Author: Jessica.F

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. 29509-06-6, name is 4-Methyl-3-oxopentanenitrile, This compound has unique chemical properties. The synthetic route is as follows., Formula: C6H9NO

General procedure: A mixture of 4-methyl-3-oxopentanenitrile 10i or 10ii (1.5eq), aldehyde 6(a-m) (1.0 eq), urea (1.5 eq) and CuCl (0.01eq) in MeOH containing concentrated H2SO4 (0.62 eq) wasstirred at reflux temperature for 3-5 days. After the reactionwas deemed complete by TLC, methanol was removed byconcentration in vacuo. The precipitated solid was extractedin dichloromethane. The dichloromethane layer was washedwithwater twice so as to removewater soluble impurities. Theorganic layerwas concentrated again to dryness in vacuo. Thecrude residue was purified by silica gel column chromatographyusing ethyl acetate: hexanes to give pyrimidine compound11(a-m).

According to the analysis of related databases, 29509-06-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Pachore, Sharad S; Ambhaikar, Narendra B; Siddaiah, Vidavalur; Khobare, Sandip R; Kumar, Sarvesh; Dahanukar, Vilas H; Kumar, U K Syam; Journal of Chemical Sciences; vol. 130; 6; (2018);,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Related Products of 1953-99-7, A common heterocyclic compound, 1953-99-7, name is 3,4,5,6-Tetrachlorobenzene-1,2-dicarbonitrile, molecular formula is C8Cl4N2, 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.

(i) Preparation of 1,2-dicyano-3,4,5,6-tetra(2-naphthoxy)benzene 1,2-Dicyano-3,4,5,6-tetrachlorobenzene (30.5 parts), potassium carbonate (62.8 parts) and 2-naphthol (98.1 parts) were stirred in dimethylformamide (140 parts) at 70 C. for 3 hours. The mixture was poured into water (300 parts) and extracted with chloroform (3*300 parts). The combined chloroform extracts were washed with dilute aqueous sodium hydroxide solution (500 parts) and then with water (500 parts). The chloroform was dried over anhydrous magnesium sulphate before evaporating under reduced pressure to leave a brown liquid which crystallized on adding butan-1-ol, cooling and standing for 2 hours. The crystallized solid was filtered, washed with butan-1-ol until the filtrates were colourless. The solid was dried to give 1,2-dicyano-3,4,5,6-tetra(2-naphthoxy)benzene (40.6 parts), m.p. 188-190 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; Zeneca, Limited; US5486274; (1996); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Related Products of 71825-51-9,Some common heterocyclic compound, 71825-51-9, name is 2-Methyl-2-(4-nitrophenyl)propanenitrile, molecular formula is C10H10N2O2, 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 cooled solution of 2-methyl-2-(4-nitrophenyl)propanenitrile (670 mg, 3.5 mmol) in THF (15 mL) was added BH3 (1M in THF, 14 mL, 14 mmol) dropwise at 0 C. The mixture was warmed to room temperature and heated at 70 C. for 2 h. 1N HCl solution (2 mL) was added, followed by the addition of NaOH until pH>7. The mixture was extracted with ether and ether extract was concentrated to give 2-methyl-2-(4-nitrophenyl)propan-1-amine (610 mg, 90%), which was used without further purification. 1H NMR (400 MHz, CDCl3) delta 8.20 (d, J=9.0 Hz, 2H), 7.54 (d, J=9.0 Hz, 2H), 2.89 (s, 2H), 1.38 (s, 6H).

The synthetic route of 71825-51-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Vertex Pharmaceuticals Incorporated; Van Goor, Fredrick F.; Burton, William Lawrence; US2015/231142; (2015); A1;,
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. 330792-69-3, name is 2-(Methoxy(4-phenoxyphenyl)methylene)malononitrile, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C17H12N2O2

1,1-Dicyano-2-methoxy-2-(4-phenoxyphenyl)ethene (22.5 g) and 1,1-dicyano-2-methoxy-2-(4-phenoxyphenyl)ethene oil (15 g) are treated with a solution of hydrazine hydrate (18 mL) in ethanol (25 mL) and heated on the steambath for 1 hour. Ethanol (15 mL) is added followed by water (10 mL). The precipitated solid is collected and washed with ethanol:water (4:1) and then dried in air to give 3-amino-4-cyano-5-(4-phenoxyphenyl)pyrazole as a pale orange solid.

According to the analysis of related databases, 330792-69-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PHARMACYCLICS, INC.; US2008/76921; (2008); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Reference of 6952-59-6, These common heterocyclic compound, 6952-59-6, name is 3-Bromobenzonitrile, 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: Aryl-halide (0.2 mmol, 1 equiv.), Ir(dtbbpy)(ppy)2PF6 (1.8 mg, 0.002 mmol, 1 mol %), NiCl2.glyme (4.4mg, 0.02 mmol, 10 mol %), DMSO (2.0 mL) was added to a 10 mL schlenk flask equipped with a magnetic stirrer bar. This resulting mixture was sealed and degassed via vacuum evacuation and subsequent backfill with ethylene for three times. Then, N,N,N?,N?-tetramethylethylenediamine, TMEDA(60 muL, 2 equiv.), N,N-diisopropylethylamine, DIPEA (70 muL, 2 equiv.) and H2O (7.2 muL, 2 equiv.) were subsequently added in this order. The mixture was then irradiated with blue LED (2 meter strip, 18 W)with ethylene balloon for 24 hours at 80oC (Figure S1). The reaction was added water (30 mL) and extracted with ethyl acetate (10 mL) three times. Combined organic layer was successively washed with brine three times and dried over Na2SO4 and concentrated under reduced pressure. The residue was then subjected to flash column chromatography (hexane or hexane/ethyl acetate) to yield theproduct

The synthetic route of 6952-59-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Li, Jiesheng; Luo, Yixin; Cheo, Han Wen; Lan, Yu; Wu, Jie; Chem; vol. 5; 1; (2019); p. 192 – 203;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Application of 42872-73-1,Some common heterocyclic compound, 42872-73-1, name is 2-Bromo-4-methylbenzonitrile, molecular formula is C8H6BrN, 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 mixture of 2-bromo-4-methylbenzonitrile (2.00 g, 10.2 mmol), 5, 5, 5′, 5′- tetramethyl-2,2′-bi(l,3,2-dioxaborinane) (3.06 g, 13.6 mmol) and potassium acetate (3.00 g, 30.6 mmol) in anhydrous DMSO (10 mL), in a sealable flask, was purged with Argon for 20 min before PdChldppfj-Cl ECl? adduct (0.25 g, 0.34 mmol) was added, the flask was sealed and the reaction heated at 80 C. After 17 hrs, the reaction was cooled to RT before being partitioned between EtOAc and brine. The layers were separated and the aqueous layer was extracted once more with EtOAc. The organic layers were combined, washed with brine, dried (MgS04), filtered and concentrated in vacuo to afford a brown oil which solidified upon standing. Purification by Isco chromatography afforded 301 A as an off-white solid (1.96 g; 84% yield). NMR (400MHz, DMSO-d6) d 7.72 – 7.63 (m, 2H), 7.43 (dd, 7=7.9, 1.1 Hz, 1H), 3.79 (s, 4H), 2.38 (s, 3H), 0.98 (s, 6H).

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

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; BALOG, James Aaron; MARKWALDER, Jay A.; SHAN, Weifang; WILLIAMS, David K.; NARA, Susheel Jethanand; ROY, Saumya; THANGAVEL, Soodamani; CHERUKU, Srinivas; SISTLA, Ramesh Kumar; (230 pag.)WO2020/23355; (2020); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Application of 3556-60-3, 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. 3556-60-3, name is 3-Methoxy-4-methylbenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Under an inert atmosphere, to a solution of 3-methoxy-4-methylbenzonitrile (2.00 g, 13.6 mmol) in tetrahydrofuran (50 mL), a methylmagnesium chloride solution (5 mL, 3M in tetrahydrofuran) was added dropwise during cooling with ice at 0-2 C, and the mixture was stirred at 40 C for 12 hours. (0195) The reaction mixture was quenched by dropwise addition of 6 M HC1 solution (3.4 mL), and was stirred stirred at 40 C for another hour. The mixture was extracted with ethyl acetate, the combined organic layer was washed with brine, dried over Na?.S04, evaporated, and the crude residue was purified with column chromatography on silica gel with gradient elution, using a mixture of dichlorom ethane and cyclohexane as eluent. Yield: 356 mg (16 %).

The synthetic route of 3-Methoxy-4-methylbenzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; RICHTER GEDEON NYRT.; LEDNECZKI, Istvan; ELES, Janos; TAPOLCSANYI, Pal; JABLONKAI, Erszebet; GABOR, Eszter; VISEGRADI, Andras; NEMETHY, Zsolt; LEVAY, Gyoergy Istvan; PETRO, Jozsef Levente; SELENYI, Gyoergy; (0 pag.)WO2020/12423; (2020); 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. 179898-34-1, name is 3-Bromo-5-fluorobenzonitrile, A new synthetic method of this compound is introduced below., Safety of 3-Bromo-5-fluorobenzonitrile

Step 1 (0915) A solution of 3-bromo-5-fluorobenzonitrile (CXVIII) (44.0 g, 220.0 mmol, 1.0 eq) was dissolved in THF (30 mL). BH3-Me2S (33.43 g, 440.0 mmol, 2.0 eq) was added to the solution at 20 C. Then it was stirred at 80 C. for 2 h, HCl (6 N, 100 mL) was added to the mixture slowly at 20 C. The mixture was stirred at 80 C. for 1 h, then it was washed with EtOAc (300 ml). The water phase was basified with 50% aqueous NaOH and it was extracted with EtOAc (300 mL×3). The combined organic layers were dried over anhydrous Na2SO4 and concentrated in vacuo to produce (3-bromo-5-fluoro-phenyl)methanamine (CXIX) (24.0 g, 117.62 mmol, 53.5% yield). 1H NMR (CDCl3, 300 MHz) 3.86 (s, 2H), 7.01 (d, J=8 Hz, 1H), 7.12 (d, J=8 Hz, 1H), 7.28 (s, 1H); ESIMS found C7H7BrFN m/z 203.9 (Br79M+H).

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; Samumed, LLC; KC, Sunil Kumar; Wallace, David Mark; Cao, Jianguo; Chiruta, Chandramouli; Hood, John; (390 pag.)US2016/90380; (2016); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Related Products of 262298-02-2,Some common heterocyclic compound, 262298-02-2, name is 4-Methoxy-2-methylphenylacetonitrile, molecular formula is C10H11NO, 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 1 Preparation of Intermediate 2-(4-methoxy-2-methylphenyl)-3-oxobutyronitrile Potassium Salt Under anhydrous conditions, (4-methoxy-2-methylphenyl)acetonitrile (25.0 kg, 155 moles, available commercially) and 68.3 kg of ethyl acetate were mixed to obtain a solution. The resulting solution was heated to 35 C. and potassium t-butoxide in THF (100 kg, 20 wt %, 178 moles) was added over a 30 to 60 minute period controlling the temperature at 35 C. Following the addition, the reaction mass was heated to 45 C. and held for 60 minutes. At the end of the hold period, a sample was analyzed by HPLC. The reaction mixture was then cooled to 25 C. and combined with 3 other batches for a total of 843 kg of solution.

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

Reference:
Patent; Gilligan, Paul J.; Rabel Riley, Shelly Renee; Meenan, Paul A.; US2005/113375; (2005); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthetic Route of 1210906-15-2, The chemical industry reduces the impact on the environment during synthesis 1210906-15-2, name is 5-Bromo-2-(trifluoromethoxy)benzonitrile, I believe this compound will play a more active role in future production and life.

Step 1A: 5-[(3R)-3-methylpiperazin-l-yll-2-(trifluoromethoxy)benzonitrile (0188) To a solution of tert-butyl (2R)-2-methylpiperazine-l-carboxylate (5.0 g, 25 mmol, 1.0 eq) and 5-bromo-2-(trifluoromethoxy)benzonitrile (3.8 mL, 25 mmol, 1 eq) in toluene (100 mL) was added sodium tert-butoxide (7.2 g, 75 mmol, 3.0 eq), racemic 2,2′-bis(diphenylphosphino)-l,l’-binaphthyl (1.6 g, 2.5 mmol, 0.10 eq), and lastly tris(dibenzylideneacetone)dipalladium(0) (2.3 g, 2.5 mmol, 0.10 eq), and the reaction mixture heated to 100 C overnight. The resulting dark reaction mixture was cooled, passed thru a pad of celite, and concentrated in vacuo. Silica gel column (80 g) was dry loaded and run using an increasing gradient of EtOAc (0-50%) in hexanes over 25 min. The chromatographed material was dissolved in dioxane (40 mL) and treated with a solution of 4M HC1 in dioxane (10 mL). The resulting thick suspension was concentrated, dissolved in MeOH, and made basic with the addition of MP-carbonate. Following removal of the resin and concentration of the filtrate, the free base of 5- [(3R)-3-methylpiperazin-l-yl]-2-(trifluoromethoxy)benzonitrile la (5.2 g, 18 mmol, 72% over two steps) was isolated as an orange oil.

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, 5-Bromo-2-(trifluoromethoxy)benzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NEUROCRINE BIOSCIENCES, INC.; HARRIOTT, Nicole; PAGANO, Nicholas; (135 pag.)WO2017/79641; (2017); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts