Month: May 2021

Synthetic Route of 129931-47-1, 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. 129931-47-1 name is 3-Chloro-2-fluoro-5-(trifluoromethyl)benzonitrile, 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.

(g) 1-(2-Chloro-6-cyano-4-trifluoromethylphenyl)-4-trifluoromethyl-2-pyridone (Compound No 14 of Table II) was prepared by reacting 3-chloro-4-fluoro-5-cyanotrifluoromethylbenzene and 4-trifluoromethyl-2-pyridone. 1 H NMR delta(CDCl3) 8.10 (1H,d); 8.0 (1H,d); 7.26 (1H,dd); 7.04 (1H,s); 6.55 (1H,dd).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Chloro-2-fluoro-5-(trifluoromethyl)benzonitrile, and friends who are interested can also refer to it.

Reference:
Patent; Imperial Chemical Industries PLC; US5109004; (1992); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Reference of 100-47-0, 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 100-47-0 as follows.

Example 1: o-trifluoromethylbenzonitrile. Dark at room temperature, the appropriate amount of the organic solvent (a mixed solvent of acetonitrile and DMSO, both the volume ratio of 1: 0.3) was added 100mmol compound of formula (II), the compound of 150mmol of formula (III), 2 mmol methylbenzene and triazole silver and 200mmol potassium t-butoxide, raising the temperature to 30 , and stirred for 30 minutes, then added dibenzo-18-crown-6, heated to 70 and the reaction was kept stirring for 5 hours; After completion of the reaction, the reaction mixture was added to 1 volume of its diluted with ethyl acetate, and washed successively with saturated aqueous sodium bicarbonate solution, and saturated brine, the organic phase was separated, which was dried over anhydrous sodium sulfate and evaporated distillation, the residue was subjected to silica gel column chromatography (eluent of ethyl acetate and n-butanol mixed solvent, a volume ratio of between 2: 1) to give the compound of the nitrile o-trifluoromethylbenzene of formula (I) (the ortho product yield 92.5%).

According to the analysis of related databases, 100-47-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Fujian Wanke Pharmaceutical Co., Ltd; Li, yibiao; Pan, MeiLing; Pan, meixia; (9 pag.)CN104649934; (2016); B;,
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 619-72-7 as follows. Recommanded Product: 4-Nitrobenzonitrile

General procedure: Photocatalytic reactions were carried out in a round bottom Pyrex flask and irradiated using four high power blue light LEDs 3W lamp or by solar light under magnetic stirring at room temperature. Reaction conditions with solar light: the aromatic nitro compounds (0.05mmol) and anhydride (0.052mmol) were carried out in the presence of TiO2-P25 (0.03g) in EtOH (10mL) and irradiated under sunlight for 1-4 h. Reaction conditions with blue LED irradiation: aromatic nitro compounds (0.002mmol) and anhydride (0.0025mmol) were carried out in the presence of TiO2-P25 (0.08g) in EtOH (4mL), and irradiated by four high power blue light LEDs 3W lamp for 30 h. While stirring, the mixture became heterogeneous as the reaction progressed. The product yields were determined by gas chromatography monitoring. The structure of products were confirmed by NMR (see ESI1).

According to the analysis of related databases, 619-72-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Zand, Zahra; Kazemi, Foad; Partovi, Adel; Journal of Photochemistry and Photobiology B: Biology; vol. 152; (2015); p. 58 – 62;,
Nitrile – Wikipedia,
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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. 2856-63-5, name is 2-(2-Chlorophenyl)acetonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Product Details of 2856-63-5

Example 30 Synthesis of 2-cyanomethylbiphenyl An oven dried resealable Schlenk tube was evacuated and backfilled with argon and charged with palladium acetate (2.2 mg, 0.01 mmol, 1.0 mol %), 2-(di-tert-butylphosphino)biphenyl (6.0 mg, 0.020 mmol, 2.0 mol %), phenylboron dihydroxide (183 mg, 1.5 mmol), and potassium fluoride (174 mg, 3.0 mmol). The tube was evacuated and backfilled with argon, and THF (1 mL) and 2-chlorobenzyl cyanide (152 mg, 1.0 mmol) were added through a rubber septum. The tube was sealed with a teflon screwcap, and the reaction mixture was stirred at room temperature until the starting aryl chloride had been completely consumed as judged by GC analysis. The reaction mixture was then diluted with ether (30 mL) and poured into a separatory funnel. The mixture was washed with 1.0 M NaOH (20 mL), and the aqueous layer was extracted with ether (20 mL). The combined organic layers were washed with brine (20 mL), dried over anhydrous magnesium sulfate, filtered, and concentrated. The crude material was purified by flash chromatography on silica gel to afford 178 mg (92%) of the title compound.

The synthetic route of 2856-63-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Buchwald, Stephen L.; Huang, Xiaohua; Zim, Danilo; US2004/171833; (2004); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthetic Route of 1528-41-2, 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. 1528-41-2, name is Ethyl 2-(4-cyanophenyl)acetate belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Preparation 50 ethyl 2-(4-cyanophenyl)-3-(dimethylamino)acrylate [0235] Combined ethyl 2-(4-cyanophenyl)acetate (25 g, 0.132 mol) with DMF-DEA (60 mL) and heated to 70C for 3 hours. The reaction mixture was cooled to room temperature and concentrated and then purified by flash chromatography to give the title compound (20 g, 62%) as a solid. XH NMR (400 MHz, DMSO-i) delta ppm 7.71 (d, J=8.4Hz, 2H), 7.59 (s, 1H), 7.29 (d, J=8.4Hz, 2H), 4.03 (q, J=6.8Hz, 2H), 2.67 (s, 6H), 1.13 (t, J=6.8Hz, 3H).

The synthetic route of Ethyl 2-(4-cyanophenyl)acetate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; BROWN, Jason, W.; DAVIS, Melinda; IVETAC, Anthony; JONES, Benjamin; KIRYANOV, Andre, A.; KUEHLER, Jon; LANIER, Marion; MIURA, Joanne; MURPHY, Sean; WANG, Xiaolun; WO2014/160810; (2014); A1;,
Nitrile – Wikipedia,
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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 31603-77-7 as follows. category: nitriles-buliding-blocks

EXAMPLE 53 (6-Biphenyl-4-yl-8-ethyl-7-imino-7,8-dihydro-pyrido[2,3-d]pyrimidin-2-yl)-phenylamine To a suspension of NaH (60% in mineral oil, 27 mg) in 5 mL of 2-ethoxyethanol was added 4-biphenylaceto-nitrile (263 mg, 1.36 mmol). After stirring for 5 minutes at room temperature, 4-ethylamino-2-phenylamino-pyrimidine-5-carboxaldehyde (300 mg, 1.24 mmol) was added and the reaction heated at 110 C. for 1 hour, resulting in a dark brown solution. Upon cooling, the solution was poured into water which caused precipitation. The resulting precipitate was removed by filtration and washed with water. The crude product was purified by flash chromatography, eluding with 5% methanol/methylene chloride, followed by 10% methanol/methylene chloride. Concentration of product fractions yielded 427 mg (83%) of (6-biphenyl-4-yl-8-ethyl-7-imino-7,8-dihydro-pyrido[2,3-d]pyrimidin-2-yl)-phenylamine; mp 245-249 C. Mass spectrum (CI) 418 (M+). Analysis calculated for C27 H23 N5: C, 77.67; H, 5.55; N, 16.78. Found: C, 76.16; H, 5.54; N, 16.36.

According to the analysis of related databases, 31603-77-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Warner-Lambert Company; US5945422; (1999); A;,
Nitrile – Wikipedia,
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Reference of 55984-93-5, 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. 55984-93-5, name is 2-Methylterephthalonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Methylterephthalonitrile (1.42 g, 1.0 mmol) and t-butoxybis(dimethylamine)methane (3.5 g, 2.0 mmol) were heated with 15 mL of DML at 75 ¡ãC for 12 h under N2. The DMF was removed and hexane was added. The precipitate formed was filtered and dried to give 1.85 g of the desired product. MS: 504.4, (M+H)+.

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-Methylterephthalonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2005/123050; (2005); A2;,
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. 13989-82-7, name is 4-(Dimethylamino)butanenitrile, This compound has unique chemical properties. The synthetic route is as follows., name: 4-(Dimethylamino)butanenitrile

To a suspension of lithium aluminum hydride (LAH) (4.74 g, 120.90 mmol) in dry ether (100 ml) was added dropwise a solution of N-(3-cyanopropyl)-N,N-dimethylamine 321 (4.10 g, 36.61 mmol) in dry ether (50 ml) at 0 C. After complete addition, the reaction mixture was stirred for two hours while allowing the temperature to raise from 0 C. to room temperature. The reaction mixture was quenched with 2N NaOH at 0 C. and the resulting white suspension was filtered through Celite and washed with ether. The ether filtrate was dried over K2 CO3, filtered and concentrated in vacuo, yielding N,N-dimethyl-1,4-diaminobutane 322 as a colorless oil (2.5 g, 60% yield). 1 H NMR (400 MHz, CDCl3) delta: 1.43 (4H, m, –CH2 –CH2 –CH2 –CH2 –), 1.93 (2H, br s, –NH2), 2.16 (6H, s, –N(CH3)2), 2.21 (2H, t, –CH2 CH2 N), 2.66 (2H, t, –CH2 CH2 NH2).

According to the analysis of related databases, 13989-82-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Magainin Pharmaceuticals, Inc.; US5637691; (1997); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

51655-39-1, name is 2-(2-Bromo-4,5-dimethoxyphenyl)acetonitrile, 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. Quality Control of 2-(2-Bromo-4,5-dimethoxyphenyl)acetonitrile

Example 7 3-(ETHOXY-HYDROXY-METHYLENE)-5,6-DIMETHOXY-3H-INDENE-1-CARBONITRILE, SODIUM SALT A solution of tricyclohexylphosphine (82.0 mg, 0.293 mmol) in ethylene glycol dimethyl ether (10 mL) under nitrogen was charged with palladium (II) acetate (43.7 mg, 0.195 mmol). The reaction was stirred at room temperature until the solution was homogeneous (approx. 15 minutes) and stirred an additional 5 minutes before cooling to 0 C. and charging with sodium tert-butoxide (996 mg, 9.75 mmol). After 5 minutes a solution of 2-bromo-4,5-dimethoxyphenylacetonitrile (1.00 g, 3.90 mmol) and ethyl-3-ethoxyacrylate (0.564 ml, 3.90 mmol) in ethylene glycol dimethyl ether (5 ml) was added dropwise over 10 minutes. Upon complete addition the reaction mixture was warmed to room temperature and then heated to 85 C. for 16 hours. The reaction was cooled to room temperature then diluted with methyl tert-butyl ether (50 mL) and poured into aqueous potassium dihydrogenphosphate (0.25 M, 100 mL). The aqueous layer was separated and solid sodium chloride was added to the aqueous layer until saturated. The aqueous layer was extracted with ethyl acetate (1*125 mL) and this organic layer was washed with aqueous saturated sodium chloride 12*35 ml), dried over sodium sulfate, filtered and concentrated in vacuo affording 3-(ethoxy-hydroxy-methylene)-5,6-dimethoxy-3H-indene-1-carbonitrile, sodium salt, as a dark brown oil (906 mg, 3.3 mmol, 85 %) which crystallized on standing. 1H NMR (400 MHz, d4-MeOH) delta7.64 (s, 1H), 7.46 (s, 1H), 6.99 (s, 1H), 4.56 (q, 2H, J=7.1), 3.86 (s, 6H), 1.38 (t, 3H, J=7.05); 13C NMR (100 MHz,d4-MeOH) delta167.8, 145.0, 144.5, 130.2, 129.4, 126.4, 123.3, 112.5, 104.0, 102.6, 100.7, 79.0, 58.4, 55.6, 14.1; IR (ATR, neat) 3499, 2164, 1629, 1482, 1449, 1282, 1207, 1157, 1124, 1076, 845, 769 cm-1.

The synthetic route of 51655-39-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Singer, Robert A.; US2003/60624; (2003); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Reference of 2112-22-3,Some common heterocyclic compound, 2112-22-3, name is 2,3-Dichloro-6-nitrobenzonitrile, molecular formula is C7H2Cl2N2O2, 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.

2,3-dichloro-6-nitrobenzonitrile, 500 gm, was dissolved in 7500 ml of THF in a clean dry RB flask maintaining a nitrogen blanket. 139.3 am of sodium borohydride was added at 25-30 C. The suspension was cooled to 15-20 C. 653 gms of Borontrifluoride etherate was added to the reaction mixture over a period of about 2 hours while maintaining the temperature between 15-30 C. After the addition was complete, the temperature was raised about 65 C. and maintained at reflux for 2 hours. The reaction mixture was cooled to about 0-5 C. A mixture of 2.0 liter water and 200 ml concentrated HCl was slowly added to the reaction mixture while maintaining the temperature below 20 C. After the addition was complete, THF was distilled from the reaction mixture under vacuum maintaining temperature below 50 C. The reaction mixture was cooled to about 10-15 C. and 2.0 liter ethylacetate was added. The pH of reaction mixture was adjusted to 10-11 using 25% aqueous sodium hydroxide solution while maintaining the temperature below 15 C. The ethylacetate layer was separated and concentrated to about half the original volume. The reaction mixture was cooled to 15-20 C. and 500 ml IPA-HC1 was added slowly, maintaining temperature below 30 C. After cooling to about 0-5 C., the solids obtained were filtered and washed with 500 ml chilled ethylacetate. The solids were dried to obtain 2,3-dichloro-6-nitrobenzyl amine hydrochloride (450 gms),

The synthetic route of 2112-22-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; WATSON PHARMA PRIVATE LIMITED; US2010/305318; (2010); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts