Tag: M.W=100-200

These common heterocyclic compound, 214623-57-1, name is 5-Amino-2-methoxybenzonitrile, 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. name: 5-Amino-2-methoxybenzonitrile

General procedure: A solution of 5-amino-2-alkoxybenzonitrile (20mmol), glacial acetic acid (50mL) and water (20mL) was added to the reaction flask at -10C under stirring, water-soluble sodium azide (30 mmol) was slowly added dropwise to the reaction mixture for 30 min, and the addition was completed,the reaction temperature is maintained steady 3h, extracted with dichloromethane, the organic layers combined, washed with brine, dried over anhydrous sodium sulfate , filtered, and concentrated to dryness under reduced pressure the crude product purified by column chromatography (ethyl acetate: petroleum ether = 1: 5) to give pure product.

The synthetic route of 5-Amino-2-methoxybenzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CHINA MEDICAL UNIVERSITY; MENG, FANHAO; ZHANG, TINGJIAN; WU, QINGXIA; WANG, LIN; SUN, QI; LIANG, JINGWEI; HE, XIN; (22 pag.)CN105294584; (2016); A;,
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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;,
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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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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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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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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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