Nitriles-buliding-blocks

A common heterocyclic compound, 16532-79-9, name is 4-Bromophenylacetonitrile, molecular formula is C8H6BrN, 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. 16532-79-9.

To a solution of (4-bromo-phenyl)-acetonitrile (1 g, 5.10 mmol) in DMF (10 mL) is added sodium hydride (0.408 g, 10.20 mmol, 60% in mineral oil) at 0 C. Thereaction mixture is stirred at 0 C for 15 minutes and then methyl iodide (0.69 mL, 11.22 mmol) is added at 0 C. The reaction mixture is stirred at room temperature forovernight. The reaction mixture is quenched with aqueous ammonium chloride solution (5 mL) and extracted with EtOAc (2×20 mL). The combined organic extracts arewashed with water (20 mL) and brine (20 mL), dried over anhydrous Na2SO4, filtered, and evaporated. The crude material is purified over silica gel column chromatography(combiflash) eluting with 5-10% EtOAc in hexanes to give an off white solid (0.9 g,78%). 1H NMR (400 MHz, CDC13) i5 7.51 (d, J = 8.4 Hz, 1H), 7.34 (d, J = 8.4 Hz, 1H),1.77 (s, 3H).

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

Reference:
Patent; ELI LILLY AND COMPANY; HAMDOUCHI, Chafiq; MAITI, Pranab; MILLER, Anne Reifel; WO2015/105779; (2015); 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 874-89-5 as follows. 874-89-5

Example 99 N-((4-(hydroxymethyl)phenyl)methyl)-N-(1-methylpiperidin-4-yl)-2-(4-methoxyphenyl)acetamide hydrochloride (57MBT72D) To a stirred suspension of LiAlH4 (285 mg, 7.52 mmol) in diethylether (10 mL) at 0 C. was added a solution of 4-cyanobenzyl alcohol (0.5 g, 3.76 mmol) in diethylether (5 mL) over 15 min. The grey reaction mixture was heated to reflux for 3 h. After cooling to r.t., the mixture was treated successively with water (1 mL), 2M NaOH (2 mL) and water (2 mL) under vigorous stirring. The resulting white slurry was filtered and washed with CH2Cl2 (20 mL). Extraction with additional CH2Cl2 (20 mL) and n-butanol (20 mL) and evaporation yielded an oil, which upon flash chromatography (0-15% MeOH in CH2Cl2) gave 152 mg (29%) of 4-(aminomethyl)benzylalcohol (57MBT52B) as a white solid. Rf=0.51 (30% MeOH in CH2Cl2+3.5% NH4OH).

According to the analysis of related databases, 874-89-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ACADIA Pharmaceuticals Inc.; ANDERSSON, Carl-Magnus A.; CROSTON, Glenn; HANSEN, Eva Louise; ULDAM, Allan Kjaersgaard; US2015/259291; (2015); A1;,
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16532-79-9, 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. 16532-79-9, name is 4-Bromophenylacetonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a suspension of NaH (2.55 g, 63.75 mmol, 60%) in dimethyl sulfoxide (50 mL) were added dropwise a mixture of 4-bromophenyl-acetonitrile (223) (5 g, 25.51 mmol) and 1,4-dibromobutane (3.04 mL, 25.51 mmol) dissolved in dimethyl sulfoxide:ether (1:1) (50 mL) at 0 C. and the reaction mixture was stirred at this temperature for 2 h. After completion of the reaction, water (20 mL) and 10% HCl solution (50 mL) were added to the mixture and the mixture was extracted with ethyl acetate (2¡Á200 ml). The organic layer was dried over Na2SO4, concentrated and purified by 100-200 silica column chromatography using hexane as the eluent to give 1-(4-bromophenyl)-cyclopentanecarbonitrile (224) (5.7 g, 89%) as a white crystalline solid. [0870] GC-MS: 250 (M+)

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

Reference:
Patent; Wolkerstorfer, Andrea; Szolar, Oliver; Handler, Norbert; Buschmann, Helmut; Cusack, Stephen; Smith, Mark; So, Sung-Sau; Hawley, Ronald Charles; Sidduri, Achyutharao; Zhang, Zhuming; US2014/194431; (2014); A1;,
Nitrile – Wikipedia,
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67515-59-7,Some common heterocyclic compound, 67515-59-7, name is 4-Fluoro-3-(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.

Preparation of BB7: 4-Fluoro-N-hydroxy-3-trifluoromethyl-benzamidine:BB7; To a solution of the 4-fluoro-3-trifluoromethyl-benzonitrile (20.0 g, 105.8 mmol) in ethanol (400 mL) a solution of the NH2OH-HCl (8.0 g, 116.4 mmmol) which was adjusted to pH=7.0 by addition of NaOH in H20 (8 mL) was added. The mixture was stirred vigorously and heated to about 65 C for about 16 h. The analysis by TLC indicated the completion of the reaction; it was concentrated to remove the solvent. The residue was redissolved in DCM (200 mL) and washed with water, brine and dried over Na2S04, concentrated in vacuum to afford 4-Fluoro-N-hydroxy-3-trifluoromethyl-benzamidine (BB7) as pale-yellow solid. 1H NMR (400 MHz, DMSO) delta ppm 9.83 (1H, s), 8.00 – 7.98 (2H, m), 7.50 (1H, t) and 6.00 (2H, s).

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-3-(trifluoromethyl)benzonitrile, its application will become more common.

Reference:
Patent; ABBOTT LABORATORIES; CUSACK, Kevin, P.; BREINLINGER, Eric, C.; FIX-STENZEL, Shannon, R.; STOFFEL, Robert, H.; WOLLER, Kevin, R.; WO2011/71570; (2011); 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. 103146-25-4, name is 4-(4-(Dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl)-3-(hydroxymethyl)benzonitrile, A new synthetic method of this compound is introduced below., 103146-25-4

To a stirred solution [OF RACEMIC 4- [4-DIMETHYLAMINO-1- (4-FLUORO-PHENYL)-1-HYDROXY-] [BUTYL]-3-HYDROXYMETHYL-BENZONITRILE] (0,29 mmol, 100 mg) and vinylbutyrate (0,29 mmol, [37 L)] in anhydrous toluene (2,925 ml) is added Novozymes 435, (0,2 mg) and 1,1 eq. Carboxylic acid. The reaction is heated to 40 degrees celcius and followed by HPLC. The enzyme is filtered off and washed with a small amount of toluene. The combined organic phases are evaporated in vacuo and subsequently analyzed on super critical fluid chromatography. Result is shown in table 19.

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; H. LUNDBECK A/S; WO2004/14821; (2004); A1;,
Nitrile – Wikipedia,
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4435-14-7,Some common heterocyclic compound, 4435-14-7, name is 2-Cyclohexylacetonitrile, molecular formula is C8H13N, 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.

Cyclohexyl acetonitrile (a-1) 18g, 2- chloro-benzoyl cyanide (b-1) It was mixed 24g and dichloromethane 700 mL, and cooled to -10 C..Then, after added dropwise over 70 min titanium tetrachloride 82g at the same temperature, was added dropwise over 2 hours N- methylmorpholine88 g, was stirred at room temperature for 15 hours. The reaction mixture was poured into water, stirred and added with chloroform, and filtered theinsoluble matter. The resulting filtrate the aqueous solution of sodium bicarbonate, washed sequentially with water, and then concentrated. By theresulting concentrate is purified by column to give the trans-1- cyclohexyl-2- (2-chlorophenyl) -1,2-dicyano ethylene (c-1) 18.1g.

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

Reference:
Patent; YAMADA CHEMICAL COMPANY LIMITED; HASE, TOMOYUKI; (19 pag.)JP2016/11348; (2016); A;,
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96606-37-0, A common heterocyclic compound, 96606-37-0, name is 2,4,6-Trifluorobenzonitrile, molecular formula is C7H2F3N, 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.

Example 3: Synthesis OF 3-AMINO-6- (4-AMINO-PIPERIDIN-1-YL)-4-FLUORO- BENZOLB] THIOPHENE-2-CARBOXYLIC acid amide H N i N O F NHZ NN O N i HN 0- HS-NH, N F N O F F THF, 50 C, 3h DMF, 15h F 0A0 F NH2 HCI NH2 na ff) / MeOH, 3 days 0 H2N~ 3 ‘3 To a solution of 1.0 g (6.4 mmol) of 2, 4,6-trifluorobenzonitrile in MEOH (25 mL) was added 1.3 g (6.5 mmol) OF 4-N-BOC-AMINO-PIPERIDINE along with 1.2 mL (6.7 mmol) of N, N-diisopropylethylamine. The mixture was stirred at room temperature for 3 days then concentrated under reduced pressure to provide a white, solid. The solid was washed with large amounts OF H20 and dried under vacuum. The solid was RECRYSTALLIZED from hexane /EtOAc to provide 1.23 g (56%) of [1- (4-CYANO-3, 5-difluoro-phenyl) -piperidin-4-yl]- carbamic acid tert-butyl ester as a white solid.

The synthetic route of 96606-37-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM PHARMACEUTICALS, INC.; WO2005/12283; (2005); A1;,
Nitrile – Wikipedia,
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1813-33-8, The chemical industry reduces the impact on the environment during synthesis 1813-33-8, name is 2-Chloro-4-(trifluoromethyl)benzonitrile, I believe this compound will play a more active role in future production and life.

General procedure: A mixture of 2-chloro-4-(trifluoromethyl)-benzonitrile (1.00 mmol) and appropriate thiol (RSH, 3.00 mmol),18-crown-6-ether (cat.) and potassium carbonate (2.00 mmol)were dissolved in acetonitrile (3 ml). The mixture was refluxedfor 12 h and then cooled to ambient temperature. The mixturewas quenched by adding water and extracted with EtOAc.Extracted organic compound was dried over MgSO4, filtered, andconcentrated in vacuo. The residue was purified by flash columnchromatography on silica gel using EtOAc/hexane (1:4) eluantcondition. (RSH = CH3CO2(CH2)2SH for 42).

The chemical industry reduces the impact on the environment during synthesis 2-Chloro-4-(trifluoromethyl)benzonitrile. I believe this compound will play a more active role in future production and life.

Reference:
Article; Ann, Jihyae; Jung, Aeran; Kim, Mi-Yeon; Kim, Hyuk-Min; Ryu, Hyungchul; Kim, Sunjoo; Kang, Dong Wook; Hong, Sunhye; Cui, Minghua; Choi, Sun; Blumberg, Peter M.; Frank-Foltyn, Robert; Bahrenberg, Gregor; Stockhausen, Hannelore; Christoph, Thomas; Lee, Jeewoo; Bioorganic and Medicinal Chemistry; vol. 23; 21; (2015); p. 6844 – 6854;,
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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. 114897-91-5, name is 2-(4-Bromo-2-fluorophenyl)acetonitrile, This compound has unique chemical properties. The synthetic route is as follows., 114897-91-5

MeOH (16MMOL, 0.81 ml), TMSCI (20mmol, 2. 13g) and (4-bromo-2-fluorophenyl) acetonitrile (10MMOL, 2. 13g) were sequentially added to a dry flask under a nitrogen atmosphere at room temperature. The reaction mixture was heated at 50 C for 4 hours. After being cooled to room temperature, water (20MMOL, 0. 36MOI) was added to the mixture, followed by the addition of NA2CO3 (10mmol, 1. 06g) and CH2Cl2 (10ml). Drying over MGSO4 and concentrating at low pressure afforded product (0.85 g, 35% YIELD). H NMR (300 MHz, CDC13) No. : 3.57 (s, 2 H), 3.65 (s, 3H), 7.08 (t, J=8.3 Hz, 1H), 7.16-7. 21 (m, 2H).

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; PFIZER INC.; WO2004/74270; (2004); A2;,
Nitrile – Wikipedia,
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17216-62-5, 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. 17216-62-5, name is Diethyl 2-(2-cyanoethyl)malonate, A new synthetic method of this compound is introduced below.

EXAMPLE 9 1,4,8,11-Tetraaza-6-(2-cyanoethyl)-5,7-dioxoundecane, 8 Diethyl 2-(2-cyanoethyl)malonate 7 (5.0 g, 23.5 mmole–Aldrich Chemical Company) was added dropwise over a one hour period to a stirred portion of freshly distilled ethylene diamine (15 g, 0.25 mole) which was maintained under nitrogen at O C. The stirred solution was allowed to warm to room temperature (25 C.) and stirring was continued over a four day period. At this point, the excess ethylene diamine was removed in vacuo with care to avoid heating over 40 C. The crude clear oil which resulted was subjected to flash chromatography using Solvent System 3 as the eluent to give 2.3 g (8.81 mmole) of 1,4,8,11-tetraaza-6-(2-cyanoethyl)-5,7-dioxoundecane as a clear viscous oil in 37 percent yield (Rf =0.39/Solvent System 3): 1 H NMR (CDCl3) delta 7.59 (t, 2H, amide H), 3.29 (m, 5H, methine H and alpha-amido CH2), 2.82 (dt, 4H), beta-amido CH2) 2.48 (t, 2H, alpha-nitrile CH2) 2.21 (q, 2H, beta-nitrile CH2),1.39 (s, 4H, amino NH); 13 C NMR (CDCl3) delta 169.6 (amide carbonyl), 118.9 (nitrile), 52.9, 42.3, 41.2, 27.1, 15.4.

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; The Dow Chemical Company; US5489425; (1996); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts