Month: January 2021

Synthetic Route of 1572-52-7, These common heterocyclic compound, 1572-52-7, name is 2-Methylenepentanedinitrile, 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.

130 g (1 M) of N-(2-hydroxyethyl)imidazolidin-2-one and 2 g of potassium hydroxide pellets are charged to a 500 cm3 reactor equipped with a mechanical stirrer, a jacket forheating, a dropping funnel and a system for rendering inertwith nitrogen. The product is brought to 80 C. and then 116g (1.1 M) of methyleneglutaronitrile are run in slowly. At theend of the reaction, when there is virtually no more methyleneglutaronitrile, the catalyst is neutralized with an acid.The expected dinitrile is obtained with a yield of 95%. Theproduct can be used as is or purified by distillation in orderto separate it from the excess methyleneglutaronitrile.

Statistics shows that 2-Methylenepentanedinitrile is playing an increasingly important role. we look forward to future research findings about 1572-52-7.

Reference:
Patent; Arkema France; Gillet, Jean-Philippe; Disson, Jean-Pierre; Van Hemelryck, Bruno; (13 pag.)US10047195; (2018); B2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 49674-16-0, name is 5-Amino-3-bromobenzonitrile, 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 49674-16-0, Product Details of 49674-16-0

Example 1.1.74: methyl 3-(aminomethyl)-5-isopropylphenylcarbamate; To a stirring solution of 97.3 mg (0.494 mmol) of 3-amino-5-bromobenzonitrile in 3 mL of pyridine at r.t. was added 0.1 mL of methyl chloroformate. After 15 h, 15 mL of H2O and EtOAc were added. The organic layer was washed with H2O and brine, dried over Na2SO4, filtered, and concentrated. Crude methyl 3-bromo-5-cyanophenylcarbamate was used in the next reaction without further purification.

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, 5-Amino-3-bromobenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; COMENTIS, INC.; PURDUE RESEARCH FOUNDATION; WO2009/42694; (2009); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

These common heterocyclic compound, 1953-99-7, name is 3,4,5,6-Tetrachlorobenzene-1,2-dicarbonitrile, 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. COA of Formula: C8Cl4N2

A reaction was performed at 270¡ã C. for 16 hours by following the procedure of Example 1 while using 80.0 g (0.301 mol) of 3,4,5,6-tetrachlorophthalonitrile in the place of pentachlorobenzonitrile and 0.1 g of sodium hydroxide in the place of potassium hydroxide. After the reaction was completed, the reaction solution was cooled to room temperature and then filtered to remove the suspended potassium chloride and the unaltered potassium fluoride. When the benzonitrile solution as the mother liquor was analyzed by gas chromatography, it was found to contain 55.4 g of 3,4,5,6-tetrafluorophthalonitrile and 0.018 g of benzoic acid fluoride (325 ppm based on the amount of 3,4,5,6-tetrafluorophthalonitrile). The stainless steel reaction vessel showed no discernible sign of corrosion.

The synthetic route of 3,4,5,6-Tetrachlorobenzene-1,2-dicarbonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Nippon Shokubai Co., Ltd.; US6392084; (2002); B1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Reference of 38487-86-4, These common heterocyclic compound, 38487-86-4, name is 2-Amino-4-chlorobenzonitrile, 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.

2-Amino-4-chlorobenzonitrile (4) (305 mg, 2 mmol)was dissolved in 94% H2SO4 (2 ml) at 20-25. Theobtained nitrile solution was cooled (5-10), stirred, andtreated by slow dropwise addition of 1-(3-bromo-4-methoxyphenyl)-2-methylpropan-1-ol (10) (518 mg, 2 mmol) asa solution in H2Cl2 (0.5 ml). The reaction mixture wasstirred for 1 h at 20-25 and further treated according tothe general method. The product was crystallized fromEtOAc, the residue was separated by chromatography (eluentpetroleum ether – EtOAc, gradient from 10:1 to 1:1). Yield90 mg (12%, general method), 420 mg (56%, method II),light-yellow crystals, mp 245.5-247, Rf 0.20 (hexane-EtOAc, 4:1). IR spectrum, nu, cm-1: 1610, 1683, 3321.1H NMR spectrum, delta, ppm (J, Hz): 1.31 (3, s, 2-3);1.36 (3, s, 2-3); 2.03 (1, d, J = 13.2, 3-2); 2.20(1, d, J = 13.2, 3-2); 2.76 (1, dd, J = 16.8, J = 3.2,7-2); 3.02 (1, dd, J = 16.8, J = 2.8, 7-2); 3.79 (1,q, J = 2.4, 7-CH); 6.62 (1, dd, J = 8.4, J = 2.0, -11);6.70 (1, d, J = 2.0, 4-CH); 6.86 (1, s, NH); 7.18 (1, d,J = 1.6, H-9); 7.62 (1, d, J = 8.4, H-12). 13C NMR spectrum,delta, ppm: 29.5; 30.9; 40.0; 47.5; 55.8; 57.0; 71.9; 113.0;113.6; 116.4; 122.2; 128.0; 136.4; 148.1; 148.2; 163.2; 188.1.Mass spectrum, m/z (Irel, %): 378 [M]+ (74), 363 [M-3]+(40), 299 [M-79Br]+ (39), 229 (13), 226 (13), 217 (40), 215(17), 193 (100), 152 (35), 148 (22), 147 (27), 119 (22).Found, %: 53.68; 4.41; Br 21.06; Cl 9.35; N 7.28.C17H16BrClN2O. Calculated, %: 53.78; 4.25; Br 21.04;Cl 9.34; N 7.38.

Statistics shows that 2-Amino-4-chlorobenzonitrile is playing an increasingly important role. we look forward to future research findings about 38487-86-4.

Reference:
Article; Rozhkova, Yuliya S.; Vshivkova, Tatyana S.; Morozov, Vyacheslav V.; Zhulanov, Vladimir E.; Gorbunov, Aleksei A.; Shklyaev, Yurii V.; Chemistry of Heterocyclic Compounds; vol. 53; 11; (2017); p. 1228 – 1241; Khim. Geterotsikl. Soedin.; vol. 53; 11; (2017); p. 1228 – 1241,14;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

147754-12-9, name is 4-Fluoro-2-methylbenzonitrile, 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. Quality Control of 4-Fluoro-2-methylbenzonitrile

In a dried reaction flask, 4-fluoro-2-methylbenzonitrile (4.055g, 30.0mmol) and hydrazine hydrate (85percent) (3.54mL, 60.0mmol) were dissolved in ethanol (15.9mL). In the protection from light and under the nitrogen atmosphere, the solution was heated under reflux at 80¡ãC for 48hr. Water was added to the reaction solution. The mixture was filtered. The filtered cake was rinsed with water to produce a pale yellow solid, which was suspended in ethyl ether. A hydrogen chloride gas was passed into the suspension under an ice-salt bath. The suspension was filtered. The filtered cake was rinsed with ethyl ether to produce an off-white solid (2.04g) in 37.0percent yield.

The synthetic route of 147754-12-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KBP Biosciences Co., Ltd.; HUANG, Zhenhua; WANG, Jinyuan; ZHANG, Dedong; EP2607363; (2013); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

67515-59-7, name is 4-Fluoro-3-(trifluoromethyl)benzonitrile, 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. Safety of 4-Fluoro-3-(trifluoromethyl)benzonitrile

A mixture of 4-fluoro-3-trifluoromethylbenzonitrile (75 mg, 0.40 mmol), sodium sulfinate (44.5 mg, 0.44 mmol) in N,N-dimethylformamide (1.5 mL) was heated at 100 C. for 2 h. The reaction mixture was cooled to room temperature, quenched with water. The resulting white solid was collected via filtration, washed with cold water, dried in a vacuum oven to give 4-methanesulfonyl-3-trifluoromethyl-benzonitrile (90 mg, 90% yield). This benzonitrile was hydrogenated in 2N NH3 in methanol with 35 mg of Raney Ni under a hydrogen balloon for 2 h. The reaction mixture was filtered through a celite plug, washed with methanol, evaporated in vacuo to give the titled compound.

The synthetic route of 67515-59-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Liu, Gang; Sham, Hing L.; Szczepankiewicz, Bruce G.; Xin, Zhili; Zhao, Hongyu; Serby, Michael D.; Liu, Bo; Liu, Mei; US2006/173050; (2006); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Reference of 64248-64-2, 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. 64248-64-2 name is 2,5-Difluorobenzonitrile, 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.

To a solution of (lR,3s,5S)-tert-butyl 3-((lr,4R)-4-hydroxycyclohexyloxy)-8- azabicyclo[3.2.1]octane-8-carboxylate (33 mg, 0.101 mmol) and 2,5-difluorobenzonitrile (18 mg, 0.129 mmol) in 0.5 mL THF, 1 M potassium teri-butoxide (0.150 mL, 0.150 mmol) was added slowly. After stirring at room temperature for 1 h, mixture was extracted with water and CH2C12. Organic phases were concentrated and residue was purified by HPLC (H20/CH3CN gradient + 0.1% TFA). Fractions containing product were partly concentrated and residue was extracted with 1 M NaOH and CH2C12. Organic phases were dried over MgS04, filtered, and concentrated to give (lR,3s,5S)-tert-butyl 3-((lr,4R)-4-(2-cyano-4-fluorophenoxy)cyclohexyloxy)-8- azabicyclo[3.2.1]octane-8-carboxylate (37.9 mg, 85.26 muiotaetaomicron?, 84.1%) as a white solid. Exact mass calculated for C25H33FN204: 444.2, found: LCMS m/z = 445.6 [M+H]+; lU NMR (400 MHz, CDC13) 5 ppm 1.41-1.69 (m, 8H), 1.47 (s, 9H), 1.87-2.10 (m, 8H), 3.50-3.56 (m, 1H), 3.77-3.85 (m, 1H), 4.16-4.31 (m, 2H), 4.33-4.39 (m, 1H), 6.92-7.00 (m, 1H), 7.20-7.26 (m, 2.4 Hz, 2H).

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

Reference:
Patent; ARENA PHARMACEUTICALS, INC.; JONES, Robert M.; BUZARD, Daniel J.; HAN, Sangdon; KIM, Sun Hee; LEHMANN, Juerg; ZHU, Xiuwen; WO2013/55910; (2013); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

These common heterocyclic compound, 147754-12-9, name is 4-Fluoro-2-methylbenzonitrile, 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. Quality Control of 4-Fluoro-2-methylbenzonitrile

2-methyl-4-fluorophenyl-carbonitrile (2g, 14.8mM, 1.0equiv) in carbon tetrachloride (24mL) was added N- bromosuccinimide (2.64g, 14.8mM, 1.0equiv ), benzoyl peroxide (BPO, 179mg, 0.74mM, 0.05equiv), and heated to reflux for 3h under nitrogen. The reaction was complete by TLC, cooled to room temperature, filtered, washed with carbon tetrachloride, the solvent was concentrated under reduced pressure to give the crude product as a white solid. It was used directly in the next reaction without purification.

The synthetic route of 4-Fluoro-2-methylbenzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chengdu Bestchiralbio Limited-Liability Company; Li, Dequn; (16 pag.)CN105272963; (2016); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

These common heterocyclic compound, 654-70-6, name is 4-Cyano-3-trifluoromethylaniline, 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. Application In Synthesis of 4-Cyano-3-trifluoromethylaniline

a 4-[(4-Chloro-2-methyl-quinolin-7-ylmethyl)-amino]-2-trifluoromethyl-benzonitrile To a solution of 4-chloro-2-methyl-quinoline-7-carbaldehyde (example 13a, 180 mg, 0.875 mmol) in ethanol (3 mL) were added 4-amino-2-trifluoromethyl-benzonitrile (163 mg, 0.875 mmol), 25% aq. hydrochloric acid solution (1.5 mL), and sodium borohydride (207 mg, 5.25 mmol). The reaction mixture was stirred 16 h at r.t., then partitioned between ethyl acetate and 1 M aq. sodium hydroxide solution. The organic layer was washed with brine, dried (MgSO4), and evaporated. Flash chromatography (SiO2, hexane/ethyl acetate 1:1 afforded the title compound (123 mg, 37%). Off-white solid, ISP-MS: m/e=376.3 ([M+H]+).

The synthetic route of 4-Cyano-3-trifluoromethylaniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Klug, Michael G.; Mattei, Patrizio; Mueller, Werner; Neidhart, Werner; Nettekoven, Matthias Heinrich; Pflieger, Philippe; Plancher, Jean-Marc; US2003/158179; (2003); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Application of 868-54-2,Some common heterocyclic compound, 868-54-2, name is 2-Aminoprop-1-ene-1,1,3-tricarbonitrile, molecular formula is C6H4N4, 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: Heterocyclic ketene aminals (1 mmol), aryl aldehydes (1.2 mmol), malononitriledimer (1.5 mmol), acetic acid (1 mmol), piperidine (1 mmol) and ethanol (10 mL)were stirred at refluxing for 1 h. After completion of the reaction (confirmed by TLC),the reaction mixture was filtered to afford the crude product, which was furtherwashed with 95% ethanol to give pure product 4.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Aminoprop-1-ene-1,1,3-tricarbonitrile, its application will become more common.

Reference:
Article; Sun, Feilong; Zhu, Fengjuan; Shao, Xusheng; Li, Zhong; Synlett; vol. 26; 16; (2015); p. 2306 – 2312;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts