Category: nitriles-buliding-blocks

Electric Literature of 658-99-1, 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. 658-99-1, name is 2-(3,4-Difluorophenyl)acetonitrile, This compound has unique chemical properties. The synthetic route is as follows.

Step A: Preparation of 2-(3,4-Difluorophenyl)-2- methylpropanenitrile; [0718] 2-(3,4-Difluorophenyl)acetonitrile (25.0 g, 163 mmol) and MeI(25.4 mL, 408 mmol) were dissolved in DMF (163 mL) and added dropwise to a suspension of sodium tert-butoxide (39.2 g, 408 mmol) in DMF at 0C. The resulting reaction mixture was stirred at 00C for 1 hour and then allowed to warm to ambient temperature for 1 hour. The reaction mixture was diluted with 400 mL of EtOAc, added to a separatory funnel, partitioned with water, washed 3 times with 200 mL of water, separated, dried over Na2SO4, and concentrated in vacuo to give the title compound (26.45 g) as a yellow oil.

The chemical industry reduces the impact on the environment during synthesis 2-(3,4-Difluorophenyl)acetonitrile. I believe this compound will play a more active role in future production and life.

Reference:
Patent; AMGEN INC.; WO2008/76427; (2008); A2;,
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Synthetic Route of 114897-91-5,Some common heterocyclic compound, 114897-91-5, name is 2-(4-Bromo-2-fluorophenyl)acetonitrile, molecular formula is C8H5BrFN, 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.

Step 1: 2- (4-BROMO-2-CHLORO-PHENYL)-2-METHYL-PROPIONITRILE (4-BROMO-2-FLUOROPHENYL) ACETONITRILE (1 g, 4.67 mmol) described in step 1 from Example A (97), benzyltriethylammonium chloride (0.02 g, 0.09 mmol) and 1,4-Dibromobutane (1.43 g, 0.79 mmol) were dissolved 50% aqueous NAOH (3 mL) and the resulting mixture was stirred for 3 hours at 50 C. Reaction was quenched with 4N HCI (50 mL extracted with EtOAc. The organic phase was dried over NA2SO4 and evaporated. The crude organic product was purified by flash column chromatography (5% EtOAc in hexanes) to give the product (1.25 g, 100%) as a clear OIL). H NMR (CDCI3) 5 : 1. 93-2. 17 (m, 4 H), 2.50-2. 55 (m, 2 H), 3.42-3. 46 (m, 2H), 7.26-7. 34 (m, 3 H).

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-Bromo-2-fluorophenyl)acetonitrile, its application will become more common.

Reference:
Patent; PFIZER INC.; WO2004/74270; (2004); A2;,
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154532-34-0, name is 3-(tert-Butyl)benzonitrile, 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. Product Details of 154532-34-0

A mixture of 0.84 g (5.1 mmol) 3-tert-butyl-benzonitrile, 1 mL (25% aq. NH3) and 0.1 g Raney-Nickel is hydrogenated at 40 C. After completion of reaction, the catalyst is filtered off and washed with MeOH. The solvent is removed in vacuo and the residue is purified by chromatography on silica gel (DCM/MeOH 90/10) to give 0.84 g of the desired product as a green oil.tR (HPLC, Nucleosil C18 column, 20-100% CH3CN/H2O/6 min, 100% CH3CN/1.5 min, 100-20% CH3CN/H2O/0.5 min, flow: 1.0 ml/min): 2.81 min.Rf: (hexane/AcOEt=95/5): 0.26MS (ES+): 164=[M+H]+ 1H-NMR (400 MHz, CDCl3): 7.40-7.33 (m, 3H), 7.20-7.18 (m, 1H), 3.90 (s, 2H), 1.60 (bs, 2H), 1.39 (s, 9H).

The synthetic route of 154532-34-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Betschart, Claudia; Lerchner, Andreas; Machauer, Rainer; Rueger, Heinrich; Tintelnot-Blomley, Marina; Veenstra, Siem Jacob; US2008/132477; (2008); A1;,
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Related Products of 873697-68-8,Some common heterocyclic compound, 873697-68-8, name is 3-Amino-2-fluorobenzonitrile, molecular formula is C7H5FN2, 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.

To 3-amino-2- fluorobenzonitrile (0.5 g, 3.67 mmol) in DCM (10 mL) cooled to 0 C, was added pyridine (1 mL) and methyl chloroformate (0.313 mL, 4.04 mmol). After 24 h, the reaction was quenched with 0 (20 mL) and extracted with EtOAc (3 x 30 mL). The combined organic layers were washed with IN HC1 (20 mL), brine (20 mL) and dried (MgS04) to afford 0.7 g (98%) of 18A as brown solid. MS (ESI) m/z: 195.2 (M+H)+.

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

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; ORWAT, Michael J.; PINTO, Donald J.P.; SMITH II, Leon M.; SRIVASTAVA, Shefali; CORTE, James R.; WO2013/55984; (2013); A1;,
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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. 7357-70-2, name is 2-Cyanothioacetamide belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Quality Control of 2-Cyanothioacetamide

To a suspension of 3-(l,2-dimethyl-lH-imidazol-5-yl)-l-(thiazol-2- yl)prop-2-en-l-one (0.31 mmol, 72 mg) and 2-cyanothioacetamide (0.93 mmol, 93 mg, 3.0 equiv.) in EtOH (1.5 mL), a few drops of piperidine were added. After being stirred at 80C for 2 h, EtOH was evaporated and crude product was redissolved in CH3CN. (0432) Butyl(chloromethyl)sulfane (0.62 mmol, 85.5 mg) and Et3N (0.93 mmol, 94.1 mg, 130 mu) were then added and the reaction mixture was stirred at 80C for 20 min. Once complete, the reaction was diluted with EtOAc and water. The organic phase was separated and aqueous layer was extracted twice with EtOAc. The combined extractions were washed with saturated NaCl solution, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography to give 99 mg of designed product (77%). H NMR (400 MHz, CDC13) delta 7.96 (d, / = 3.1 Hz, 1H), 7.85 (s, 1H), 7.56 (d, / = 3.1 Hz, 1H), 7.37 (s, 1H), 4.49 (s, 2H), 3.60 (s, 3H), 2.72 (t, / = 7.4 Hz, 2H), 2.48 (s, 3H), 1.62 (p, / = 7.3 Hz, 2H), 1.40 (h, / = 7.3 Hz, 2H), 0.90 (t, / = 7.3 Hz, 3H). ESI- MS (m/z): 416.6 [M+H]+.

The synthetic route of 7357-70-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CASE WESTERN RESERVE UNIVERSITY; MARKOWITZ, Sanford; GERSON, Stanton; DESAI, Amar; HO, Won Jin; (185 pag.)WO2016/144958; (2016); A1;,
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Electric Literature of 13388-75-5, A common heterocyclic compound, 13388-75-5, name is 2-(3,5-Dimethoxyphenyl)acetonitrile, molecular formula is C10H11NO2, 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.

Example 487 Preparation of the intermediate 5-bromo-3-(3,5- dimethoxy-phenyl)-pyrazolo[1 ,5-a]pyrimidineExample 487a Preparation of 2-(3,5-dimethoxy-phenyl)-3- dimethylamino-acrylonitrileA mixture of (3,5-dimethoxy-phenyl)-acetonitrile (19.9 g, 112 mmol), N,N,N’,N’-tetramethyl-ethane-1 ,2-diamine (2.86 mL, 19.09 mmol) and dimethyl formamide dimethyl acetal (72 mL) were heated at reflux for 4 h. On cooling, the reaction was partitioned between EtOAc and saturated aqueous ammonium chloride solution, and the mixture filtered, and the residue washed with EtOAc and dried to give 2-(3,5-dimethoxy-phenyl)-3- dimethylamino-acrylonitrile (7.1 g, 27%). The filtrates were combined, extracted and the combined organic phase washed with brine and concentrated in vacuo. The crude product was purified by chromatography on silica gel to give 2-(3,5-dimethoxy-phenyl)-3-dimethylamino-acrylonitrile (11.1 g, 43%). 1H-NMR (300 MHz, d6-DMSO): delta = 7.44 (1H, s), 6.42 (2H, d), 6.20 (1 H, t), 3.69 (6H, s), 3.15 (6H, s) ppm.

The synthetic route of 13388-75-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER SCHERING PHARMA AKTIENGESELLSCHAFT; WO2007/147647; (2007); A1;,
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Related Products of 3939-09-1, 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. 3939-09-1 name is 2,4-Difluorobenzonitrile, 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.

To a mixture of 2,4-difluorobenzonitrile (10.0 g, 72 mmol) and 1,1-dioxo-1?6-[1,2]thiazin-2-ane (8.84 g, 65.4 mmol) in 1:1 tetrahydrofuran/dimethylformamide (40 mL) was added potassium carbonate (9.0 g, 65.4 mmol). The mixture was stirred at 90 C. for 18 h then filtered and concentrated. The residue was purified by flash chromatography (SiO2) eluting with 10%-50% ethyl acetate/hexanes followed by recrystallization from hot ethyl acetate/hexane to give the title compound as white needles (0.537 g, 3% yield). 1H NMR (500 MHz, CD3OD) ? ppm: 7.70 (1H, dd, J=8.8, 5.8 Hz), 7.30 (1H, dd, J=8.8, 2.4 Hz), 7.15-7.12 (1H, m), 3.27 (2H, t, J=5.3 Hz), 3.33 (2H, t, J=6.1 Hz), 2.40-2.35 (2H, m), 2.05-2.01 (2H, m). LCMS (M+H) calcd for C11H16N2OF: 255.06; found: 255.19.

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

Reference:
Patent; Naidu, B. Narasimhulu; Banville, Jacques; Beaulieu, Francis; Connolly, Timothy P.; Krystal, Mark R.; Matiskella, John D.; Ouellet, Carl; Plamondon, Serge; Remillard, Roger; Sorenson, Margaret E.; Ueda, Yasutsugu; Walker, Michael A.; US2005/267105; (2005); A1;,
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Synthetic Route of 40497-11-8, A common heterocyclic compound, 40497-11-8, name is Ethyl 2,3-dicyanopropanoate, molecular formula is C7H8N2O2, 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.

250 mL round bottom three-necked flask0.01 mol of 4-methylaniline and a small amount of ethanol,3.0 mL (0.035 mol) of concentrated hydrochloric acid was added dropwise under ice-cooling with stirring.0.018 mol of sodium nitrite was dissolved in 10 mL of water,Slowly dropping into the flask,After the reaction was completed 0.5h yellow diazonium salt solution.0.01 mol of ethyl 2,3-dicyanopropionate was added to a three-necked flask,The prepared diazonium salt solution was dropped into the flask,After dropping the reaction 2 h. Adding ammonia,Adjust the pH to 9-10,Reaction at room temperature for 2h.After completion of the reaction, the reaction mixture was extracted with 40 mL of dichloromethane,The organic layer was washed with water (2 x 30 mL)Washed with saturated sodium chloride solution (1 x 40 mL)Dried over anhydrous magnesium sulfate,A portion of the solvent was evaporated under reduced pressure to crystallize to yield 1.20 g of product,Yield 60.5%

The synthetic route of 40497-11-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Nanjing University of Technology; Wan, Rong; Wu, Shaohua; Guo, Chunwei; Wang, Xinlin; Chen, Fuli; Han, Zhenyu; Fu, Xiaohuan; (13 pag.)CN105820167; (2016); A;,
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Adding a certain compound to certain chemical reactions, such as: 654-70-6, name is 4-Cyano-3-trifluoromethylaniline, 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 654-70-6, Recommanded Product: 4-Cyano-3-trifluoromethylaniline

To the reaction kettle, was introduced nitrogen gas, to which were added 4-cyano-3-(trifluoromethyl)phenylamine (200 g), n-heptane (450 mL), and water (500 mL), followed by stirring to produce suspension. Thiophosgene (148 g) was drop added. The mixture was stirred at 40 C. for 16 hours, then stood for liquid separation. The water phase was extracted with n-heptane (500 mL) once, and the organic phase was combined. The solvent was removed by concentrating under reduced pressure, followed by reduced pressure distillation to provide the target compound (220 g), with a yield of 89.8%. 1HNMR (DMSO, 400 MHz): 7.52 (1H, dd, J=1.7, 8.3), 7.60 (1H, d, J=1.7 Hz), 7.87 (1H, d, J=8.3 Hz).

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:
Patent; HINOVA PHARMACEUTICALS INC.; CHEN, Yuanwei; DU, Wu; KUANG, Tongtao; GENG, Xi; (10 pag.)US2020/87261; (2020); A1;,
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Reference of 5216-17-1,Some common heterocyclic compound, 5216-17-1, name is 2,3,5,6-Tetrafluorobenzonitrile, molecular formula is C7HF4N, 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.

General procedure: CZ-CZO (3.90 g, 4.08 mmol) and sodium hydride (0.6 g, 24.3 mmol) were added to dry tetrahydrofuran (THF, 20 mL), and the mixture was stirred at room temperature for 0.5 h.Further, 2,3,5,6-tetrafluorobenzonitrile (0.089 g, 0.51 mmol) was added, and the reaction was stirred at room temperature for 12 h. After completion of the reaction, the mixture was quenched with water and extracted with dichloromethane. Purification by column chromatography gave the final product C5, yield 75%

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2,3,5,6-Tetrafluorobenzonitrile, its application will become more common.

Reference:
Patent; Southeast University; Jiang Wei; Huang Suli; Sun Yueming; (21 pag.)CN108586318; (2018); A;,
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