Month: February 2021

Electric Literature of 115661-37-5, The chemical industry reduces the impact on the environment during synthesis 115661-37-5, name is 2-Amino-3-fluorobenzonitrile, I believe this compound will play a more active role in future production and life.

2-Amino-3-fluorobenzonitrile (9.8 g, 71.9 mmol) was bromo-deaminated as described in Example 1 to afford 2-bromo-3-fluorobenzonitrile as a pale brown solid: 1H NMR (360 MHz, CDCl3) delta 7.62-7.68 (1H, m), 7.74-7.85 (1H, ddd, J 9, 9, 1 Hz), 7.74-7.85 (1H, ddd, J 8, 1, 1 Hz).

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

Reference:
Patent; Carling, William Robert; Hallett, David James; Russell, Michael Geoffrey Neil; Street, Leslie Joseph; US2003/55060; (2003); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

628-20-6, name is 4-Chlorobutyronitrile, 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. SDS of cas: 628-20-6

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 628-20-6 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;,
Nitrile – Wikipedia,
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Electric Literature of 98730-77-9, A common heterocyclic compound, 98730-77-9, name is 1-(Hydroxymethyl)cyclopropanecarbonitrile, molecular formula is C5H7NO, 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.

Intermediate 19: (1-Cyanocyclopropyl)methyl 4-methylbenzenesulphonate (0699) (0700) Et3N (8.97 mL, 64.36 mmol) was added to 1-(hydroxymethyl)cyclopropane-1-carbonitrile (5 g, 51.48 mmol) and TsCl (11.78 g, 61.78 mmol) in DCM (100 mL) cooled to 0 C. under nitrogen. The resulting solution was stirred at room temperature for 2 hours. The reaction mixture was quenched with water (20 mL), extracted with DCM (3¡Á20 mL), the organic layer was dried over Na2SO4, filtered and evaporated to afford white solid. The crude product was purified by flash silica chromatography, elution gradient 0 to 100% DCM in petroleum ether. Pure fractions were evaporated to dryness to afford (1-cyanocyclopropyl)methyl 4-methylbenzenesulfonate (5.20 g, 40%). (0701) LC/MS: m/z=252 [M+H]+. 1H NMR (300 MHz, CDCl3) delta 1.09 (dd, J=7.5, 5.7 Hz, 2H), 1.38 (dd, J=7.5, 5.4 Hz, 2H), 2.48 (s, 3H), 4.01 (s, 2H), 7.40 (d, J=8.1 Hz, 2H), 7.84 (d, J=8.1 Hz, 2H).

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; AstraZeneca AB; NARJES, Frank; OLSSON, Roine Ingemar; VON BERG, Stefan; LEVER, Sarah; (112 pag.)US2017/166527; (2017); A1;,
Nitrile – Wikipedia,
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Synthetic Route of 3759-28-2, A common heterocyclic compound, 3759-28-2, name is 2-(Cyanomethyl)benzonitrile, molecular formula is C9H6N2, 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: A mixture of 1-aryl/alkyl-3,3-bis-methylsulfanyl-propenone (1.0 mmol), 2-cyanomethyl-benzonitrile (1 mmol, 142.0 mg), and powdered KOH (2 mmol, 112.0 mg) in dry DMSO (5 mL) was stirred at room temperature for 2 h. Completion of reaction was monitored by TLC. After completion, reaction mixture was poured onto ice-water with constant stirring and then neutralized with 10% HCl. The precipitate obtained was filtered, washed with water and dried over dry sodium sulfate. Many compounds were purified by recrystallization in dry methanol. Some compounds were purified through column chromatography using 15% ethylacetate in hexane as an eluent. Characterization data for some of the synthesized compounds are reported earlier.17

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:
Article; Singh, Surjeet; Althagafi, Ismail; Yadav, Pratik; Panwar, Rahul; Kumar, Abhinav; Pratap, Ramendra; Tetrahedron; vol. 70; 46; (2014); p. 8879 – 8884;,
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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 4088-84-0 as follows. HPLC of Formula: C8H3F4N

Heat a solution [OF 2-FLUORO-5-TRIFLUOROMETHYL-BENZONITRILE (L. OG,] 5.74 mmol) with 4,5-difluoro-2-nitro-phenylamine (1.09g, 5.74 mmol) and lithium hydroxide monohydrate (0. [48G,] 11.49 mmol) in DMSO (12 ml) to 55 [C] for 16 hours. Cool the reaction to ambient temperature and then add approximately 150 ml of ice water and stir the mixture for one hour. Extract with three 200 ml portions of dichloromethane. Combine organic layers, dry over sodium sulfate and evaporate solvent. Purify the residue via flash chromatography eluting with a linear gradient starting with 100% hexanes and going to 70% hexanes: 30% ethyl acetate to obtain 0.995g (2.90 mmol, 50% yield) of the title compound as a yellow amorphous solid: Mass Spectrum [(M/E)] : 344 [(M+1).]

According to the analysis of related databases, 4088-84-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ELI LILLY AND COMPANY; WO2004/14895; (2004); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthetic Route of 179897-89-3,Some common heterocyclic compound, 179897-89-3, name is 5-Bromo-2-fluorobenzonitrile, molecular formula is C7H3BrFN, 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.

Add 5-bromo-2-fluoro-benzonitrile (0.5 g, 2.5 mmol), benzophenone imine (0.543 g, 3 mmol), (¡À)-2,2′-bis(diphenylphosphino)-l,l’-binaphthalene (BetaGammaNuAlphaRho, 60 mg, 0.1 mmol), tris(dibenzylideneacetone)dipalladium [Pd2(dba)3, 50 mg, 0.05 mmol], and Cs2C03 (1.6 g, 4.9 mmol) in 1,4-dioxane (20 mL). Stir the reaction under N2 at 110C for 16 hrs. Cool to room temperature, filter the solid, and concentrate the filtrate to give the crude product. Purification by chromatography (silica gel, EtOAc_PE=l :3) affords the title compound (0.78 g, 99%). MS: (M+1): 301.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Bromo-2-fluorobenzonitrile, its application will become more common.

Reference:
Patent; CROWN BIOSCIENCE INC. (TAICANG); ZHANG, Deyi; ZHANG, Ruihao; ZHONG, Boyu; SHIH, Chuan; WO2014/418; (2014); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthetic Route of 1885-38-7, A common heterocyclic compound, 1885-38-7, name is (E)-Cinnamonitrile, molecular formula is C9H7N, 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: In a typical reaction, 0.015 g of catalyst and 2 mmol of the reactant were taken in 10 mL of ethanol under hydrogen atmosphere. The reaction was monitored by thin-layer chromatography (TLC). After complete disappearance of the starting material, the catalyst was separated by simple filtration and the solvent was removed under reduced pressure to obtain the pure product.

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:
Article; Lakshmi, Kantam M.; Parsharamulu; Manorama; Journal of Molecular Catalysis A: Chemical; vol. 365; (2012); p. 115 – 119;,
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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. 1194-02-1, name is 4-Fluorobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 4-Fluorobenzonitrile

General procedure: To the solution of NaOH (5.93 g, 0.15 mol) in water (20 mL) and ethanol (120 mL), hydroxylamine hydrochloride (10.33 g, 0.15 mol) was added in one portion at room temperature. The resulting mixture was then stirred for 10 min, followed by the addition of 4-substituted cyanobenzene (1, 0.12 mol) and then heated to reflux for 4 h. After cooled to room temperature, the reaction mixture was evaporated in vacuo to remove ethanol. The obtained slurry was dissolved in ethyl acetate and filtered. The filtrate was collected, dried over anhydrous Na2SO4, and then concentrated to give corresponding compound 2, which was used in next step without any purification.

According to the analysis of related databases, 1194-02-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Dai, Hong; Chen, Jia; Li, Gang; Ge, Shushan; Shi, Yujun; Fang, Yuan; Ling, Yong; Bioorganic and Medicinal Chemistry Letters; vol. 27; 4; (2017); p. 950 – 953;,
Nitrile – Wikipedia,
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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. 5922-60-1, name is 2-Amino-5-chlorobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C7H5ClN2

2-Amino-5-chlorophenyl)r4-fluorophenyl)methanone (5-1)To a O0C solution of 1.0M 4-fluorophenylmagnesium bromide in THF (196.6 mL, 196.6 mmol) was added a THF solution (100 mL) of 2-amino-5-chlorobenzonitrile (10.0 gm, 65.5 mmol) over 0.5h. The ice bath was removed and the reaction stirred at ambient temperature for 17 h. The brown solution was cooled in an ice bath, treated with a drop wise addition of aqueous IN HCl (300 mL) and extracted with ether (2x 250 mL). The combined organic extracts were washed with aqueous IN HCl (100 mL), water (2x 150 ml), saturated aqueous sodium bicarbonate (150 ml), brine (100 mL), dried over MgSO4, filtered, concentrated in vacuo to 30 mL and diluted with 60 mL hexane. The resulting precipitate was filtered to give (2-amino-5-chlorophenyl)(4-fluorophenyl)methanone as a yellow solid. IH NMR (CDCl3, 400 MHz) 7.67 (m, 2H); 7.37 (d, J= 2.38 Hz, IH); 7.25 (m, IH); 7.16 (m, 2H); 6.70 (d, J= 8.79 Hz, IH); 5.99 (s). MS (Electrospray): m/z 250.1 (M+H)

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 5922-60-1.

Reference:
Patent; MERCK & CO., INC.; WO2006/98969; (2006); A2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 4426-11-3, These common heterocyclic compound, 4426-11-3, name is Cyclobutanecarbonitrile, 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.

Example 253A 1-(2-methylbenzyl)cyclobutanecarbonitrile n-BuLi (0.018 mol, 7.2 ml, 2.5M) was added to a solution of diisopropylamine (1.7 g, 0.017 mol) in THF (15 mL) at -78 C. After 5 minutes neat cyclobutancarbonitrile (1.2 g, 0.015 mol) 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)

The synthetic route of 4426-11-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AbbVie Inc.; Bayburt, Erol K.; Clapham, Bruce; Cox, Phil B.; Daanen, Jerome F.; Dart, Michael J.; Gfesser, Gregory A.; Gomtsyan, Arthur; Kort, Michael E.; Kym, Philip R.; Schmidt, Robert G.; Voight, Eric A.; US2013/131036; (2013); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts