Month: August 2021

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

Electric Literature 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.

Example 107a; (2- (4-Amino-phenyl)-2-methyl-propionitrile; 3.8 g (20 mmol) of 2-methyl-2- (4-nitro-phenyi)-propionitrile (Example 10b) and 1 g of Raney-Ni are shacked in 50 mL of THF-MeOH (1: 1) under 1.1 bar of H2 for 4 h at RT. After completion of the reaction, the catalyst is filtered-off and the filtrate is evaporated to dryness. The residue is purified by flash chromatography on silica gel (hexane-EtOAc 3: 1 to 1: 2) to give the title compound as an oil : ES-MS: 161 (M+H) + ; analytical HPLC: tret= 2.13 minutes (Grad 2).

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

Reference:
Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2005/54238; (2005); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 6136-68-1, A common heterocyclic compound, 6136-68-1, name is 3-Acetylbenzonitrile, molecular formula is C9H7NO, 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: To a 1:1 chloroform and methanol solution (16ml) of aldehyde 1 (10.2 mg, 18.5 mumol) and p-nitroacetophenone (0.98 g, 5.9 mmol), was added 28% sodium methoxide in methanol (1 ml, 5 mmol). After being stirred in an ice bath for 30 min, the reaction mixture was washed with an aqueous 2% hydrochloric acid solution, an aqueous saturated sodium hydrogen carbonate solution and distilled water, and dried over sodium sulfate. The solvents were evaporated and the residue was purified with FCC (5-6% Et2O-CH2Cl2) and recrystallization (CH2Cl2-hexane) to give 2i (4.3 mg, 6.2 mumol, 33% isolated yield).

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; Ohashi, Kota; Kinoshita, Yusuke; Tamiaki, Hitoshi; Tetrahedron; vol. 74; 22; (2018); p. 2703 – 2715;,
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. 326-62-5, name is 2-(2-Fluorophenyl)acetonitrile, A new synthetic method of this compound is introduced below., COA of Formula: C8H6FN

General procedure: To a solution of 9 (20 mmol) in anhydrous DMF (100 mL) was added appropriate aryl acetonitriles (22 mmol) at room temperature. After the mixture was stirred for 0.5 h, 60% NaH (1.0 g, 24 mmol) was added portion wise at -10C under a nitrogen atmosphere. The whole mixture was stirred at the same temperature for 1 h, warmed to room temperature and then reacted for 48-72 h. The resulting mixture was acidified with acetic acid under ice cooling and concentrated under reduced pressure to afford the crude intermediate 10. Then, without further purification, EtOH (300 mL) was added at room temperature. After stirred for 0.5 h, 10% NaOH (100 mL) was added dropwise under ice cooling. The reaction mixture was then stirred at room temperature for 24-48 h and then acidified to pH 5-6 with acetic acid. After most of the solvent was removed under reduced pressure, the resulting residue was poured into water and extracted with CH2Cl2. The organic layer was dried over Na2SO4 and concentrated in vacuo to give the crude product, which was first purified by flash chromatography (eluent: CH2Cl2) and followed by recrystallization from MeOH or AcOEt, to afford target compounds 3a-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:
Article; Chen, Guo-Shen; Du, Fen; Zhao, Tian-Sheng; Xiong, Yuan-Zhen; Indian Journal of Heterocyclic Chemistry; vol. 28; 2; (2018); p. 255 – 260;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthetic Route 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.

To a 100L reaction vessel were added ethanol (40L) and 2-chloro-4-fluorobenzonitrile (7kg). Then hydrazine hydrate (4 L) was added. The resulting mixture was heated to reflux for 5 hours, then cooled, and subjected to centrifugal filtration. The resulting solid was introduced into a 100L reaction vessel. Anhydrous ethanol (40L) was added, and then concentrated hydrochloric acid (7.5L) was slowly added. The resulting mixture was heated to reflux for 2 hours, subjected to centrifugal filtration, and dried to produce 2-chloro-4-hydrazinobenzonitrile hydrochloride (7kg), yield: 76.2%.

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

Reference:
Patent; KBP Biosciences Co., Ltd.; JIANG, Chen; WANG, Aichen; ZHANG, Dedong; EP2937348; (2015); 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. 4553-07-5, name is Ethyl 2-cyano-2-phenylacetate, A new synthetic method of this compound is introduced below., HPLC of Formula: C11H11NO2

General procedure: To a solution of methyleneindolinone (0.1 mmol, 1equiv) and isocyanide 1a (0.15 mmol, 1.5 equiv) in DCM (0.2 mL) was added catalyst VI (0.01 mmol, 0.1 equiv). The resulting mixture was stirred at room temperature (23 C). After thereaction completed, the mixture was quenched with water (5 mL) and extracted with DCM (2 x 5mL). The combined organic layer was washed with brine and dried over Na2SO4. The solvent was then removed under reduced pressure. The product was afforded by silica gel flash chromatography using gradient elution (EtOAc/Hexane = 1:10 to 1:6).

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; Tan, Bin; Zhang, Xuan; Zhong, Guofu; ARKIVOC; vol. 2014; 3; (2014); p. 124 – 142;,
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. 50712-68-0, name is 4-Chloro-2-methylbenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 50712-68-0

In a 500 mE round-bottom flask, 4-chloro-2-meth- ylbenzonitrile (10 g, 66 mmol) was dissolved in 200 mE of methanol. To the mixture was added hydroxylammonium chloride (4.56 g, 66 mmol) followed by DIEA (diisopropylethylamine) (23 mE, 132 mmol). The mixture was heated at reflux for overnight. The solvents were removed. The residue was dissolved in 200 mE of CHC13. To the mixture was added 2-throyl chloride (10.5 ml, 66 mmol) followed by DIEA (23 mE, 132 mmol). Afier reaction completion, the mixture was extracted with chloroform and watet The organic layer was separated, washed with brine, dried over Na2SO4, filtered and evaporated to dryness. The residue was dissolved in 200 mE of dioxanes. To the mixture was added 1 eq of DId (N, N?-diisopropylcarbodiimide) followed by 1 eq of DIEA. The mixture was then heated at reflux overnight. Afier reaction completion, the mixture was cooled down. The solvents were removed in vacuo. The residue was then extracted with ethyl acetate and watet The organic layer was separated, washed with brine, dried over Na2SO4, filtered and evaporated to dryness. The crude was purified by flash chromatography on silica gel in a 0-20% ethyl acetate hexanes gradient to afford 4.96 g of the desired compound 3-(4-Chloro-2-methyl-phenyl)-5-thran-2-yl-[1 ,2,4-]oxadi- azole as a white powder in an overall yield of 28.8%.

According to the analysis of related databases, 50712-68-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Monsanto Technology LLC; Shortt, Barry J.; South, Michael S.; Wideman, Al S.; Williams, Deryck Jeremy; (34 pag.)US2018/228158; (2018); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Reference of 60702-69-4, 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. 60702-69-4, name is 2-Chloro-4-fluorobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows.

Anhydrous p-toluene sulfonic acid (41.99 g, 220.76 mmol) was melted at 120 C and 3-amino-4-methoxy benzoic acid methyl ester (20 g, 110.38 mmol) obtained in step 1 of Preparation Example 1 and 2-chloro-4- fluorobenzonitrile (25.76 g, 165.57 mol) were added thereto and stirred at 160 C for 8 hours. The resulting solution was cooled to room temperature and the reaction was stopped by adding NaHCO3 thereto. The resulting mixture was extracted with ethyl acetate, the extract was dried over MgSO4 and concentrated under a reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain the title compound (26.70 g, 79.47 mmol) in a yield of 72 %. 1H NMR (CDCl3): delta 7.92-7.75 (4H, m), 7.15-7.02 (3H, m), 3.87-3.81 (6H, d) MW: 336

The chemical industry reduces the impact on the environment during synthesis 2-Chloro-4-fluorobenzonitrile. I believe this compound will play a more active role in future production and life.

Reference:
Patent; CRYSTALGENOMICS, INC.; YUYU INC.; WO2004/65370; (2004); 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. 52798-01-3, name is Methyl (4-cyanophenyl)acetate, A new synthetic method of this compound is introduced below., Product Details of 52798-01-3

Step S2:Compound 2 (212 g) was added to the reactor under nitrogen, and THF (3 L) and PMHS (269 g) were added and cooled to 0 C;NaBEt3H (120.7 g) was added dropwise with stirring at 0 to 10 C, warmed to room temperature and stirred for 20 hours (the product of this stage was analyzed by IPC).Cool to 0 ~ 10 C, slowly add 500 ml of methanol at 0 C, add 2 L of saturated NaCl aqueous solution,Stir for 15 minutes, separate, and the aqueous phase was extracted with 1L ethyl acetate.The combined organic layers were dried over Na2SO4, concentrated, and then applied107 g of Compound 3 (IPC retention time: 1.61 min) was obtained as a yellow solid.

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; Huidingzhiyao (Beijing) Technology Co., Ltd.; Wang Zaiqi; Yang Lihu; (20 pag.)CN108864114; (2018); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts