Month: June 2021

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. 4640-66-8, name is 4-Chlorophenacylcyanide belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. HPLC of Formula: C9H6ClNO

General procedure: To a 0.5-2.0ml vial with 1 mmol ketone (1 eq) issolved in 2-pentanol (1.66 M) was added 1.1 eq of aromatic aldehyde and catalytic piperidine (0.08 eq), stirring vigorously. After heating under muWave for 15min at 120 C, the reaction was cooled to r.t. and precipitate was vacuum filtered and washed with minimal, cold hexanes. After drying under vacuum, solid was analyzed via NMR, IR, and mp.

The synthetic route of 4640-66-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Deshpande, Shyam J.; Leger, Paul R.; Sieck, Stephen R.; Tetrahedron Letters; vol. 53; 14; (2012); p. 1772 – 1775;,
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Electric Literature of 6136-93-2, 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. 6136-93-2, name is 2,2-Diethoxyacetonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

a) To a solution of sodium methoxide (3.54 ml of a 25% wt. solution in methanol, 15.5 mmol) in methanol (80 ml) was added diethoxyacetonitrile (215 ml, 155 mmol) and the reaction mixture stirred for 4 hours at room temperature. Solid carbon dioxide was added and most of the methanol was removed in vacuo. Diethyl ether (30 ml) was added and the sodium carbonate removed by filtration. The residue was concentrated to afford methyl diethoxyacetimidate as a colourless oil (22 g, 92% yield) which was used with no further purification. MS (+ve ESI): 162 (M+H)+.

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

Reference:
Patent; AstraZeneca AB; US7235559; (2007); B1;,
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Synthetic Route of 39581-21-0, The chemical industry reduces the impact on the environment during synthesis 39581-21-0, name is N-Butyl-2-cyano-acetamide, I believe this compound will play a more active role in future production and life.

Example 11. Synthesis of 1,5-dibutyl-6-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile (AA11) [Show Image] Under the nitrogen gas atomosphere, a mixture of 28% sodium methoxide methanol solution (39 mL, 202 mmol) and ether (260 mL) was cooled to 3C in an ice bath, and the mixture of 2-heptanone (22.84 g, 200 mmol) and ethyl formate (16.15 g, 218 mmol) was dropped in about 20 minutes. After that, being stirred at the same temperature for 30 minutes, then the mixture was returned to be at room temperature and was further stirred for 20 hours afterwards. The precipitated product was removed by filtration and washed enough with ether (about 620 g). The mother liquor and the washing layer were combined and concentrated to give a crude product of 29.34 g. This crude product was repeatedly washed with hexane and ether, and powdered yellow ocher sodium salt of 3-[1-hydroxymethylidyne]-heptan-2-one (11.33 g, 34.5%) was obtained. This salt (2.13 g, 13 mmol) was suspended in DMF (10 mL), and n-butylcyanoacetamide (1.40 g, 10mmol), acetic acid (0.75 mL, 13.1 mmol), piperidine (0.20 mL, 2.02 mmol) were added in order at room temperature, and the mixture was refluxed at 135C for 7 hours. After that, the reaction mixture was let alone at room temperature for 13 hours and then poured into ice water, and the obtained mixture was extracted with ethyl acetate two times. The organic layer was washed with diluted hydrochloric acid one time and with water two times, and then died with anhydrous magnesium sulfare. The solvent was removed by distillation under reduced pressure, and a red oily crude product of 2.03 g was obtained. This crude product was refined by the silica gel chromatography, and the desired 1, 5-dibutyl-6-methyl-2-oxo-1, 2-dihydropyridine-3-carbonitrile (AA11, 420 mg, 17.3%) and 1-butyl-2-oxo-6-pentyl-1,2-dihydropyridine-3-carbonitrile (230 mg, 9.4%) were obtained. AA11 NMR:(CDC13) 0.95 (t, 3H, J=6.9, 0.98 (t, 3H, J=6.9), 1:5-1.7 (m, 8H), 2.42 (s, 3H), ca 2.4 (m, 2H), 4.08 (2H, m), 7.57 (1H, s)) 1-butyl-2-oxo-6-pentyl-1,2-dihydropyridine-3-carbonitrile NMR: (CDCl3) 0.94 (t, 3H, J=6.8), 0.98 (t, 3H, J=7.2), 1.3-1.7 (m, 10H), 2.66 (m, 2H), 4.04 (m, 2H), 6.11 (ABd, 1H, J=7.5), 7.67 (ABd, 1H, J=7.5)) was obtained.

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, N-Butyl-2-cyano-acetamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SHIONOGI & CO., LTD.; EP1806342; (2007); A1;,
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Electric Literature of 69395-13-7,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.

PREPARATION 13 Preparation of 4-carbamoylphenethyl bromide and 4-cyanophenethyl bromide STR36 A solution of phosphorus tribromide (5 g) in carbon tetrachloride (10 ml) was added, dropwise, to a solution of 4-cyanophenethyl alcohol (8.06 g) in carbon tetrachloride (60 ml). The mixture was heated under reflux for 4 hours. On cooling to room temperature, the mixture was poured onto ice (200 g). The layers were separated and the organic layer was washed with 10% aqueous sodium carbonate (50 ml) and brine (50 ml), dried (MgSO4) and concentrated in vacuo to give a colourless oil which solidified on standing. The solid was chromatographed on silica eluding with ethyl acetate containing hexane (20%). The fractions containing the less polar (higher Rf) product were combined and concentrated in vacuo to give 4-cyanophenethyl bromide as a yellow oil which solidified on standing, yield 8.9 g. The fractions containing the more polar (lower Rf) product were combined and concentrated in vacuo to give 4-carbamoylphenethyl bromide as a colourless solid, yield 0.47 g, m.p. 152-153.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-(2-Hydroxyethyl)benzonitrile, its application will become more common.

Reference:
Patent; Pfizer Inc.; US5340831; (1994); 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. 36282-26-5, name is 2-Bromo-4-fluorobenzonitrile, A new synthetic method of this compound is introduced below., COA of Formula: C7H3BrFN

To a solution of 2-bromo-4-fluorobenzonitrile (0.30 g, 1.5 mmol) and cyclopropanol (0.14 g, 2.4 mmol) in DMF (4 mL) wasadded Cs2CO3 (0.88 g, 2.7 mmol) in a 25 mL single-necked round-bottom flask. After that, themixture was stirred at 25 C under nitrogen. After stirring for 4 h, the resulting mixture was dilutedwith H2O (30 mL) and extracted with MTBE (10 mL×3). Then the combined organic phase waswashed with saturated aqueous NaCl (10 mL×3) and dried over Na2SO4 for 0.5 h. After that, theorganic phase was filtered under reduced pressure and the filtrate was concentrated underreduced pressure to give product as a yellow sticky substance. Then a mixture of 30 mL MTBE and100 mL n-hexane was added to dissolve the yellow sticky substance. Subsequently, the solutionwas cooled for 30 minutes with the mixture of water and ethanol. Lastly, the solution was filteredunder reduced pressure and the filtrate was dried naturally to obtain desired product in 80.3%yield (0.29g).

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:
Article; Jin, Hao; Gao, Zhuo; Zhou, Shaodong; Qian, Chao; Synlett; vol. 30; 8; (2019); p. 982 – 986;,
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Synthetic Route of 118431-88-2, The chemical industry reduces the impact on the environment during synthesis 118431-88-2, name is 3-Cyclopropyl-3-oxopropanenitrile, I believe this compound will play a more active role in future production and life.

3-Cyclopropyl-3-oxopropanenitrile (2.61 g, 24 mmol) and 4-hydrazinylbenzoic acid (3.0 g, 20 mmol) were dissolved in ethanol and the solution was heated at reflux for 12 h. The reaction mixture was concentrated and re-dissolved in methanol (30 mL) followed by addition of CF3CO2H (15 mL). The reaction mixture was stirred at room temperature for 12 h and the volatile components were removed on a rotary evaporator. The remaining residues were washed with ethyl acetate and 4-(5-amino-3-cyclopropyl- 1H-pyrazol-1-yl)benzoic acid was collected by filtration as a solid (6.44 g). ?H NMR (400 MHz, DMSO-d6): 8.02 (d, I = 8.70 Hz, 2H), 7.74 (d, I = 8.70 Hz, 2H), 5.30 (s, 1H), 1.85-1.75 (m, 1H), 0.95-0.85 (m, 2H), 0.73-0.65 (m, 2H). ESI-MS calculated for C,3H,4N302[M+Hj+ = 244.11; Observed: 244.1.

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-Cyclopropyl-3-oxopropanenitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; THE REGENTS OF THE UNIVERSITY OF MICHIGAN; WANG, Shaomeng; ZHAO, Yujun; ZHOU, Bing; AGUILAR, Angelo; (114 pag.)WO2016/138332; (2016); A1;,
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Related Products of 5414-21-1, A common heterocyclic compound, 5414-21-1, name is 5-Bromovaleronitrile, molecular formula is C5H8BrN, 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.

General procedure: To a solution of the tetrabutylammonium salt of 10-methylthio-7,8-dicarba-nido-caborane [1] (0.40 g, 0.95 mmol) in ethanol (10ml) chloroacetonitrile (0.06 ml, 0.95 mmol) was added. After stirring for 15 min, r.t., the mixture was heated under reflux for about 15 h and the solvent was evaporated under reduced pressure. The column chromatography on silica gel was used for the purification of the substance with CH2Cl2 as an eluent. Finally the solvent was removed in a vacuum to yield white solid (0.14 g, 68% yield).

The synthetic route of 5414-21-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Erokhina, Svetlana A.; Stogniy, Marina Yu.; Suponitsky, Kyrill Yu.; Kosenko, Irina D.; Sivaev, Igor B.; Bregadze, Vladimir I.; Polyhedron; vol. 153; (2018); p. 145 – 151;,
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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. 7357-70-2, name is 2-Cyanothioacetamide, A new synthetic method of this compound is introduced below., Application In Synthesis of 2-Cyanothioacetamide

[00288] 2-(((butylthio)methyl)thio)-4-(l,2-dimethyl-lH-imidazol-5-yl)-6-(thiazol-2- yl)nicotinonitrile. To a suspension of 3-(l,2-dimethyl-lH-imidazol-5-yl)-l-(thiazol-2- yl)prop-2-en-l-one (0.31 mmol, 72 mg) and 2-cyanothioacetamide (0.93 mmol, 93 mg, 3.0 equiv.) in EtOH (1.5 mL), a few drops of piperidine were added. After being stirred at 80C for 2 h, EtOH was evaporated and crude product was redissolved in CH3CN. Butyl(chloromethyl)sulfane (0.62 mmol, 85.5 mg) and Et3N (0.93 mmol, 94.1 mg, 130 mu,) were then added and the reaction mixture was stirred at 80C for 20 min. Once complete, the reaction was diluted with EtOAc and water. The organic phase was separated and aqueous layer was extracted twice with EtOAc. The combined extractions were washed with saturated NaCl solution, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography to give 99 mg of designed product (77%). FontWeight=”Bold” FontSize=”10″ H NMR (400 MHz, CDC13) delta 7.96 (d, / = 3.1 Hz, 1H), 7.85 (s, 1H), 7.56 (d, J = 3.1 Hz, 1H), 7.37 (s, 1H), 4.49 (s, 2H), 3.60 (s, 3H), 2.72 (t, / = 7.4 Hz, 2H), 2.48 (s, 3H), 1.62 (p, / = 7.3 Hz, 2H), 1.40 (h, / = 7.3 Hz, 2H), 0.90 (t, / = 7.3 Hz, 3H). ESI- MS (m/z): 416.6 [M+H]+.

The synthetic route of 7357-70-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CASE WESTERN RESERVE UNIVERSITY; BOARD OF REGENTS OF THE UNIVERSITY OF TEXAS SYSTEM; MARKOWITZ, Sanford D.; READY, Joseph; ZHANG, Yongyou; ANTCZAK, Monika; WILLSON, James K.V.; POSNER, Bruce A.; GREENLEE, William; (254 pag.)WO2016/168472; (2016); A1;,
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Adding a certain compound to certain chemical reactions, such as: 36282-26-5, name is 2-Bromo-4-fluorobenzonitrile, 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 36282-26-5, Recommanded Product: 2-Bromo-4-fluorobenzonitrile

Example 21 1-amino-6-fluoro-isoquinoline-4-carbonitrile; Palladium acetate (II) (0.556 g, 2.5 mmol) is added to a degassed solution of 2-bromo-4-fluoro-benzonitrile (10 g, 50 mmol), 3-ethoxyacrylonitrile (10.3 mL, 100 mmol) and triethylamine (14 mL, 100 mmol) in toluene (75 mL). The reaction mixture is stirred in an oil bath at 100 C. for 1 day. The reaction mixture is cooled to RT, filtered through a pad of Celite, and the filter cake is rinsed with EtOAc. After evaporation of the solvent, the residue is purified using a Biotage column eluted with 0-50% EtOAc/hexanes (20 CV) to afford 8.77 g (94%) of 2-(1-cyano-2-ethoxy-vinyl)-4-fluoro-benzonitrile. LC/MS: RT=3.38 min, no ionization.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Bromo-4-fluorobenzonitrile, and friends who are interested can also refer to it.

Reference:
Patent; Huang, Kenneth He; Veal, James; Barta, Thomas; Smith, Emilie D.; Ma, Wei; Ommen, Andy; US2008/70935; (2008); A1;,
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Reference of 2469-99-0, 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 2469-99-0 as follows.

General procedure: A mixture of(tetrahydropyran-4-yl)hydrazine (2.32 g, 20 mmol), 3-oxobutyronitrile (1.66 g, 20 mmol) in ethanol (50 mL) was stirred at 90 C for overnight. The reaction was cooled to room temperature and was concentrated. The residue was purified by flash HPLC(MeCN / H20 = 5/100 to 95/100) to afford the desired product 5-methyl-2-(tetrahydropyran-4-yl)-2H-pyrazol-3-ylamine (2.6 g yield: 72%) as white solid. MS: m/z 182.3 (M+H).

According to the analysis of related databases, 2469-99-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SANFORD-BURNHAM MEDICAL RESEARCH INSTITUTE; PINKERTON, Anthony, B.; HASSIG, Christian, A.; JACKSON, Michael, R.; ARDECKY, Robert, John; PASS, Ian; (436 pag.)WO2016/123392; (2016); A2;,
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