Category: nitriles-buliding-blocks

Electric Literature of 5922-60-1, The chemical industry reduces the impact on the environment during synthesis 5922-60-1, name is 2-Amino-5-chlorobenzonitrile, I believe this compound will play a more active role in future production and life.

General procedure: Under a N2 atmosphere, a Schlenk tube was charged with 2-aminobenzonitrile 1 (0.3 mmol),sodium arylsulfinate 2 (0.6 mmol), Pd(OAc)2 (10 mol percent), bpy (20 mol percent), p-NBSA (10 equiv), THF (2 mL), and H2O (1 mL) at room temperature. The reaction mixture was stirred vigorously at 80 °C for 48 h. The mixture was poured into ethyl acetate, which was washed with saturated NaHCO3 (2 × 10 mL) and then brine (1 × 10 mL). After the aqueous layer was extracted with ethyl acetate, the combined organic layers were dried over anhydrous MgSO4 and evaporated under reduced pressure. The residue was purified by flash column chromatography (hexane/ethyl acetate) to afford the desired products 3.

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-Amino-5-chlorobenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Chen, Jiuxi; Li, Jianjun; Su, Weike; Molecules; vol. 19; 5; (2014); p. 6439 – 6449;,
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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. 75344-77-3, name is 4-Bromo-3,5-dimethylbenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., name: 4-Bromo-3,5-dimethylbenzonitrile

Under a nitrogen atmosphere, Add the previous step in a 250 ml three-neck round bottom reaction bottle. 10-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-10H-phenoxazine, 420 mg of 4-bromo-3,5-dimethylbenzonitrile, 120 ml of toluene, 40 ml of absolute ethanol and 40 ml of a 2 molar solution of potassium carbonate per liter, Stir and dissolve. After 15 minutes of aeration, 50 mg of tetrakis(triphenylphosphine)palladium(0) catalyst was added, and after aeration for 30 minutes, it was heated to 85 C and refluxed for 24 hours. After the reaction was stopped and the reaction was stopped, the solvent of the reaction system was removed by steaming. The reaction system was extracted with a dichloromethane solvent. It was washed three times with deionized water, three times with saturated brine, and dried over anhydrous magnesium sulfate for 1 hour. Purification of the product by column chromatography, The eluent is a mixed solvent of petroleum ether and dichloromethane in a ratio of 3:1. The yield of the solid product was finally 77%.

According to the analysis of related databases, 75344-77-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; South China University of Technology; Su Shijian; Cai Xinyi; Qiu Weidong; Qiao Zhenyang; (32 pag.)CN108530376; (2018); A;,
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Electric Literature of 3288-99-1, A common heterocyclic compound, 3288-99-1, name is 2-(4-(tert-Butyl)phenyl)acetonitrile, molecular formula is C12H15N, 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.

(RS)-2-(4-tert-butylphenyl)-2-cyanoacetic acid methyl ester at room temperature, To a solution of 4-tert-butylbenzeneacetonitrile (0.1mol) Tetrahydrofuran (150 mL) and sodium hydride (0.12 mol) in a mixed solution, Dimethyl carbonate (0.15 mol) was added dropwise, After the drop, Heated to reflux reaction 3 ~ 6hr. After cooling, the reaction mixture was poured into ice water, With 20% hydrochloric acid solution to adjust its pH to 6 ~ 7, Ethyl acetate, dried over anhydrous sodium sulfate, decompressed under reduced pressure, Take the oily title compound 19.2 g.

The synthetic route of 3288-99-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hunan research institute of chemical industry company; Wang, XiaoGuang; Liu, AiPing; Liu, XingPing; Gao, deliang; Bai, JianJun; Luo, LiangMing; Huang, Lu; He, Liying; Zhou, Bo; Cheng, LiJun; (15 pag.)CN105777580; (2016); 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. 75344-77-3, name is 4-Bromo-3,5-dimethylbenzonitrile, A new synthetic method of this compound is introduced below., Computed Properties of C9H8BrN

To a solution of 4-bromo-3,5-dimethylbenzonitrile (1 g) in N,N-dimethylformamide (10 ml_) is added NH4CI (770 mg) and NaN3 (800 mg) and the mixture is heated to 100C for 12 hours. After cooling to room temperature the mixture is diluted with water. The formed precipitate is filtered off, washed with water and dried to give the title compound. Yield: 650 mg; Mass spectrum (ESI+): m/z = 253 [M+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; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; ECKHARDT, Matthias; FRATTINI, Sara; HAMPRECHT, Dieter; HIMMELSBACH, Frank; LANGKOPF, Elke; LINGARD, Iain; PETERS, Stefan; WAGNER, Holger; WO2013/144097; (2013); A1;,
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Synthetic Route of 1835-65-0,Some common heterocyclic compound, 1835-65-0, name is 3,4,5,6-Tetrafluorophthalonitrile, molecular formula is C8F4N2, 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.

One hundred (100) g of the benzonitrile solution as the mother liquor obtained in Example 8 and 80 g of an aqueous 70percent sulfuric acid solution added thereto were stirred together at room temperature for 2 hours. Then, the resultant reaction solution was left standing at rest and allowed to separate into an organic layer (benzonitrile solution layer) and a water layer. When the organic layer was analyzed, it was found to contain absolutely no benzoic acid fluoride.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3,4,5,6-Tetrafluorophthalonitrile, its application will become more common.

Reference:
Patent; Nippon Shokubai Co., Ltd.; US6392084; (2002); B1;,
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Synthetic Route of 42872-74-2, The chemical industry reduces the impact on the environment during synthesis 42872-74-2, name is 3-Bromo-4-methylbenzonitrile, I believe this compound will play a more active role in future production and life.

Heat a mixture of 3-bromo-4-methylbenzonitrile (25.0 g, 127.5 mmol, 1.0 equiv) and n-bromosuccinimide (NBS) (5.53 g, 306.1 mmol, 2.4 equiv) in carbon tetrachloride (200 mL) to 95 C. for two days. Cool the resulting suspension, and remove the solids by filtration. Concentrate the filtrate under reduced pressure, and purify the resulting crude material by chromatography on silica gel eluting with a gradient of 2-5% THF/hexanes to furnish the title compound (37.09 g, 82% yield). 1H NMR (400 MHz, CDCl3) delta 8.10 (d, 1H, J=8.2 Hz), 7.79 (d, 1H, J=1.3 Hz), 7.67 (dd, 1H, J=8.2, 1.3 Hz), 6.99 (s, 1H).

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-Bromo-4-methylbenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ELI LILLY AND COMPANY; US2012/302608; (2012); 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. 39581-21-0, name is N-Butyl-2-cyano-acetamide, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 39581-21-0

Exemplary Synthesis 9 Method of Synthesizing Exemplary Compound 9 (0236) (0237) Intermediate 3 (5.0 g), N-butyl-2-cianoacetamide (2.1 g), triethylamine (1.3 g) and acetonitrile (50 ml) were placed in a flask, and the content was stirred at 50 C. for 5 hours. Acetonitrile was removed, the residue was purified by column chromatography, and the eluate was recrystallized from ethanol to obtain a target product. The crystal was dried at 50 C. under air flow, to obtain 1.4 g of Exemplary Compound 9. (0238) lambdamax=369 nm (AcOEt) (0239) 1H-NMR (CDCl3) delta: 8.30 (d, 1H), 5.96 (s, 1H), 4.84 (d, 2H), 4.18 (s, 2H), 3.32 (q, 2H), 2.83 (s, 3H), 1.51 (m, 2H), 1.36 (m, 2H), 1.33 (s, 6H), 0.92 (t, 3H)

According to the analysis of related databases, 39581-21-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; FUJIFILM CORPORATION; NORIZUKI, Yutaro; WATANABE, Yukie; TAKAHASHI, Kazutaka; (21 pag.)US2016/16919; (2016); A1;,
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Electric Literature of 939-80-0, The chemical industry reduces the impact on the environment during synthesis 939-80-0, name is 4-Chloro-3-nitrobenzonitrile, I believe this compound will play a more active role in future production and life.

3-Nitro-4-(4,4,4-trifluorobutylamino)benzonitrileA mixture of 4-chloro-3-nitro-benzonitrile (1.36 g, 7.43 retool, 1 eq), 4,4,4-trifluorobutan-1-amine (945 rag, 7.43 retool, 1 eq) and triethylamine (1.04 mL, 7.43 retool, 1 eq) inacetonitrile (30 mL) was stirred at room temperature. After 16 h the reaction wasconcentrated in vacuo to dryness. The residue was dissolved in CH2C12 (30 mL), washedwith water (3 x 15 mL), dried (MgSO4), filtered and concentrated in vacuo to yield the titlecompound as a yellow solid (1.99 g, 98%).1H NMR (250MHz, CDC13): c2.10 (m, 2H), 2.33 (m, 2H), 3.51 (q, 2H), 6.95 (d, 1H), 7.68(m, 1H), 8.44 (br.s, 1H), 8.57 (d, 1H). LC/MS 274 (MH+).

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-Chloro-3-nitrobenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ASTRAZENECA UK LIMITED; ARROW THERAPEUTICS LIMITED; BLADE, Helen; CARRON, Elisa, Ann; JACKSON, Heather, Marie; LUMLEY, James, Andrew; PILKINGTON, Christopher, John; TOMKINSON, Gary, Peter; THOMAS, Alexander, James, Floyd; WARNE, Justin; WO2010/103306; (2010); A1;,
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Related Products of 1000339-52-5, 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. 1000339-52-5, name is 3-Fluoro-2-nitrobenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: To a solution of fluorine substituted 2-nitrobenzonitrile (18.06 mmol, 3 g) in DMF (50 mL) was added 1-Boc-piperazine (36.12 mmol, 6.727 g) and K2CO3 (18.06 mmol, 2.496 g), and the mixture solution was stirred for 5 h at 160 C. The mixture was extracted with DCM. The organic layer was separated and dried over Na2SO4. Removal of the solvent produced a residue which was purified using column chromatography, eluted with a mixture of MeOH:CH2Cl2 (1:30, v:v), to afford intermediate 7a-1, 7c-1.

The synthetic route of 3-Fluoro-2-nitrobenzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Article; Liu, Wenwen; Wang, Huan; Li, Xiaokang; Xu, Yixiang; Zhang, Jian; Wang, Wei; Gong, Qi; Qiu, Xiaoxia; Zhu, Jin; Mao, Fei; Zhang, Haiyan; Li, Jian; Bioorganic and Medicinal Chemistry; vol. 26; 12; (2018); p. 3117 – 3125;,
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Application of 53312-80-4, 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. 53312-80-4 name is 4-Amino-2-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.

Sodium cyanide (0.74 g, 15 mmol) was added to a mixture of 4-amino-2- fiuorobenzonitrile (1.36 g, 10 mmol) and cyclopentanone (1.26 g, 15 mmol) in 90% acetic acid (10 ml). The reaction mixture was stirred at room temperature for 3 hours and then the medium was hearted to 80 0C and stirred for an additional 5 hours. The medium was washed with water and extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, concentrated and chromatographed (dichloromethane:acetone, 97:3) to yield 4-(l-cyanocyclopentylamino)-2-fluorobenzonitrile (54b) (2.07 g, 9.03 mmol, 90%) as a yellow solid. 1H NMR (CDCl3, 400 MHz) delta 1.69-1.91 (m, 4H), 2.13-2.18 (m, EPO 2H), 2.37-2.42 (m, 2H), 5.08 (bs, IH), 6.54-6.62 (m, 2H), 7.39 (t, J= 7.3 Hz, IH); 13C NMR (CDCl3, 100 MHz) delta 23.7, 39.8, 56.8, 89.6 (d, J = 15.8 Hz), 101.2 (d, J= 23.8 Hz), 110.9, 115.2, 120.8, 134.1 (d, /= 2.4 Hz), 150.3 (d, J= 11.2 Hz), 164.5 (d, J= 254.1 Hz).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Amino-2-fluorobenzonitrile, and friends who are interested can also refer to it.

Reference:
Patent; THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; WO2006/124118; (2006); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts