Month: August 2021

Synthetic Route of 3556-60-3,Some common heterocyclic compound, 3556-60-3, name is 3-Methoxy-4-methylbenzonitrile, 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.

C.14.e. 4-Bromomethyl-3-methoxybenzonitrile 14.7 g (0.1 mol) of 3-methoxy-4-methylbenzonitrile were dissolved in 210 ml of 1,2-dichloroethane, brominated in portions with 19.1 g (0.11 mol) with NBS over the course of 1 h in the presence of catalytic amounts of AIBN at 82 C. and, after the addition was complete, stirred at 82 C. for a further 30 min. After addition of n-heptane, precipitated succinimide was removed, and the solvent was stripped off. The product contained traces of the corresponding benzal bromide in addition to small amounts of precursor. 1H-NMR (DMSO-d6; delta in ppm): 7.60 (dd, 1H); 7.50 (d, 1H); 7.40 (dd, 1H); 4.68 (s, 2H); 3.96 (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 3-Methoxy-4-methylbenzonitrile, its application will become more common.

Reference:
Patent; Abbott Laboratories; US6455671; (2002); B1;,
Nitrile – Wikipedia,
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Related Products of 50670-64-9, 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. 50670-64-9, name is 5-Amino-2-methylbenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example 22 5-Bromo-2-methylbenzonitrile Water (13.5 mL), HBr (74%, 14.4 mL) and 5-amino-2-methylbenzonitrile (2.0 g, 15.1 mmol) dissolved in water (24 mL) was added to a flask and heated to 50 C. for 20 min. Then the mixture was cooled to 0~5 C., and a solution of NaNO2 (1.2 g, 17.4 mmol) in water was added. The reaction mixture was stirred for 10 min at 0~5 C., then was warmed to 40 C. A solution of CuBr (6.5 g, 45.1 mmol) in water (36 mL) and HBr (7.2 mL) was added to the mixture, and refluxed for 2 h. The mixture was extracted with AcOEt, and the organic layer was washed by saturated NaHCO3 solution and brine, and dried over Na2SO4. The crude product was purified by flask chomatograph (PE:EA=50:1), obtaining 2.3 g of 5-bromo-2-methylbenzonitrile as a white solid (yield: 77%). 1H NMR (400 MHz, CDCl3) delta 7.72 (s, 1H), 7.59 (d, J=8.0 Hz, 1H), 7.19 (d, J=8.0 Hz, 1H), 2.51 (s, 3H).

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-2-methylbenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Glaxo Group Limited; US2009/203677; (2009); A1;,
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Related Products of 621-50-1, A common heterocyclic compound, 621-50-1, name is 2-(3-Nitrophenyl)acetonitrile, molecular formula is C8H6N2O2, 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.

To a solution of 3-nitro-phenyl-acetonitrile (3.20 g, 19.7 mmol) in MeOH(50 mL) was added Pd/C (10% wt, -50% H20, 0.32 g) and the mixture was placed under H2 (80 psi) and stirred for 2 days at 22 0C. The reaction mixture was filtered through Celite and the filtrate concentrated in vacuo to give crude product as a yellow oil. The residue was purified by silica gel chromatography (ISCO, elution with 0-10% ethyl acetate in hexanes) to give xix-1-1 (1.15 g, 44%): MS m/z = 133 (M-H).

The synthetic route of 621-50-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MILLENNIUM PHARMACEUTICALS, INC.; WO2006/41773; (2006); A2;,
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Related Products of 2469-99-0, The chemical industry reduces the impact on the environment during synthesis 2469-99-0, name is 3-Oxobutanenitrile, I believe this compound will play a more active role in future production and life.

General procedure: 3-Acetyl-2-aminothiophene Derivatives; General Procedure Carbonyl compound (0.025 mol) was added to freshly prepared cya-noacetone (0.03 mol) in either MeOH or EtOH (40 mL). Sublimed sul-fur S8 (0.03 mol) and piperidine (0.03 mol) were added and the mix-ture was stirred and heated to 55-65 C for 24 h. Ice was then addedand the formed precipitate was filtered under vacuum and washedwith water. The obtained solid was crystallised from a suitable sol-vent, with the exception of 4g and 4j, which were collected directlywithout further purification. 1-(2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophen-3-yl)ethan-one (4a)Yield: 2.7 g (61%); brown solid; mp 230 C (toluene). 1H NMR (400 MHz, CDCl3): delta = 6.82 (s, 2 H), 2.92-2.87 (m, 2 H), 2.78-2.72 (m, 2 H), 2.44-2.38 (m, 2 H), 2.38 (s, 3 H).13C NMR (100 MHz, CDCl3): delta = 193.7, 168.6, 141.0, 121.3, 112.2,31.74, 29.1, 28.7, 27.3.HRMS (ESI): m/z calcd for [C9H11NOS + Na]+: 204.0454; found:204.0464.Anal. Calcd for C9H11NOS: C, 59.64; H, 6.12; N, 7.73; S, 17.69. Found: C,60.14; H, 6.10, N, 7.48; S, 17.25.

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-Oxobutanenitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Abdelwahab, Ahmed B.; Hanna, Atef G.; Kirsch, Gilbert; Synthesis; vol. 48; 17; (2016); p. 2881 – 2888;,
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Some common heterocyclic compound, 1080-74-6, name is 2-(3-Oxo-2,3-dihydro-1H-inden-1-ylidene)malononitrile, molecular formula is C12H6N2O, 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. Safety of 2-(3-Oxo-2,3-dihydro-1H-inden-1-ylidene)malononitrile

To a solution of 7-bromo-benzo[1 ,2,5]thiadiazole-4-carbaldehyde (2.0 g, 8.2 mmol) in anhydrous chloroform (875 cm3) is added pyridine (46.5 cm3, 576 mmol). The mixture is then degassed with nitrogen before 3- (dicyanomethylidene) indan-1 -one (4.0 g, 21 mmol) is added. The solution is then further degassed and stirred for 20 minutes. The mixture is stirred at 40 C for 17 hours. The solid collected by filtration and washed with acetone (200 cm3), water (200 cm3), diethyl ether (200 cm3) and dichloromethane (200 cm3) to give intermediate 29 (3.0 g, 86%) as a pale yellow solid with very limited solubility.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1080-74-6, its application will become more common.

Reference:
Patent; MERCK PATENT GMBH; MORSE, Graham; NANSON, Lana; MITCHELL, William; KROMPIEC, Michal; D’LAVARI, Mansoor; PRON, Agnieszka; (327 pag.)WO2018/65350; (2018); A1;,
Nitrile – Wikipedia,
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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. 7251-09-4, name is 4-Amino-2-methoxybenzonitrile, A new synthetic method of this compound is introduced below., SDS of cas: 7251-09-4

Example 152, Part A 2-Amino-5-cyano-4-methoxybenzoic Acid Compound 152A was prepared by an analogous method as that of 118B starting from 3-methoxy-4-cyanoaniline.

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; Iwanowicz, Edwin J.; Watterson, Scott H.; Dhar, T.G. Murali; Pitts, William J.; Gu, Henry H.; US2002/40022; (2002); A1;,
Nitrile – Wikipedia,
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Electric Literature of 10406-25-4, 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 10406-25-4 as follows.

(S) -l- (2-bromopyridin-4-yl) piperidine-3-carboxylic acid (4a) (290 mg, 1.02 mmol)Was dissolved in 8 mL of anhydrous DMF,Was added to CDI (198 mg, 1.23 mmol) under nitrogen,Heated to 50 C for 21 h,Cooled to room temperature, 4-cyanobenzylamine (202 mg, 1.53 mmol) was added,Continue to nitrogen protection, heating to 50 reaction 24h,After cooling to room temperature, quenched with 1M HClThe reaction was carried out by adding 50 mL of water and extracting three times with dichloromethane. The combined organic phases were dried over anhydrous sodium sulfate and subjected to gradient gradient chromatographyThe column (ethyl acetate / petroleum ether = 5% to 100%) gave 289 mg of a white solid in 71% yield.

According to the analysis of related databases, 10406-25-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Southern Medical University; Li Zhonghuang; Wang Guangfa; Wu Xiaoyun; Tian Yuanxin; Wan Shanhe; Zhang Tingting; Hu Xiang; Hou Ju; Long Lifan; Liu Siming; Zhu Zhengguang; Zhang Jiajie; (22 pag.)CN107089968; (2017); A;,
Nitrile – Wikipedia,
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Some common heterocyclic compound, 7048-38-6, name is (5-Chloro-2-methoxyphenyl)acetonitrile, molecular formula is C9H8ClNO, 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. HPLC of Formula: C9H8ClNO

(a) 2-Methoxy-5-chloro-alpha-isopropylbenzyl cyanide To a stirred suspension of sodium hydride (2.4 g) in dimethylformamide (100 ml) was added a solution of 2-bromopropane and 2-methoxy-5-chlorobenzyl cyanide (18.2 g) in dry dimethylformamide (50 ml), keeping the temperature at 20°-30° C. The mixture was then stirred for 30 minutes, water was added cautiously, and the mixture was then poured into ice-water. Hydrochloric acid was then added and the mixture was extracted with dichloromethane, washed with water then with sodium chloride solution, then dried over magnesium sulphate, filtered, and the solvent was then removed to give 25 g of a brown oil. Distillation gave the title product (15 g) as a colourless oil, bp 180° C./20 mm Hg.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 7048-38-6, its application will become more common.

Reference:
Patent; Fisons Limited; US4263037; (1981); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Some common heterocyclic compound, 127946-77-4, name is 1-Amino-1-cyclopropanecarbonitrile hydrochloride, molecular formula is C4H7ClN2, 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. Computed Properties of C4H7ClN2

A mixture of 2-((trans-3-(3-cyclopropyl-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyrazin-1-yl)cyclobutyl)amino)thiazole-5-carboxylic acid, (EXAMPLE 149), (0.070 g, 0.188 mmol), (benzotriazol-1-yloxy)tripyrrolidinophosphonium hexafluorophosphate (0.147 g, 0.282 mmol), diisopropylethylamine (0.049 ml, 0.282 mmol), and 1-amino-1-cyclopropanecarbonitrile hydrochloride (0.033 g, 0.282 mmol) in DCM (5 mL) was stirred at room temperature for 12 hours. Purification of the reaction mixture using silica chromatography with ISCO eluting with 0-80% EtOAc/hexanes gave the title compound N-(1-cyanocyclopropyl)-2-((trans-3-(3-cyclopropyl-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyrazin-1-yl)cyclobutyl)amino)thiazole-5-carboxamide (0.060 g, 0.137 mmol, 73.1% yield). m/z: 437 (M+1); 1H NMR (400 MHz, DMSO-d6) delta: ppm 8.78 (s, 1H) 8.32 (d, J=6.65 Hz, 1H) 7.93-8.05 (m, 2H) 7.40 (s, 1H) 5.18 (quin, J=8.51 Hz, 1H) 4.31-4.53 (m, 1H) 3.21-3.41 (m, 2H) 2.88-3.05 (m, 1H) 2.29-2.44 (m, 2H) 1.44-1.60 (m, 2H) 1.23-1.35 (m, 2H) 0.93-1.10 (m, 4H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 127946-77-4, its application will become more common.

Reference:
Patent; AMGEN INC.; Allen, Jennifer R.; Amegadzie, Albert; Andrews, Kristin L.; Brown, James; Chen, Jian J.; Chen, Ning; Harrington, Essa Hu; Liu, Qingyian; Nguyen, Thomas T.; Pickrell, Alexander J.; Qian, Wenyuan; Rumfelt, Shannon; Rzasa, Robert M.; Yuan, Chester Chenguang; Zhong, Wenge; US2013/225552; (2013); A1;,
Nitrile – Wikipedia,
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Application of 3215-64-3, 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 3215-64-3 as follows.

Step 22-Cyano-(2,6-dichlorophenyl)-acetic acid methyl ester: A 500 mL round-bottom flask was charged with absolute methanol (100 mL) and sodium (6.2 g, 269.57 mmol). After all of sodium was dissolved, the mixture was evaporated to dryness. Then, 30 mL tolune was added and the mixture was dried down again by evaperation to give fresh NaOMe. To this was added dimethyl carbonate (300 mL) and 2-(2,6- dichlorophenyl)acetonitrile (25 g, 134.41 mmol). The resulting solution was allowed to reflux for 2 hours. The reaction progress was monitored by TLC (AcOEt: PE=I :4). The mixture was quenched by the addition of of 100 mL ice H2O. Then, the pH was adjusted to ca. 6 by the addition of AcOH . The resulting mixture was then extracted with EtOAc (3 x 100 ml). Combined organic layers were then concentrated down in vacuo to afford a residue that was purified by a column chromatography eluted with a 20:1 PE / AcOEt. This resulted in 27.8 g (85%) of methyl 2-cyano-2-(2,6-dichlorophenyl)acetate as a white solid. This was used for next step without further purification.

According to the analysis of related databases, 3215-64-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; KALYPSYS, INC.; WO2007/15866; (2007); A2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts