Month: August 2021

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. 103146-25-4, name is 4-(4-(Dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl)-3-(hydroxymethyl)benzonitrile, A new synthetic method of this compound is introduced below., Safety of 4-(4-(Dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl)-3-(hydroxymethyl)benzonitrile

Process for the preparation of citalopram (by double Grignard method): A solution of 4-fluorophenyl magnesium bromides prepared from 153. 33g 4-flour bromobenzene (0.876 moles) and 25.33g magnesium turnings (1. 055 moles) and iodine (0.05gm) in dry 300mi tetrahydrofuran was added to a suspension of 100g 5- cyanophthalide (0.628 moles) in 900ml dry methylene dichloride at-4 to-2C. After the completion of the reaction a solution of 3-N, N dimethylaminopropyl magnesiumchloride in toluen/THF mixture [generated in situ by reacting 175g 3-N, N dimethylamiopropyl chloride (1. 446mole) in 350ml toluene with 41. 6gm magnesium turnings (9. 733moles) and iodine (0. 05g) in dry 75ml tetrahydrofuran and dibromoethane] was added between 0- 5C. The reaction mass was then maintained at-5 to 0C for 3-4 hours. After completion of the reaction, the reaction mass was quenched with 200ml 20% aqueous ammonium chloride solution. The toluene layer was separated and washed with 200ml water. Methylene dichloride and THF was distilled. 189g sulphuric acid and 60ml of water was added to the toluene layer and heated to 85-90C. The same temperature was maintained for additional 4-5 hours. After completion of the reaction the reaction mass was diluted with 200ml water and the pH was adjusted to basic with liquor ammonia below 10-15C. The toluene layer was separated, washed with 200moi water and extracted with 400ml 20% acetic acid (80mi acetic acid and 320ml water). The aq. acid extract was cooled to 5- 10C and the pH was adjusted to 8.5 to 9.0 using liquor ammonia (85ml) at 5-10C and extracted with toluene 3x600m1. The toluene layer was washed with water, dried over anhydrous sodium sulphate. The dried toluene layer was treated with carbon (10g) and filtered. The filtrate toluene was subjected to salt formation in accordance with the following methods:

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; JUBILANT ORGANOSYS LIMITED; WO2005/77927; (2005); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthetic Route of 10406-25-4,Some common heterocyclic compound, 10406-25-4, name is 4-(Aminomethyl)benzonitrile, molecular formula is C8H8N2, 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.

a) Preparation of N-benzenesulfonyl-D-leucyl-L-proline- [(4-cyanophenyl)methyl] amide[0170] N- benzenesulfonyl- D- leucyl- L- proline (737mg) , p- aminomethyl cyanophenyl hydrochloride (337mg) andDIEA (569mg) were dissolved in DMF (20ml) , cooled down to 0C under the protection of nitrogen, HOBt (270mg) andEDCI (460mg) were added. The resulting mixture was stirred at 0C for 20min and allowed to warm up naturally to roomtemperature and react for 5 hours. The organic layer was washed in turn with 5% potassium hydrosulphate solution,saturated sodium hydrogencarbonate solution and saturated saline solution, dried over anhydrous sodium sulfate, filteredand concentrated under reduced pressue to give 1.1g crude product, which was purified with column chromatographyto give a colourless oil (650mg, yield: 67.3%) .Rf = 0.65Developer: petroleum ether: ethyl acetate = 1: 1Color development: ultraviolet and iodineMS: 505 (M+Na+)

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

Reference:
Patent; Shanghai Institute of Pharmaceutical Industry; Li, Min; LI, Min; SHAN, Hanbin; HUANG, Yu; YUAN, Zhedong; YU, Xiong; EP2639230; (2013); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 501-00-8,Some common heterocyclic compound, 501-00-8, name is 2-(3-Fluorophenyl)acetonitrile, 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.

[0245] To a solution of compound 1 (100 g, 0.74 mol) in dry DMF (1000 ml) was added 1,5-dibromopentane (170 g, 0.74 mol). NaH (65 g, 2.2 eq) was added dropwise while the reaction was cooled in an ice bath. The resulting mixture was vigorously stirred overnight at 50 C. The suspension was carefully quenched with ice water and extracted with ethyl acetate (3×500 ml). The combined organic layers were concentrated to afford the crude product, which was purified by flash column chromatography to give compound 2 as pale solid (100 g, 67%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-(3-Fluorophenyl)acetonitrile, its application will become more common.

Reference:
Patent; Acetylon Pharmaceuticals, Inc.; Tamang, David Lee; Yang, Min; Jones, Simon S.; US2015/99744; (2015); A1;,
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. 31643-49-9, name is 4-Nitrophthalonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 31643-49-9

Under inert gas (N2), 4-nitro-o-phthalonitrile (9.2 g), phenol (5.0 g), K2CO3 (7.3 g) and DMSO (40 mL) were added into a flask, and were stirred and reacted at room temperature for 48 hrs., then heated to 60 C. and reacted for 2 his. After cooled down, the reaction mixture was filtered and the resulted yellow solid was dried to obtain 11.6 g of Compound 1.

The synthetic route of 31643-49-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Kang, Xinshan; Long, Wei; Zhang, Jianxi; Hu, Yunyan; Wang, Yinxiang; US2015/31721; (2015); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Related Products of 1835-49-0, A common heterocyclic compound, 1835-49-0, name is Tetrafluoroterephthalonitrile, molecular formula is C8F4N2, 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.

Water-wet tetrafluoroterephthalonitrile 56. 69 G (10% water content, 98% pure, 50.0 g in terms of tetrafluoroterephthalonitrile), water-wet 5% Pd/C 1.18 g (58% water content, 0.5 g in terms of Pd), and toluene 200.0 g were introduced into a 500 ml three-necked glass flask equipped with a stirrer, a thermometer, a Claisen tube and a cooling tube. The contents were heated to distill away toluene and water together in an amount of 187.5 g. After cooling, toluene 187.5 g was added and the water content was measured to be 150 ppm. The resultant reaction solution was introduced into a 500 ml stainless steel autoclave (NU-4 model produced by Nitto Koatu Co., Ltd. ), and further Zeolite 5A powder 45 g (Molecular Sieve 5A produced by Union Showa K. K. ) was added thereto. Then the autoclave was purged with nitrogen. THEREAFTER THE CONTENTS WERE HEATED TO 160C under stirring, and hydrogen pressurized at a pressure higher than that in the autoclave at the above temperature by 0.1 MPa was supplied to initiate hydrogenolysis. The rate of hydrogen absorption lowered in approximately 5 hours and 30 minutes of reaction time, and the supply of hydrogen was terminated to end the reaction. The hydrogen absorption was 116 MOL% (based on the mol of tetrafluoroterephthalonitrile under standard conditions). Cooled to room temperature, the reaction slurry was filtered, and the filtrate was analyzed with the gas chromatography analyzer. The analysis gave a conversion of 97. 8% and a reaction yield of 84.4 % (product: 2,3, 5,6-tetrafluorobenzonitrile). Example 5 Reaction was conducted basically in the same manner as in Example 4 except that the amount of 5% Pd/C was altered to 2.38 g (58% water content, 1.0 g in terms of Pd) and that the amount of the Zeolite 5A powder was altered to 37.5 g (Molecular Sieve 5A produced by Union Showa K. K. ). The results were that the hydrogenolysis reaction was completed in 5 hours and 30 minutes and the hydrogen absorption was 114%. The analysis gave a conversion of 98. 2% and a reaction yield of 87. 5% (product: 2,3, 5, 6-tetrafluorobenzonitrile).Example 6 Reaction was conducted basically in the same manner as in Example 4 except that the amount of 5% Pd/C was altered to 1.43 g (58% water content, 0.6 g in terms of Pd). The results were that the hydrogenolysis reaction was completed in 5 hours and 20 minutes and the hydrogen absorption was 121%. The analysis gave a conversion of 99.4% and a reaction yield of 86. 2% (product: 2,3, 5, 6-tetrafluorobenzonitrile). Example 7 Reaction was conducted basically in the same manner as in Example 4 except that the hydrogenolysis temperature was altered to 170C. The results were that the hydrogenolysis reaction was completed in 5 hours and 30 minutes and the hydrogen absorption was 111%. The analysis gave a conversion of 99. 3% and a reaction yield of 87. 5% (product: 2,3, 5,6-tetrafluorobenzonitrile). Example 8 Reaction was conducted basically in the same manner as in Example 4 except that the hydrogenolysis temperature was altered to 180C. The results were that the hydrogenolysis reaction was completed in 5 hours and 10 minutes and the hydrogen absorption was 114%. The analysis gave a conversion of 99. 3% and a reaction yield of 89. 1% (product: 2,3, 5, 6-tetrafluorobenzonitrile). Example 9 Reaction was conducted basically in the same manner as in Example 4 except that the additional toluene was used in an amount of 147.5 g. The results were that the hydrogenolysis reaction was completed in 5 hours and 30 minutes and the hydrogen absorption was 112%. The analysis gave a conversion of 98. 9% and a reaction yield of 87. 0% (product: 2,3, 5,6-tetrafluorobenzonitrile). Example 10 Reaction was conducted basically in the same manner as in Example 4 except that the additional toluene was used in an amount of 107.5 g. The results were that the hydrogenolysis reaction was completed in 5 hours and 30 minutes and the hydrogen absorption was 108%. The analysis gave a conversion of 98.7% and a reaction yield of 86.5% (product: 2,3, 5,6-tetrafluorobenzonitrile).

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; SHOWA DENKO K.K.; WO2004/9535; (2004); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthetic Route of 42872-74-2, 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 42872-74-2 as follows.

5-C. 3-Bromo-4-(bromomethyl)benzonitrile; [00161] A solution of 3-bromo-4-methylbenzonitrile (1 g, 5.10 mmol) in chloroform (20 mL) was heated to 40-50 0C and N-bromosuccinimide (0.953 g, 5.36 mmol) was added in one portion followed by AIBN (8.38 mg, 0.051 mmol). After 1.5 hr. additional AIBN (20mg) was added and the reaction was allowed to stir at 50 0C overnight. Additional AIBN (20mg) and N-bromosuccinimide (l.lg) were added, a reflux condenser was attached and the solution was heated to reflux. After several hours, additional AIBN (20mg) was added and the reaction was allowed to stir at reflux overnight. The reaction was quenched by the addition of water and sat. aq. sodium bicarbonate. The organic phase was separated, concentrated in vacuo and purified by flash column chromatography (12Og silica, eluting with 0%-20% Ethyl Acetate in hexanes) to afford 3-bromo-4-(bromomethyl)benzonitrile as a pale yellow solid (800 mg, 2.88 mmol). 1H NMR (500 MHz, MeOD) delta ppm 4.70 (s, 2H), 7.71 (d, J= 8.0 Hz, IH), 7.73 (d, J= 8.0 Hz, IH), 8.04 (s, IH).

According to the analysis of related databases, 42872-74-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WATTERSON, Scott, Hunter; DYCKMAN, Alaric, J.; PITTS, William, J.; SPERGEL, Steven, H.; WO2010/85581; (2010); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 5414-21-1, name is 5-Bromovaleronitrile, 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 5414-21-1, name: 5-Bromovaleronitrile

EXAMPLE 1 5-{4-[2-(4-Pyridinyl)-ethenyl]-phenoxy}-valeronitrile To the solution of 1.16 g (50 mmol) sodium in 250 ml 2-propanol one adds 10.0 g (50 mmol) 4-[2-(4-pyridinyl)-ethenyl]-phenol, heats under reflux for 10 min, allows to cool, adds thereto 8.1 g (50 mmol) 5-bromovaleronitrile and heats to reflux for 16 h. One evaporates, mixes with water, extracts with dichloromethane, dries the extract, evaporates and triturates the residue with ether. One obtains 11.9 g of title compound (86% of theory) of the m.p. 85-87 C.

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

Reference:
Patent; Boehringer Mannheim GmbH; US5399575; (1995); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 70484-01-4, name is 4-Bromophthalonitrile, 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 70484-01-4, SDS of cas: 70484-01-4

4-bromo-phthalonitrile (0.414 g), 4-borate-4′,4′-dimethoxytriphenylamine (1.725 g), Tetrakis(triphenylphosphine)palladium (0.231 g) and potassium carbonate (2.764 g) were placed in a mixed solution of water (3 mL) and tetrahydrofuran (50 mL). Nitrogen gas was used as a shielding gas, and aeration-degassing was carried out three times to obtain a nitrogen atmosphere. Then, the mixture was stirred at 80 C for 12 hours. After the reaction was completed, the reaction solution was cooled to room temperature, and magnesium sulfate was added to remove water; the solution after water removal was dried. To obtain a solid product, The obtained solid product was subjected to column chromatography using an eluent (petroleum ether: ethyl acetate: dichloromethane in a volume ratio of 20:1:2); after column chromatography, The obtained solution was spin-dried to obtain an phthalic acid derivative, which was confirmed by nuclear magnetic analysis.Its structure is as shown in Formula I, which is 4-o-phenylenedicyano-4′,4′-dimethoxytriphenylamine. The nuclear magnetic analysis chart is shown in Figure 1;

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

Reference:
Patent; South University of Science and Technology of China; Xu Zongxiang; Feng Yaomiao; Hu Qikun; (18 pag.)CN109651197; (2019); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Reference of 1953-99-7, These common heterocyclic compound, 1953-99-7, name is 3,4,5,6-Tetrachlorobenzene-1,2-dicarbonitrile, 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.

In a 100 ml flask, 3,4,5,6-tetrachlorophthalonitrile (5 g), 2,6-dichlorophenol (2.45 g), K2CO3 (3.9 g) and N,N-dimethylformamide And the mixture was stirred while heating to 70°C. After completion of the reaction, the reaction mixture is extracted with EA (ethyl acetate). After extraction and concentration, a solid can be obtained. The resulting solid is dissolved in a small amount of dichloromethane, washed several times with hexane, filtered, and vacuum dried to obtain 3,4,6-trichloro-5-(2,6-dichloro-phenoxy)-phthalonitrile.

The synthetic route of 1953-99-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Samsung SDI Co., Ltd; Seo Hye-won; Shin Myeong-yeop; Jeong Ui-su; Han Gyu-seok; (56 pag.)KR2019/11995; (2019); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Application of 103146-25-4, 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. 103146-25-4, name is 4-(4-(Dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl)-3-(hydroxymethyl)benzonitrile, This compound has unique chemical properties. The synthetic route is as follows.

A test tube equipped with a stopper was charged with 10 mg (0.029 m mol) of [(=T :)-4-] [4-dimethylamino-1- (4′-fluorophenyl)-1-hydroxybutyl]-3-hydroxymethylbenzonitrile, 10 mg of Novozym 435 (product of NOvozymes), 33 mg (0.29 [M MOL)] of vinyl butyrate and 1 ml of various kinds of solvents, and stirred at [30C] for 16 hours. After the reaction, converted ratios and optical purities were analyzed and E-values were calculated. The results are shown in Table 9.

The chemical industry reduces the impact on the environment during synthesis 4-(4-(Dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl)-3-(hydroxymethyl)benzonitrile. I believe this compound will play a more active role in future production and life.

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