Category: nitriles-buliding-blocks

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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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;,
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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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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;,
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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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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 123-06-8 as follows. 123-06-8

To a solution of ethoxymethylenemalonodinitrile (S) (80 mmol) in benzene is added hydrazine (150 mmol). The reaction is stirred at reflux for 1 hr, diluted into ethyl acetate, washed with sodium bicarbonate solution and concentrated under vacuum, to provide T.

According to the analysis of related databases, 123-06-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CONCERT PHARMACEUTICALS INC.; WO2008/5471; (2008); A2;,
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114897-91-5, A common heterocyclic compound, 114897-91-5, name is 2-(4-Bromo-2-fluorophenyl)acetonitrile, molecular formula is C8H5BrFN, 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.

(11-2) According to a method similar to Example (8-1), from (4-bromo-2-fluorophenyl)acetonitrile (3.0 g, 14 mmol) obtained in Example (11-1) and 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (3.45 g, 14 mmol), (3-fluoro-4′-hydroxy-1,1′-biphenyl-4-yl)acetonitrile was obtained as a colorless solid (2.9 g, yield: 91%). 1H-NMR (400MHz, MeOH-d4): delta 7.50-7.34 (5H, m), 6.87 (2H, d, J=8.8Hz), 3.92 (2H, s).

The synthetic route of 114897-91-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Daiichi Sankyo Company, Limited; EP1806332; (2007); A1;,
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These common heterocyclic compound, 13388-75-5, name is 2-(3,5-Dimethoxyphenyl)acetonitrile, 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. 13388-75-5

General procedure: A 50 mL round-bottomed flask was charged with 3 (0.177 g, 1 mmol), aromatic aldehyde or substituted aromatic aldehyde (1 mmol) and 10 mL methanol with stirring, and the mixture was heated to 60 C. After 30 min, sodium methoxide (0.027 g, 0.5 mmol) was added to the mixture and keep the temperature for 4-6 h. After completion of the reaction as indicated by TLC, the reaction mixture was cooled to RT, and the precipitate was separated by filter and recrystallized from methanol to give 4a-4z and 5a-5d.

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 13388-75-5.

Reference:
Article; Ma, Jun; Li, Jiajun; Tian, Yu-Shun; Bioorganic and Medicinal Chemistry Letters; vol. 27; 1; (2017); p. 81 – 85;,
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A common heterocyclic compound, 103146-25-4, name is 4-(4-(Dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl)-3-(hydroxymethyl)benzonitrile, molecular formula is C20H23FN2O2, 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. 103146-25-4.

Example 2 (Preparation of the mixture used in example 1) (S)-4-[4-Dimethylamino-1-(4′-fluorophenyl)-1-hydroxybutyl]-3-hydroxymethyl- benzonitrile To a stirred solution of racemic 4- [4-Dimethylamino-l- (4-fluorophenyl)-l-hydroxy- butyl] -3-hydroxymethylbenzonitrile (29 mmol, 10 g) and vinylbutyrate (58 mmol, 7,5 ml) in anhydrous 1,4-dioxane (142,5 ml) is added lipoprotein lipase pseudomonas sp. (160 U, 250 mg). The reaction is heated to 50 C and followed by HPLC. After 192 hours at a conversion of 41%, additional 250 mg lipase was added. After 504 hours, at a conversion of 63 % the reaction was stopped. The enzyme is filtered off and washed with a small amount of 1,4-dioxane. The combined organic phases are evaporated in vacuo and subsequently analyzed on super critical fluid chromatography. Obtained ee-value ( (S-diol) = 95% (S-diol/R-diol = 40: 1).

The synthetic route of 4-(4-(Dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl)-3-(hydroxymethyl)benzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; H. LUNDBECK A/S; WO2005/77891; (2005); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts