Category: nitriles-buliding-blocks

Synthetic Route of 20249-16-5,Some common heterocyclic compound, 20249-16-5, name is 3-Oxocyclobutanecarbonitrile, molecular formula is C5H5NO, 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.

[0467] Synthesis of 3-hydroxy-3-((trimethylsilyl)ethynyl)cyclobutanecarbonitrile (108B): At -78C, n-BuLi (1.6M in hexane, 3.8ml) was added dropwise to a stirred solution of trimethylsilylacetylene (0.99ml, 7.0mmol) in THF(4ml) over 3 minutes. The reaction was stirred for 55rnin at -78C. Compound 108A in 1ml THF was added. The reaction was stirred at -78C for 2 hours. The reaction was quenched with saturated aqueous NH4CI solution, extracted with EtOAc. The organic layer was dried with MgSC and concentrated. The resultant crude was purified by column chromatography on silica to afford compound 108B.

The synthetic route of 20249-16-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GILEAD SCIENCES, INC.; BRIZGYS, Gediminas; CANALES, Eda; HALCOMB, Randall, L.; HU, Yunfeng, Eric; KATO, Darryl; LINK, John, O.; LIU, Qi; SAITO, Roland, D.; TSE, Winston, C.; ZHANG, Jennifer, R.; (253 pag.)WO2016/33243; (2016); A1;,
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Reference of 53312-79-1, The chemical industry reduces the impact on the environment during synthesis 53312-79-1, name is 3-Amino-4-chlorobenzonitrile, I believe this compound will play a more active role in future production and life.

General procedure: Sodium ethanethiolate (362 mg, 4.3 mmol) was added to a solution of 5-bromo-2-fluorobenzaldehyde (546 mg, 2.7 mmol) in DMF (1.08 ml), and the mixture was stirred at 60C. After one hour, sodium ethanethiolate (123 mg, 1.5 mmol) was added thereto. After 15 minutes, the reaction solution was returned to room temperature, and a 1 N aqueous hydrochloric acid solution was added thereto, and extraction was performed with ethyl acetate. The organic layer was sequentially washed with a saturated aqueous sodium bicarbonate solution and brine, and dried over anhydrous sodium sulfate. The drying agent was removed by filtration, and the residue obtained by concentration under reduced pressure was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (163 mg, 24%) as a yellow oil. The title compound was synthesized from 3-amino-4-chloro-benzonitrile under the same conditions as for Compound 4. However, the reaction was performed by heating at 80C with microwave irradiation.

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-Amino-4-chlorobenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Chugai Seiyaku Kabushiki Kaisha; MURATA, Takeshi; KAWADA, Hatsuo; NIIZUMA, Satoshi; HARA, Sousuke; HADA, Kihito; SHIMADA, Hideaki; TANAKA, Hiroshi; MIO, Toshiyuki; EP2842946; (2015); A1;,
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Synthetic Route of 77668-42-9, 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. 77668-42-9 name is 2,3-Dichlorobenzoyl cyanide, 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.

6. Synthesis of lamotrigine via the tetrafluoroborate salt as a one-pot reactionThe condensation step was performed as described in example 5, with the exception that the isolation of the tetrafluoroborate intermediate was omitted. After the condensation step the solvents were removed on a rotary evaporator, then an equal volume of acetonitrile was added and the subsequent cyclization step was performed as described in example 2.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2,3-Dichlorobenzoyl cyanide, and friends who are interested can also refer to it.

Reference:
Patent; LONZA AG; WO2008/19798; (2008); A1;,
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Adding a certain compound to certain chemical reactions, such as: 2469-99-0, name is 3-Oxobutanenitrile, 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 2469-99-0, Product Details of 2469-99-0

Example 1 (E)-2-[(dimethylamino)-methylene]-3-oxobutanenitrile A 2000 ml 3-neck Morton flask was equipped with an overhead stirrer, a N2 inlet, and a thermocouple. The flask was charged with water (500 g) and 36% hydrochloric acid (192.00 g, 12.18 mol). The resultant clear solution was stirred and cooled to room temperature, whereupon 3-aminocrotononitrile (100.19 g, 1.17 mol) was added portion-wise over about 15 minutes. The resultant solution was stirred at room temperature for about 1 h. The aqueous reaction mixture was then extracted twice with ethyl acetate (450.2 g portions).The organic extracts were then charged to a clean 2000 ml 3-neck Morton flask equipped with an overhead stirrer, an addition funnel, and a thermocouple. Stirring was initiated and dimethylformamide dimethyl acetal (165:11 g, 1.39 mol) was added dropwise via the addition funnel over about 18 minutes, while maintaining the internal temperature at <34 C. The resultant solution was stirred at room temperature for about 2 h.A solution of sodium bicarbonate (20.14 g, 0.24 mol) in water (200.0 g) was then added and the resultant biphasic mixture was stirred vigorously at room temperature for about 20 minutes. The layers were separated and the organic layer was dried over MgSO4, filtered and concentrated by rotary evaporation to yield an oil, which rapidly crystallized to yield the title compound as a low melting solid.1H NMR (300 MHz, CDCl3): delta 7.82 (s, 1H), 3.41(s, 3H), 3.25(s, 3H), 2.35 (s, 3H)MS: (Cl): m/z 139 (M++1), 161 (M++Na)Elemental Analysis for C7H10N2O¡Á0.17 H2O: Calculated: C, 59.53; H, 7.38; N, 19.84, H2O, 2.17. Found: C, 59.12; H, 7.62; N, 19.85, H2O, 2.04. If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it. Reference:
Patent; Cesco-Cancian, Sergio; Chen, Hongfeng; Grimm, Jeffrey S.; Mani, Neelakandha S.; Mapes, Christopher M.; Palmer, David C.; Pippel, Daniel J.; Sorgi, Kirk L.; Xiao, Tong; US2010/4450; (2010); A1;,
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Adding a certain compound to certain chemical reactions, such as: 64248-62-0, name is 3,4-Difluorobenzonitrile, 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 64248-62-0, Recommanded Product: 64248-62-0

To THF (18 ml) was added cerium(III) chloride (2.84 g, 11.50 mmol) and the solution was purged, backfilled with nitrogen and warmed to 45 C. for 3 h. The reaction was cooled to rt and 3,4-difluorobenzonitrile (0.8 g, 5.75 mmol) was added. The solution was cooled further to -25 C. and methyl lithium/lithium bromide (1.5 M in diethyl ether, 9.59 ml, 14.38 mmol) was added slowly. The reaction was stirred at this temperature for 1 h and ammonium hydroxide solution (28% in water, 4.00 ml, 28.8 mmol) was added and the mixture was allowed to sit overnight at rt. The cerium salts were filtered off and washed with THF. The obtained THF solution was dried with MgSO4, filtered and concentrated. The product was diluted with ethyl ether and THF and HCl (4M in dioxane, 1.438 mL, 5.75 mmol) were added. The residue was concentrated, diluted with hexane and filtered affording the title compound.

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, 3,4-Difluorobenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Clements, Matthew J.; Debenham, John S.; Hale, Jeffrey J.; Madsen-Duggan, Christian B.; Walsh, Thomas F.; US2009/239876; (2009); A1;,
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Related Products of 14533-86-9, 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 14533-86-9 as follows.

General procedure: A mixture of benzylidenecyanoacetates 1 (X = COOR2,3 mmol), dialkyl malonate 2 (3 mmol), aromatic aldehyde 3 (3 mmol) and ammonium acetate (0.46 g, 6 mmol) was refluxed in methanol (10 mL) for 2 h. Then, the reaction mixture was cooled to – 10 C for 30 min. The target dialkyl (2SR,3RS,4RS,5SR)-3-cyano-6-oxo-2,4-diarylpiperidine-3,5-dicarboxylates 5 were isolated by simple filtration. Dimethyl(¡À)-3-cyano-6-oxo-2,4-diphenylpiperidine-3,5-dicarboxylate (5a) White solid. 1.02 g (87%). M.p 237-239 C. 1H-NMR (300.13 MHz DMSO-d6): 3.40(s, 3H, CH3O2C),3.51 (s, 3H, CH3O2C),4.10 (d, J = 12.4 Hz, 1H, CH), 4.20 (d,J = 13.3 Hz, 1H, CH), 5.41 (s, 1H, CH), 7.36-7.42 (m, 10H, 2Ph), 8.94 (s, 1H,NH) ppm. 13C-NMR (75.47 MHz, DMSO-d6): 47.5 (1C), 52.0 (1C), 52.4 (1C), 53.5(1C), 58.6 (1C), 60.7 (1C), 114.7 (1C), 127.4 (2C), 127.8 (2C), 128.6 (2C), 129.0(2C), 129.1 (1C), 129.5 (1C), 134.1 (1C), 134.8 (1C), 164.8 (1C), 165.3 (1C), 168.1(1C) ppm. IR (upsilonmax) (KBr) 3176, 3061, 2930, 2245, 1746, 1677, 1457 cm-1. MS(ESI) m/z (M + H)+ 393.1436, calcd. for C22H20N2O5 393.1445.

According to the analysis of related databases, 14533-86-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; Vereshchagin, Anatoly N.; Karpenko, Kirill A.; Elinson, Michail N.; Goloveshkin, Alexander S.; Dorofeeva, Evgeniya O.; Egorov, Mikhail P.; Research on Chemical Intermediates; vol. 46; 2; (2020); p. 1183 – 1199;,
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Some common heterocyclic compound, 935-02-4, name is 3-Phenylpropiolonitrile, molecular formula is C9H5N, 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. Safety of 3-Phenylpropiolonitrile

4.3.1 (Z)-3-(3-Methyl-2-thioxo-2,3-dihydro-1H-imidazol-1-yl)-3-phenyl-2-propenenitrile (3a) To a mixture of acetylene 2 (127 mg, 1 mmol) and S (32 mg, 1 mmol) was added 1-methylimidazole (1a; 82 mg, 1 mmol). The mixture was stirred at 20-25 C for 24 h. Column chromatography afforded thione 3a (132 mg, 67%), yellow microcrystalline powder, mp 159-161 C (washed with ether). Initial imidazole 1a was recovered (15 mg, conversion was 82%). 1H NMR (400.13 MHz, CDCl3): delta=7.45-7.25 [m, 5H, Ho,m,p from C(6)-Ph], 6.89 (s, 1H, 4-H), 6.80 (s, 1H, 5-H), 6.05 (s, 1H, 7-H), 3.63 (s, 3H from N-CH3) ppm. 13C NMR (100.62 MHz, CDCl3): delta=164.4 (C-2), 154.2 (C-6), 132.5 [Ci from C(6)-Ph], 131.8 [Cp from C(6)-Ph], 129.1 [Cm from C(6)-Ph], 126.8 [Co from C(6)-Ph], 119.8 (C-4), 116.9 (C-5), 114.6 (CN), 97.0 (C-7), 35.3 (N-CH3) ppm. 15N NMR (40.55 MHz, CDCl3): delta=-110.6 (CN), -207.8 (N-3), -217.9 (N-1) ppm. IR (KBr): 2220 (CN), 1621 (C=C), 1383 (C=S) cm-1. Anal. Calcd for C13H11N3S (241.31): C, 64.70; H, 4.59; N, 17.41; S, 13.29. Found: C, 64.44; H, 4.32; N, 17.72; S, 13.34.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 935-02-4, its application will become more common.

Reference:
Article; Belyaeva, Kseniya V.; Andriyankova, Ludmila V.; Nikitina, Lina P.; Mal’Kina, Anastasiya G.; Afonin, Andrei V.; Ushakov, Igor A.; Bagryanskaya, Irina Yu.; Trofimov, Boris A.; Tetrahedron; vol. 70; 5; (2014); p. 1091 – 1098;,
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Synthetic Route of 67515-59-7, 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. 67515-59-7, name is 4-Fluoro-3-(trifluoromethyl)benzonitrile, This compound has unique chemical properties. The synthetic route is as follows.

A solution of vanillin (1.65 g, 10.86 mmol) and 4-fluoro-3-trifluoromethyl-benzonitrile (10.26 mmol) in DMF (15 mL) was treated with K2CO3 (2.83 g, 21.72 mmol), and the mixture was heated in an oil bath at 80 C. for 12 h. The reaction was cooled to RT and partitioned between EtOAc and H2O. The organic phase was washed with water (3¡Á), dried over Na2SO4 and concentrated in vacuo. Silica gel chromtagraphy (EtOAc/hexanes) afforded the title compound. 1H NMR (400 Hz, CDCl3) delta 10.00 (s, 1H), 8.00 (m, 1H), 7.68 (dd, 1H), 7.58-7.53 (m, 2H), 7.29 (d, 1H), 6.75 (d, 1H), 3.83 (s, 3H); LC/MS (m/z) [M+1]+ 322.1 (calculated for C16H11F3NO3, 322.06).

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

Reference:
Patent; Gaul, Michael; Searle, Lily Lee; Rentzeperis, Dionisios; US2008/286265; (2008); A1;,
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Application of 72115-09-4, These common heterocyclic compound, 72115-09-4, name is 5-Amino-2-bromobenzonitrile, 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.

5-Amino-2-bromobenzonitrile (500 mg, 2.54 mmol), 4-(4,4,5,5-tetramethyl-1 ,3,2- dioxaborolan-2-yl)-3,6-dihydro-2H-pyran (559 mg, 2.67 mmol) and potassium carbonate (701 mg, 5.08 mmol) were dissolved in DME (10 mL) and water (5 mL). The reaction mixture was degassed under a stream of nitrogen before bis(triphenylphosphine) palladium(ll) dichloride (89 mg, 0.13 mmol) was added. The reaction mixture was stirred at 100 C for 2 hours. After this time the reaction was complete and the reaction mixture was cooled to room temperature. Water (15 mL) was added to the reaction mixture and this was extracted with DCM (3 x 10 mL). The combined organics were dried (MgS04), filtered and concentrated under reduced pressure. The crude material was purified by flash chromatography (Si02, EtOAc/heptane 0-100%) to afford 270 mg (50% yield) of the title compound.1H NMR (250 MHz, DMSO-d6) delta [ppm] 2.29 – 2.40 (m, 2H), 3.79 (t, J = 5.4 Hz, 2H), 4.18 (q, J = 2.8 Hz, 2H), 5.59 (s, 2H), 5.82 – 5.96 (m, 1 H), 6.71 – 6.90 (m, 2H), 7.14 (d, J = 8.3 Hz, 1 H).LCMS (Analytical Method A): Rt = 0.92 mins; MS (ESIpos) m/z = 201 (M+H)

The synthetic route of 72115-09-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; BAeURLE, Stefan; DAVENPORT, Adam, James; STIMSON, Christopher; CARR, James, Lindsay; BUBERT, Christian, Abingdon; MARLIN, Frederic, Jacques; NAGEL, Jens; SCHMIDT, Nicole; ROTGERI, Andrea; IRLBACHER, Horst; (378 pag.)WO2018/114783; (2018); A1;,
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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. 328-87-0, name is 2-Chloro-5-trifluoromethylbenzonitrile, A new synthetic method of this compound is introduced below., name: 2-Chloro-5-trifluoromethylbenzonitrile

Preparation of 2-cyano-alpha,alpha,alpha-trifluoro-p-tolyl-4-nitro phenyl ether A solution of potassium hydroxide (3.2 g. 0.05 mole of 89.3% purity) and p-nitrophenol (7.0 g. 0.05 mole) in methanol (25 ml.) is stripped under reduced pressure. The residue is dissolved in sulfolane, 4-chloro-3-cyano alpha,alpha,alpha-trifluorotoluene (10.3 g. 0.05 mole) added, and the resulting solution heated at 150 C for 5 hours. After cooling, the solution is diluted with benzene (350 ml.) washed with water (6 * 250 ml.), dried, and the solvent removed. The residue (12.5 g.) is recrystallized from isopropanol to give 2-cyano-alpha,alpha,alpha-trifluoro-p-tolyl-4-nitrophenyl ether (7.6 g., 49%) m.p. 93-98 C.

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; Rohm and Haas Company; US4076741; (1978); A;,
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