Month: March 2021

Adding a certain compound to certain chemical reactions, such as: 193290-27-6, name is 3-(2-Hydroxyethyl)benzonitrile, belongs to nitriles-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 193290-27-6, Safety of 3-(2-Hydroxyethyl)benzonitrile

To a solution of 3-(2-hydroxy-ethyl)-benzonitrile (1 g; 6.79 mmol) in toluene (20 ml_), was added tetrabutylammonium hydrogen sulfate (230.70 mg; 0.68 mmol; 0.10 eq.) and NaOH (20 ml 5 M; 10 mmol) followed by the addition of tert-butyl bromoacetate (2 ml 13.59 mmol). Reaction mixture was stirred at RT under vigorous stirring for 9h. After this time, the aqueous phase was removed and the organic phase was diluted with EtOAc (50 ml_), washed with water (50 ml_) and brine (50 ml_). The combined organic layers were dried over magnesium sulfate, filtered and concentrated to give the title compound as a yellow powder (1.42 g; 80%). 1H NMR (DMSO-d6, 300 MHz) delta 7.74-7.73 (m, 1 H), 7.68-7.65 (m, 1 H), 7.63- 7.59 (m, 1 H), 7.51-7.46 (m, 1 H), 3.97 (s, 2H), 3.69 (t, J = 6.5 Hz, 2H), 2.88 (t, J = 6.5 Hz, 2H), 1.40 (s, 9H). LC/MS (Method B): 262.1 (M+H)+.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; MERCK SERONO S.A.; WO2009/43889; (2009); A2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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. 6136-93-2, name is 2,2-Diethoxyacetonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Computed Properties of C6H11NO2

Step 1 To a stirred solution of 2,2-diethoxyacetonitrile (XXVIII) (5.0 g, 38.71 mmol) in dry MeOH (80 mL) was added a 25% solution of sodium methoxide (1 mL). After the addition, the reaction mixture was stirred at room temperature for 24 h, quenched with dry ice, and then concentrated under vacuum. The resulting residue was diluted with water and EtOAc. The organic layer was separated and aqueous was extracted with EtOAc (3*100 mL). The combined organic layers were dried (Na2SO4) and the solvent was removed in vacuo to produce the product methyl 2,2-diethoxyacetimidate as colorless oil (XXIX) (4.7 g, 29.2 mmol, 75.3% yield).

The synthetic route of 6136-93-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Samumed, LLC; KC, Sunil Kumar; Mak, Chi Ching; Cao, Jianguo; Bollu, Venkataiah; Chiruta, Chandramouli; Mittapalli, Gopi Kumar; Eastman, Brian Walter; Hofilena, Brian Joseph; (960 pag.)US2019/127370; (2019); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 6011-14-9, name is 2-Aminoacetonitrile hydrochloride, belongs to nitriles-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 6011-14-9, name: 2-Aminoacetonitrile hydrochloride

The coupling of an aminonitrile to a carboxylic acid and subsequentBoc-deprotection is described and is referred to as General Method 6. To a solution ofCompound 101-N (180 mg, 0.15 mmol), aminoacetonitrile hydrochloride (31 mg, 0.33 mmol) and DIPEA (38 mg, 0.29 mmol) in DCM/DMF (3 mL, 2:1) at 0C, HATU (56 mg, 0.15 mmol) was added while stirring. The resulting mixture was stirred at room temperature for lh. Most DCM was removed under reduced pressure and the residue was poured into water (10 mL),which was extracted with EtOAc (20 mL x 3). The combined organic layers were washed with brine (50 mL), dried over Na2504, concentrated to the residue, which was purified by flash chromatography column to afford Compound 101-0 (140 mg, 76%) as a white solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Aminoacetonitrile hydrochloride, and friends who are interested can also refer to it.

Reference:
Patent; RQX PHARMACEUTICALS, INC.; GENENTECH, INC.; CHEN, Yongsheng; SMITH, Peter Andrew; ROBERTS, Tucker Curran; HIGUCHI, Robert I.; PARASELLI, Prasuna; KOEHLER, Michael F. T.; SCHWARZ, Jacob Bradley; CRAWFORD, James John; LY, Cuong Q.; HANAN, Emily J.; HU, Huiyong; YU, Zhiyong; (424 pag.)WO2017/84630; (2017); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Application of 97165-77-0, 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 97165-77-0 as follows.

To a flask was added 3,5-dibromobenzonitrile (3 g, 11.6 mmol), 4-(1-naphthyl)-benzenesulfonic acid (2.9 g, 11.6 mmol), potassium carbonate (4.1 g, 30 mmol)tetraphenyllphosphine palladium (0.1 g),tetrahydrofuran (30 mL) and water (15 mL)heated to reflux under nitrogen for 12 hours, cooled, extracted with dichloromethane, dried and concentrated. The crude product was purified by column chromatography to give 2.5 g of product in 57% yield.

According to the analysis of related databases, 97165-77-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Shanghai Daoyi Chemical Technology Co., Ltd.; Huang Jinhai; Su Jianhua; (29 pag.)CN107033143; (2017); A;,
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. 170230-87-2, name is 4-Amino-3-ethylbenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 170230-87-2

Description 25; 4-bromo-3-ethylbenzonitrile (D25); A mixture of 4-amino-3-ethylbenzonitrile (3.00 g, 20.5 mmol) and copper (II) bromide (6.88 g, 30.8 mmol) in acetonitrile (115 ml.) was stirred under argon before addition of isoamylnitrite (3.60 g, 30.8 mmol) dropwise through a condenser and the mixture was heated to 60 0C for 2.5 h. The mixture was stood at room temperature overnight under argon before it was concentrated. Diethyl ether was added and the mixture washed with saturated aqueous ammonium chloride followed by 2M sodium hydroxide. The aqueous was extracted with further diethyl ether before the combined organic fractions were dried (phase separator) and evaporated. Purification of the material in three batches was by reverse phase chromatography, eluting 5-100 % acetonitrile in water to give the title compound 787 mg, 3.74 mmol). deltaH (MeOD, 400 MHz): 7.74 (1 H, d), 7.67 (1 H, d), 7.45 (1 H, dd), 2.82 (2H, q), 1.24 (3H, t) ppm

According to the analysis of related databases, 170230-87-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXO GROUP LIMITED; WO2008/74820; (2008); 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. 3215-64-3, name is 2-(2,6-Dichlorophenyl)acetonitrile, A new synthetic method of this compound is introduced below., Safety of 2-(2,6-Dichlorophenyl)acetonitrile

Example 9a Preparation of 2-(2,6-dichlorophenyl)-2-methylpropanenitrile To a 1 M solution of potassium tert-butoxide (403 mL, 403 mmol) at -66 C. (acetone/dry ice) was slowly added 2-(2,6-dichlorophenyl)acetonitrile (25.0 g, 134 mmol) in anhydrous THF (150 mL). The mixture was stirred at -66 C. for 20 minutes. Then, iodomethane (33.6 mL, 538 mmol) was added drop-wise over 25 minutes at -66 C. At this stage, it was exothermic and a large amount of light yellow precipitate was observed. The suspension was stirred at -60 C. for 30 minutes. The reaction mixture was quenched with 200 mL ice water, and extracted with ether (3*150 mL). The organics were combined, washed with 150 mL brine, dried over Na2SO4, and concentrated on a rotary evaporator. The crude product (30 g, yellow oil) was purified by column chromatography (ISCO, 330 g silica, 20% EtOAc in hexanes) to afford 2-(2,6-dichlorophenyl)-2-methylpropanenitrile (28.2 g, 132 mmol, 98% yield) as a light yellowish oil. 1H-NMR (CDCl3, 400 MHz) delta 7.35 (d, 2H, J=8.03 Hz), 7.16 (t, 1H, J=8.0 Hz), 2.09 (s, 6H); 13C-NMR (CDCl3, 126 MHz) delta 134.6, 133.8, 131.4, 129.0, 124.1, 38.6, 29.2; MS m/e 214.10 (M+H+); HPLC (XBridge 5mu C18 4.6*50 mm, 4 mL/min, Solvent A: 10% MeOH/water with 0.2% H3PO4, Solvent B: 90% MeOH/water with 0.2% H3PO4, gradient with 0-100% B over 4 minutes): 3.16 minutes.

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; BRISTOL-MYERS SQUIBB COMPANY; EXELIXIS PATENT COMPANY LLC; Busch, Brett B.; Stevens, JR., William C.; Kick, Ellen K.; Zhang, Haiying; Bollu, Venkataiah; Martin, Richard; Mohan, Raju; US2015/299136; (2015); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 60758-86-3, 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 60758-86-3 as follows.

The reaction flask was charged with 400 mL of tetrahydrofuran and 62.5 g (0.8 mol) of dimethylsulfoxide,Stirring down to 0 to 5 ,500 mL (0.8 mol) of 1.6 M n-butyllithium n-hexane solution at a temperature of 0 C to 5 C was added,Stirring reaction for 1.5 hours,179.0 g (0.55 mol) of tributyltin chloride and 88.6 g (0.5 mol) of 3-ethoxy-4-methoxybenzonitrile (formula III) in 450 mL of tetrahydrofuran were added,Stirring for 0.5 hours,The temperature was raised to 15 C to 20 C for 2 hours,1000 mL of purified water was added,The incubation was continued at 15 C to 20 C for 12 hours.Stop the reaction,The solid obtained in the reaction solution was filtered, washed with purified water,N-hexane, tetrahydrofuran 100mL each washing cake.Dried to afford 109.6 g of a white solid,The molar yield was 85.2%, HPLC purity was 98.1% and ee was 97.3%.

According to the analysis of related databases, 60758-86-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Peking University Fangzheng Group Co., Ltd.; Chongqing Southwest Synthetic Pharmaceutical Co., Ltd.; Peking University Medical Treatment Industrial Group Co., Ltd.; Fu Biao; Wang Fenglin; Luo Li; (9 pag.)CN106866493; (2017); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Related Products of 52798-01-3,Some common heterocyclic compound, 52798-01-3, name is Methyl (4-cyanophenyl)acetate, molecular formula is C10H9NO2, 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 methyl 4-cyanobenzeneacetate (2.646 g, 15.1 mmol) and iodomethane (2.4 ml) in N,N-dimethylformamide (50 ml) was slowly added 60% oily sodium hydride (1.55 g, 38.8 mmol) under ice-cooling. The reaction mixture was stirred for 2 hours at room temperature. The reaction solution was slowly added to ice water, and extracted with ethyl acetate. The extracts were washed with a saturated aqueous solution of sodium chloride, dried, and concentrated under reduced pressure. The residue was subjected to a silica gel column chromatography (ethyl acetate/hexane 3:1) to give the title compound (2.996 g, yield 98%). 1H NMR (CDCl3) delta 1.59 (6H, s), 3.67 (3H, s), 7.42-7.47 (2H, m), 7.61-7.65 (2H, m).

The synthetic route of 52798-01-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Takeda Pharmaceutical Company Limited; EP1541576; (2005); 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. 4513-77-3, name is 2-Oxocyclohexanecarbonitrile, A new synthetic method of this compound is introduced below., Safety of 2-Oxocyclohexanecarbonitrile

To a solution of (2-methylphenyl) hydrazine hydrochloride (464 mg, 2.92 mmol) in ethanol (2 mL) was added 2-oxocyclohexanecarbonitrile (300 mg, 2.44 MMOL), and the mixture was heated to 60C and stirred for 16 h. The flask was then cooled to rt and the solvent was evaporated to give a solid. The crude residue of 2-(2-methylphenyl)-4, 5,6, 7- tetrahydro-2H-indazol-3-amine hydrochloride (449 mg, 70%) was used in the next step with no further purification. ES-MS m/z 228.2 (MH+) ; HPLC RT (min) 1.22.

The synthetic route of 4513-77-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER PHARMACEUTICALS CORPORATION; WO2004/50650; (2004); 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. 115279-57-7, name is 2-(4-Aminophenyl)-2-methylpropanenitrile, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 2-(4-Aminophenyl)-2-methylpropanenitrile

To a solution of compound 1 (4.3 g, 15 mmol) in acetic acid (100 mL) at 250C, was added 2-(4-aminophenyl)-2-methylpropanenitrile (2.4 g, 15 mmol). The reaction mixture was stirred at 250C for 30 mins. The reaction mixture was quenched with ice-water and the solid was filtered, washed with 10% cold aqueous NaHCtheta3 solution and cold water, and dried under vacuum to provide 14 (5.5 g, 89% ) as a yellowish solid. MS (m/z) (Nf +H): 411, 413; 1H-NMR (400Mz, DMSO-d, ppm) 10.13 (s, IH), 9.08 (s, IH), 8.72 (s, IH), 8.01 (d, IH, J=8.55Hz), 7.94 (d, IH, J=8.97Hz), 7.47 (d, 2H, J=8.55Hz), 7.14 (d, 2H, J=8.55Hz),1.68 (s, 6H).

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 115279-57-7.

Reference:
Patent; PROGENICS PHARMACEUTICALS, INC.; WO2009/155527; (2009); A2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts