Category: nitriles-buliding-blocks

Application of 60702-69-4,Some common heterocyclic compound, 60702-69-4, name is 2-Chloro-4-fluorobenzonitrile, molecular formula is C7H3ClFN, 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 3) To a solution of the compound obtained in Step 2 (500 mg, 1.54 mmol) and 2-chloro-4-fluorobenzonitrile (240 mg, 1.54 mmol) in THF (15 mL) was added potassium t-butoxide (432 mg, 3.85 mmol) at room temperature, and the mixture was stirred for 14 hr. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and dried, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (solvent gradient; 5 to 75% ethyl acetate/hexane) to give the title compound (458 mg, 0.996 mmol, 64.6%) as a colorless powder. 1H-NMR (300MHz,DMSO-d6):delta1.03 (3H,d,J=6.0Hz), 1. 20-1.42(3H,m), 1.56-1.79(1H,m), 1.79-2.00(1H,m), 2.14-2.33(2H,m), 2.33-2.48(1H,m), 4.04-4.31(2H,m), 4.41(2H,q,J=6.9Hz), 7.00-7.26(2H,m), 7.35(1H,d,J=2.3Hz), 7.38-7.49(1H,m), 7.49-7.66(3H,m), 7.85(1H,d,J=8.7Hz), 8.04(1H,d,J=7.9Hz), 8.40(1H,s), 9.91(1H,s).

The synthetic route of 60702-69-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Takeda Pharmaceutical Company Limited; YAMAMOTO, Satoshi; SHIRAI, Junya; FUKASE, Yoshiyuki; TOMATA, Yoshihide; SATO, Ayumu; OCHIDA, Atsuko; YONEMORI, Kazuko; NAKAGAWA, Hideyuki; EP2759533; (2014); A1;,
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Electric Literature of 4421-09-4, 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. 4421-09-4, name is 3,4-(Methylenedioxy)benzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

2H-l,3-benzodioxole-5-carbonitrile (1.73 g, 11.75 mmol) in diethyl ether (15 ml) was added portion wise to a mixture of lithium aluminiumhydride (55.2 mmol hydride, 13.8 mmol, 525 mg) in diethyl ether (15 ml). The mixture was refluxed for 2 hours, then cooled and worked up (H20, 15 % NaOH, 3 x H20) and gave crude benzyl amine (1.77 g, quant.). This amine (1.0 g, 6.6 mmol) and pyridine (1.1 equiv., 17.6 mmol, 1.43 ml) was dissolved in dichloromethane (5.0 ml) and added dropwise to an ice cooled mixture of triphosgene (2.7 mmol, 801 mg,) in dichloromethane (5.0 ml). The mixture was stirred for 1 hour, then partitioned between cold 0.5 M sulfuric acid and dichloromethane. The organic phase was separated, dried and evaporated to give crude 5-(isocyanatomethyl)-2H-l,3-benzodioxole (1.08 g, 92 % yield). (0987) [00644] N-[(2,4-difluorophenyl)methyl]-l-methylpiperidin-4-amine (250 mg, 1.01 mmol) was dissolved in dichloromethane (1 ml) and 5-(isocyanatomethyl)-2H-l,3-benzodioxole (215 mg, 1.21 mmol) in dichloromethane (1 ml) was added in one portion. The mixture was stirred at room temperature for 1 hour and then purified by column chromatography using silicon dioxide gel, eluting with methanol to afford the title compound (275 mg, 66 % yield): NMR (400 MHz, Chloroform-;/) delta 7.21 (q, 1H), 6.87 – 6.73 (m, 2H), 6.73 – 6.59 (m, 3H), 5.92 (s, 2H), 4.57 (t, 1H), 4.40 (s, 2H), 4.29 (d, 2H), 4.26 (m, 1H), 2.88 (d, 2H), 2.27 (s, 3H), 2.07 (m, 2H), 1.75- 1.60 (m, 4H); LC-MS : 418.2 [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, 3,4-(Methylenedioxy)benzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ACADIA PHARMACEUTICALS INC.; BURSTEIN, Ethan, S.; OLSSON, Roger; BORGSTROeM, Bjoern, Gustav; JANSSON, Karl, Erik; SKOeLD, Niklas, Patrik; VON WACHENFELDT, Henrik; WAHLSTROeM, Larisa, Yudina; (250 pag.)WO2019/40107; (2019); A1;,
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Electric Literature of 55490-87-4, 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. 55490-87-4, name is 2-(Anthracen-9-ylmethylene)malononitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: The mixture of beta-cyanostyrenes 1 (1.0 mmol) and PIDA 2a (386 mg, 1.2 equiv) in acetonitrile and water (1:1) (5 mL) was irradiated in ultrasonic bath (Power dissipation as 50 W and frequency of 40 kHz) at room temperature for 30-60 min. The course of reaction was monitored by TLC. After completion of reaction, water (5 mL) was added to the reaction mixture and extracted with dichloromethane (3 X 5 mL). The combined organic layer was dried over anhydrous sodium sulphate and concentrated under vacuum. The crude products were purified by column chromatography on silica gel using EtOAc-hexane (1:49) and isolated products were characterized as beta-cyanoepoxides 3 by their spectroscopic analysis.

The synthetic route of 2-(Anthracen-9-ylmethylene)malononitrile has been constantly updated, and we look forward to future research findings.

Reference:
Article; Singh, Fateh V.; Mangaonkar, Saeesh R.; Kole, Priyanka B.; Synthetic Communications; vol. 48; 17; (2018); p. 2169 – 2176;,
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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 1897-52-5 as follows. COA of Formula: C7H3F2N

4.00 g (35.65 mmol) of potassium tert-butoxide and 2.60 g (34.64 mmol) of acetohydroxamic acid are dissolved in 50 ml of dry dimethylformamide and stirred at room temperature for 45 minutes. After the addition of 3.30 g (23.72 mmol) of 2,6-difluorobenzonitrile, the mixture is stirred at 50 C. for 16 hours. The mixture is concentrated under reduced pressure, and the residue is dissolved in dichloromethane and washed with water. After drying and concentration of the organic phase, 3.2 g of a yellow resin are obtained, which, according to 1H NMR, is about 85% pure

According to the analysis of related databases, 1897-52-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BAYER CROPSCIENCE AG; US2010/267703; (2010); A1;,
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Related Products of 56043-01-7, A common heterocyclic compound, 56043-01-7, name is 2-Amino-6-methylbenzonitrile, molecular formula is C8H8N2, 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.

PREPARATION 9; Preparation of 1 ,8-bis(bromomethyl)-9/-/-fluoren-9-one; A. Preparation of 2-(imino(o-tolyl)methyl)-3-methylaniline; To a cooled (0 0C) solution of 2-amino-6-methylbenzonitrile (5.00 g, 37.81 mmol) in anhydrous tetrahydrofuran (50 mL) was added dropwise a solution of 2- methylphenylmagnesium bromide (77.5 ml_ of a 2 M solution in diethyl ether, 155.0 mmol). The resultant mixture was then heated at reflux for 16 h and allowed to cool to ambient temperature. The reaction mixture was then poured into ice-water (500 mL) and concentrated hydrochloric acid (100 mL) was added. The mixture was transferred to a separatory funnel and was washed with diethyl ether (3 chi 100 mL). The aqueous phase was rendered alkaline by the addition of solid sodium hydroxide (8.0 g) and was extracted with dichloromethane (3 x 150 mL). The combined dichloromethane extract was washed with brine (150 mL), dried over sodium sulfate and filtered. The filtrate was concentrated in vacuo to dryness to afford 2-(imino(o-tolyl)methyl)-3-methylaniline: MS (ES+) m/z 225.3 (M + 1 ).

The synthetic route of 56043-01-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; XENON PHARMACEUTICALS INC.; WO2008/109840; (2008); A1;,
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Application of 222978-02-1, 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. 222978-02-1 name is 2-Fluoro-4-(hydroxymethyl)benzonitrile, 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.

Step D Preparation of 4-Bromomethyl-2-fluoro-benzonitrile N-Bromosuccinimide (6.6 g, 0.037 mol) was dissolved in CH2Cl2 (150 mL), cooled to 0 C. and treated with dimethylsulfide (3.27 mL, 0.0446 mol). The solution was cooled to -20 C. then treated dropwise with a solution of 2-fluoro-4-hydroxymethylbenzonitrile, as described in Step C above, (3.74 g, 0.0248 mol) in CH2Cl2 (30 mL). After the addition, the reaction mixture was stirred at 0 C. for 2 h then left to warm to ambient temperature overnight. The reaction mixture was added to ice/H2O, extracted with EtOAc, the organic layer separated, washed with brine and dried (MgSO4). Filtration and concentration to dryness gave the title compound which was purified after chromatography (silica gel, 5-10% EtOAc/hexane). 1H NMR (CDCl3) delta 7.61 (dd, 1H, J=8, 8 Hz), 7.26-7.30 (m, 2H), 4.45 (s, 2H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Fluoro-4-(hydroxymethyl)benzonitrile, and friends who are interested can also refer to it.

Reference:
Patent; Merck & Co., Inc.; US6284755; (2001); B1;,
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Related Products of 874-97-5, These common heterocyclic compound, 874-97-5, name is 3-Cyanobenzyl alcohol, 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.

The compound of Reference Example 1 3- (hydroxymethyl) benzonitrile (0.043 mL, 0.37 mmol) and sodium hydride (17 mg, 0.40 mmol) were added to a DMF (0.32 mL) solution of sodium hydride (50 mg, 0.16 mmol) And the mixture was stirred at 100 C. for 14 hours. Water (10 mL) was added to the reaction mixture at room temperature and extracted with ethyl acetate (10 mL × 2). The organic layers were combined, dried over sodium sulfate and concentrated. The resulting concentrate was purified by silica gel column chromatography (eluent: ethyl acetate / n-hexane = 30/70) to give the intermediate as a yellow oil (48 mg).To a solution of the obtained intermediate (48 mg) in 1,4-dioxane (0.32 mL) was added 4 N hydrogen chloride 1,4-dioxane solution (0.80 mL) at room temperature, and the mixture was stirred at room temperature for 2 hours. Acetonitrile (2.0 mL) was added to the reaction mixture at room temperature, diethyl ether (4.0 mL) was added dropwise at room temperature, and the mixture was stirred at room temperature for 1 hour. The solid was collected by filtration and dried under reduced pressure at room temperature to give 3 – (((6- (1,4-diazepan-1 -yl) pyrazin-2-yl) oxy) methyl) benzonitrile dihydrochloride Compound of Example 5) as a white solid (43 mg, yield 70%).

The synthetic route of 874-97-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TORAY INDUSTRIES INCORPORATED; KIKUCHI, TSUKASA; OKANO, TSUBASA; (24 pag.)JP2017/14121; (2017); A;,
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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. 35704-19-9, name is N-(4-Cyanophenyl)acetamide, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C9H8N2O

General procedure: In a double-necked round bottom flask (100 mL) equippedwith a condenser was added a mixture consisting ofnitrile (0.005 mol), NaN3 (0.006 mol), and monodisperse Pt NPsVC in DMF (1.5 mL). The mixture washeated at reflux until TLC monitoring indicated no furtherimprovement in the conversion. The reaction mixture wasthen cooled to room temperature, vacuum-filtered usinga sintered-glass funnel and the residue was washed withethyl acetate (3×10 mL). The filtrate was treated with5 mL HCl (4 mol L-1 to reach pH= 3 and it was allowedto stir for 30 minutes. Subsequently, the organic layer wasseparated, dried over anhydrous Na2SO4 and evaporated.The crude product was purified by recrystallization and/orcolumn chromatography on silica gel eluted with propersolvents to get pure 5-Phenyl 1H-tetrazole.

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 35704-19-9.

Reference:
Article; Baskaya, Gaye; Esirden, Ibrahim; Erken, Esma; Sen, Fatih; Kaya, Muharrem; Journal of Nanoscience and Nanotechnology; vol. 17; 3; (2017); p. 1992 – 1999;,
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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. 6621-59-6, name is 6-Bromohexanenitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Product Details of 6621-59-6

General procedure: A solution of the corresponding precursor (4-chlorobutyronitrile for compounds 1, 5-chlorovaleronitrile for compounds 3 and 6-bromohexanenitrile for compounds 6) (2.5 mmol) in dimethylformamide (1 mL) was added during 1.5 h to a mixture of the arylamine (2.5 mmol), Cs2CO3(2.5 mmol) and KI (5 mmol) in dimethylformamide (2.5mL). The mixture was stirred at the indicated temperature and time. After completion of the reaction, as indicated by TLC, the mixture was treated with ethyl ether (50 mL) and water (10 mL). The aqueous phase was separated and extracted with ethyl ether (30 mL). The combined organic layers were dried over anhydrous sodium sulfate and filtered. The solvent was evaporated in vacuo. The crude product was purified by column chromatography (silica gel, hexane:DCM).

The synthetic route of 6621-59-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Diaz, Jimena E.; Mollo, Maria C.; Orelli, Liliana R.; Beilstein Journal of Organic Chemistry; vol. 12; (2016); p. 2026 – 2031;,
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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. 42872-74-2, name is 3-Bromo-4-methylbenzonitrile, A new synthetic method of this compound is introduced below., Computed Properties of C8H6BrN

Dissolve 3-bromo-4-methylbenzonitrile (10g, 51mmol) in carbon tetrachloride (100mL), add NBS (22.6g, 127.5mmol) and benzoyl peroxide (272mg, 2.5mmol), and reflux 14h, the raw materials disappeared. Cool to room temperature, add water (400 mL), extract with DCM (200 mL × 2), and obtain column chromatography (P / E = 20: 1) to obtain 16.17 g of white solid with a yield of 89.6% and melting point: 48-49 C.

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; Chinese Academy Of Medical Sciences Pharmaceutical Institute; Xu Boling; Chen Xiaoguang; Cui Guonan; Lai Fangfang; Zhou Jie; Ji Ming; Wang Xiaoyu; Du Tingting; Li Ling; Jin Jing; (144 pag.)CN110483366; (2019); A;,
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