Category: nitriles-buliding-blocks

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;,
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

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 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;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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,
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,
Nitriles – Chemistry LibreTexts

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

Reference of 3939-09-1,Some common heterocyclic compound, 3939-09-1, name is 2,4-Difluorobenzonitrile, molecular formula is C7H3F2N, 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.

To a solution of 2,4-difluorobenzonitrile (10 g, 72 mmol) dissolved in tetrahydrofuran (20 mL), and dimethylformamide (40 mL) was added the sodium salt of 1,2,4-triazole (6.3 g, 70 mmol) and the mixture was stirred at 90 C. for 3 h, filtered and concentrated. The residue was adsorbed onto Silica gel and purified by flash chromatography eluting with 0%-10%-30% ethylacetate/hexanes to give 4-fluoro-2-(1H-1,2,4-triazol-1-yl)benzonitrile as colorless needles (2.46 g, 18%) and 4-(1H-1,2,4-triazol-1-yl)-2-fluorobenzonitril as a white solid (0.746 g, 6%). 4-Fluoro-2-(1H-1,2,4-triazol-1-yl)benzonitrile. Colorless needles (2.46 g, 18% yield) 1H NMR (500 MHz, CDCl3) delta 8.89 (1H, s), 8.19 (1H, s), 7.85 (1H, dd, J=8.7, 5.6 Hz), 7.60 (1H, dd, J=8.8, 2.4 Hz), 7.28-7.24 (1H, m). LCMS (M+H) calcd for C9H6N4F: 189.05; found: 189.13. 4-(1H-1,2,4-Triazol-1-yl)-2-fluorobenzonitrile. White solid (0.746 g, 6% yield) 1H NMR (500 MHz, CDCl3) delta 8.66 (1H, s), 8.15 (1H, s), 7.79 (1H, dd, J=8.5, 6.7 Hz), 7.69 (1H, dd, J=9.5, 1.8 Hz), 7.65-7.63 (1H, m). LCMS (M+H) calcd for C9H6N4F: 189.05; found: 189.13.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2,4-Difluorobenzonitrile, its application will become more common.

Reference:
Patent; Bristol-Myers Squibb Company; US2007/111984; (2007); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

These common heterocyclic compound, 67515-59-7, name is 4-Fluoro-3-(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. Recommanded Product: 67515-59-7

b. 3-Dimethoxymethyl-1-(2-trifluoromethyl-4-cyano-phenyl)-1,4,5,6-tetrahydro-cyclopentapyrazole 0.7 g (17.5 mmol) of sodium hydride are added at 0 C. to a solution of 3.2 g (17 mmol) of 4-fluoro-3-trifluoromethyl-benzonitrile and 3.1 g (17 mmol) of 3-dimethoxymethyl-1,4,5,6-tetrahydro-cyclopentapyrazole in 20 ml of dimethylformamide. After 3 hours at ambient temperature the reaction solution is poured onto ice water and extracted with ethyl acetate. The organic phase is washed with water and with saturated saline solution, dried and evaporated down. The crude product is recrystallized from diisopropylether/petroleum ether. Yield: 3.2 g (54% of theory) Rf value: 0.33 (silica gel; petroleum ether/ethyl acetate=7:3+1% conc. ammonia)

The synthetic route of 4-Fluoro-3-(trifluoromethyl)benzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Nar, Herbert; Priepke, Henning; Ries, Uwe; Stassen, Jean Marie; Wienen, Wolfgang; US2002/183519; (2002); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Some common heterocyclic compound, 34667-88-4, name is 2-Fluoro-4-nitrobenzonitrile, molecular formula is C7H3FN2O2, 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. HPLC of Formula: C7H3FN2O2

2-fluoro-4-nitrobenzonitrile (0.125 g, 0.751 mmol) was hydrogenated at 50 psi in the presence of 10percent Pd/C (40 mg) in EtOH/EtOAc (15mL) for 1 h. Filtered through Celite? and concentrated to an orange solid that was carried onto next step. MS (ESI) m/z: 137 (M+H)+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 34667-88-4, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; ORWAT, Michael J.; PINTO, Donald J.P.; SMITH II, Leon M.; SRIVASTAVA, Shefali; CORTE, James R.; WO2013/55984; (2013); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts