Month: September 2021

Electric Literature of 5312-97-0, A common heterocyclic compound, 5312-97-0, name is 2,5-Dimethoxybenzonitrile, molecular formula is C9H9NO2, 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: Dry HCl (g) was bubbled into a stirred solution of nitrile (10 mmol) in propargyl alcohol (1 equiv.) at 0 C for 10 minutes. The vial was capped and stirred warming to rt overnight (18 h). Air was bubbled through the resulting mixture for 10 minutes. The mixture was then diluted with Et2O (20 mL), and the resulting precipitate was collected by vacuum filtration, and washed with Et2O (20 mL). This salt was suspended in CHCl3 (50 mL), to which saturated NaHCO3 (50 mL) was then added. After mixing, the layers were separated, and the aqueous layer was extracted with an additional amount of CHCl3 (20 mL). The combined organic layers were dried over Na2SO4 and concentrated to afford the imidate.

The synthetic route of 5312-97-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Fricke, Patrick J.; Stasko, Jenna L.; Robbins, Dylan T.; Gardner, Alexander C.; Stash, Jacqueline; Ferraro, Mark J.; Fennie, Michael W.; Tetrahedron Letters; vol. 58; 48; (2017); p. 4510 – 4513;,
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Synthetic Route of 89001-53-6, A common heterocyclic compound, 89001-53-6, name is 2-Methyl-4-nitrobenzonitrile, 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.

b) Preparation of 5,6-Dihydro-5-oxo-9-nitro-indeno[1,2-c]isoquinoline (53a); To a refluxing mixture of 2-methyl-4-nitro-benzonitrile (32.4 g, 0.2 mol) and NBS (44.470 g, 0.25 mol) in CCl4 (300 ml) was added AIBN (0.325 g) and the resultant reaction mixture was refluxed for 4 hours. The reaction mixture was treated with AIBN (0.325 g, 31 mmol) and refluxed further for 4 hours. The reaction mixture was filtered, and the filtered succinimide was washed with CCl4. The filtrate was concentrated in vacuo to provide a bromo compound (46 g). The bromo compound was dissolved in MeCN (200 ml), and to the reaction mixture was added homophthalic anhydride (30.780 g, 0.19 mol) at room temperature and under inert atmosphere. The reaction mixture was then treated with a solution of triethylamine (84 ml, 0.6 mol) in acetonitrile (100 ml). The reaction mixture was refluxed for 8 hours. The precipitate that formed was removed by filtration and washed with MeCN (100 ml). The washed precipitate was suspended in DMF (300 ml), which was heated at 130 C., then cooled and filtered. The resultant solid was washed with DMF (100 ml) and dried under vacuum to provide Compound 53a as a pale yellow solid (18.310 g, 33%). 1H-NMR (DMSO-d6): delta, 4.09 (s, 2H), 7.56 (m, 1H), 7.81-7.82 (m, 2H), 8.17 (d, J=8.4 Hz, 1H), 8.26-8.34 (m, 2H), 8.44 (s, 1H), 12.47 (s, 1H).

The synthetic route of 89001-53-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Inotek Pharmaceuticals Corporation; US2006/287313; (2006); A1;,
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Synthetic Route of 103146-25-4, These common heterocyclic compound, 103146-25-4, name is 4-(4-(Dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl)-3-(hydroxymethyl)benzonitrile, 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 test tube equipped with a stopper was charged with 10 mg (0.029 m mol) of [(=T :)-4-] [4-dimethylamino-1- (4′-fluorophenyl)-1-hydroxybutyl]-3-hydroxymethylbenzonitrile, 10 mg of Novozym 435 (product of NOvozymes), 33 mg (0.29 [M MOL)] of vinyl butyrate and 1 ml of various kinds of solvents, and stirred at [30C] for 16 hours. After the reaction, converted ratios and optical purities were analyzed and E-values were calculated. The results are shown in Table 9.

The synthetic route of 103146-25-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; H. LUNDBECK A/S; WO2004/14821; (2004); A1;,
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Adding a certain compound to certain chemical reactions, such as: 3598-13-8, name is 2-(4-Chlorophenoxy)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 3598-13-8, HPLC of Formula: C8H6ClNO

2-(3-(hydroxymethyl)-6-nitro-2,3-dihydrobenzo[b][l,4]dioxin-5-yl)acetonitrile: A solution of racemic (7-nitro-2,3-dihydrobenzo[b][l,4]dioxin-2-yl)methanol (1.00 g, 4.73 mmol) and 4-chlorophenoxyacetonittauile (827 mg, 4.94 mmol) in DMF (12 mL) was added dropwise to a solution of potassium tert-butoxide (2.12 g, 18.9 mmol) in DMF (20 mL) at -5- 00C. After the addition was complete (7 minutes), the reaction mixture was stirred for 1 hour at -5-00C. The reaction mixture was acidified with 1 N HCl before drowning into water (200 mL). The mixture was extracted with EtOAc (3 x 100 mL) and the combined organic layers were washed with IN NaOH (3 x 50 mL) to remove most of the 4-chlorophenol. After removal of solvent, the residue was purified by flash chromatography on silica gel, gradient elution using 2:3, 1 :1, 3:2, 100:0 ethyl acetate/hexane, to give 139 mg, 14% recovered starting material and 804 mg, 68% yield of the title compound as a solid. 1H NMR (CDCl3) 5 7.77 (IH, d, J=9.12 Hz); 7.01 (IH, d, J=9.12 Hz); 4.50-4.40 (2H, m); 4.30-3.91 (5H, m); 2.25-2.21 (IH, m). 13C NMR (CDCl3) 5 148.07, 141.71, 141.55, 119.44, 117.07, 116.96, 115.71 , 74.36, 65.31, 61.18, 14.89.

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-Chlorophenoxy)acetonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; WYETH; WO2007/139998; (2007); A2;,
Nitrile – Wikipedia,
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Related Products of 50594-78-0, A common heterocyclic compound, 50594-78-0, name is 5-Fluoro-2-nitrobenzonitrile, molecular formula is C7H3FN2O2, 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 5-fluoro-2-nitrobenzonitrile (9.7Og, 58mmol) and 10% palladium on charcoal (Ig) in MeOH (20OmL) was stirred under an atmosphere of hydrogen for 5h. The mixture was filtered through a pad of celite and evaporated. The residue was triturated with Et2O-hexane EPO (4OmL / 1:3) and filtered. Evaporation of the filtrate afforded the product as a pale yellow solid (4.65g, 58%). 1H NMR (CDCl3) 7.09 (2H, m), 6.71 (IH5 m), 4.29 (2H, bs).

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; JAMES BLACK FOUNDATION; WO2006/129120; (2006); A2;,
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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. 630-18-2, name is Pivalonitrile, A new synthetic method of this compound is introduced below., Computed Properties of C5H9N

H. 7-(3-(1,1-Dimethylethyl-1,2,4-oxadiaz-5-yl)-1-(4-methylpiperazin-1-yl)naphthalene Sodium (0.112 g, 4.9 mmol), hydroxylamine hydrochloride (0.35 g, 5 mmol), and trimethylacetonitrile (0.334 g, 2.0 mmol) and methanol (5 mL) were used to prepare trimethylacetamidoxime (0.35 g, 100%) as described above.

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; Pfizer Inc.; US6166020; (2000); A;,
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Reference of 118431-88-2, A common heterocyclic compound, 118431-88-2, name is 3-Cyclopropyl-3-oxopropanenitrile, molecular formula is C6H7NO, 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.

Methyl hydrazine (lmL) was added to a solution of 3-cyclopropyl-3-oxopropanenitrile (lg, 9.l7mmol) in ethanol (l5mL). The resulting reaction mass was heated to reflux for 12h. The reaction mass was quenched with ice cold water and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulphate and concentrated under reduced pressure to afford the title compound (1.lg, 97%) LCMS: mlz = 138 (M+H)t

The synthetic route of 118431-88-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AURIGENE DISCOVERY TECHNOLOGIES LIMITED; SAMAJDAR, Susanta; PODDUTOORI, Ramulu; PANDIT, Chetan; MUKHERJEE, Subhendu; GOSWAMI, Rajeev; (126 pag.)WO2016/193939; (2016); A1;,
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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. 78473-00-4, name is 4-Amino-3,5-dichlorobenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. HPLC of Formula: C7H4Cl2N2

nto a 1000 mL three-neck flask were put 9.4 g (50 mmol) of 4-amino-3,5-dichlorobenzonitrile, 26 g (253 mmol) of isobutylboronic acid, 54 g (253 mmol) of tripotassium phosphate, 2.0 g (4.8 mmol) of 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (S-phos), and 500 mL of toluene. The atmosphere in the flask was replaced with nitrogen, and this mixture was degassed while being stirred under reduced pressure. After the degassing, 0.88 g (0.96 mmol) of tris(dibenzylideneacetone)palladium(0) was added, and the mixture was stirred under a nitrogen stream at 130 C. for 8 hours to be reacted. Toluene was added to the obtained reacted solution, and the mixture was filtered through a filter aid in which Celite (Catalog No. 531-16855, manufactured by Wako Pure Chemical Industries, Ltd. (the same applies to Celite in the following description)), aluminum oxide, and Celite were stacked in this order. the obtained filtrate was concentrated to give an oily substance. The obtained oily substance was purified by silica column chromatography. Toluene was used as a developing solvent. The resulting fraction was concentrated to give 10 g of a yellow oily substance in a yield of 87%. The obtained yellow oily substance was identified as 4-amino-3,5-diisobutylbenzonitrile by nuclear magnetic resonance (NMR).

The synthetic route of 78473-00-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Semiconductor Energy Laboratory Co., Ltd.; Watabe, Takeyoshi; Watabe, Satomi; Yoshizumi, Hideko; Hara, Tomoka; Yamada, Yui; Ishisone, Takahiro; Kido, Hiromitsu; Suzuki, Kunihiko; Seo, Satoshi; (88 pag.)US2018/62084; (2018); A1;,
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Adding a certain compound to certain chemical reactions, such as: 147754-12-9, name is 4-Fluoro-2-methylbenzonitrile, 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 147754-12-9, Recommanded Product: 4-Fluoro-2-methylbenzonitrile

a) 1.35 g 4-Fluoro-2-methyl-benzonitrile, dissolved in DMF, was added to 2.11 g 4-Hydroxy-piperidine-1-carboxylic acid tert-butyl ester and 0.6 g sodium hydride in 30 mL DMF. The mixture was stirred at room temperature (rt) until the reaction was complete. The reaction was quenched with water. The aqueous layer was extracted with ethylacetate (AcOEt) or methyl tert. butyl ether (MTB ether). The combined organic layers were washed with brine, dried and concentrated to to give 2.6 g (yield 81percent) 4-(4-Cyano-3-methyl-phenoxy)-piperidine-1-carboxylic acid tert-butyl ester. Mass: (C18H24N2O3): calcd. 316, found 261 [M+H-t(C4H9)]+

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; SANOFI; GESSLER, Simon; WOLLMANN, Theo; US2013/12711; (2013); A1;,
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Adding a certain compound to certain chemical reactions, such as: 1572-52-7, name is 2-Methylenepentanedinitrile, 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 1572-52-7, Product Details of 1572-52-7

(0099) At 0 C., 8.96 g (56.07 mmol) of bromine are slowly added dropwise to a solution of 7.0 g (65.96 mmol) of 2-methylenepentanedinitrile. The reaction mixture is then stirred at 35 C. for 2 hours. The reaction mixture is then once more cooled to 0 C., and 6.52 g (85.75 mmol) of 1-hydroxyurea are added. A solution of 7.13 g (178.09 mmol) of NaOH in 15 ml of water is then slowly added dropwise at 0 C., and the mixture is boiled under reflux for 3.5 hours. The solvents are concentrated and the residue is then dissolved in 20 ml of water and extracted three times with in each case 10 ml of dichloromethane. The combined organic phases are dried over sodium sulfate and concentrated. Yield: 2.8 g (29%). (0100) 1H-NMR, DMSO-d6, 400 MHz: 8.24 (s, 1H), 5.56 (bs, 2H), 2.71 (t, 2H), 2.60 (t, 2H).

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

Reference:
Patent; BAYER CROPSCIENCE AG; KOEHN, Arnim; AHRENS, Hartmut; BRAUN, Ralf; HEINEMANN, Ines; TIEBES, Joerg; WALDRAFF, Christian; DIETRICH, Hansjoerg; GATZWEILER, Elmar; ROSINGER, Christopher Hugh; SCHMUTZLER, Dirk; US2015/307462; (2015); A1;,
Nitrile – Wikipedia,
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