Tag: M.W=100-200

Application 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: In a typical experiment, a solution of sodium hydrogen carbonate (62.72 mmol) in 20 mL of water was stirred for 10 min and to it was added dichloromethane (20 mL) followed by substituted aniline (15.68 mmol). The reaction mixture was cooled to 0 C, thiophosgene (23.52 mmol) was introduced dropwise over a period of 30 min and continuously stirred at room temperature for 1 h. The reaction mixture was washed with brine solution; the organic layer was dried over anhydrous sodium sulphate and concentrated to get a crude gummy compound which was recrystalized in hexane under cold condition. The precipitate was filtered and dried to get the desired compound. The products were characterized by analytical and spectral methods.

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; Khatik, Gopal L.; Kaur, Jasmine; Kumar, Varun; Tikoo, Kulbhushan; Venugopalan; Nair, Vipin A.; European Journal of Medicinal Chemistry; vol. 46; 8; (2011); p. 3291 – 3301;,
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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 591769-05-0 as follows. Computed Properties of C8H11N

Racemic 3-cyclopentyl-3-{4-[7-(2-trimethylsilanylethoxymethyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]pyrazol-1-yl}propionitrile (9, racemic SEM-protected compound).; Method A.; 3-Cyclopentylacrylonitrile (8, 273.5 g, 2.257 mol, 1.20 equiv) and DBU (28 mL, 0.187 mol, 0.10 equiv) was added to a suspension of 4-(1H-pyrazol-4-yl)-7-(2-trimethylsilanylethoxymethyl)-7H-pyrrolo[2,3-d]pyrimidine (5, 591.8 g, 1.876 mol) in acetonitrile (4.7 L) at room temperature. The resulting reaction mixture was heated to 50-60¡ã C. for 17 hours (a clear solution developed midway through heating) then to 70-80¡ã C. for 8 hours. When LCMS analysis showed the reaction was deemed complete, the reaction mixture was cooled to room temperature. The cooled solution was then concentrated under reduced pressure to give the crude product (9) as a thick amber oil. The crude product was dissolved in dichloromethane (DCM) and absorbed onto silica gel then dry-loaded onto a silica column (3 Kg) packed in 33percent EtOAc/heptanes. The column was eluted with 33percent EtOAc/heptanes (21 L), 50percent EtOAc/heptanes (28 L), 60percent EtOAc/heptanes (12 L) and 75percent EtOAc/heptanes (8 L). The fractions containing the desired product (9) were combined and concentrated under reduced pressure to generate a yellow oil, which was transferred to a 3 L flask with EtOAc. The solvent was removed under reduced pressure and the residual EtOAc by co-evaporating with heptanes. The residue was further dried under high vacuum for overnight to afford racemic 3-cyclopentyl-3-{4-[7-(2-trimethylsilanylethoxymethyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]pyrazol-1-yl}propionitrile (9, racemic SEM-protected compound, 800 g, 819.1 g theoretical, 97.7percent yield) as an extremely viscous yellow oil. For 9: 1H NMR (DMSO-d6, 400 MHz) delta ppm 8.83 (s, 1H), 8.75 (s, 1H), 8.39 (s, 1H), 7.77 (d, 1H, J=3.7 Hz), 7.09 (d, 1H, J=3.7 Hz), 5.63 (s, 2H), 4.53 (td, 1H, J=19.4, 4.0 Hz), 3.51 (t, 2H, J=8.1 Hz), 3.23 (dq, 2H, J=9.3, 4.3 Hz), 2.41 (m, 1H), 1.79 (m, 1H), 1.66-1.13 (m, 7H), 0.81 (t, 2H, J=8.2 Hz), 0.124 (s, 9H); C23H32N6OSi (MW, 436.63), LCMS (EI) m/e 437 (M++H) and 459 (M++Na).

According to the analysis of related databases, 591769-05-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Zhou, Jiacheng; Liu, Pingli; Lin, Qiyan; Metcalf, Brian W.; Meloni, David; Pan, Yongchun; Xia, Michael; Li, Mei; Yue, Tai-Yuen; Rodgers, James D.; Wang, Haisheng; US2010/190981; (2010); A1;,
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These common heterocyclic compound, 555-21-5, name is 4-Nitrophenylacetonitrile, 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: 555-21-5

To a solution of (4-nitro-phenyl)-acetonitrile (5.00 g; 30.9 mmol) in dry DMF (30 mL) cooled at 0 C, under N2 atmosphere, was added NaH (60% dispersion in mineral oil; 1.23 g; 30.9 mmol) portionwise and the mixture was stirred for 15 min at 0C. Then iodomethane (1.92 mL; 30.9 mmol) was added and the mixture was stirred at room temperature for 1.5 hour. The reaction was re-cooled at 0C and NaH (60% dispersion in mineral oil; 1.23 g; 30.9 mmol) was added again portionwise. After stirring at 00C for 15 min, iodomethane (1.92 mL; 30.9 mmol) was added and the reaction was stirred at room temperature for 16 hours. The solvent was evaporated under vacuum and the residue was taken up with EtOAc, washed with brine, dried over Na2SO4, filtered and concentrated under vacuum. The crude was purified by chromatography [SiO2, Petroleum ether/EtOAc (95/5 to 8/2)] to give the title compound as a yellow solid (3.50 g, 60 % yield). LCMS (RT): 1.42 min (Method A); MS (ES+) gave m/z: 191.1 (MH+).

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

Reference:
Patent; ADDEX PHARMA SA; WO2008/117175; (2008); A2;,
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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. 796600-15-2, name is 2-Chloro-4-fluoro-3-methylbenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Safety of 2-Chloro-4-fluoro-3-methylbenzonitrile

Example 4 2-Chloro-4-(3-endo-hydroxy-8-azabicyclo[3.2.1]octan-8-yl)-3-methylbenzonitrile, hydrochloride (165RL90) 2-Chloro-4-fluoro-3-methylbenzonitrile (165RL87a, 55 mg, 0.32 mmol) and nortropine (165 mg, 1.29 mmol) was dissolved in pyridine (2 mL) and the mixture irradiated at 220 C. for 2 hours in a microwave oven. Dichloromethane (50 mL) was added and the mixture washed with hydrochloric acid (0.4 M, 2¡Á30 mL) followed by sat. sodium hydrogen carbonate (20 mL). The organic layer was dried over sodium sulfate, filtered and evaporated. The product was further purified by column chromatography using dichloromethane to give the title compound (16.2 mg, 18%). Rf=0.45 (CH2Cl2). LC/MS m/z 277 [M+H]+. 1H-NMR (CDCl3, 300 MHz) delta 7.37 (d, 1H, J=8.6, Ar-H), 6.78 (d, 1H, J=8.6, Ar-H), 4.20 (m, 1H, Tr-H), 3.80 (m, 2H, Tr-H), 2.37 (s, 3H, Ar-CH3), 2.32-2.22 (m, 4H, Tr-H), 1.98-1,81 (m, 4H, Tr-H).

The synthetic route of 796600-15-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Schlienger, Nathalie; Thygesen, Mikkel Boas; Pawlas, Jan; Badalassi, Fabrizio; Lewinsky, Rasmus; Lund, Birgitte Winther; Olsson, Roger; US2006/160845; (2006); A1;,
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Electric Literature of 3759-28-2,Some common heterocyclic compound, 3759-28-2, name is 2-(Cyanomethyl)benzonitrile, molecular formula is C9H6N2, 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 solution of homophthalonitrile 2 (129 mg, 0.82 mmol) in PriOH (4 ml), salicylaldehyde 1 (2.46 mmol) and NH4OAc (143 mg, 1.64 mmol) were added. The mixture was placed into a microwave reactor and heated at 150 C for 10 min. The vessel was opened, MeNO2 (0.439 ml, 8.2 mmol) and Et3N (0.114 ml, 0.82 mmol) were added, the mixture was heated again in the microwave reactor at 150 C for 10 min. The solvent was evaporated under reduced pressure, the residue was chromatographed on silica gel (EtOAc-hexane, 1:5-1:1) (method A) or was dissolved in asmall volume of Et2O or CH2Cl2 and extracted with HCl aqueous solution(0.6 m, 3 30 ml). The aqueous layer was neutralized with Na2CO3. The precipitate was filtered off and washed with H2O several times and once with a small amount (1.5 ml) of PriOH and dried in air (method B).

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

Reference:
Article; Festa, Alexey A.; Storozhenko, Olga A.; Bella Ndoutoume, Delphine R.; Varlamov, Alexey V.; Voskressensky, Leonid G.; Mendeleev Communications; vol. 27; 5; (2017); p. 451 – 453;,
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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. 39581-21-0, name is N-Butyl-2-cyano-acetamide, A new synthetic method of this compound is introduced below., category: nitriles-buliding-blocks

General procedure: A mixture of a salicylaldehyde (1a or 1b, 1 mmol), N-alkyl-2-cyanoacetamides (2a-2f,1 mmol), and {Mo132} (0.05 g) was heated in an oil bath at 110 C for 5-15 min. Aftercompletion of the reaction, monitored by TLC on silica gel (n-hexane-ethyl acetate,3:2), the mixture was cooled to room temperature and hot ethanol (10 ml) was added.The catalyst was collected by filtration and washed with a small portion of hot ethanol(5 ml). The combined filtrate was concentrated by half and allowed to stand at roomtemperature. The precipitated solid was collected by filtration, and recrystallized from96% ethanol to give compounds 3a-3i in high yields (see Table 2).

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:
Article; Jooya, Arsalan; Davoodnia, Abolghasem; Fattahi, Mehri; Tavakoli-Hoseini, Niloofar; Organic Preparations and Procedures International; vol. 50; 6; (2018); p. 565 – 574;,
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Related Products of 2973-50-4,Some common heterocyclic compound, 2973-50-4, name is 2-(2-Aminophenyl)acetonitrile, molecular formula is C8H8N2, 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.

(2-Aminophenyl)acetonitrile (9) (2.64 g, 20.0 mmol) was dissolved in 50 mL of acetic acid. KI (3.65 g, 22.0 mmol) was added followed by dropwise addition of 30% H2O2 (2.24 mL, 22.0 mmol). The reaction mixture was then stirred under nitrogen for 90 min, poured into 200 mL of 0.1 M sodium thiosulfate solution, and extracted with ethyl acetate (3 ¡Á 200 mL). The organic fractions were combined, washed with 0.1 M sodium thiosulfate (2 ¡Á 200 mL), satd sodium bicarbonate (2 ¡Á 200 mL) and brine (2 ¡Á 200 mL), dried over sodium sulfate, filtered, and concentrated in vacuo. Purification by automated flash chromatography (400 g silica gel, 25% ethyl acetate/hexanes) afforded 10 (3.5 g, 68%). 1H NMR (400 MHz, DMSO-d6) delta ppm: 5.41 (s, 2H), 6.53 (d, J = 8.34 Hz, 1H), 7.30 (dd, J = 8.59, 2.02 Hz, 1H), 7.39 (d, J = 2.02 Hz, 1H), NH2 protons not resolved.

The synthetic route of 2973-50-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Bobko, Mark A.; Evans, Karen A.; Kaura, Arun C.; Shuster, Leanna E.; Su, Dai-Shi; Tetrahedron Letters; vol. 53; 2; (2012); p. 200 – 202;,
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Application of 149793-69-1,Some common heterocyclic compound, 149793-69-1, name is 3-Fluoro-5-(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.

General procedure: General procedure for nucleophilic substitution: A solution of 3-fluoro-5-trifluoromethyl-benzonitrile (1 eq) and the corresponding amine (3eq) in DMA was stirred at 145C during 3h. NaCl(aq) was added. The product was taken off into ethyl acetate. The organic layer was washed two times with water then dried over Na2S04 and evaporated under reduced pressure to give a white solid. 3 -(4-Methyl-imidazo 1- 1 -yl)-5 -trifluoromethyl-benzonitrile Yield: 74%. HPLC: 100% ESI-MS: [M+H]+= 252 Da.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Fluoro-5-(trifluoromethyl)benzonitrile, its application will become more common.

Reference:
Patent; ORIBASE PHARMA; CHEVE, Gwenael; DAYDE-CAZALS, Benedicte; FAUVEL, Benedicte; BORIES, Cedric; YASRI, Abdelaziz; WO2014/102376; (2014); A1;,
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1080-74-6, name is 2-(3-Oxo-2,3-dihydro-1H-inden-1-ylidene)malononitrile, 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. category: nitriles-buliding-blocks

To a degassed mixture of compound 9-3 (192 mg, 0.14 mmol), anhydrous chloroform (15 cm3) and pyridine (0.77 cm3) was added 2-(3-oxo-indan-1 – ylidene)-malononitrile (185 mg, 0.95 mmol). The solution was then degassed for a further 10 minutes and then stirred at 23 C for 160 minutes. Methanol (300 cm3) was added and after stirring for 20 minutes the solid was collected by filtration. The solid was then washed with methanol (3 x 10 cm3), acetone (3 x 10 cm3) and diethyl ether (2 x 10 cm3) to give compound 9 (179 mg, 75%) as a solid. 1H-NMR (400 MHz, CDCIs) 0.80 – 0.90 (12H, m), 1.18 – 1.43 (72H, m), 1.49 – 1.64 (8H, m), 2.48 – 2.60 (8H, m), 7.06 – 7.19 (16H, m), 7.53 (2H, s), 7.70 (2H, s), 7.73 – 7.83 (4H, m), 7.90 – 7.95 (2H, m), 8.65 – 8.70 (2H, m), 8.81 (2H, s).

The synthetic route of 1080-74-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK PATENT GMBH; MORSE, Graham; HEARD, Kane; MITCHELL, William; KROMPIEC, Michal; D’LAVARI, Mansoor; PRON, Agnieszka; (260 pag.)WO2019/52935; (2019); A1;,
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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 21883-13-6 as follows. name: 4-Methoxy-2-methylbenzonitrile

Decanethiol (261 mg, 1.5 mmol) and t-BuOK (168 mg, 1.5 mmol) were added to a solution of 4-methoxy-2-methylbenzonitrile (147 mg, 1 mmol) in DMF (5 mL). The reaction mixture was stirred at 110 C for 3 h. The mixture was then diluted with water (30 mL) and extracted with EtOAc (10 mL x 3). The extracts were washed with brine (10 mL x 3), dried over Na2SO4, and concentrated under reduced pressure. The resulting residue was purified by silica gel column with (petroleum ether:EtOAc = 10:1) to provide 4-hydroxy-2-methylbenzonitrile (70 mg, yield: 52.6%). LC-MS (011): 134.70 [M+H]+; Rt: 1.44 min, Purity: 80% (254 nm).

According to the analysis of related databases, 21883-13-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; TEMPERO PHARMACEUTICALS, INC.; BALOGLU, Erkan; GHOSH, Shomir; LOBERA, Mercedes; SCHMIDT, Darby, R.; WO2013/19621; (2013); A1;,
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