Category: nitriles-buliding-blocks

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. 60710-80-7, name is 3-Amino-4-methylbenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. category: nitriles-buliding-blocks

(Boc)20 (50 g, 227 mmol) was added portion-wise to a stirred solution of 3-amino-4- methylbenzonitrile (7) (10 g, 75.7 mmol) and DMAP (0.5 g) in THF (250 ml_). After 30 minutes, the reaction was heated at 60 C overnight. The crude reaction mixture was purified over silica gel to obtain a white solid tert-butyl 5-cyano-2-methylphenylcarbamate (34) (17.5 g, quantitative yield). MS m/z 233.1 (M+1 )+. NH2OH (20 ml_, 50% in water) was added to a stirred solution of tert-butyl 5-cyano-2- methylphenylcarbamate (34) (17.5 g, 75.3 mmol) in EtOH (200 ml_) and the resulting solution was heated at 50 C for 10 hours. The solvent was then evaporated and the product was titurated with EtOAc and hexane to obtain a white solid (Z)-tert-butyl 5-(N’- hydroxycarbamimidoyl)-2-methylphenylcarbamate (35) in a quantitative yield which was used without further purification. MS m/z 266.1 (M+1 )+.

The synthetic route of 60710-80-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; IRM LLC; LIU, Xiaodong; LI, Xiaolin; LOREN, Jon; MOLTENI, Valentina; NABAKKA, Juliet; NGUYEN, Bao; PETRASSI, Hank Michael James; YEH, Vince; WO2013/33116; (2013); 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. 288251-96-7, name is 2-Isobutyl-5-nitrobenzonitrile, A new synthetic method of this compound is introduced below., Computed Properties of C11H12N2O2

To a mixture of 2-isobutyl-5-nitrobenzonitrile (500 mg, 2.9 mmol), cuprous bromide (86 mg, 0.6 mmol), cupric bromide (1.3 g, 5.8 mmol), hydrobromic acid (364 muL, 6.7 mmol) and acetonitrile (20 mL) in a 100 mL single-neck flask cooled in an ice bath was added a solution of sodium nitrite (242 mg, 3.0 mmol) in acetonitrile slowly. After stirred in the ice bath for half an hour, the mixture was slowly warmed to room temperature and stirred overnight. After the materials had all reacted when being determined by TLC, solvent was removed in vacuo, and saturated sodium chloride (20 mL) was added. The mixture was extracted with ethyl aceate (8 mL) and dried over anhydrous sodium sulfate. The organic layers were combined and concentrated in vacuo, and the cruded product was separated by a silica gel column (eluent: 100% of petroleum ether) to give a product (white solid, 260 mg), with a yield of 37.8%. 1H NMR (400 MHz, CDCl3) delta 7.72 (s, 1H), 7.61 (d, J = 8.4 Hz, 1H), 7.16 (d, J = 8.4 Hz, 1H), 2.66 (d, J = 7.3 Hz, 2H), 2.01 – 1.88 (m, 1H), 0.94 (d, J = 6.6 Hz, 6H).

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; Fudan University; WANG, Yonghui; HUANG, Yafei; QIU, Ruomeng; TANG, Ting; (68 pag.)EP3581561; (2019); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Reference of 4426-11-3, The chemical industry reduces the impact on the environment during synthesis 4426-11-3, name is Cyclobutanecarbonitrile, I believe this compound will play a more active role in future production and life.

General procedure: l-(2-methylbenzyl)cyclobutanecarbonitrile[579] n-BuLi (0.018mol, 7.2ml, 2.5M) was added to a solution of diisopropylamine (1.7 g, 0.017 mol) in THF (15 mL) at -78C. After 5 minutes neat cyclobutancarbonitrile (1.2g, 0.015mol) was added and the mixture was stirred at -78 C for 1 hour. Then a solution of 1 -(bromomethyl)-2-methylbenzene (3.3 g, 0.018 mol) in THF (3 mL) was added and the mixture was stirred at -78 C for 1 hour. The mixture was quenched with water and extracted with EtOAc. The organic phase was concentrated and the residue was directly used to the next step without further purification. MS: m/z 186 (M+H)

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, Cyclobutanecarbonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ABBVIE INC.; BAYBURT, Erol K.; CLAPHAM, Bruce; COX, Phil B.; DAANEN, Jerome F.; GOMTSYAN, Arthur; KORT, Michael E.; KYM, Philip R.; VOIGHT, Eric A.; SCHMIDT, Robert G.; DART, Michael J.; GFESSER, Gregory; WO2013/62966; (2013); A2;,
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Related Products of 194853-86-6, These common heterocyclic compound, 194853-86-6, name is 4-Fluoro-2-(trifluoromethyl)benzonitrile, 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 4-fluoro-2-(trifluoromethyl)benzonitrile (7.00 g, 37.1 mmol), tert- butyl N-(5-aminopentyl)carbamate (10 g, 49.43 mmol), and Nu,Nu-diisopropylethyl amine (11 g, 85.11 mmol) in DMF (100 mL) stirred for 6 h at room temperature. The resulting solution was diluted with 400 mL of ethyl acetate, washed with 2x200mL brine, dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum. The residue was purified via column chromatography with silica gel (eluting with ethyl acetate/petroleum ether (1 : 1)) to give tert- butyl 5-(4-cyano-3-(trifluoromethyl)phenylamino)pentylcarbamate (11 g, 60%) as colorless oil. MS: (ESI, m/z): 372[M+H]+.

Statistics shows that 4-Fluoro-2-(trifluoromethyl)benzonitrile is playing an increasingly important role. we look forward to future research findings about 194853-86-6.

Reference:
Patent; FORMA THERAPEUTICS, INC.; H. LEE MOFFITT CANCER CENTER AND RESEARCH INSTITUTE, INC.; LEE, Jennifer; BURNETTE, Pearlie; CHELLAPPAN, Srikumar; BARCZAK, Nicholas; CONTI, Chiara; ESCOBEDO, Jaime A.; HAN, Bingsong; LANCIA, David R., Jr.; LIU, Cuixian; MARTIN, Matthew W.; NG, Pui Yee; RUDNITSKAYA, Aleksandra; THOMASON, Jennifer R.; ZHENG, Xiaozhang; (322 pag.)WO2018/75959; (2018); A1;,
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Adding a certain compound to certain chemical reactions, such as: 31643-49-9, name is 4-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 31643-49-9, category: nitriles-buliding-blocks

10 g of 2-mercaptopyridine, 14.2 g of 4-nitrophthalonitrile, and 22.6 g of potassium carbonate were suspended in 250 ml of acetone and heated at reflux temperature for 4 hours. The solution was filtered through a pad of celite and a course glass filter to remove residual solids. The solution was concentrated to a crude residue and purified by column chromatography on silica gel eluting the product with a gradient of 0-10% ethyl acetate in dichloromethane. 6.4 g of product was recovered; 1H NMR (200 Mz, CDCl3) delta=8.49-8.53 (m, 1H), 7.84-7.83 (dd, 1H), 7.76-7.71 (m, 2H), 7.68-7.64 (dd, 1H), 7.40-7.36 (dt, 1H), 7.27-7.20 (m, 1H).

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

Reference:
Patent; FibroGen, Inc.; US2004/254215; (2004); A1;,
Nitrile – Wikipedia,
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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. 105942-08-3, name is 4-Bromo-2-fluorobenzonitrile, A new synthetic method of this compound is introduced below., Computed Properties of C7H3BrFN

4-Bromo-2-phenoxy-benzonitrile (5c). Sodium hydride (12 g, 300 mmol) (60% by wt) was weighed into a flask and washed free of oil with several hexane rinsings. The hexanes were decanted and discarded and DMF was added to the flask. A solution of phenol (23.5 g, 250 mmol) in DMF (100 ml_) was added dropwise and the mixture was stirred at room temperature. To the mixture was added a solution of 4-bromo-2-fluoro-benzonitrile (50 g, 250 mmol, 100 ml_ DMF), dropwise. Upon complete addition, the reaction was refluxed for 20 h. The reaction was cooled to room temperature and poured into cold 1 N NaOH. A fine, tan precipitate formed and was collected by vacuum filtration to give Compound 5c. MS m/z (MH+) 277.

The synthetic route of 105942-08-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA N.V.; WO2007/30089; (2007); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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. 455-18-5, name is 4-(Trifluoromethyl)benzonitrile, A new synthetic method of this compound is introduced below., Application In Synthesis of 4-(Trifluoromethyl)benzonitrile

N-Hydroxy-4-trifluoromethylbenzimidamide (47c). 4-Trifluoromethylbenzonitrile 46c (1.37 g, 8.0 mmol) in ethanol (30 mL) was added to hydroxylamine hydrochloride (3.34 g, 48 mmol) and sodium hydrogen carbonate (2.54 g, 24 mmol) in water (30 mL) and the mixture was stirred at 100C for 3 h. The ethanol was evaporated from the cooled mixture and the residue was poured into ice-cold water. The precipitate was collected by filtration, washed (water) and dried to give N-hydroxy-4-trifluoromethyl- benzimidamide 47c (1.60 g, 98%) as a white powder: 1 18-120C (lit.95 128-129C); 1H NMR ((CD3)2SO) delta 6.01 (2 H, br, NH2), 7.79 (2 H, d, J = 8.4 Hz, Ph 2,6-H2), 7.94 (2 H, d, J = 8.4 Hz, Ph 3,5-H2), 9.96 (1 H, s, OH); 13C NMR ((CD3)2SO) delta 124.98 (q, J = 3.1 Hz, 3,5-C2), 125.54 (q, J = 331 Hz, CF3), 126.05 (2,6-C2), 129.17 (1 -C), 137.28 (q, J = 28 Hz, 4-C), 149.76 (C=N); 19F NMR (CDCI3) delta -62.84 (CF3); MS m/z 205.0610 (M + H)+ (C8H8N2OF3 requires 205.0589).

The synthetic route of 455-18-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UNIVERSITY OF BATH; THREADGILL, Michael David; LLOYD, Matthew David; THOMPSON, Andrew Spencer; NATHUBHAI, Amit; WOOD, Pauline Joy; PAINE, Helen Angharad; KUMPAN, Ekaterina; SUNDERLAND, Peter Thomas; CHUE YEN WOON, Esther; WO2014/87165; (2014); A1;,
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Synthetic Route of 120351-94-2,Some common heterocyclic compound, 120351-94-2, name is 3-(2-Aminoethoxy)benzonitrile, molecular formula is C9H10N2O, 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 Synthesis of N-[2-(3-cyanophenoxy)ethyl]-(1R)-10-camphorsulfonamide: The title compound was obtained from 700 mg (4.32 mmol) of 3-(2-aminoethoxy)benzonitrile and 1.08 g (4.32 mmol) of (1R)-(-)-10-camphorsulfonyl chloride in the same manner as that of step 1 in Example 106. Yield: 1.33 g (3.54 mmol) (82 %) MS (ESI, m/z) 377 (MH+)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-(2-Aminoethoxy)benzonitrile, its application will become more common.

Reference:
Patent; Ajinomoto Co., Inc.; EP976722; (2000); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthetic Route of 95-11-4, 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. 95-11-4 name is 5-Norbornene-2-carbonitrile, 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.

Ortho-dichlorobenzene (958 g) was added into a five-neck flask which is equipped with a reflux cooling tube,stirring blades, a thermometer, a gas-blowing tube and a raw material-injecting tube, and had an inner volume of 2 liter,154.2 g (1.0 mol) of 2,5-bisaminomethyl-bicyclo[2.2.1]heptane and 2,6-bisaminomethyl-bicyclo[2.2.1]heptane which hadbeen obtained in Example 2 and ortho-dichlorobenzene (702 g) were prepared in a raw material tank. Next, a reactioncontainer was heated to 120C at 0.1 MPa, adding of hydrochloric acid gas from a hydrochloric acid-blowing tube at arate of 43.8 g/hr and adding of an amine diluted by a solvent from the raw material tank using a raw material-injectingpump at a rate of 428.1 g/hr were initiated at the same time, and the total amount was added over 2 hours. Furthermore,aging was carried out for 1 hour while adding hydrochloric acid gas at 20 g/hr. After the completion of the reaction,subsequently, hydrochloride reaction mass was heated to 160C, phosgene was blown in from a phosgene-blowingtube at 100 g/hr (1.0 mol/hr), and a reaction was caused for 6 hours while maintaining the temperature. After thecompletion of the reaction, unreacted phosgene and hydrochloric acid gas in the system were purged using nitrogen,and the solvent was removed, thereby obtaining a solution (200.9 g) including 2,5-bisisocyanate methyl-bicyclo[2.2.1]heptane and 2,6-bisisocyanate methyl-bicyclo[2.2.1]heptane. Furthermore, distillation was carried out under reducedpressure, and a mixture (175.7 g) of 2,5-bisisocyanate methyl-bicyclo[2.2.1]heptane and 2,6-bisisocyanate methylbicyclo[2.2.1]heptane having a purity of 99.0% was obtained. An 1H-NMR chart is illustrated in Fig. 3.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Norbornene-2-carbonitrile, and friends who are interested can also refer to it.

Reference:
Patent; Mitsui Chemicals, Inc.; KUMA, Shigetoshi; SAKATA, Michiharu; TOKUNAGA, Kouichi; SHIMAKAWA, Chitoshi; KAKINUMA, Naoyuki; FURUYA, Masayuki; TANAKA, Mamoru; EP2708527; (2014); A1;,
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Electric Literature of 76469-88-0, A common heterocyclic compound, 76469-88-0, name is Methyl 4-(cyanomethyl)benzoate, molecular formula is C10H9NO2, 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.

Step 1; Methyl 4-(cyanomethyl)benzoate (1.8 g, 10 mmol, 1 eq) was dissolved in THF (100 mL) and cooled to 0C. Sodium hydride (60% w/w in mineral oil, 820 mg, 20 mmol, 2 eq) was added portionwise and the mixture was stirred for 10 minutes. Methyl iodide (1.3 mL, 20 mmol, 2 eq) was added dropwise and the reaction was stirred at 0C until the starting material was consumed by TLC (2 hours). The reaction mixture was quenched with water and was partitioned between EtOAc and brine. The aqueous layer was discarded, and the organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered, and evaporated to afford a crude residue which was chromatographed on silica gel (gradient elution, 0% to 50% EtOAc in hexanes, Si02) to afford the desired product as a white crystalline solid (1.88g, 74%).

The synthetic route of 76469-88-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SCHERING CORPORATION; WONG, Michael, K.; LAVEY, Brian, J.; YU, Wensheng; KOZLOWSKI, Josheph, A.; DEMONG, Duane, E.; DAI, Xing; STAMFORD, Andrew, W.; MILLER, Michael, W.; ZHOU, Guowei; YANG, De-Yi; GREENLEE, William, J.; WO2011/119559; (2011); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts