Month: March 2021

Synthetic Route of 75344-77-3,Some common heterocyclic compound, 75344-77-3, name is 4-Bromo-3,5-dimethylbenzonitrile, molecular formula is C9H8BrN, 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.

Under a nitrogen atmosphere, Add 420 mg to a 250 ml three-neck round bottom reaction bottle4-bromo-3,5-dimethylbenzonitrile and 10-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-10H-phenoxazine, Then, 120 ml of toluene, 40 ml of absolute ethanol and 40 ml of a 2 mol-liter potassium carbonate aqueous solution were sequentially added thereto, followed by stirring to dissolve. After 15 minutes of aeration, 50 mg of tetrakis(triphenylphosphine)palladium(0) catalyst was added, and after aeration for 30 minutes, it was heated to 85 C and refluxed for 24 hours. After the reaction was stopped and the reaction was stopped, the solvent of the reaction system was removed by steaming. The reaction system was extracted with a dichloromethane solvent. It was washed three times with deionized water, three times with saturated brine, and dried over anhydrous magnesium sulfate for 1 hour. Purification of the product by column chromatography, The eluent is a mixed solvent of petroleum ether and dichloromethane in a ratio of 3:1. Finally, a white solid product was obtained with a yield of 69%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Bromo-3,5-dimethylbenzonitrile, its application will become more common.

Reference:
Patent; South China University of Technology; Su Shijian; Cai Xinyi; Qiu Weidong; Qiao Zhenyang; (32 pag.)CN108530376; (2018); A;,
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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. 103146-25-4, name is 4-(4-(Dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl)-3-(hydroxymethyl)benzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. HPLC of Formula: C20H23FN2O2

R-enriched cyanodiol (lOg, 0.029 moles) was dissolved in MDC (30ml) at 20-40 C. To the obtained clear reaction mass imidazole (5.96g, 0.0438 moles) followed by a solution of t-butyldimethylsilylchloride (TBDMSC1) (6.60g, 0.04 moles) in dichloromethane (10ml) was added at 20-40 C and the reaction mass stirred further at 20-30C for 1-2 hours. Then the reaction mass was directly washed with water (30ml x 3) after which the lower organic layer was separated and concentrated under vacuum at 35-40 C which yielded l l .Ogm title compound ( lib) as a off white solid. 1H-NMR in DMSO at 300MHz (ppm):0.23-0.24 (d,3H), 0.17-0.18(d,3H), 0.76- 0.77 (s, 9H), 0.83-0.85 (d, lH), 1.17-1.22 (m,lH), 1.41-1.45 (m,lH), 2.03 (s,6H), 2.08-2.25 (m,4H), 4.27-4.33 (dd,lH), 4.74-4.79 (dd,lH), 7.07-7.13 (t,2H), 7.23- 7.27 (m,2H),7.80-7.83 (d,3H) FT-IR as such (cm”1): 2952, 2855, 2227, 1599, 1506, 1470, 1253, 1216, 1160, 1122, 1109, 1092, 1035, 1016, 958, 897 Mass Analysis (ESI, +ve mode): Molecular ion peak observed at 457.47 a.m.u which corresponds to (M+H)+ peak of title compound DSC Analysis: Two Endotherm peaks observed at 124.89 and 136.30 C XRPD Analysis (Observed 2Theta values):8.09, 9.32, 10.45, 11.44, 12.34, 13.29, 14.02, 15.57, 16.26, 16.87, 17.51, 18.18, 18.71, 19.34, 19.87, 20.39, 20.99, 21.47, 22.13, 22.49, 23.01, 23.29, 24.49, 24.87, 25.33, 25.74, 26.29, 26.78, 27.03, 27.52, 28.26, 28.69, 29.05, 29.41, 29.61, 30.13, 31.44, 32.09, 32.37, 32.86, 33.17, 33.77, 34.78, 35.16, 35.81, 36.74, 37.54, 38.33, 38.64, 39.45, 40.16, 41.24, 41.59, 42.24, 43.03, 44.29, 45.79, 47.81, 48.49 Purity by HPLC : 91 27%

The synthetic route of 103146-25-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; IPCA LABORATORIES LIMITED; REGURI, Buchi Reddy; PRASAD, Ashok; RAWAT, Ajay Singh; RAJPUT, Sandip; SANTAN, Rohit B; (36 pag.)WO2017/9866; (2017); A1;,
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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. 1897-52-5, name is 2,6-Difluorobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 2,6-Difluorobenzonitrile

To a solution of A3.l (500 g, 3.6 mol) in 2.5 L MeOH was added sodium methoxide (388 g, 7.2 mol) in portions slowly. The mixture was stirred at rt overnight. The reaction mixture was poured into 15 L H20 andthe precipitate was filtered off and washed twice with 2.0 L H20 to give the title compound (1140 g) as a white solid, the crude product will be used in next step without further purification. 1H NMR (500 MHz, CDCI3) O ppm 3.96 (5, 3H), 6.79 (dd, 2H), 7.52 (dd, 1H).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 1897-52-5.

Reference:
Patent; NOVARTIS AG; CHAN, Ho Man; FU, Xingnian; GU, Xiang-Ju Justin; HUANG, Ying; LI, Ling; MI, Yuan; QI, Wei; SENDZIK, Martin; SUN, Yongfeng; WANG, Long; YU, Zhengtian; ZHANG, Hailong; ZHANG, Ji Yue (Jeff); ZHANG, Man; ZHANG, Qiong; ZHAO, Kehao; (148 pag.)WO2017/221100; (2017); A1;,
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Some common heterocyclic compound, 120351-94-2, name is 3-(2-Aminoethoxy)benzonitrile, molecular formula is C9H10N2O, 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: 120351-94-2

Step 1 Synthesis of 3-[2-(2-naphthalenesulfonylamino)ethoxy]benzonitrile: 163 mg of 3-(2-aminoethoxy)benzonitrile and 0.5 ml of diisopropylethylamine were dissolved in 10 ml of dimethylformamide. A solution of 250 mg (1.1 mmol) of 2-naphthalenesulfonyl chloride in dimethylformamide was added to the obtained solution under cooling with ice, and they were stirred under cooling with ice for 2 hours. The title compound was obtained by the same isolation process as that of step 1 in Example 1 with ethyl acetate as the extractant. Yield: 320 mg (0.91 mmol) (91 %) H-NMR (CDCl3) delta 3.45 (2H, dt), 4.00(2H, t), 5.05(1H, br), 6.96 (1H, s),6.97 (1H, d), 7.20 (1H, d), 7.30 (1H, t), 7.59-7.70 (2H, m), 7.82-7.98(4H, m), 8.46 (1H, s)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 120351-94-2, its application will become more common.

Reference:
Patent; Ajinomoto Co., Inc.; EP976722; (2000); 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 2042-37-7 as follows. Recommanded Product: 2-Bromobenzonitrile

Preparation 6 A solution of 1.5M butyllithium in hexane (25 ml) in tetrahydrofuran (25 ml) was cooled at -78C by using dry ice-acetone bath under nitrogen atmosphere and a solution of 4-bromotoluene (6.40 g) in tetrahydrofuran (25 ml) was added dropwise to the solution. After being stirred at -78C for 1 hour, a solution of freshly fused zinc chloride (5.15 g) in tetrahydrofuran (25 ml) was added in a slow stream via cannula and the resulting mixture was allowed to warm to room temperature. The mixture was stirred at room temperature for 1 hour and the resulting solution was added to a solution of 2-bromobenzonitrile (4.55 g) and tetrakis(triphenylphosphine)palladium(0) (400 mg) in tetrahydrofuran (25 ml) at room temperature. The solution was stirred at room temperature overnight. The solution was diluted with ethyl acetate (300 ml) and washed successively with 1N-hydrochloric acid, water, and brine. The organic solution was dried over magnesium sulfate and the solvent was evaporated in vacuo. The residue was purified by silica gel column chromatography with a mixture of ethyl acetate and n-hexane (1:20) as eluent to give 2-cyano-4–methylbiphenyl (4.43 g) as white powders. mp: 44-47C NMR (CDCl3, delta): 2.42 (3H, s), 7.25-7.35 (2H, m), 7.35-7.5 (4H, m), 7.62 (1H, dt, J=1, 7.5Hz), 7.85 (1H, dd, J=1, 7.5Hz)

According to the analysis of related databases, 2042-37-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; FUJISAWA PHARMACEUTICAL CO., LTD.; EP426021; (1991); A1;,
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Reference of 10406-25-4, These common heterocyclic compound, 10406-25-4, name is 4-(Aminomethyl)benzonitrile, 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.

General procedure: A sealed tube is charged with 7-chloro-5-(1 -methyl- 7 – -indol-6-yl)-quinoxaline (60.00 mg; 0.20 mmol; 1.0 eqr.) (Intermediate 4), 1-pyridin-3-yl-ethylamine (0.05 ml0.41 mmol; 2.0 eqf.), NaOtBu (58.77 mg; 0.61 mmol; 3.00 eqf.) and toluene (2.0 ml_). RM is purged with argon and then BINAP (25.39 mg; 0.04 mmol; 0.20 eqf.) and Pd2(dba)3 (18.67 mg; 0.02 mmol; 0.10 eq.) are added. RM is sealed and heated at 1 10C for 16 h. After this time, the mixture is filtered through a Celite pad and the filtrate is diluted with EtOAc and extracted with water. Combined organic phases are washed with brine, dried over Na2S04. Solvent is evaporated and the residue is purified by FCC (hexane/EtOAc; gradient). [8-(1 -Methyl- 7H-indol-6-yl)-quinoxalin-6-yl]-(1 – pyridin-3-yl-ethyl)-amine is obtained as a yellow powder (60.00 mg; yield 79%; 97% by HPLC).

Statistics shows that 4-(Aminomethyl)benzonitrile is playing an increasingly important role. we look forward to future research findings about 10406-25-4.

Reference:
Patent; SELVITA S.A.; FABRITIUS, Charles-Henry Robert Yves; NOWAK, Mateusz Oktawian; WIKLIK, Katarzyna Anna; SABINIARZ, Aleksandra Barbara; BIE?, Marcin Dominik; BUDA, Anna Ma?gorzata; GUZIK, Pawel Szczepan; JAKUBIEC, Krzysztof Roman; MACIUSZEK, Monika; KWIECI?SKA, Katarzyna; TOMCZYK, Mateusz Micha?; GA??ZOWSKI, Micha? Miko?aj; GONDELA, Andrzej; DUDEK, ?ukasz Piotr; (681 pag.)WO2016/180536; (2016); A1;,
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Some common heterocyclic compound, 7357-70-2, name is 2-Cyanothioacetamide, molecular formula is C3H4N2S, 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. Product Details of 7357-70-2

To a suspension of 3-(1,2-dimethyl-1H-imidazol-5-yl)-1-(thiazol-2- yl)prop-2-en-1-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 80oC for 2 h, EtOH was evaporated and crude product was redissolved in CH3CN. (0383) Butyl(chloromethyl)sulfane (0.62 mmol, 85.5 mg) and Et3N (0.93 mmol, 94.1 mg, 130 muL) 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%). 1H NMR (400 MHz, CDCl3) delta 7.96 (d, J = 3.1 Hz, 1H), 7.85 (s, 1H), 7.56 (d, J = 3.1 Hz, 1H), 7.37 (s, 1H), 4.49 (s, 2H), 3.60 (s, 3H), 2.72 (t, J = 7.4 Hz, 2H), 2.48 (s, 3H), 1.62 (p, J = 7.3 Hz, 2H), 1.40 (h, J = 7.3 Hz, 2H), 0.90 (t, J = 7.3 Hz, 3H). ESI- MS (m/z): 416.6 [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 7357-70-2, its application will become more common.

Reference:
Patent; CASE WESTERN RESERVE UNIVERSITY; UNIVERSITY OF TEXAS SOUTHWESTERN MEDICAL CENTER; UNIVERSITY OF IOWA RESEARCH FOUNDATION; MARKOWITZ, Sanford; READY, Joseph; PIEPER, Andrew; (168 pag.)WO2018/17582; (2018); A1;,
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Related Products of 135748-35-5, These common heterocyclic compound, 135748-35-5, name is 4-Chloro-2,5-difluorobenzonitrile, 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.

b [3-(5-Chloro-2-cyano-4-fluorophenoxy)-3-cyclopentylpropyl]methylcarbamic Acid, 1,1-dimethylethyl Ester The subtitle compound was prepared according to the method of Example 3 step (b) using (3-cyclopentyl-3-hydroxypropyl)methylcarbamic acid, 1,1-dimethylethyl ester and 4-chloro-2,5-difluorobenzonitrile in N,N-dimethylformamide. 1H NMR 300 MHz (CDCl3) 7.32 (1H, d), 7.04 (1H, bm), 4.28 (1H, m), 3.35 (2H, bm), 2.83 (3H, s), 2.28 (1H, m), 1.95 (2H, q), 1.50-1.80 (6H, m), 1.42 (9H, s), 1.26-1.45 (2H, m).

Statistics shows that 4-Chloro-2,5-difluorobenzonitrile is playing an increasingly important role. we look forward to future research findings about 135748-35-5.

Reference:
Patent; Cheshire, David; Connolly, Stephen; Cox, David; US2003/65174; (2003); 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. 5653-62-3, name is 2,3-Dimethoxybenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. COA of Formula: C9H9NO2

EXAMPLE III STR33 To a solution of 1,1,1,3,3,3-hexamethylsisilazane (20 g) in dry ether (150 mL) was added 2.4M n-butyllithium in hexane (5 mL). After 10 min at room temperature, 2,3-Dimethoxybenzonitrile (16.3 g) was added in one portion and the mixture was kept at room temperature for 16 h. The reaction mixture was the poured onto excess 3N HCl. The aqueous layer was separated, basified with 50% NaOH and the product was extracted three times with 10% methanol in methylene chloride. The combined organic extracts were dried over magnesium sulfate and the solvents removed in vacuo to afford 2,3-Dimethoxy-benzamidine as a glassy solid.

The synthetic route of 5653-62-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Neurogen Corporation; US5633376; (1997); A;,
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Electric Literature of 3672-47-7, 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. 3672-47-7, name is 3-(4-Methoxyphenyl)-3-oxopropanenitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A mixture of 2 (2.0 g, 11.4 mmol), N,N-diethylchloroacetamide (1.7 g, 11.4 mmol) and NaI (5.1 g, 34 mmol) were added to a solution of NaOH (0.5 g, 12.5 mmol) in 80% EtOH (80 ml) whilst being stirred continuously. The mixture was stirred at room temperature for 7 hours and monitored by t.l.c. Once the reaction was complete it was allowed to cool and was filtered to remove the inorganic material. The filtrate was concentrated and the residue was purified by column chromatography (CH2Cl2 as eluent) to yield 3 (2.1 g, 64 %) as a dark yellow oil; 1H n.m.r. (CDCl3, 300 MHz) delta 1.06-1.30 (m, 6H, N(CH2CH3)2), 2.85 (dd, J= 4.5, 16.2 Hz5 IH, CH2), 3.21-3.43 (m, 5H: 4H, N(CH2CH3)2 : IH, CH2), 3.90 (s, 3H, OCH3), 4.89-5.02 (m, IH, CH), 6.98 (d, J= 8.7, 2H5 Ph)5 8.05 (d, J= 9.O5 2H, Ph). Mass Spectrum: CI5 m/z 289 (M + 1).

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-Methoxyphenyl)-3-oxopropanenitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; THE UNIVERSITY OF SYDNEY; WO2007/134362; (2007); A1;,
Nitrile – Wikipedia,
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