Month: June 2021

Related Products of 52516-37-7, These common heterocyclic compound, 52516-37-7, name is 2-(3,5-Dichlorophenyl)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.

A mixture of 3, 5-dichlorophenylacetonitrile (2gm, prepared according to the procedure described in WO00/58292), ethanol (25mL), potassium hydroxide (3. 95gm) and water (1 OmL) was heated under reflux for 4hr then evaporated to dryness under vacuum. The residue was partitioned between water (20mL) and diethyl ether and the aqueous layer was acidified to pH1 by addition of concentrated hydrochloric acid. The mixture was extracted with diethyl ether (3 x 25mL), the organic layer dried over anhydrous sodium sulfate and evaporated under vacuum. The carboxylic acid was dissolved in methanol (20mL) and TRIMETHYLSILYLDIAZOMETHANE (2M solution in hexanes, 30mL, Aldrich Chemical Company, Milwaukee, WI) was added slowly. After 1 hr the solvent was removed under vacuum, the residue dissolved in diethyl ether, washed with aqueous sodium carbonate solution (2M), dried over anhydrous sodium sulfate and evaporated to dryness to give the title compound (2. 1 GM). 1H-NMR (CDCI3) 6 7. 27 (s, 1H), 7. 17 (s, 2H), 3. 71 (S, 3H), 3. 57 (s, 2H).

The synthetic route of 52516-37-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER PRODUCTS INC.; WO2004/85401; (2004); A1;,
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Some common heterocyclic compound, 403-54-3, name is 3-Fluorobenzonitrile, molecular formula is C7H4FN, 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 C7H4FN

The 4chloro-6-(2-methylimidazol-1-yl)quinazoline used as a starting material was obtained as follows: 3-Fluorobenzonitrile (25 g) was added dropwise to a stirred mixture of potassium nitrate (21.1 g) and concentrated sulphuric acid (150 ml) which had been cooled in a mixture of salt and ice. The mixture was stirred at ambient temperature for 45 minutes. The mixture was poured onto ice (800 ml) and the precipitate was isolated. The solid so obtained was dissolved in methylene chloride, dried (MgSO4) and the solution was evaporated to give 5-fluoro-2-nitrobenzonitrile (19 g).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 403-54-3, its application will become more common.

Reference:
Patent; Zeneca Limited; US5955464; (1999); A;,
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Reference of 25978-68-1, These common heterocyclic compound, 25978-68-1, name is Methyl 4-cyano-3-methylbenzoate, 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.

Lithium borohydride (33 mg, 1.54 mmol) was added into a solution of methyl 4-cyano-3- methylbenzoate (245 mg, 1.40 mmol) in THF (3 ml.) and the resulting mixture was stirred at RT for 4 hours. The reaction mixture was diluted with water (10 ml.) and extracted with EtOAc (4×20 ml_). The combined organic fractions were dried (MgSO4) and concentrated under vacuum. The residue was purified by flash chromatography (silica, petrol ether/EtOAc) to give the title compound as a colorless gum (195 mg, 95%). 1H NMR (CDCI3, 400 MHz) delta 7.58 (1 H, d, J=7.9 Hz), 7.33 (1 H, s), 7.26 (1 H, m), 4.74 (2H, s), 2.55 (3H, s), 1.95 (1 H, s). LC/MS (Method A): 144 (M+H)+. HPLC (Method F) Rt 3.95 min (Purity: 95.3%).

The synthetic route of 25978-68-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SERONO S.A.; QUATTROPANI, Anna; MONTAGNE, Cyril; SAUER, Wolfgang; CROSIGNANI, Stefano; BOMBRUN, Agnes; WO2010/112461; (2010); A1;,
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Electric Literature of 134450-56-9, 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. 134450-56-9, name is 4,5-Difluorophthalonitrile, This compound has unique chemical properties. The synthetic route is as follows.

Synthesis of compound of formula XVIII is illustrated in Scheme 3 below. (0146) Reaction of 0.5 molar equivalents of carbazole with 4,5-difluorophthalonitrile affords compound 8 which is then reacted with 4 to provide intermediate 9. Hydrolysis of the nitrile functions provides dicarboxylic acid 10 on acidification. Methylation with iodomethane and anion metathesis with saturated NH4PF6 solution provides the product XVIII.

The chemical industry reduces the impact on the environment during synthesis 4,5-Difluorophthalonitrile. I believe this compound will play a more active role in future production and life.

Reference:
Patent; UNIVERSITY COURT OF THE UNIVERSITY OF ST ANDREWS; Zysman-Colman, Eli; Wong, Michael Yin; (41 pag.)US2017/352818; (2017); A1;,
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Synthetic Route of 20249-16-5,Some common heterocyclic compound, 20249-16-5, name is 3-Oxocyclobutanecarbonitrile, molecular formula is C5H5NO, 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 mixture of lithium (Z)-l-(5-bromo-2-methoxypyridin-3-yl)-2- (dimethoxvphosphoryl)ethenolate (2.0 g, 5.8 mmol) and 3-oxocyclobutanecarbonitrile (1.1 g, 12 mmol) in p-dioxane (6 ml) was heated at 1200C by Microwave in Ih. The mixture was cooled, taken up in H2O, extracted with EtOAc (3x), dried over MgSO4, concentrated to provide the title compound. MS (m+1): 307.0.

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

Reference:
Patent; AMGEN INC.; WO2008/147544; (2008); A1;,
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Related Products of 60899-34-5,Some common heterocyclic compound, 60899-34-5, name is 1-Oxo-2,3-dihydro-1H-indene-4-carbonitrile, molecular formula is C10H7NO, 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 the stirred mixture of 50.0 gm of 4-cyano-l-indanone (Formula 3) (0.318 moles) and 500 ml of heptane, 60 gm of (S)-(-)-l-(4-methoxyphenyl)ethylamine (Formulal3) (0.398 moles, 1.25eq.) was added at ambient temperature. The resulting mixture was heated to 100-105C and water was removed azeotropically. After 15.0 hrs, the reaction mass was cooled to 25-30C and stirred for 1.0 hr. The product was filtered, washed with heptane and dried to obtain a light brown solid of compound of Formulal4(84.0 g, 90.93% yield) with HPLC purity 94.35% & SOR -72 (c=0.1 in CHC13at 20C).MR: 130.4-132.1C; IR (KBr, cm”1): 2226, 1661, 1611, 1513, 1245, 1030; 1H- NMR(CDC13): delta 8.11-8.09 (d, 1H, J=7.74Hz), 7.66-7.64 (d, 1H, J=7.47Hz),7.41-7.89 (m, 3H), 6.89-6.87 (d, 2H, J=8.50Hz), 4.66-4.61 (q, 1H, J=6.46, 12.96 Hz), 3.79 (s, 3H), 3.26-3.21 (m, 2H), 2.90-2.88 (m, 1H), 2.78-2.73 (m, 1H), 1.56-1.55 (d, 3H, J=6.49Hz);13C-NMR(CDCl3): 169.99, 158.48, 152.56, 141.66, 137.59, 134.28, 127.72, 127.66 (2C),127.15,117.12, 113.87(2C), 109.93, 61.56, 55.32, 27.85, 27.67, 24.77;MS (m/z): 291.1 [M+l]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Oxo-2,3-dihydro-1H-indene-4-carbonitrile, its application will become more common.

Reference:
Patent; SUVEN LIFE SCIENCES LIMITED; CHINNAPILLAI, Rajendiran; PERIYANDI, Nagarajan; JASTI, Venkateswaralu; (33 pag.)WO2019/58290; (2019); A1;,
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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. 4592-94-3, name is 3-(4-Bromophenyl)-3-oxopropanenitrile, This compound has unique chemical properties. The synthetic route is as follows., Safety of 3-(4-Bromophenyl)-3-oxopropanenitrile

General procedure: A dry 50 mL round flask equipped with a magnetic stirring bar was charged with a solution of 3-oxo-3-phenylpropanenitrile (0.87 g, 6.0 mmol), benzaldehyde (0.61 mL, 6.0 mmol), piperidine (0.12 mL, 0.2 equiv), and acetic acid (0.069 mL, 0.2 equiv) in toluene (20 mL). The mixture was heated at 60 C for 12 h. After cooling to room temperature, the mixture was washed with water (10 mL) and the aqueous phase was extracted with ethyl acetate (3×10 mL). The crude mixture was subjected to column chromatography (PE/EA 98:2) to yield 0.68 g (2.9 mmol, 48%) of the desired product as a white solid.

According to the analysis of related databases, 4592-94-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Liu, Wen; Zhou, Jing; Zheng, Changwu; Chen, Xingkuan; Xiao, Hua; Yang, Yingquan; Guo, Yinlong; Zhao, Gang; Tetrahedron; vol. 67; 10; (2011); p. 1768 – 1773;,
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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. COA of Formula: C12H6N2O

As shown in the above reaction formula,The compound of the formula (2-9-1) obtained in the above Preparation Example 2 (157.4 mg,0.1mmol),a compound of the formula (a-2-1) (78 mg, 0.4 mmol; purchased from TCI),Pyridine (0.8 mL, 0.96 mmol)Add chloroform (30 mL) to the reaction vessel and pass argon for 25 min.It was then refluxed at 65 C for 15 h.After cooling to room temperature (about 25 C), the reaction product was poured into 200 mL of methanol and filtered, and the resulting precipitate was chromatographed on silica gel (using 200-300 mesh).Separation of silica gel with eluent in a volume ratio of 1:2 petroleum ether/dichloromethane to give a blue solid(173.6 mg, yield 90.1%)

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; Peking University; Zhan Xiaowei; Wang Jiayu; (33 pag.)CN108794504; (2018); A;,
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Reference of 766-84-7, 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 766-84-7 as follows.

General procedure: An equimolar mixture of 2-aminoethanol (1.0 mmol) and sulfur(1.0 mmol) was heated under solvent-free condition at 50C. Nitrile (1.0 mmol) was then added to reaction mixture and refluxed at 80C. The progress of the reaction was monitored through TLC (n-hexane: EtOAc, 8:2). After completion of the reaction, excess of water was added, and the product was filtered (for solid). Further chromatographic purification afforded pure product. All the compounds were characterizedby infrared (IR) and 1H NMR and 13C NMR spectroscopic data, as well as by comparison with data of reported compounds.

According to the analysis of related databases, 766-84-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Bansal, Shivani; Gupta, Poonam; Halve; Phosphorus, Sulfur and Silicon and the Related Elements; vol. 191; 7; (2016); p. 971 – 974;,
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Related Products of 1558-82-3, A common heterocyclic compound, 1558-82-3, name is Ethyl N-cyanoacetimidate, molecular formula is C5H8N2O, 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 7 Preparation of 6-cyano-3,4-dihydro-2,2-dimethyl-trans-4-[N-methyl-(N-cyano-acetimidoyl)amino]-2H-benzo[b]pyran-3-ol To 2.80 g of ethyl N-cyanoacetimidate, 4.65 g of 6-cyano-3,4-dihydro-2,2-dimethyl-trans-4-methylamino-2H-benzo[b]pyran-3-ol was added, and the mixture was reacted under stirring at a temperature of from 100 to 120 C. for 2 hours. The reaction mixture was cooled, then dissolved in 100 ml of ethyl acetate, washed twice with a saturated sodium chloride aqueous solution and then dried over anhydrous sodium sulfate. Then, ethyl acetate was distilled off under reduced pressure. The residual solid was recrystallized from ethanol to obtain 2.34 g of the above identified compound in the form of crystals. Melting point: 250-251 C.

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; Kaken Pharmaceutical Co., Ltd.; US5095016; (1992); A;,
Nitrile – Wikipedia,
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