Month: June 2021

Related Products of 4435-14-7,Some common heterocyclic compound, 4435-14-7, name is 2-Cyclohexylacetonitrile, molecular formula is C8H13N, 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 (2) Preparation of 4-[(3-Benzofuranyl)methyl]-3H-1,2,3,5-oxathiadiazole 2-Oxide According to Scheme I illustrated by Example 4, 3-benzofuranylacetonitrile was converted to the desired product as beige crystals, m.p. 138.5-140 C. temperature. Cyclohexylacetonitrile (14.7 g, 120 mmol) was added in one portion and the resulting mixture was heated to reflux for 12 hours. The mixture was cooled to room temperature and concentrated to give a yellow solid. The solid was collected by filtration, washed with water, EtOAc/hexane (2:8), and dried in vacuo to give 7.4 g (40%) of the product of sufficient purity for use in the next reaction. NMR (DMSO-d6, 200 MHz): delta 0.85 (m, 2H), 1.10 (m, 3H), 1.64 (m, 6H), 1.80 (d, J=7.0, 2H), 5.25 (br s, 2H), 8.30 (br s, 1H).

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

Reference:
Patent; American Home Products Corporation; US4895860; (1990); A;,
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 79463-77-7 as follows. Safety of Diphenyl N-cyanocarbonimidate

A mixture of 4-(4-amino-2,6-dimethoxy-phenoxy)-piperidine-1-carboxylic acid benzyl ester (57.8 mg, 0.180 mmol) and diphenyl cyanocarbonimide (42.8 mg, 0.180 mmol) in toluene (1.0 mL) was heated at 100 C overnight. The mixture was concentrated and purified by silica gel column chromatograghy eluted with EtOAc:hexanes (40 to 60% EtOAc) to give the title compound (65.3 mg, 82%) as a colorless oil. MS (ES+): m/z = 531.2.

According to the analysis of related databases, 79463-77-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; WO2004/46120; (2004); A2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

19924-43-7, name is 2-(3-Methoxyphenyl)acetonitrile, 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: 2-(3-Methoxyphenyl)acetonitrile

Example 1 Synthesis of Exemplified Compound 4 (A) Synthesis of Compound 4-a In a nitrogen atmosphere, 15.5 g of metallic sodium, 200 ml of 1-methyl-2-pyrrolidinone (NMP), and 66.8 g of diphenyldisulfide (PhSSPh) were placed into a flask, and the mixture was refluxed under heating at an outside temperature of 200 C. for 30 minutes. Thereto, added was a solution prepared by dissolving 75 g of (3-methoxyphenyl)acetonitrile in 200 ml of 1-methyl-2-pyrrolidinone, while being refluxed at the same temperature, followed by refluxing under heating at an outside temperature of 200 C. for additional 3 hours. After completion of the reaction,the reaction liquid was cooled to room temperature (r.t.), and 200 ml of hexane and 400 ml of a 0.5M aqueous sodium hydroxide solution were added thereto. The resultant mixture was stirred and transferred into a separatory funnel, and the resultant hexane layer was separated and removed. To the obtained aqueous layer, was added 3M hydrochloric acid to adjust the solution to be acidic, and was subjected to extraction by ethyl acetate. The solution was separated, and an ethyl acetate layer was obtained. The ethyl acetate layer was washed with 1M hydrochloric acid and then a saturated saline solution, dried over anhydrous magnesium sulfate, followed by distilling off the solvent, and being purified by silica gel column chromatography, to thereby obtain 70.4 g (100% yield) of Compound 4-a. 1H NMR (300 MHz, CDCl3) ? (ppm): 3.73 (2H, s), 6.16 (1H, s), 6.80 to 6.89 (3H, m), 7.20 to 7.30 (1H, m)

The synthetic route of 19924-43-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FUJI PHOTO FILM CO., LTD.; US2006/142553; (2006); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Related Products of 90401-84-6,Some common heterocyclic compound, 90401-84-6, name is 6-Cyano-1-tetralone, molecular formula is C11H9NO, 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.

alpha”l ) delta-Hvdroxy-delta-d-trityl-I H-imidazol^-vD-delta.thetaJ.S-tetrahydronaphthalene^-carbonitrile 12 mmol of ethylmagnesium chloride (3M in diethyl ether) are added to a solution of 10 mmol of 4-iodo-1-trityl-1 H-imidazole [96797-15-8] in 40 ml of dichloromethane. The mixture is stirred for 45 minutes, and a solution of 10 mmol of 5-oxo-5,6,7,8-tetrahydronaphthalene- 2-carbonitrile [90401-84-6] in 15 ml of dichloromethane is added. The reaction mixture is stirred at room temperature overnight and quenched with saturated ammonium chloride solution. The phases are separated, and the aqueous phase is extracted with dichloromethane (3x). The combined organic phases are washed with brine, dried with sodium sulphate and evaporated. The title compound is identified from the residue on the basis of the Rf by flash chromatography (SiO2 60F).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6-Cyano-1-tetralone, its application will become more common.

Reference:
Patent; SPEEDEL EXPERIMENTA AG; WO2007/116098; (2007); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 75279-55-9, A common heterocyclic compound, 75279-55-9, name is 2-Chloro-6-fluorophenylacetonitrile, molecular formula is C8H5ClFN, 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.

Similar results are obtained when the above reaction is repeated using substituted-phenylacetonitriles. For example, when 1,4-dichlorobutene-2 is reacted with 6-chloro-2-fluorophenylacetonitrile or 4-nitrophenylacetonitrile in accordance with the above process 1-cyano-1-(6-chloro-2-fluorophenyl)-2-vinylcyclopropane and 1-cyano-1-(4-nitrophenyl)-2-vinylcyclopropane are respectively produced.

The synthetic route of 75279-55-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; National Distillers and Chemical Corporation; US4399076; (1983); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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. 874-97-5, name is 3-Cyanobenzyl alcohol, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 3-Cyanobenzyl alcohol

To a solution of 7-chloro-2,2-dimethyl-1-(methylsulfonyl)-2,3-dihydroimidazo[1,2-c]pyrimidin-5(1H)-one (200 mg, 0.720 mmol) and 3-(hydroxymethyl)benzonitrile (288 mg, 2.16 mmol) in N,N-dimethylformamide (DMF) (3.5 mL) was added K2CO3 (299 mg, 2.16 mmol). The reaction mixture was sealed in a microwave vial and irradiated with a microwave using initial normal to 100 C. for 1 h. Purification via mass-directed auto-preparation afforded the title product as a white solid. LCMS (ESI): m/z 297 [M+H]+; 2.24 min (ret time)

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 874-97-5.

Reference:
Patent; GlaxoSmithKline Intellectual Property Development Limited; WAN, Zehong; Sang, Yingxia; Zhang, Qing; US2014/213599; (2014); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Related Products of 6393-40-4,Some common heterocyclic compound, 6393-40-4, name is 4-Amino-3-nitrobenzonitrile, molecular formula is C7H5N3O2, 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.

(1) 4-Amino-3-nitrobenzonitrile (25 g) was dissolved in methanol (200 mL) and tetrahydrofuran (200 mL). The mixture was stirred in the presence of 10% palladium/carbon (3.0 g) under a hydrogen atomosphere (1 atm) for 20 hr. The reaction mixture was filtrated and the filtrate was concentrated under reduced pressure to give 3,4-diaminobenzonitrile (20 g) as a charcoal brown solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Amino-3-nitrobenzonitrile, its application will become more common.

Reference:
Patent; WELFIDE CORPORATION; EP1308439; (2003); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 177476-76-5, These common heterocyclic compound, 177476-76-5, name is 4-Amino-3-methoxybenzonitrile, 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.

4-Amino-3-methoxybenzonitrile (5.93 g, 40 mmol), acetic acid (40 mL) and methanol (100 mL) were added to a 250 mL single neck flask, then bromine (7.03 g, 44 mmol) was added dropwise at 0C. The reaction mixture was stirred for 2 h at rt. To the mixture was added saturated aqueous sodium carbonate (200 mL). The mixture was extracted with ethyl acetate (100 mL x 2). The combined organic phases were washed with saturated brine (100 mL), dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography (ethyl acetate/petroleum ether (v/v) = 1/10) to give the title compound as a pale yellow solid (7.63 g, 84%).MS (ES-API, pos. ion) m/z: 227.9 [M + 2]t

Statistics shows that 4-Amino-3-methoxybenzonitrile is playing an increasingly important role. we look forward to future research findings about 177476-76-5.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; YANG, Xinye; HUANG, Changwei; MA, Facheng; ZHANG, Ji; WANG, Xiaojun; ZHANG, Yingjun; (162 pag.)WO2017/36404; (2017); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Some common heterocyclic compound, 6587-24-2, name is Methyl 2-cyanobenzoate, molecular formula is C9H7NO2, 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. SDS of cas: 6587-24-2

To a solution of methyl 2-cyanobenzoate (322 mg, 2.0 mmol)) in MeOH (6 mL), Pd/C (10% by weight, 61 mg) and 4.0 N HCl in dioxane (0.875 mL, 1.75 eq) were added. This mixture was hydrogenated with a H2 balloon for 2.0 h. After filtration and concentration, 23A was obtained as HCl salt. 1H NMR (400 MHz, DMSO-d6) delta ppm 3.86 (s, 3 H) 4.30 (d, J=5.71 Hz, 2 H) 7.55 (m, 1 H) 7.65 (m, 2 H) 7.99 (d, J=7.91 Hz, 1 H) 8.49 (s, 3 H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6587-24-2, its application will become more common.

Reference:
Patent; Bristol-Myers Squibb Company; US2007/3539; (2007); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 16588-02-6, 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. 16588-02-6, name is 2-Chloro-5-nitrobenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 2-chloro-5-nitrobenzonitrile (1 g, 5.49 mmol) and 3,5- difluorobenzenethiol (960 mg, 6.6 mmol) in DIVIF (20 mL) was added K2C03 (2.3 g, 16 mmol). The reaction was stirred at 80 C overnight. The residue was poured into H20 (20 mL) and the aqueous phase was extracted with EA (30 mL x2). The organic layer was washed with brine (20 mL), dried over Na2SO4 and concentrated. The residue was purified by silica gel column (PE/EA = 10/1) to give 2-((3,5-difluorophenyl)thio)-5-nitrobenzonitrile (620 mg, yield: 39%) as a yellow solid.

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, 2-Chloro-5-nitrobenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SANFORD BURNHAM PREBYS MEDICAL DISCOVERY INSTITUTE; GARDELL, Stephen; PINKERTON, Anthony B.; SERGIENKO, Eduard; SESSIONS, Hampton; (428 pag.)WO2018/132372; (2018); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts