Month: February 2021

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. 5332-06-9, name is 4-Bromobutanenitrile, This compound has unique chemical properties. The synthetic route is as follows., name: 4-Bromobutanenitrile

General procedure: To a stirred solution of 7,8-dimethoxy-2,3,4,5-tetrahydro-1H-benzo[d]azepine20 (11) (1.36 g, 6.6 mmol) and 4-bromobutyronitrile (0.98 g, 6.6 mmol) in DMF (40 mL), NaI (1.00 g, 6.6 mmol) and K2CO3 (2.75 g, 19.9 mmol) were added and the mixture was stirred at 60 C overnight. The solvent was removed under reduced pressure and the residue was diluted with H2O (150 mL) and extracted with ethyl acetate (3 ¡Á 100 mL) to give 4-(7,8-dimethoxy-4,5-dihydro-1H-benzo[d]azepin-3(2H)-yl)butanenitrile (1.66 g, 92%) as a yellow oil. 1H NMR (CDCl3) d: 6.64 (s, 2H), 3.85 (s, 6H), 2.86-2.82 (m, 4H), 2.63-2.59 (m, 4H), 2.58 (t, J = 6.8 Hz, 2H), 2.47 (t, J = 6.8 Hz, 2H), 1.84 (tt, J = 6.9 Hz, 6.9 Hz, 2H). This material (1.58 g, 5.7 mmol) was used without further purification and dissolved in dry THF (20 mL) for the following reaction. A solution of LiAlH4 (0.65 g, 17.1 mmol) in dry THF (20 mL) was added dropwise at 0 C. The mixture was stirred at rt overnight under N2. The mixture was cooled to 0 C and quenched by adding H2O (1 mL), 10% aqueous NaOH (2 mL), and H2O (2.5 mL) successively. The inorganic salts were washed with EtOAc and filtered. The filtrate was evaporated under reduced pressure to give 12 (1.18 g, 75%) as yellow oil.

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 5332-06-9.

Reference:
Article; Fan, Kuo-Hsien; Lever, John R.; Lever, Susan Z.; Bioorganic and Medicinal Chemistry; vol. 19; 6; (2011); p. 1852 – 1859;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthetic Route of 403-54-3, 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 403-54-3 as follows.

4.12 mL (8.24 mmol) of trimethyl aluminum (2.0 M toluene solution) was added to a 10 mL of toluene containing 441 mg (8.24 mmol) of ammonium chloride at room temperature. After stirring for 1.5 hours, 2 g (28.9 mmol) of isobutyronitrile was added EPO thereto and the resulting mixture was heated to 85C for 9 hours. After completion of a reaction, the reaction solution was poured into 200 mL of chloroform containing 200 g of silicagel and filtered off. The residue was washed with 100 mL of methanol and distillation was conducted to give 731 mg (5.29 mmol) of the title compound in a yield of 64%.[936] NMR: 1H-NMR(CD OD) delta 7.71~7.44(4H, m)[937] Mass(EI) 139(M++.)

According to the analysis of related databases, 403-54-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; LG LIFE SCIENCES, LTD.; WO2006/104356; (2006); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Reference of 1080-74-6, A common heterocyclic compound, 1080-74-6, name is 2-(3-Oxo-2,3-dihydro-1H-inden-1-ylidene)malononitrile, molecular formula is C12H6N2O, 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.

The compound represented by Formula (2-11A-1) obtained in the above Preparation Example 2 (163.1 mg, 0.1 mmol), the compound represented by Formula (a-2-1) (78 mg, 0.4 mmol; purchased from TCI), Pyridine (0.8 mL, 0.96 mmol) and chloroform (30 mL) were added to the reaction vessel, argon was passed for 25 min, and then refluxed at 65 C. for 15 h. After cooling to room temperature (approximately 25 C), the reaction product was poured into 200 mL of methanol and filtered. The obtained precipitate was subjected to a silica gel chromatography column (200-300 mesh silica gel was used, and the eluent was petroleum ether with a volume ratio of 1: 2. / Dichloromethane) and chromatographically separated to obtain a green solid (178.3 mg, yield 90.0%), which is a two-dimensional fused ring conjugated macromolecule represented by the formula (1-11A-1).

The synthetic route of 1080-74-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Peking University; Zhan Xiaowei; Wang Jiayu; (34 pag.)CN110386943; (2019); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthetic Route of 123-06-8, 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. 123-06-8 name is Ethoxymethylenemalononitrile, 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.

General procedure: Hydrazine monohydrate (26.7 mul, 0.55 mmol) was added to a solution of (ethoxymethylene)malonic acid derivatives 4a-d (0.50 mmol) in EtOH (0.5 ml), and the solution was subjected to microwave irradiation (4a: 80C, 4b: 150C, 4c,d: 120C; 150W; 10 min). Afterwards, water (0.5 ml), aldehydes 2a-j (0.55 mmol), TFA (7.7 mul, 0.10 mmol) and isocyanides 3a-d (0.55 mmol) were sequentially added to the solution, and the reaction was stirred for 10-60 min at room temperature. The precipitated product was filtered, washed with hexane or diethyl ether (1-3 ml) and dried in vacuo, yielding the corresponding final products 6-41 and 46-51. In case of 42-45, the crude reaction mixtures were purified by flash chromatography with hexane-EtOAc as eluent.

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

Reference:
Article; Demjn, Andrs; Gyuris, Mri; Woelfling, Jnos; Pusks, Lszl G.; Kanizsai, Ivn; Beilstein Journal of Organic Chemistry; vol. 10; (2014); p. 2338 – 2344;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthetic Route of 89642-49-9, A common heterocyclic compound, 89642-49-9, name is 4-Bromo-3-nitrobenzonitrile, molecular formula is C7H3BrN2O2, 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.

3.48. Compound 49: (lR,2R)-N-(6-(5-cyano-2-ethylphenylamino)-l-methyl-lH-imidazo[4,5- 3.48.1. Step i : 3-Nitro-4-vinyl-benzonitrile A mixture of 4-bromo-3-nitro-benzonitrile (1.0 eq, 1.0 g), potassium vinyl trifluoroborate (1.5 eq, 0.89 g), PdCl2(dppf).DCM (0.05 eq, 201 mg), K2C03 (3.0 eq, 1.82 g) in THF/water (10: 1; 20 mL) is heated at 80 C. After 1 h, the resulting mixture is diluted with DCM and aq. sat. NaHCOs, passed through a phase separator and concentrated. The residue is used as such in the next step.

The synthetic route of 89642-49-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GALAPAGOS NV; MENET, Christel, Jeanne, Marie; MAMMOLITI, Oscar; QUINTON, Evelyne; JOANNESSE, Caroline, Martine, Andree-Marie; DE BLIECK, Ann; BLANC, Javier; (263 pag.)WO2017/12647; (2017); 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. 654-70-6, name is 4-Cyano-3-trifluoromethylaniline, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C8H5F3N2

A mixture of 750 mg of the compound, produced under 7b, and 920 mg of 4-amino-2-(trifluoromethyl)benzonitrile in 10 ml of ethanol was mixed under a nitrogen atmosphere with 0.5 g of an activated molecular sieve (0.3 nm) and stirred for 2 days at 90 C. For working-up, the molecular sieve was filtered off after cooling, washed with ethanol, and the combined ethanol solutions were concentrated by evaporation. The residue was taken up in ethyl acetate and washed with water as well as saturated sodium chloride solution. After drying on sodium sulfate and concentration by evaporation, it was chromatographed on silica gel with ethyl acetate/hexane, and 731 mg of the title compound was thus obtained as a colorless oil. ESI-MS: 320

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 654-70-6.

Reference:
Patent; Schering AG; US2004/9969; (2004); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

These common heterocyclic compound, 939-80-0, name is 4-Chloro-3-nitrobenzonitrile, 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. COA of Formula: C7H3ClN2O2

6-Methoxybenzothiazol-2-amine (0.5 g, 2.8 mmol; Compound 8a) was suspended in aqueous potassium hydroxide solution and refluxed overnight. The reaction solution was cooled to room temperature and then added dropwise to a solution of 4-chloro-3-nitrobenzonitrile (0.51 g, 2.8 mmol; Compound 7a) in ethanol (20 mL)/acetic acid (50 mL) in a water bath. The reaction mixture was stirred for an additional 3 hours. The precipitate was filtered and washed with a 1:1 mixture of water:ethanol to give 4-((2-Amino-5-methoxyphenyl)thio)-3-nitrobenzonitrile (Compound 9a) as a red solid. (0.51 g, 60%). 1H NMR (CDCl3): delta=3.77 (s, 3H), 3.99 (b, 2H), 6.85 (d, 1H, J=8.4 Hz), 6.98 (m, 3H), 7.58 (d, 1H, J=8.7 Hz), 8.56 (s, 1H); mp 163.6-165.1 C.

The synthetic route of 4-Chloro-3-nitrobenzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Washington University; Tu, Zhude; Mach, Robert; Yu, Lihai; Kotzbauer, Paul; US2013/315825; (2013); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Reference of 79463-77-7,Some common heterocyclic compound, 79463-77-7, name is Diphenyl N-cyanocarbonimidate, molecular formula is C14H10N2O2, 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.

Diphenyl cyanocarbonimidate (5.3 g, 21.56 mmol) in DCM (50 mL) was added to a sol. of l-(4methoxyphenyl)-2,2-dimethylpiperazine (5 g, 21.56 mmol) in DCM (190 mL). The r.m. was stirred at r.t. for 24 h. Water was added and the mixture was extracted with DCM. The separated organic layer was dried (MgS04), filtered and the solvent was evaporated. The residue was suspended in DIPE, filtered off and dried in the oven. Yield: 6.12 g of intermediate 1 (77 %).

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

Reference:
Patent; JANSSEN PHARMACEUTICALS, INC.; BISCHOFF, Francois, Paul; VELTER, Adriana, Ingrid; VAN BRANDT, Sven, Franciscus, Anna; BERTHELOT, Didier, Jean-Claude; WO2012/126984; (2012); 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. 5332-06-9, name is 4-Bromobutanenitrile, A new synthetic method of this compound is introduced below., Safety of 4-Bromobutanenitrile

To a suspension of K2CO3 (8.28 g, 60 mmol) and morpholine (4.35 g, 50 mmol) in acetonitrile (50 mL) was added 4-bromobutyronitrile (7.40 g, 50 mmol) dropwise at rt under N2. The mixture was stirred at rt for 6 h, filtered and concentrated in vacuo to give the title compound (7.26 g, 94.2%).

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; SUNSHINE LAKE PHARMA CO., LTD.; Zhang, Yingjun; Zhang, Jiancun; Wang, Xiaojun; Lin, Runfeng; Cao, Shengtian; Wang, Zhaohe; Li, Jing; US2015/87639; (2015); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 19179-31-8, name is 3,5-Dimethoxybenzonitrile, 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 19179-31-8, Computed Properties of C9H9NO2

Step 1: Cyclopentyl-(3,5-dimethoxy-phenyl)-methanone To a solution of 3,5-dimethoxybenzonitrile (5.0 g) in anhydrous THF (60 mL) were added a solution of cyclopentylmagnesium chloride (20 mL of 2 M solution in diethyl ether) and cuprous bromide (88 mg). The resulting reaction mixture was refluxed for 1 h. Then water (10 mL) and 10% sulfuric acid (20 mL) were added and the resulting mixture was stirred at room temperature overnight. Then the reaction mixture was diluted with diethyl ether and washed with water and brine. The organic extract was dried over anhydrous sodium sulfate, concentrated and purified on a silica gel column using ethyl acetate and hexanes to yield 5.9 of the title compound (82% yield). HRMS calcd for C14H18O3 [M+H]+ 253.1329, observed 253.1328.

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, 3,5-Dimethoxybenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Dominique, Romyr; Goodnow, JR., Robert Alan; Kowalczyk, Agnieszka; Qiao, Qi; Sidduri, Achyutharao; Tilley, Jefferson Wright; US2010/240678; (2010); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts