Month: January 2021

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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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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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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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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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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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 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 2338-75-2,Some common heterocyclic compound, 2338-75-2, name is 4-(Trifluoromethyl)phenylacetonitrile, molecular formula is C9H6F3N, 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: To a stirred solution of MeONa in MeOH (5%,1.5 mL) was added 3a (ca. 122 mg, 0.5 mmol, 1 eq), immediatelyfollowed by cyano derivative (1.1 eq) at room temperature. Thereaction mixture was heated under reflux for 1.5 h. After coolingfor 1 h in ice bath, the solid was filtered and washed with a minimumof cold MeOH. If not pure, crude product was purified by columnchromatography on silica gel with CH2Cl2/MeOH: 99:1?90:10 as eluent.

The synthetic route of 2338-75-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; N’Guessan, Jean-Paul Deto Ursul; Delaye, Pierre-Olivier; Penichon, Melanie; Charvet, Claude L.; Neveu, Cedric; Ouattara, Mahama; Enguehard-Gueiffier, Cecile; Gueiffier, Alain; Allouchi, Hassan; Bioorganic and Medicinal Chemistry; vol. 25; 24; (2017); p. 6695 – 6706;,
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Application of 194853-86-6,Some common heterocyclic compound, 194853-86-6, name is 4-Fluoro-2-(trifluoromethyl)benzonitrile, molecular formula is C8H3F4N, 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.

Reference Example 3 t-Butyl 4-(4-cyano-3-trifluoromethylphenyl)-3-methylpiperazine-1-carboxylate A 4.46 g portion of t-butyl 3-methylpiperazine-1-carboxylate synthesised in Reference Example 2, 6.74 g of 4-fluoro-2-trifluoromethylbenzonitrile and 7.76 ml of diisopropylethylamine were stirred in 50 ml of DMF at 100C for 2 days. The reaction solution was diluted with water and extracted with ethyl acetate, the organic layer was washed and dried and then the solvent was evaporated under reduced pressure. The residue was subjected to a silica gel column chromatography and eluted with hexane-ethyl acetate (3:1, v/v) to obtain 5.6 g of the title compound as white crystals.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Fluoro-2-(trifluoromethyl)benzonitrile, its application will become more common.

Reference:
Patent; YAMANOUCHI PHARMACEUTICAL CO. LTD.; EP1122242; (2001); A1;,
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Synthetic Route of 332-25-2, 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. 332-25-2, name is 4-(Trifluoromethoxy)benzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

4-Trifluoromethoxybenzaldehyde Diisobutylaluminium hydride (11.8 ml. 1M solution in toluene) was added to a stirred solution of 4-cyanophenyl trifluoromethyl ether (2.0 g., Fairfield) in dry diethyl ether (100 ml.). The mixture was refluxed with stirring for 3 hours. The mixture was cooled and dioxane (5 ml.) containing water 1.0 ml.) was added. Dilute hydrochloric acid was added (60 ml. of 10percent solution). The mixture was stirred for 30 minutes and extracted with diethyl ether. The ethereal extracts were washed with water and dried over anhydrous magnesium sulphate. The solvent was removed in vacuo and the residue was purified by chromatography on silica, eluding with 9:1 hexane:diethyl ether. 4-Trifluoromethoxybenzaldehyde was obtained as a colourless liquid (1.65 g.).

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-(Trifluoromethoxy)benzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; The Wellcome Foundation; The Regents of the University of California; US5502073; (1996); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts