Month: July 2021

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. 32703-80-3, name is 4-(tert-Butyl)phthalonitrile, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 4-(tert-Butyl)phthalonitrile

A mixture of 3.0 g (16.3 mmol) of 4-tert-butylphthalonitrile and 0.12 g (17.1 mmol) of lithium in 20 mL of anhydrous quinoline was re uxed for 3 h. The mixture was cooled, 30 mL of concentrated aqueous HCl and 150 mL of water were added with stirring, and the precipitate was ltered off, washed with water, and dried. The product was dissolved in chloroform and subjected to chromatography on aluminum oxide (activity grade III). The eluate was evaporated, and compound 1 was precipitated with methanol. Yield 0.8 g (36.2%), R f 0.52 (CHCl 3 -hexane, 3 : 1). Electronic absorption spectrum (CHCl 3 ), lambda max , nm (log epsilon): 342 (4.81), 603 (4.41), 645 (4.59), 664 (5.03), 701 (5.10). 1 H NMR spectrum (CDCl 3 ), delta, ppm: 2.60 br.s (2H, NH), 1.90 m (36H, t-Bu), 8.15 m (4H, 5-H), 8.86 m (4H, 3-H), 9.16 m (4H, 6-H). Mass spectrum (MALDI-TOF): m/z 739.156 [M] + .

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 32703-80-3.

Reference:
Article; Dmitrieva, O. A.; Ivanova, Yu. B.; Khrushkova, Yu. V.; Lyubimova, T. V.; Mamardashvili, N. Zh.; Semeikin, A. S.; Russian Journal of General Chemistry; vol. 90; 5; (2020); p. 852 – 857; Zh. Obshch. Khim.; vol. 90; 5; (2020); p. 760 – 766,6;,
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Application of 3759-28-2, 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. 3759-28-2, name is 2-(Cyanomethyl)benzonitrile, This compound has unique chemical properties. The synthetic route is as follows.

A solution of 2-cyanophenylacetonitrile (1 g, 7 mmol) and hydroxylamine (1.7 cm3, 28.1 mmol, 4 eq) in EtOH (25 cm3) were stirred under reflux for 60 hours, after which the volatiles were removed under reduced pressure. The residue was recrystallized from EtOH-water (1:4, 15 cm3) to give the cyclised product 3-aminoisoquinolin-1(4H)-one oxime or 3-(hydroxyamino)-3,4-dihydroisoquinolin-1-amine (1.15 g, 85.9%) as a solid, mp 92.5-94.5 C.

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

Reference:
Patent; Lee, Wai Mun; US2009/112024; (2009); A1;,
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Some common heterocyclic compound, 499983-13-0, name is 4-Bromo-3-fluorophenylacetonitrile, molecular formula is C8H5BrFN, 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. category: nitriles-buliding-blocks

A suspension of (4-bromo-3-fluorophenyl)acetonitrile (20 g; see step (ii) above) in cone. HCl (100 mL) was stirred at 8O0C overnight. The reaction mixture was basified with saturated NaHCO3 (aq.) and then extracted with ethyl acetate. The aqueous layer was acidified with cone. HCl and filtered to provide 8.2 g of the sub-title compound as a pink solid. This was employed directly in the next step without further purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 499983-13-0, its application will become more common.

Reference:
Patent; ASTRAZENECA AB; WO2007/69986; (2007); A1;,
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Some common heterocyclic compound, 69395-13-7, name is 4-(2-Hydroxyethyl)benzonitrile, molecular formula is C9H9NO, 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. Recommanded Product: 69395-13-7

To a solution of 4- (2- hydroxyethyl) benzonitrile (120 mg, 0.816 mmol) in acetone (3 ML), Jone’s reagent (1. 5ML, 4.005 mmol) was added.. After stirring for 10 minutes at room temperature, the crude reaction mixture was poured into water (10 ML) and extracted with CHC13 (6 x 10 mL). Combined organics were dried over magnesium sulfate, filtered, and concentrated to give (4-cyanophenyl- acetic acid which was used without purification. To a solution of (4-cyanophenyl) acetic acid (131 MG, 0.816 mmol) in ETOH (0.5 ML) at 0C was bubbled HCl (g) until saturation. Reaction mixture was allowed to warm to room temperature slowly. After overnight stirring, the crude reaction mixture was concentrated in vacuo. This residue was taken up in ETOH (4 ML) and ethylene diamine (0.1 mL, 1.49 mmol) was added. After stirring at room temperature for two hours, the crude reaction mixture was concentrated under reduced pressure and then re-dissolved in DMF (2 mL). To this solution was added 1M NAOH (2 mL, 2 mmol) and the reaction stirred at room temperature for three hours. Crude reaction mixture was neutralized with 1M HC1 to a pH 6 and extracted with CHC13 (4 x 15 ML). Product was found in the water layer, so combined all layers and concentrated in vacuo, re-dissolved in CHCL3/MEOH, and filtered to remove precipitate. Concentration of the filtrate gives [4- (4, 5-dihydro-lH-imidazol-2-yl) phenyl] acetic acid, which was used without further purification. LCMS (ES) 205.1 771/Z (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 69395-13-7, its application will become more common.

Reference:
Patent; MERCK & CO., INC.; WO2004/54584; (2004); A1;,
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Reference of 1897-41-2,Some common heterocyclic compound, 1897-41-2, name is 2,3,5,6-Tetrachloroterephthalonitrile, molecular formula is C8Cl4N2, 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.

0.60 g (0.015 mol) of sodium hydroxide was added to a solution of 1.22 g (0.0075 mol) of 2,5-dichloropyridin-3-amine in 40 mL of DMF, followed by addition of 2 g (0.0075 mol) of 2,3,5,6-tetrachloroterephthalonitrile under stirring, the mixture was stirred for 5 h after addition at room temperature. After the reaction was over by Thin-Layer Chromatography monitoring, the reaction mixture was poured into water and extracted with ethyl acetate, the organic phase was washed with water and saturated brine, dried over anhydrous magnesium sulfate, filtered and then concentrated under reduced pressure. The residue was purified through silica column (ethyl acetate/petroleum ether (boiling point range 60-90° C.)=1:3, as an eluent) to give 2.21 g of compound C-118 as yellow solid, m.p. 202-204° C. [0194] 1H-NMR (300 MHz, internal standard TMS, solvent CDCl3) delta (ppm): 7.36 (d, J=2.4 Hz, 1H, Py-4-1H), 7.97 (d, J=2.4 Hz, 1H, Py-5-1H), 8.89 (br, 1H, NH).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2,3,5,6-Tetrachloroterephthalonitrile, its application will become more common.

Reference:
Patent; SHENYANG RESEARCH INSTITUTE OF CHEMICAL INDUSTRY CO., LTD.; SINOCHEM CORPORATION; Liu, Changling; Huang, Guang; Lan, Jie; Hao, Shulin; Li, Zhinian; Li, Huichao; Guan, Aiying; Jiang, Airu; Xu, Ying; US2014/213598; (2014); A1;,
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Adding a certain compound to certain chemical reactions, such as: 3544-25-0, name is 2-(4-Aminophenyl)acetonitrile, 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 3544-25-0, HPLC of Formula: C8H8N2

To a solution of 2-(4- m op^r^l) eton ^ (3D g, 22.70 mmol) i 40 mL dimemylformamide cooled with ice bathwas added N-bromosuccinimide (4.04 g, 22.70 mmol) in portions . The mixture was stirred at 0 for 30 minutes and then at a b ie t tenperature for 1 hour. Waterwas added. The precipitate was collected by filtranon, washed with water, and dried in a vacuum oven at 40 “C to give the title compound (35fjg, 16.9 mmol. 74.4 % yield).

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, 2-(4-Aminophenyl)acetonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ABBVIE INC.; ABBVIE PHARMACEUTICAL TRADING (SHANGHAI) CO., LTD.; FIDANZE, Steven D.; LIU, Dachun; MANTEI, Robert A.; MCDANIEL, Keith F.; PRATT, John; SHEPPARD, George S.; WANG, Le; BOGDAN, Andrew; HOLMS, James H.; DIETRICH, Justin D.; MARJANOVIC, Jasmina; HASVOLD, Lisa A.; DAI, Yujia; WO2014/139324; (2014); A1;,
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Reference of 19472-74-3,Some common heterocyclic compound, 19472-74-3, name is 2-Bromophenylacetonitrile, molecular formula is C8H6BrN, 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.

A 100 mL round bottom flask was evacuated and back-filled byargon 3 times, and charged with 0.84 mL of o-bromophenylacetonitrile(6.5 mmol) and 25 mL of toluene under a positive pressure ofargon. After being cooled in an ice bath for 5 min, 7.5mL of a solutionof NaHMDS in THF (1 M, 7.5 mmol) was added to this toluenesolution, and the ice bath was removed. After 30 min, 0.47mL of 2-chloropyridine (5.0 mmol) was added, and the mixture was heatedin a 70 C oil bath for 6 h. The progress of reactionwas monitored byTLC. Upon completion, reaction was quenched by adding 50 mL ofsaturated aqueous ammonium chloride solution reaction, then extracted by 30 mL of ethyl acetate for three times. The combinedorganic extract was dried (anhydrous sodium sulfate), filtered(celite plug), and concentrated under a reduced pressure. A silicagel column chromatography purification (9:1 Hexanes/EtOAc)afforded 0.84 g of 1h in 64% yield.1h: 1H NMR (400 MHz, CDCl3) delta ppm 8.63-8.62 (1H, m),7.70-7.59 (m, 3H), 7.59e7.35 (m, 1H), 7.38-7.20 (m, 3H), 5.80 (s,1H). 13C NMR (101 MHz, CDCl3) delta ppm 153.95, 150.23, 137.38, 134.17,133.40, 130.44, 130.26, 128.40, 123.70, 123.27, 122.51, 118.53, 44.74.13C-DEPT 135 NMR (101 MHz, CDCl3) delta ppm 150.23, 137.37, 133.39,130.43, 130.24, 128.39, 123.26, 122.50, 44.72.

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

Reference:
Article; Chuentragool, Padon; Li, Zhou; Randle, Katrina; Mahchi, Faraj; Ochir, Ishmael; Assaf, Shadi; Gevorgyan, Vladimir; Journal of Organometallic Chemistry; vol. 867; (2018); p. 273 – 277;,
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Reference of 1187-42-4,Some common heterocyclic compound, 1187-42-4, name is Diaminomaleonitrile, molecular formula is C4H4N4, 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: AlCl3 (15 molpercent) was added to a solution of DAMN (1 mmol), ketone (1 mmol) and isocyanide (1 mmol), in 5 ml of CH3CN. The resulting mixture was stirred for an appropriate time at room temperature. After completion of the reaction, as indicated by thin-layer chromatography (TLC; ethyl acetate=n-hexane 3=1), the product was precipitated by addition of 10 ml of water. The precipitate was filtered off, washed with water, and then recrystallized from acetone. In the case of aromatic aldehyde, precipitate after filtration was loaded on column chromatography with 20percent ethyl acetate?hexane as an eluent system to furnish the product.

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

Reference:
Article; Bhosale, Shrikar M.; Naik, Nilesh H.; Kusurkar, Radhika S.; Synthetic Communications; vol. 43; 23; (2013); p. 3163 – 3169;,
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Electric Literature of 76469-88-0, A common heterocyclic compound, 76469-88-0, name is Methyl 4-(cyanomethyl)benzoate, molecular formula is C10H9NO2, 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.

Step 1; Methyl 4-(cyanomethyl)benzoate (1.8 g, 10 mmol, 1 eq) was dissolved in THF (100 mL) and cooled to 0C. Sodium hydride (60% w/w in mineral oil, 820 mg, 20 mmol, 2 eq) was added portionwise and the mixture was stirred for 10 minutes. Methyl iodide (1.3 mL, 20 mmol, 2 eq) was added dropwise and the reaction was stirred at 0C until the starting material was consumed by TLC (2 hours). The reaction mixture was quenched with water and was partitioned between EtOAc and brine. The aqueous layer was discarded, and the organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered, and evaporated to afford a crude residue which was chromatographed on silica gel (gradient elution, 0% to 50% EtOAc in hexanes, Si02) to afford the desired product as a white crystalline solid (1.88g, 74%).

The synthetic route of 76469-88-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SCHERING CORPORATION; WONG, Michael, K.; LAVEY, Brian, J.; YU, Wensheng; KOZLOWSKI, Josheph, A.; DEMONG, Duane, E.; DAI, Xing; STAMFORD, Andrew, W.; MILLER, Michael, W.; ZHOU, Guowei; YANG, De-Yi; GREENLEE, William, J.; WO2011/119559; (2011); A1;,
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Synthetic Route of 95-11-4, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 95-11-4 name is 5-Norbornene-2-carbonitrile, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Ortho-dichlorobenzene (958 g) was added into a five-neck flask which is equipped with a reflux cooling tube,stirring blades, a thermometer, a gas-blowing tube and a raw material-injecting tube, and had an inner volume of 2 liter,154.2 g (1.0 mol) of 2,5-bisaminomethyl-bicyclo[2.2.1]heptane and 2,6-bisaminomethyl-bicyclo[2.2.1]heptane which hadbeen obtained in Example 2 and ortho-dichlorobenzene (702 g) were prepared in a raw material tank. Next, a reactioncontainer was heated to 120C at 0.1 MPa, adding of hydrochloric acid gas from a hydrochloric acid-blowing tube at arate of 43.8 g/hr and adding of an amine diluted by a solvent from the raw material tank using a raw material-injectingpump at a rate of 428.1 g/hr were initiated at the same time, and the total amount was added over 2 hours. Furthermore,aging was carried out for 1 hour while adding hydrochloric acid gas at 20 g/hr. After the completion of the reaction,subsequently, hydrochloride reaction mass was heated to 160C, phosgene was blown in from a phosgene-blowingtube at 100 g/hr (1.0 mol/hr), and a reaction was caused for 6 hours while maintaining the temperature. After thecompletion of the reaction, unreacted phosgene and hydrochloric acid gas in the system were purged using nitrogen,and the solvent was removed, thereby obtaining a solution (200.9 g) including 2,5-bisisocyanate methyl-bicyclo[2.2.1]heptane and 2,6-bisisocyanate methyl-bicyclo[2.2.1]heptane. Furthermore, distillation was carried out under reducedpressure, and a mixture (175.7 g) of 2,5-bisisocyanate methyl-bicyclo[2.2.1]heptane and 2,6-bisisocyanate methylbicyclo[2.2.1]heptane having a purity of 99.0% was obtained. An 1H-NMR chart is illustrated in Fig. 3.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Norbornene-2-carbonitrile, and friends who are interested can also refer to it.

Reference:
Patent; Mitsui Chemicals, Inc.; KUMA, Shigetoshi; SAKATA, Michiharu; TOKUNAGA, Kouichi; SHIMAKAWA, Chitoshi; KAKINUMA, Naoyuki; FURUYA, Masayuki; TANAKA, Mamoru; EP2708527; (2014); A1;,
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