Category: nitriles-buliding-blocks

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. 41963-20-6, name is 4-Bromo-3-methylbenzonitrile, A new synthetic method of this compound is introduced below., Safety of 4-Bromo-3-methylbenzonitrile

(E)-methyl 3-(4-cyano-2-methylphenyl)acrylateTo a solution of 4-bromo-3-methylbenzonitrile (0.784 g, 4 mmol) in DMF (20 ml_) was added methyl acrylate (1.812 ml_, 20.00 mmol), DIPEA (1.747 ml_, 10.00 mmol), Pd(OAc)2(0.090 g, 0.400 mmol) and tri-o-tolylphosphine (0.243 g, 0.800 mmol). The reaction mixture was then heated with microwave irradiation at 150 C under N2atmosphere for 1 h. The reaction mixture was evaporated under vacuum to remove remaining methyl acrylate, then diluted with H20 (20 ml_), extracted with EtOAc (3 x 40 ml_). The combined organic layer was washed with brine (50 ml_), dried over MgS04, filtered, evaporated down under vacuum, and purified by flash chromatography to afford desired product (E)-methyl 3-(4-cyano-2-methylphenyl)acrylate (0.8815 g, 4.38 mmol, 110 % yield). H-NMR (400 MHz, CHLOROFORM-d) delta ppm 2.47 (s, 3 H) 3.84 (s, 3 H) 6.43 (d, J=15.81 Hz, 1 H) 7.47 – 7.55 (m, 2 H) 7.61 (d, J=8.53 Hz, 1 H) 7.92 (d, J=15.81 Hz, 1 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; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; ASTEX THERAPEUTICS LIMITED; BOEHM, Jeffrey Charles; DAVIES, Thomas Glanmor; WOOLFORD, Alison Jo-anne; GRIFFITHS-JONES, Charlotte Mary; WILLEMS, Hendrika Maria Gerarda; NORTON, David; SAXTY, Gordon; HEIGHTMAN, Thomas Daniel; LI, Tindy; KERNS, Jeffrey K.; DAVIS, Roderick S.; YAN, Hongxing; WO2015/92713; (2015); A1;,
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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. 101184-73-0, name is 2-(4-Bromophenyl)-2-methylpropanenitrile, A new synthetic method of this compound is introduced below., Recommanded Product: 101184-73-0

To degassed toluene (200 mL) was added palladium acetate (0.30 g, 1.3 mmol) and x-phos (1.3 g, 2.7 mmol) and the mixture degassed a further 5 minutes. To the reaction mixture was then added cesium carbonate (35.0 g, 107 mmol), beta alanine ethyl ester hydrochloride (6.2 g, 40.4 mmol) and 2-(4-bromophenyl)-2-methylpropanenitrile (6.0 g, 26.8 mmol). The reaction mixture was heated at reflux for 2 hours, cooled and filtered through celite. Filtrate concentrated and the residue further purified on silica eluding with 25% ethyl acetate in heptane to give ethyl 3-(4-(2-cyanopropan-2-yl)phenylamino)propanoate (4.05 g, 58%) as a yellow solid. 1H NMR (300 MHz, CDCl3): delta ppm 1.26 (t, 3H), 1.66 (s, 6H), 2.60 (t, 2H), 3.44 (t, 2H), 4.15 (q, 2H), 4.18 (br s, 1H), 6.61 (d, 2H), 7.26 (d, 2H).

The synthetic route of 101184-73-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; pfizer Inc; US2010/197591; (2010); A1;,
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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. 3441-01-8, name is 3-Cyanobenzamide, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C8H6N2O

Example 100 3-cyano-A-[10,ll-dichloro-4-oxo-3-(trifluoromethyl)-2,5,7-triazatricyclo[6.4.0.02’6]dodeca- l(8),6,9,ll-tetraen-3-yl]benzamide (ABR 239453) To a stirred solution of 3-cyanobenzamide (650 mg, 4.45 mmol) in DMF (7 mL) was added pyridine (378 mu, 4.45 mmol) followed by ethyl 3,3,3-trifluoro-2-oxopropanoate (590 mu, 4.45 mmol) at room temperature under argon. The reaction mixture was stirred at room temperature for 1 h. Thionyl chloride (323 mu, 4.45 mmol) was added at 0¡ãC. The reaction mixture was then stirred at room temperature for a further 16 h and before the reaction mixture was concentrated. The acyl intermediate that remained was dissolved in DMF (5 mL) under argon. 5,6-Dichloro- lH-l,3-benzodiazol-2-amine (674 mg, 3.34 mmol) and triethylamine (934 mu, 6.67 mmol) were added and the reaction mixture was stirred at room temperature for 16 h. The reaction mixture was diluted with water and extracted with EtOAc. The organic phase was washed with brine, dried (Na2SC>4), filtered and concentrated. The crude product was purified by silica chromatography, using 3percent MeOH in DCM as eluent. Further purification was carried out by trituration in DCM/MeOH and then pentane to afford the title compound as a white solid (25 mg, 1percent).

According to the analysis of related databases, 3441-01-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ACTIVE BIOTECH AB; WELLMAR, Ulf; LIBERG, David; EKBLAD, Maria; BAINBRIDGE, Marie; EAST, Stephen; HARGRAVE, Jonathan; PREVOST, Natacha; WO2015/177367; (2015); A1;,
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These common heterocyclic compound, 628-20-6, name is 4-Chlorobutyronitrile, 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. name: 4-Chlorobutyronitrile

1L three-necked flask 600ml of anhydrous ethanol under ice four hours continuously fed ammonia to saturation;pressurized cylinders ethanol was added a saturated solution of ammonia had been prepared, and then added 103.5g 4-chlorobutyronitrile (lmol), sealed in an oil bath heated 100-120 C, 10 hours;After completion of the reaction, cooled to room temperature, the reaction solution was spin to 70% ethanol, the precipitated solid was filtered, and the mother liquor was recrystallized with ether to give a solid, solids were combined to give a pale yellow solid drying 89.2g,No. HHC-014-A, Yield 74%

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

Reference:
Patent; Nanjing Pharmatechs Co., Ltd; Zhang, Xiaowen; Yang, Jie; (5 pag.)CN103435617; (2016); B;,
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Some common heterocyclic compound, 147754-12-9, name is 4-Fluoro-2-methylbenzonitrile, molecular formula is C8H6FN, 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. Computed Properties of C8H6FN

[0144] 4-Fluoro-2-methylbenzonitrile (2.9g), 5N NaOH (50 mL), and MeOH (50 mL) were set stirring at 100 ¡ãC for 18 hours. The solvent was removed under reduced pressure and the product was washed with CH2CI2 and acidified to pH 1. The reaction was partitioned between ethyl acetate and water and the organic layer was washed with brine and dried overanhydrous Na2S04 to yield a while solid (1.6 g). *H NMR (300 MHz, CDC13): 5 8.07-8.14 (m, 1H), 6.96-7.01 (m, 1H), 6.79-6.82 (m, 1H), 2.73 (br s, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 147754-12-9, its application will become more common.

Reference:
Patent; ASTRAZENECA AB; NPS PHARMACEUTICALS, INC.; WO2006/20879; (2006); A1;,
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Synthetic Route of 25309-65-3, 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. 25309-65-3, name is 4-Ethylbenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

EXAMPLE 27 Preparation of 2-(p-ethylphenyl)-5(6)-methoxybenzimidazole 5.0 g. of p-ethylbenzonitrile in 40 ml. of methanolic hydrochloric acid was stirred at room temperature overnight. The reaction mixture was diluted with water, neutralized with sodium carbonate and extracted with n-hexane. The extract was evaporated in vacuo to remove n-hexane. The remaining alkoxyimine compound was dissolved in methanol and 4.7 g. of p-anisidine was added thereto. The mixture was warmed for 30 minutes and evaporated in vacuo to remove methanol, whereby N-(p-methoxyphenyl)-4-ethylbenzamidine was recovered. This product was dissolved in water and then acidified with hydrochloric acid.

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

Reference:
Patent; Kanebo, Ltd.; US4188486; (1980); A;,
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Synthetic Route of 89001-53-6, 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. 89001-53-6, name is 2-Methyl-4-nitrobenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Step 3: To a stirred solution of 2-methyl-4-nitrobenzonitrile (407 mg, 2.510 mmol) in tetrahydrofuran was added 2M BH3-SMe2 in tetrahydrofuran (2.1 ml_). The reaction mixture was stirred for 15 h at 70 C. The mixture was cooled to room temperature, then quenched by water. The mixture dissolved in ethyl acetate and washed with water and brine. The organic layer was dried over magnesium sulfate and filtered. The filtrate removed in vacuo. The crude was purified by column chromatography to give (2-methyl-4- nitrophenyl)methanamine (178 mg, 43 %).

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-Methyl-4-nitrobenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GRUeNENTHAL GMBH; FRANK, Robert; BAHRENBERG, Gregor; CHRISTOPH, Thomas; LESCH, Bernhard; LEE, Jeewoo; WO2013/45447; (2013); A1;,
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Synthetic Route of 96606-37-0,Some common heterocyclic compound, 96606-37-0, name is 2,4,6-Trifluorobenzonitrile, molecular formula is C7H2F3N, 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.

Trimethylaluminium (2M solution in toluene, 4.69 ml) was added to a stirred solution of 6-chloro-2,3-methylenedioxyaniline (1.07 g) in toluene (10 ml) and the resultant solution was stirred at ambient temperature for 15 minutes. A solution of 2,4,6-trifluorobenzonitrile (0.98 g) in toluene (10 ml) was added dropwise and the resultant mixture was stirred at ambient temperature for 10 minutes and then heated to 900C for 3 hours. The reaction mixture was cooled to ambient temperature and stirred for 16 hours. The reaction mixture was washed with water (20 ml). The organic solution was extracted with 10% aqueous citric . acid solution. The aqueous solution was basified with 2M aqueous sodium hydroxide and extracted with methylene chloride (50 ml). The organic solution was dried over magnesium sulphate and evaporated. There was thus obtained ^-(-chloro^S-methylenedioxyphenyi)- 2,4,6-trifluorobenzamidine (0.92 g).Formamidine acetic acid salt (0.185 g) was added to a stirred solution of ./^-(-chloro- 2,3-methylenedioxyphenyl)-2,4,6-trifluorobenzamidine (0.204 g) in toluene (5 ml) and the reaction mixture was heated to reflux for 16 hours. A second portion (0.185 g) of formamidine acetic acid salt was added and the reaction mixture was heated to reflux for a further 16 hours. Triethylamine (0.25 ml) was added and the reaction mixture was heated to reflux for a further 3 days. The resultant reaction mixture was cooled to ambient temperature and partitioned between methylene chloride (25 ml) and a saturated aqueous sodium bicarbonate solution (25 ml). The organic solution was washed with 10% aqueous citric acid (25 ml), dried over magnesium sulphate and evaporated. The resultant oil was purified by column chromatography on silica gel using increasingly polar mixtures of isohexane and ethyl acetate as eluent. There was thus obtained 4-(6-chloro-2,3-methylenedioxyanilino)- 5,7-difluoroquinazoline (0.068 g).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2,4,6-Trifluorobenzonitrile, its application will become more common.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2006/64217; (2006); A2;,
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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. 3544-25-0, name is 2-(4-Aminophenyl)acetonitrile, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C8H8N2

Take carbazole monoaldehyde 0.502g (2mmol)Add about 3 mL of dichloromethane to a 100 mL round bottom flask to dissolve completely.Then, 0.3 g of p-aminophenylacetonitrile and 30 mL of ethanol were added to the flask.1.5 mL of TBAH (tetrabutylammonium hydroxide) was added dropwise as a catalyst.The progress of the reaction was monitored by thin layer chromatography and reacted at 80 C for 12 hours.The reaction mixture was cooled and a small amount of yellow precipitate was precipitated.Dry the organic phase to a yellow solid, dissolve it with a small amount of dichloromethane and pour it into a beaker.Add 100mL of ethanol and stir. A large amount of yellow solid precipitates and is quickly filtered.The solid obtained by suction filtration was washed three times with ethanol.The collected solid was dried and weighed 0.44 g of an orange-red solid with a yield of about 60%.

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 3544-25-0.

Reference:
Patent; Anhui University; Zhu Weiju; Fang Min; Liu Xiaonan; Ge Jialong; Li Cun; Wu Zhenyu; (12 pag.)CN108640867; (2018); A;,
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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. 179897-89-3, name is 5-Bromo-2-fluorobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 179897-89-3

To a solution of zinc chloride (50 mL, 1. OM in diethyl ether, 50 mmol) was added neopentylmagnesium chloride (50 mL, 1. OM in THF, 50 mmol) dropwise at 0 C. During the addition, the generated magnesium salts formed a white precipitate. The reaction was removed from the ice bath and allowed to stir for 1h, then 1- bromo-2-fluorobenzonitrile (5 g, 25 mmol) was added followed by bis (tri-tert- butylphosphine) palladium (0.127 g, 0.25 mmol, 1%). The reaction began to reflux and was placed back into the ice bath. After 1 h, the reaction was diluted with 200 mL of diethyl ether and washed with 1N HCI (2 x 100 mL), brine (100 mL), dried over magnesium sulfate and concentrated to give an oily solid (4.3 g, 22 mmol, 90%). H NMR (400 MHz, CDC13) 8 7.38-7. 30 (m, 2H), 7.11 (dt, J=8.5, 1.4 Hz, 1 H), 2.49 (s, 2H), 0.90 (s, 9H).

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 179897-89-3.

Reference:
Patent; ELAN PHARMACEUTICALS, INC.; WO2005/87751; (2005); A2;,
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