Month: April 2021

21883-13-6, name is 4-Methoxy-2-methylbenzonitrile, 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: 21883-13-6

Example 3 Methyl 3-(4-methoxy-2-methylphenyl)-2-methyl-3-oxopropanoate Methyl 2-bromopropanoate (0.3 mL) was added to anhydrous tetrahydrofuran (100 mL) of zinc powder (11 g) under argon gas atmosphere, followed by refluxing by heat for 15 minutes. 4-methoxy-2-dimethylbenzonitrile (5.0 g) was added to the resultant reaction solution, and further methyl 2-bromopropanoate (15 mL) was dropped thereinto taking 40 minutes, followed by refluxing by heat for 1 hour. The resultant reaction solution was cooled into room temperature, and was diluted with tetrahydrofuran (50 mL) and 50% potassium carbonate solution (30 mL), followed by stirring for 30 minutes. The supernatant of the reaction solution was separated, and concentrated under reduced pressure. The residual was poured to water, and was extracted with ethyl acetate. The extracted solution was washed by a saturated saline solution, and concentrated under reduced pressure after drying with anhydrous magnesium sulfate. Methanol (110 mL) and IN hydrochloric acid (33 ml) were added to the residue, and stirred at room temperature for 15 hours. The resultant reaction solution was concentrated under reduced pressure, was poured to water, and was extracted with ethyl acetate. The extracted solution was washed by a saturated solution of sodium chloride, and concentrated under reduced pressure after drying with anhydrous magnesium sulfate. The obtained residue was purified by silica gel chromatography (hexane:ethyl acetate=100:0?71:29), to thereby obtain a title compound (5.4 g) having the following physical properties. TLC: Rf 0.55 (hexane:ethyl acetate=3:1); 1H-NMR(300 MHz, CDCl3): delta 7.72 (d, J=9.3 Hz, 1H), 6.81-6.73 (m, 2H), 3.85 (s, 3H), 3.68 (d, J=0.6 Hz, 3H), 2.54 (s, 3H), 1.56 (d, J=0.6 Hz, 3H), 1.45 (dd, J=7.2, 0.3 Hz, 3H).

The synthetic route of 21883-13-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ONO PHARMACEUTICAL CO., LTD.; EP1961754; (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. 151-18-8, name is 3-Aminopropanenitrile, A new synthetic method of this compound is introduced below., name: 3-Aminopropanenitrile

oBromonium iodobenzene(4.0 g, 14.1 mmol) in dimethylsulfoxide (40 mL) was added 3-aminopropionitrile(1.5 mL, 20 mmol), cuprous iodide (2.8 g, 15 mmol), cesium carbonate (7.0 g, 21.5 mmol) and N, N-dimethylglycine(1.5 g, 14 mmol), reacted at 70 C for 5 hours, quenched with water (40 mL), extracted with dichloromethane (40 mL x 3), dried over anhydrous sodium sulfate (Eluent: PE / EtOAc (v / v) = 2/1) to give 3.0 g of a pale yellow oil, and the residue was subjected to column chromatography , Yield: 94%.

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; Guangdong East Sunshine Pharmaceutical Co., Ltd; Liu, Bing; Huang, Jiuzhong; Zhang, Yingjun; Xue, Yaping; Xing, Wei; Xu, Juan; Wu, Zuping; Yu, Tianxi; (106 pag.)CN106432246; (2017); A;,
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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. 2338-75-2, name is 4-(Trifluoromethyl)phenylacetonitrile, A new synthetic method of this compound is introduced below., Quality Control of 4-(Trifluoromethyl)phenylacetonitrile

To a solution of 4-trifluoromethyl phenylacetonitrile (40 g, 215 mmol) in 2N NH3/MeOH (400 mL) was added Raney Ni (4.0 g). The reaction mixture was placed in a par-shaker and shook under 50 Lb pressure overnight. The solution was filtered through celite and concentrated in vacuo to yield the desired amine (38 g, 95%). ESI-MS calc. For C9H10F3N: 189; Found: 190 (M+M).

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; Goble, Stephen D.; Yang, Lihu; Zhou, Changyou; Kothandaraman, Shankaran; Guiadeen, Deodialsingh; Butora, Gabor; Pastemak, Alexander; Mills, Sander G.; US2007/117797; (2007); A1;,
Nitrile – Wikipedia,
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Electric Literature of 327056-73-5, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 327056-73-5 name is 3-Chloro-5-fluorobenzonitrile, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

A solution of 19 (1.07 g, 5 mmol), 16 (1.3 g, 7.56 mmol), K2CO3 (2.07 g, 15.0 mmol) and NMP (10 mL) was stirred and heated to 110 C. for 6 h. The reaction mixture was cooled to RT and diluted with H2O (50 mL) and twice extracted with EtOAc. The combined organic extracts were washed sequentially with water and brine, dried (Na2SO4), filtered and concentrated in vacuo. The crude product was purified by SiO2 chromatography eluting with EtOAc/hexane (10:90) to afford 0.328 g of 31.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Chloro-5-fluorobenzonitrile, and friends who are interested can also refer to it.

Reference:
Patent; Roche Palo Alto LLC; US2007/88053; (2007); 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 4435-14-7 as follows. HPLC of Formula: C8H13N

The isopropyl cyclohexylacetimidate hydrochloride used as the starting material was prepared as follows: In a manner analogous to that described in Example 1, from cyclohexylacetonitrile, there was obtained isopropyl cyclohexylacetimidate hydrochloride in the form of a pale pink solid of melting point 108-110 C.

According to the analysis of related databases, 4435-14-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Hoffmann-La Roche Inc.; US5399712; (1995); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Related Products of 2469-99-0,Some common heterocyclic compound, 2469-99-0, name is 3-Oxobutanenitrile, molecular formula is C4H5NO, 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.

Weighing 0.22 muM of sodium cyanide (2.2 equiv) in 250 ml three-neck bottle in, under ice bath by adding 110 ml THF, then adding 0.1 muM 1 a (1 equiv) and 0.1 muM 1 d (1 equiv), 65 C reflow 12 h. After the reaction, under the ice, with a certain amount of reaction water quenching, adjusting solution PH value to 4 – 5, ethyl acetate extraction, the organic phase is dried with anhydrous sodium sulfate, and steaming and get products 2 ad. 250 Ml three-neck bottle is added to the product of the 1st step 2 ad, 100 ml ethanol and 0.9 muM 2 g, 85 C reflow 18 h. Stopping the reaction, steaming and out ethanol, saturated sodium hydroxide solution to adjust the residue for the PH in 9 – 10. DCM extraction, the organic phase is dried with anhydrous sodium sulfate, and steaming and, column chromatography purification (dichloromethane: ethyl acetate=20:1) to obtain the product B3.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Oxobutanenitrile, its application will become more common.

Reference:
Patent; China Agricultural University; Hou Shicong; Gao Gui; Chen Xiangzhu; Liu Jingjing; Zhang Yuanyuan; Zhang Xueyan; (10 pag.)CN107980784; (2018); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

These common heterocyclic compound, 6136-93-2, name is 2,2-Diethoxyacetonitrile, 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: 2,2-Diethoxyacetonitrile

To a vial was added 2,2-diethoxyacetonitrile (XIX) (1.0 g, 7.74 mmol) dissolved MeOH (7.74 mL) followed by addition of MeONa/MeOH (0.18 mL, 0.77 mmol) dropwise. The reaction was stirred at room temperature for 20 h. HOAc (44.3 muL, 0.77 mmol) was added until pH=7-8 (using pH strips). (4-Bromo-3-fluoro-phenyl)methanamine hydrochloride (XX) (1.86 g, 7.74 mmol) was added and stirred at 40 C. for 4 h. The solvent was removed under vacuum. Sulfuric acid (12.6 mL, 232.3 mmol) was added and stirred at 40 C. for 16 h. NH4OH (30.8 mL, 240.0 mmol) was added dropwise at 0 C. The solvent was removed under vacuum and the residue was purified by C18 silica gel (240 g) [0?50% H2O/MeCN (0.1% Formic acid)] to produce 6-bromo-7-fluoro-isoquinolin-3-amine (XXI) (1.33 g, 5.50 mmol, 71.1% yield) as an off-white solid. 1H NMR (499 MHz, DMSO-d6) delta ppm 6.07 (2H, s), 6.61 (1H, s), 7.76 (1H, d, J=9.33 Hz), 8.01 (1H, d, J=6.86 Hz), 8.80 (1H, s); ESIMS found for C9H6BrFN2 m/z 242.9 (81BrM+H).

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

Reference:
Patent; Samumed, LLC; KC, Sunil Kumar; Mak, Chi Ching; Hofilena, Brian Joseph; Mittapalli, Gopi Kumar; Eastman, Brian Walter; Cao, Jianguo; Bollu, Venkataiah; Chiruta, Chandramouli; (149 pag.)US2019/125740; (2019); A1;,
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Synthetic Route of 75344-77-3, A common heterocyclic compound, 75344-77-3, name is 4-Bromo-3,5-dimethylbenzonitrile, molecular formula is C9H8BrN, 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.

3-(4-Bromo-3,5-dimethyl-phenyl)-1H-tetrazole 4-Bromo-3,5-dimethyl benzonitrile (3.0 g, 14.3 mmol), sodium azide (2.32 g, 35.7 mmol) and ammonium chloride (2.3 g, 42.84 mmol) are suspended in dry N,N-dimethylformamide and heated at 140 C. for 7 hours. The mixture is allowed to cool to room temperature, diluted with water and the precipitated solid collected by filtration, washed with water and dried to give the title compound (yield 1.74 g). The mother liquor was saturated with sodium chloride and repeatedly extracted with ethyl acetate. The organic extracts were combined and the solvent removed to give a second crop of title compound (yield 1.39 g, total yield 3.13 g). LC (MIL-07-002): tR=0.83 min; Mass spectrum (ES+): m/z=253/255 [M+H]+.

The synthetic route of 75344-77-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; HAMPRECHT, Dieter; FRATTINI, Sara; LINGARD, Iain; PETERS, Stefan; US2013/324514; (2013); A1;,
Nitrile – Wikipedia,
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147754-12-9, name is 4-Fluoro-2-methylbenzonitrile, 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. Recommanded Product: 4-Fluoro-2-methylbenzonitrile

Preparation 7; 2-(bromomethyl)-4-fluorobenzonitrile; A solution of 2-methyl-4-fluoro-benzonitrile (3.5 g, 25.9mmol) in 4OmL of carbon tetrachloride was treated with N-bromosuccinimide (4.6g, 25.9 mmol) and benzoylperoxide (157mg, 0.65 mmol). The mixture was heated to reflux for 3 hours, cooled to room temperature and allowed to stir overnight. The solids were filtered off and washed with carbon tetrachloride. The filtrate was condensed and purified by normal phase flash column chromatography on a 50 g silica gel column (5 – 50percent ethyl acetate/hexanes gradient). Two peaks separated. It was determined that the second eluting peak is the desired product. Pure fractions of this peak were pooled and concentrated in vacuo to yield 2-(bromomethyl)-4- fluorobenzonitrile (1.35g, 0.63 mmol, 25percent yield) as a white solid. 1H NMR (400 MHz, DMSO-dbeta) delta ppm 4.79 (s, 2 H), 7.44 (dt, J=8.59, 2.69 Hz, 1 H), 7.68 (dd, J=9.53, 2.55 Hz, 1 H), 8.01 (dd, J=8.59, 5.64 Hz, 1 H).

The synthetic route of 147754-12-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER PRODUCTS INC.; WO2008/53300; (2008); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Reference of 103146-25-4, 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. 103146-25-4, name is 4-(4-(Dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl)-3-(hydroxymethyl)benzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

In a 200-ml four-necked flask equipped with a stirrer and a thermometer, 1.5 g [(4.] [38] m mol) of [()-4- [4-DIMETHYLAMINO-1- (4′-FLUOROPHENYL)-1-HYDROXYBUTYL]-3-] hydroxymethylbenzonitrile was dissolved in 30 ml of toluene, then 0.45 g of Novozym 435 (product [OF NOVOZYMES),] 0.347 g (4.38 m mol) of pyridine, 4.38 m mol of various kinds of acids and 1.00 g (8.76 m mol) of vinyl butyrate were added, and stirred at [40C] for between 16 and 21.5 hours. The result is shown in Table 4.

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, 4-(4-(Dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl)-3-(hydroxymethyl)benzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; H. LUNDBECK A/S; WO2004/14821; (2004); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts