Author: Jessica.F

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. 76469-88-0, name is Methyl 4-(cyanomethyl)benzoate, A new synthetic method of this compound is introduced below., Application In Synthesis of Methyl 4-(cyanomethyl)benzoate

General procedure: To a solution of potassium tert-butoxide (8.0 g, 0.08 mmol,2.5 equiv) in THF (25 ml) at 30 C was added a solution of methyliodide (5.35 ml, 0.09 mmol, 3.0 equiv) and methyl 4-(cyanomethyl)benzoate (5.0 g, 0.03 mmol,1.0 equiv) in THF (25 ml) under nitrogen atmosphere over 20 min. The cooling bath was removed and the reaction mixture was allowed to warm to rt and stirred for 2 h.Following this the reaction was quenched with water (10 ml) and ethyl acetate was added and the organic and aqueous layers were separated. The organic layer was washed with water, brine, anddried over sodium sulfate. The organic solvent was removed under vacuum to obtain a violet residue that was purified by column chromatography using 20:80 EtOAc:Pet ether to obtain an off white solid that was crystallized in CHCl3:Pet ether to afford the title compound (4.0 g, 69%) as a white solid.

The synthetic route of 76469-88-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Kadam, Kishorkumar S.; Jadhav, Ravindra D.; Kandre, Shivaji; Guha, Tandra; Reddy, M. Mahesh Kumar; Brahma, Manoja K.; Deshmukh, Nitin J.; Dixit, Amol; Doshi, Lalit; Srinivasan, Shaila; Devle, Jayendra; Damre, Anagha; Nemmani, Kumar V. S.; Gupte, Amol; Sharma, Rajiv; European Journal of Medicinal Chemistry; vol. 65; (2013); p. 337 – 347;,
Nitrile – Wikipedia,
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Reference of 41963-20-6,Some common heterocyclic compound, 41963-20-6, name is 4-Bromo-3-methylbenzonitrile, molecular formula is C8H6BrN, 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 17 (10.0 g, 49.5 mmol) in carbon tetrachloride (200 mL) were added N-bromosuccinimide (8.81 g, 49.5 mmol) and 2,2′-azobis(isobutyronitrile) (414 mg, 5 mol %), and the mixture was refluxed for 3 h. Water was added, and the mixture was extracted with chloroform. The organic layer was washed with brine and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure. To the residue were added dimethylformamide (150 mL) and sodium acetate (20.5 g, 250 mmol), and the mixture was stirred at 80 C. overnight. Water was added, and the mixture was extracted with ether. The organic layer was washed with water and brine, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure. To the residue was added methanol (150 mL) and 1 mol/L sodium hydroxide (50 mL), and the mixture was stirred at room temperature for 1 h. The reaction mixture was concentrated to about a third of volume under reduced pressure. Water and hydrochloric acid were added, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the residue was purified by silica gel column chromatography (3:1 hexane/ethyl acetate) followed by trituration with dichloromethane to give 2-bromo-5-cyanobenzyl alcohol (4.63 g, overall 44%): 1H NMR (300 MHz, DMSO-d6) delta (ppm) 4.51 (d, J=5.9 hz, 2H), 5.67 (t, J=5.6 Hz, 1H), 7.67 (dd, J=8.2, 2.0 Hz, 1H), 7.80 (s, J=8.2 Hz, 1H), 7.83 (d, J=2.0 Hz, 1H).

The synthetic route of 41963-20-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Anacor Pharmaceuticals; US2007/265226; (2007); A1;,
Nitrile – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 1835-49-0, name is Tetrafluoroterephthalonitrile, 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 1835-49-0, name: Tetrafluoroterephthalonitrile

[Comparative Example 1]; The same operations as in Example 1 were carried out, except that the amount of the catalyst used was changed from 0.25 g to 0.05 g on a dry weight basis. After a lapse of 7.0 hours, absorption of hydrogen ceased. The quantity of hydrogen absorbed was 83% of the theoretical quantity of hydrogen absorbed. Treatment of the reaction solution was carried out in the same manner as in Example 1. EPO From the toluene extract, a small amount of a sample was withdrawn, and it was subjected to GC analysis. As a result of the analysis, the tetrafluoroterephthalonitrile as a raw material remained in an amount of 21.0 mol%, and tetrafluoroterephthalaldehyde was obtained in an amount of only 5.0 mol%. The amount of 2, 3, 5, 6-tetrafluorobenzene was 0.65 mol%, the amount of 2,3,5,6- tetrafluorobenzonitrile was 0.53 mol%, and 1-cyano- 2, 3, 5, 6-tetrafluorobenzaldehyde wherein a nitrile group on only one side had reacted was obtained in an amount of 63.1 mol%. On the other hand, the aqueous phase was neutralized and then subjected to GC analysis. As a result of the analysis, presence of 2.88 mol% of 2,3,5,6- tetrafluorobenzylamine was confirmed. The results are set forth in Table 2.; [Comparative Example 3]; The same operations as in Example 1 were carried out, except that the amount of sulfuric acid used was changed from 20.6 g to 5.15 g (50 mmol). After a lapse of 4.2 hours, absorption of hydrogen ceased. The quantity of hydrogen absorbed was 47% of the theoretical quantity of hydrogen absorbed. Treatment of the reaction solution was carried out in the same manner as in Example 1.From the toluene extract, a small amount of a sample was withdrawn, and it was subjected to GC analysis. As a result of the analysis, a peak of the tetrafluoroterephthalonitrile as a raw material was below EPO the detection limit, and tetrafluoroterephthalaldehyde was obtained in an amount of only 14.5 mol%. The amount of 2, 3, 5, 6-tetrafluorobenzene was 0.81 mol%, the amount of 2, 3, 5, 6-tetrafluorobenzonitrile was 0.67 mol%, and 1- cyano-2, 3, 5, 6-tetrafluorobenzaldehyde wherein a nitrile group on only one side had reacted was obtained in an amount of 54.0 mol%. On the other hand, the aqueous phase was neutralized and then subjected to GC analysis. As a result of the analysis, presence of 0.04 mol% of 2,3,5,6- tetrafluorobenzylamine was confirmed. The results are set forth in Table 2.

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

Reference:
Patent; SHOWA DENKO K.K.; WO2006/137347; (2006); A2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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. 3598-14-9, name is Phenoxyacetonitrile, A new synthetic method of this compound is introduced below., Quality Control of Phenoxyacetonitrile

(a) 5 millimoles (0.665 g) of phenoxy-acetonitrile are dissolved in 8 ml of anhydrous toluene at 0 C., under an argon atmosphere 7.5 millimoles of a toluenic solution 1.5 M of diisobutylaluminum hydride (5 ml) are added dropwise, at this temperature. The stirring is maintained for 1 hour at 0 C., then 5.9 ml (1.3 eq) of diethylaluminum cyanide are added. The reaction mixture is stirred for 3 hours at room temperature, then hydrolyzed with 4 ml of methanol and pasty sodium sulfate. After purification by high pressure liquid chromatography on silica, there are obtained 0.182 g of 2-amino-3-phenoxy-propionitrile, in form of a cream-colored solid-state product; M.P. 65 C., yield: 22%.

The synthetic route of 3598-14-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Albert Rolland S.A.; US4942221; (1990); A;,
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. 630-18-2, name is Pivalonitrile, A new synthetic method of this compound is introduced below., Product Details of 630-18-2

General procedure: To a solution of 4-bromobiphenyl 1a (3.0 mmol, 699.3 mg) in THF (3.0 mL) was added n-BuLi (4.5 mmol, 1.55 M in hexane, 2.87 mL) at 50 C. The obtained mixture was stirred for 30 min at 50 C under an argon atmosphere. Pivalonitrile (6.0 mmol, 498.8 mg) in THF (2.0 mL) was added to the mixture at 50 C and the obtained mixture was stirred for 30 min in the temperature range of 50 C to room temperature. MeOH (2.0 mL) was added to the mixture. Then, I2 (12.0 mmol, 3045.6 mg) and K2CO3 (12.0 mmol, 1658.4 mg) were added to the mixture at room temperature, and the obtained mixture was stirred for 6 h at 70 C. Sat. aq. Na2SO3 solution (20.0 mL) was added to the reaction mixture, and the product was extracted with AcOEt (10.0 mL x 3). The organic layer was dried over Na2SO4. After filtration and removal of the solvent, the residue was purified by silica-gel column chromatography (chloroform: n-hexane 1:1) to give 4-cyanobiphenyl 2a (451.6 mg, 84%).

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; Uchida, Ko; Togo, Hideo; Tetrahedron; vol. 75; 39; (2019);,
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654-70-6, name is 4-Cyano-3-trifluoromethylaniline, 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. category: nitriles-buliding-blocks

General procedure: A solution of NaHCO3 (0.82 g) in distilled water (4 mL) wasstirred for 10 min and to it was added DCM (4 mL) followed by thedifferent aniline 7e12 (2.4 mmol). The reaction mixture was cooledto 0 C, thiophosgene (0.3 mL, 3.7 mmol) was added dropwise over10 min and the reaction was then stirred at r.t. overnight. Themixture was then diluted with DCM (20 mL), washed with brine(20 mL), the organic layer was dried over Na2SO4 and concentratedto dryness.

The synthetic route of 654-70-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Pertusati, Fabrizio; Ferla, Salvatore; Bassetto, Marcella; Brancale, Andrea; Khandil; Westwell, Andrew D.; McGuigan, Christopher; European Journal of Medicinal Chemistry; vol. 180; (2019); p. 1 – 14;,
Nitrile – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 327-74-2, name is 2-Amino-5-cyanobenzotrifluoride, 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 327-74-2, Computed Properties of C8H5F3N2

Intermediate I-IX-6 (I-19): 4-iodo-3-(trifluoromethyl)benzonitrile To a slurry of 4-amino-3-(trifluoromethyl)benzonitrile (5.48 g; 29.5 mmol) in HBF4 (50 mL; 48%) at -10 C. was added NaNO2 (2.24 g; 32.4 mmol), portionwise over 10 min. The mixture was stirred 30 min, precipitated solids were collected by filtration (Note 1) and (without delay) added portionwise to a solution of KI (7.84 g; 47.2 mmol) in acetone/water (50 mL of a 40% v/v solution). The mixture was decolorized by addition of 10 wt % Na2S2O3, precipitate was collected by filtration, washed with water and slurried in PhMe. The slurry was concentrated to dryness, affording the title compound as a pale orange solid, used without further purification. 1H NMR (400 MHz, DMSO-d6) delta 7.83 (dd, J=8.1, 1.6 Hz, 1H), 8.27 (d, J=1.5 Hz, 1H), 8.37 (d, J=8.1 Hz, 1H). Note 1 Solid was not allowed to dry completely on the filter.

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

Reference:
Patent; Smithkline Beecham Corporation; US2011/124559; (2011); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 4640-66-8,Some common heterocyclic compound, 4640-66-8, name is 4-Chlorophenacylcyanide, molecular formula is C9H6ClNO, 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: Benzoyl acetonitrile (1, 0.5 mmol), cyclic 2-diazo-1,3-dicarbonyl compound (2, 1.25 mmol), [RhCp*Cl2]2 (0.025 mmol), CsOAc (0.25 mmol), Cu(OAc)2*H2O (1.0 mmol) and DCE (2 mL) were sequentially charged into a reaction tube. The tube was then sealed and the mixture was stirred at 80 C. Upon completion, it was cooled to room temperature, quenched with saturated brine (10 mL), and extracted with EtOAc (10 mL * 3). The combined organic phase was dried over anhydrous Na2SO4, and concentrated under reduced pressure. The residue was purified by silica gel chromatography using petroleum ether/ethyl acetate (5:1) as eluent to afford 3.

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

Reference:
Article; Zhang, Beibei; Li, Bin; Guo, Chenhao; Zhang, Xinying; Fan, Xuesen; Tetrahedron Letters; vol. 59; 32; (2018); p. 3094 – 3099;,
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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. 626-17-5, name is 1,3-Dicyanobenzene, A new synthetic method of this compound is introduced below., HPLC of Formula: C8H4N2

EXAMPLE 1 Hydrogenation of Isophthalonitrile Into a 100-ml autoclave, were charged 3.2 g of isophthalonitrile, 10.4 g of mesitylene, 10.0 g of liquid ammonia and 2.0 g of Pd-alumina pellets (manufactured by N.E. Chemcat Corporation; Pd content = 5% by weight), and the inner pressure was raised to 4.9 MPa by hydrogen gas. Then, the autoclave was shaken at 50C until the change of pressure was no longer appreciated. The analysis on the reaction product solution showed that the conversion of isophthalonitrile was 95.7 mol%, the yield of 3-cyanobenzylamine was 87.3 mol% and the yield of m-xylynenediamine was 7.7 mol%. The reaction solution separated from the catalyst was charged into a 100-ml autoclave together with 10.0 g of liquid ammonia and 2.0 g of Ni-diatomaceous earth pellets (manufactured by Nikki Chemical Co., Ltd.; Ni supported amount = 46% by weight). The inner pressure was raised to 4.9 MPa by hydrogen gas. Then, the autoclave was shaken at 50C until the change of pressure was no longer appreciated. The analysis on the reaction product solution showed that the conversion of isophthalonitrile was 100 mol%, the yield of 3-cyanobenzylamine was 0.2 mol% and the yield of m-xylynenediamine was 89.4 mol% EXAMPLE 4 Hydrogenation of Isophthalonitrile Into a 100-ml autoclave, were charged 3.2 g of isophthalonitrile, 10.4 g of mesitylene, 10.0 g of liquid ammonia and 2.0 g of Pd-alumina pellets (manufactured by N.E. Chemcat Corporation; Pd content = 5% by weight), and the inner pressure was raised to 4.9 MPa by hydrogen gas. Then, the autoclave was shaken at 50C until the change of pressure was no longer appreciated. The analysis on the reaction product solution showed that the conversion of isophthalonitrile was 95.7 mol%, the yield of 3-cyanobenzylamine was 87.3 mol% and the yield of m-xylynenediamine was 7.7 mol%. The reaction solution separated from the catalyst was charged into a 100-ml autoclave together with 10.0 g of liquid ammonia and 2.0 g of the catalyst A. The inner pressure was raised to 4.9 MPa by hydrogen gas. Then, the autoclave was shaken at 50C until the change of pressure was no longer appreciated. The analysis on the reaction product solution showed that the conversion of isophthalonitrile was 100 mol%, the yield of 3-cyanobenzylamine was 0.0 mol% and the yield of m-xylynenediamine was 91.1 mol%.

The synthetic route of 626-17-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MITSUBISHI GAS CHEMICAL COMPANY, INC.; EP1449825; (2004); A1;,
Nitrile – Wikipedia,
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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. 6011-14-9, name is 2-Aminoacetonitrile hydrochloride, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 2-Aminoacetonitrile hydrochloride

Example 6 N-(BOC) amino Acetonitrile To a stirred suspension of aminoacetonitrile hydrochloride (0.1 mol) and triethyl amine (0.25 mol) in THF (150 ml) is added a solution of di-t-butyldicarbonate in THF (75 ml) at room temperature under argon. After stirring overnight, the reaction mixture is filtered and concentrated to give the title compound as an oil.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 6011-14-9.

Reference:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts