Tag: M.W=100-200

These common heterocyclic compound, 63069-50-1, name is 4-Amino-3-fluorobenzonitrile, 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. SDS of cas: 63069-50-1

General procedure: 1.4.1. MethodAlj00243j A mixture of the amino aromatic or heteroaromatic starting material (1 eq), Ag2SO4 (1 eq) and 12 (1 eq) in EtOH is stirred at temperatures ranging from room temperature to 50C for a period which can vary from 1 h to approximately 16 h. The mixture is filtered, concentrated and diluted in an organic solvent. The organic mixture undergoes aqueous work up. The solvent is removed under reduced pressure and the residue is purified by flash column chromatography to yield the desired product.1.4.2. Illustrative example ofmethodAl: synthesis of 4-Amino-3-fluoro-5-iodo-benzonitrile (Int.4).N NH2 NI H2j00244j A mixture of 4-amino-3-fluorobenzonitrile (147 mmol), 12 (147 mmol) and Ag2SO4 (147 mmol) in EtOH (700 mL) was stirred at room temperature for 1.5 h. The mixture was filtered and concentrated. The residue was dissolved in EtOAc and washed (sat. Na2S2O3 x 3). The organic layer was dried (Na2SO4) and concentrated. The residue was purified by flash column chromatography (Si02, 95:5 to 70:3 0 cyclohexane/EtOAc) to yield the desired product.

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

Reference:
Patent; GALAPAGOS NV; MENET, Christel, Jeanne, Marie; MAMMOLITI, Oscar; BLANC, Javier; OR?ULIC, Mislav; RO?CIC, Maja; WO2015/110378; (2015); A1;,
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Some common heterocyclic compound, 5922-60-1, name is 2-Amino-5-chlorobenzonitrile, molecular formula is C7H5ClN2, 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. SDS of cas: 5922-60-1

Example 3: Synthesis of 6-chloro-2,4-diamino-quinazolineA mixture of 2-amino-5-chlorobenzonitrile (1.07 g, 7.0 mmol), chloro- formamidine hydrochloride (1.6 g, 14 mmol), sulfolane (0.5 ml) and dimethylsulfone(3 g) was heated at 165 0C for 30 minutes. Then, water (30 ml) was added to the reaction mixture. The pH was adjusted to 7-8 by the addition of a 33 percent aqueous ammonia solution in water. The precipitate was collected by filtration, washed with water and dried over P2O5, yielding the title compound as a yellowish solid (1.35 g, yield: 99 percent) which was characterized by its mass spectrum as follows: MS (m/z): 195([M+H]+, 100).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5922-60-1, its application will become more common.

Reference:
Patent; GILEAD SCIENCES, INC.; WO2008/9077; (2008); A2;,
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Related Products of 52798-01-3, A common heterocyclic compound, 52798-01-3, name is Methyl (4-cyanophenyl)acetate, molecular formula is C10H9NO2, 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.

a. Methyl 2-(4-cyanophenyl)-tert.butyl malonate 1.7 g (0.01 mol) of methyl 4-cyanophenylacetate are dissolved in 30 ml tetrahydrofuran, 0.48 g (0.01 mol) of sodium hydride (60% in oil) are added in batches thereto and stirred for 15 minutes at 60 C. Then 1.5 ml (0.01 mol) of tert.butyl bromoacetate are added dropwise at ambient temperature. The reaction mixture is refluxed for 5 hours, cooled and poured onto water and extracted with methylene chloride. The combined organic extracts are dried and evaporated down. The residue is chromatographed on silica gel and eluted with petroleum ether/ethyl acetate (4:1). Yield: 1.5 g (52% of theory), Rf value: 0.7 (silica gel; petroleum ether/ethyl acetate=7:3).

The synthetic route of 52798-01-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Boehringer Ingelheim Pharma KG; US6114532; (2000); A;,
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Related Products of 16588-02-6,Some common heterocyclic compound, 16588-02-6, name is 2-Chloro-5-nitrobenzonitrile, molecular formula is C7H3ClN2O2, 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.

Conc. HC1 (15.6 ml) was added dropwise to 2-chioro-5- nitrobenzonitrile (3.38 g, 18.5 mmol) and SnC12.2H20 (18.9 g, 83.9 mmol, 4.5 eq.) in isopropanol (35 ml). The mixture was heated at 120 C. for 2 h and then cooled to room temperature and made basic using aq. NaOH. The mixture wasextracted with dichloromethane, dried over Na2SO4 and filtered through silica gel. Concentration under reduced pressure gave 5-amino-2-chlorobenzonitrile (2.58 g, 91%).55?H NMR (300 MHz, CDC13): oe=3.90 (br. s, 2H), 6.79 (dm, 1H), 6.91 (m, 1H), 7.22-7.26 (m, 1H) ppm.

The synthetic route of 16588-02-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER INTELLECTUAL PROPERTY GMBH; Maue, Michael; Kapferer, Tobias; Muehlthau, Friedrich August; Malsam, Olga; US9204645; (2015); B2;,
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Application of 64248-62-0, 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 64248-62-0 as follows.

In a 500mL three-necked flask,Add 3,4-difluorobenzonitrile (50.0 g, 0.28 mol)And 200mL of absolute ethanol,Control temperature 0~5 C,Pass dry HCl gas to saturation,The reaction was kept for 30 hours, a large amount of white solid was precipitated, and suction filtration was applied. The filter cake was washed with 0 to 5 C anhydrous ethanol, and dried under vacuum to give (VI-11) 52.5 g, yield 65.9%.

According to the analysis of related databases, 64248-62-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; China Pharmaceutical University; Hefei Medical Engineering Pharmaceutical Co., Ltd.; Xu Yungen; He Guangwei; Liu Kun; Chu Zhaoxing; Zhu Qihua; Zhao Yan; Liu Weizhong; Wang Kui; Zhang Luyong; (26 pag.)CN108456152; (2018); A;,
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Reference of 654-70-6, The chemical industry reduces the impact on the environment during synthesis 654-70-6, name is 4-Cyano-3-trifluoromethylaniline, I believe this compound will play a more active role in future production and life.

General procedure: Thionyl chloride (4.3 g, 36 mmol) was added dropwise under argon to a solution of bromoacid 39 (5.5 g, 30 mmol) in 35 mL of DMA at -5 to -10 C. The resulting mixture was stirred for 2 h under the same conditions. A solution of the appropriate aniline (30 mmol) in 40 mL of DMA was added dropwise to the above solution, and the resulting mixture was stirred overnight at room temperature. The solvent was removed on rotavapor using high vacuum oil pump; the residue was diluted with saturated NaHCO3 solution, and extracted with ethyl ether (3 x 100 mL). Combined extracts were dried over anhydrous Na2SO4, filtered through celite, and purified by flash chromatography on silica gel, using DCM as eluent to afford the desired product. The data are in accordance with literature data [ref]. 1H-NMR (CDCl3): 9.09 (s,1H), 8.12 (d, J = 2.0 Hz, 1H), 7.98 (dd, J = 8.5 Hz, 2.0 Hz, 1H), 7.83 (d, J = 8.5 Hz,1H), 4.02 (d, J = 10.6 Hz, 1H), 3.62 (d, J = 10.6 Hz, 1H), 1.66 (s, 3H); 19F-NMR(CDCl3): -63.59 (s, 3F).

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-Cyano-3-trifluoromethylaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Bassetto, Marcella; Ferla, Salvatore; Pertusati, Fabrizio; Kandil, Sahar; Westwell, Andrew D.; Brancale, Andrea; McGuigan, Christopher; European Journal of Medicinal Chemistry; vol. 118; (2016); p. 230 – 243;,
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Synthetic Route of 119584-73-5, 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. 119584-73-5, name is 2-Ethoxy-6-fluorobenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example 8: Synthesis of 3-amino-4-ethoxy-7-methanesulfonylamino- benzo [B] THIOPHENE-2-CARBOXYLIC acid amide To a stirred solution of 2-ethoxy-6-fluorobenzonitrile (J. Hynes, J.Heterocycl.Chem. 1988, 25, 1173) (10. 0 G, 60. 54 mmol) in THF (150mL) at-78C was added lithium diisopropylamide (1. 8 M, 44.1 mL, 79. 4MMOL). The mixture was stirred AT-78 C for lh. Then it was poured slowly onto dry ice and stirred until it reached room temperature. The mixture was concentrated to about 10 mL, then diluted with 6N HCI (200mL), and extracted with dichloromethane (3X100 mL). The solvent was washed with brine and dried over NA2S04. The solvent was removed to give product 3-CYANO-4-ETHOXY-2- fluorobenzoic acid (4.2 g, 33.2%).

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-Ethoxy-6-fluorobenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BOEHRINGER INGELHEIM PHARMACEUTICALS, INC.; WO2005/12283; (2005); A1;,
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42872-73-1, name is 2-Bromo-4-methylbenzonitrile, 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. Safety of 2-Bromo-4-methylbenzonitrile

F. Methyl 3-(4-cyanobenzyloxy)-5-isoxazolecarboxylate. A mixture of o-bromo-p-tolunitrile (18.8 mmol, 3.69 g), methyl 3-hydroxy-5-isoxazolecarboxylate (18.8 mmol, 2.69 g) and potassium carbonate (25 mmol, 3.5 g) was heated at 50 C. overnight. After cooling to room temperature, the solution was added to 1% citric acid and the precipitate was filtered, washed with water and cold ether several times and dried. Yield 4.2 g (87%). NMR (DMSO-d6): delta 7.90 (d, 2H); 7.68 (d, 2H); 7.18 (s, 1H); 5.43 (s, 2H); 3.90 (s, 3H).

The synthetic route of 42872-73-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; The Dupont Merck Pharmaceutical Company; US5563158; (1996); A;,
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Some common heterocyclic compound, 873-74-5, name is 4-Aminobenzonitrile, molecular formula is C7H6N2, 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. Recommanded Product: 873-74-5

EXAMPLE 25 PREPARATION OF 4-AMINO-3,5-DIBROMOBENZONITRILE STR37 To a stirred solution of 100 mg (0.847 mmoles) of p-aminobenzonitrile in 3.6 mL dioxane chilled in an ice-bath was added sequentially 356 muL (1.78 moles) of 5N sodium hydroxide solution and mg (1.78 mmoles) of bromine. The ice-water bath was removed and the reaction mixture was stirred further for 1.5 hours. After this time, 21.8 muL (0.423 mmoles) of bromine was added to drive the reaction to completion and stirring was continued for 10 minutes. The mixture was partitioned between ethyl acetate and ice-water and the organic phase was separated. It was washed with brine, dried over anhydrous sodium sulfate, filtered, and evaporated. Purification by plate layer chromatography using hexane-ethyl acetate (7:3) as the eluant provided 175 mg (74%) of the entitled product. NMR(CDCl3) delta5.1 (bs, 2H), 7.66 (s, 2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 873-74-5, its application will become more common.

Reference:
Patent; Merck & Co. Inc.; US5455239; (1995); A;,
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Electric Literature of 16213-85-7, The chemical industry reduces the impact on the environment during synthesis 16213-85-7, name is 2-(2,5-Dimethylphenyl)acetonitrile, I believe this compound will play a more active role in future production and life.

The organic layer obtained in the second step above,250g (1.5mol) of 60% sulfuric acid aqueous solution and 50g (0.8mol) of glacial acetic acid,Add to the 500mL four-necked bottle in sequence,Heat up to 120-130 ,Insulation reaction for 10h.GC detected that the reaction material 2,5-dimethylacetonitrile was completely reacted.After the reaction,After cooling to room temperature,Using para-xylene extraction,Add anhydrous magnesium sulfate to the organic layer to dry,After filtration, proceed directly to the next step.

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-(2,5-Dimethylphenyl)acetonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Dalian Qikai Pharmaceutical Technology Co., Ltd.; Yang Yongzheng; Pei Xiong; Zhang Hongxue; Jiang Dianbao; (10 pag.)CN111072470; (2020); A;,
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