) was added 2-amino-5-chloro-benzonitrile (1.53 g, 10.0 mmoL) portionwise at 0¡ã C. After the addition, the mixture was stirred at room temperature overnight. The reaction was quenched with 1 N HCl (30 mL) and reflux for 1 hr. The aqueous phase was extracted with DCM (30 mL*2). The extracts were dried over Na2SO4 and concentrated to dryness. The residue was purified by silica gel column (PE/EtOAc=10/1) to give (2-amino-5-chlorophenyl)(4-fluorophenyl)methanone (1.8 g, yield: 72percent) as a yellow solid. 1HNMR (400 MHz, DMSO-d6): delta=7.67 (dd, J=8.8, 5.2 Hz, 2H), 7.37 (d, J=2.8 Hz, 1H), 7.25 (dd, J=8.0, 2.4 Hz, 1H), 7.17 (d, J=8.4 Hz, 2H), 6.70 (d, J=8.8 Hz, 1H), 5.99 (brs, 2H).

The chemical industry reduces the impact on the environment during synthesis 2-Amino-5-chlorobenzonitrile. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Sanford-Burnham Medical Research Institute; The Royal Institution for the Advancement of Learning / McGill University; The Government of the United States of America as Represented by the Secretary of the Department of; RONAI, Ze’ev; PINKERTON, Anthony B.; FENG, Yongmei; TOPISIROVIC, Ivan; BROWN, Kevin; HASSIG, Christian A.; (155 pag.)US2018/44324; (2018); 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. 36282-26-5, name is 2-Bromo-4-fluorobenzonitrile, A new synthetic method of this compound is introduced below., Recommanded Product: 2-Bromo-4-fluorobenzonitrile

Method 10B: the bromophenol was prepared using the appropriate fluorobromobenzene with methanesulfonylethanol.Under inert atmosphere, to a solution of the fluorinated derivative in dimethylformamide was added methylsulfonylethanol (1.5eq). The mixture was stirred at 0 C. before adding sodium hydride (5eq). The reaction mixture was stirred at room temperature, then acidified with 1M hydrochloric acid solution to pH 2, and then extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate and evaporated under reduced pressure. The residue was chromatographed over silica gel.Example 10.4. 2-bromo-4-hydroxybenzonitrile Prepared following the method previously described (Method 10B) using 2-bromo-4-fluorobenzonitrile. The product was chromatographed over silica gel (elution gradient petroleum ether/ethyl acetate 90/10 to 80/20). The product was obtained as a white solid. Yield: 95% Rf (petroleum ether/ethyl acetate 70/30): 0.25 NMR 1H (CDCl3): 5.95 (s, 1H); 6.87 (dd, 1H, J=8.5 Hz, J=2.4 Hz); 7.17 (d, 1H, J=2.4 Hz); 7.54 (d, 1H, J=8.5 Hz).

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; GENFIT; US2010/4159; (2010); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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 628-20-6 as follows. category: nitriles-buliding-blocks

4-chloro-nitrile (103.5mg, 1.0mmol, 5.0equiv. ) And Na 2 S 2 O 3 ¡¤ 5H 2 O (248.2mg, 1.0mmol, 5.0equiv. After) was added to the reaction tube, followed by addition of the reaction solvent of ethanol / water (0.25mL / 0.5mL), and stirred at a reaction temperature of 100 C for 2 hours. Then the reaction system was cooled, the solvent was removed under reduced pressure, followed by addition of Sodium trifluoromethylbenzene (46.5mg, 0.2mmol, 1.0equiv.), Then added to the reaction solvent, 1,4-dioxane ring (1.0mL), and stirred at a reaction temperature of 110 C for 11 hours. The reaction solution was cooled to room temperature. Methylbenzoate was then added triphenylphosphine (36.5mg, 0.12mmol, 0.6equiv.), Stirred at room temperature for 4 hours, the reaction solution under reduced pressure and finally the solvent removed to give product 20 after column chromatography (elution agent polarity: stone ether / ethyl acetate 40:1). Yield: 62%

According to the analysis of related databases, 628-20-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; East China Normal University; JIANG, XUEFENG; XIAO, XIAO; FENG, MINGHAO; (30 pag.)CN104387303; (2016); B;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts