Author: Jessica.F

Synthetic Route of 868-54-2,Some common heterocyclic compound, 868-54-2, name is 2-Aminoprop-1-ene-1,1,3-tricarbonitrile, molecular formula is C6H4N4, 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: In a 20 mL reaction vial, 4-hydroxycarbazole 1{1} (0.183g, 1mmol) with benzaldehyde 2{1} (0.106g, 1mmol), and 2-aminoprop-1-ene-1,1,3-tricarbonitrile 3 (0.132g, 1mmol) and ethanol (3 mL), as well as EtONa (0.064g, 1mmol)were mixed and then capped (the automatic mode stirring helped the mixing and uniform heating of the reactants). The mixture was heated for 15 min at 80 C under microwave irradiation. Upon completion, confirmed by TLC, the reaction mixture was cooled to room temperature. The crystalline solid product was collected by Buchner filtration, subsequently washed with two different solvents of ethanol and ethylether in sequence to give the pure product 4{1,1}.

The synthetic route of 868-54-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhang, Wenhui; Wang, Jianqiang; Mao, Jingpeng; Hu, Li; Wu, Xiaohua; Guo, Cheng; Tetrahedron Letters; vol. 57; 18; (2016); p. 1985 – 1989;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 2338-76-3, name is 3-(Trifluoromethyl)phenylacetonitrile, 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 2338-76-3, COA of Formula: C9H6F3N

A suspension of 56 g of sodium hydride at a concentration of 60percent in oil in 750 ml of DMSO and 250 ml of THF is admixed dropwise under an inert atmosphere and at AT with a solution of 120 g of 3-(trifluoromethyl)phenylacetonitrile in 250 ml of DMSO and then, slowly with a solution of 150 g of the compound obtained in the preceding step in 250 ml of DMSO and heated at 60° C. overnight. The reaction mixture is poured into an ice/H2O mixture and extracted with ether, the organic phase is washed with water and with saturated NaCl solution and dried over Na2SO4 and the solvent is evaporated under vacuum. The residue is chromatographed on silica gel, eluting with DCM and then with a DCM/AcOEt (80/20; v/v) mixture. This gives 191 g of the expected product, which crystallizes; m.p.=72-73° C.

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-(Trifluoromethyl)phenylacetonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; sanofi-aventis; US2005/176722; (2005); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

These common heterocyclic compound, 501-00-8, name is 2-(3-Fluorophenyl)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. Formula: C8H6FN

3-Fluorophenylacetonitrile (135 mg, 1 mmol),Benzyl alcohol (119 mg, 1.1 mmol), [Rh (cod) Cl] 2 (4.9 mg, 0.01 mmol, 1 mol%),Triphenylphosphine (26 mg, 0.1 mmol, 10 mol%),Potassium hydroxide (22 mg, 0.4 mmol, 40 mol%) were added successively to 10 ml of a microwave reaction tube.The mixture was reacted at 130 C for 2 hours and then cooled to room temperature. The solvent was removed by rotary evaporation and then the title compound was obtained by column chromatography (developing solvent: ethyl acetate / petroleum ether) in 89% yield.

The synthetic route of 2-(3-Fluorophenyl)acetonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Nanjing University of Science and Technology; Li, Feng; Lu, Lei; Wang, Nana; (15 pag.)CN105985256; (2016); A;,
Nitrile – Wikipedia,
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Reference of 612-24-8, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 612-24-8 name is 2-Nitrobenzonitrile, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

General procedure: The mixture of nitroarene 2 (1.0 mmol), PhSTMS 1(1.2 mmol, 1.2 equiv.), and TBAF (1.2 mmol, 1.2 equiv.) in degassedacetonitrile (2 mL) was stirred at room temperature under N2 for2 h and the reaction was monitored by TLC. After completion of thereaction, the solvent was evaporated under reduced pressure andthe residue purified by flash column chromatography on silica gelto give 3.

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

Reference:
Article; Yu, Xiao-Chun; Li, Bo; Yu, Bao-Hua; Xu, Qing; Chinese Chemical Letters; vol. 24; 7; (2013); p. 605 – 608;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Reference of 69395-13-7, A common heterocyclic compound, 69395-13-7, name is 4-(2-Hydroxyethyl)benzonitrile, molecular formula is C9H9NO, 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.

The following examples were prepared in a similar manner to that described in Scheme 38.; The mesylate prepared in step 1 (63 mg), piperazine Example 304 (80 mg), K2CO3 (97 mg), and NaI (40 mg) were taken up in CH3CN and heated at reflux (90 C., 18 h). The solution was partitioned between EtOAc and water. The aqueous layer was extracted with EtOAc. The combined organic layers were washed with brine and dried (MgSO4). Filtration and concentration gave a yellow oil. Purification via thin-layer preparative chromatography (7% EtOAc in CH2Cl2, SiO2) gave 100 mg (90%) of Example 323 as a colorless oil.

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; Gilbert, Eric J.; Greenlee, William J.; Miller, Michael W.; Scott, Jack D.; Stamford, Andrew W.; US2013/72468; (2013); A1;,
Nitrile – Wikipedia,
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Some common heterocyclic compound, 17626-40-3, name is 3,4-Diaminobenzonitrile, molecular formula is C7H7N3, 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. Recommanded Product: 3,4-Diaminobenzonitrile

To a solution of 3,4-diaminobenzonitrile (350 mg) in toluene (5.5 ml) was added CDI (554 mg), followed by stirring at 125C for 2 hours. To the reaction mixture was added a 1 M aqueous NaOH solution (0.117 ml), followed by extraction with EtOAc. The organic layer was dried over anhydrous MgsO4, and then filtered, and the filtrate was concentrated. It was powdered/washed with IPE/IPA to obtain 2-oxo-2,3-dihydro-1H-benzimidazole-5-carbonitrile (423 mg) as colorless powders.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 17626-40-3, its application will become more common.

Reference:
Patent; Astellas Pharma Inc.; EP2003132; (2008); A1;,
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Electric Literature of 6587-24-2,Some common heterocyclic compound, 6587-24-2, name is Methyl 2-cyanobenzoate, molecular formula is C9H7NO2, 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 2 2-{2-[6-Fluoro-3-(2-methyl-pyridin-3-yl)-4-oxo-3,4-dihydro-quinazolin-2-yl]-1-hydroxy-vinyl}-benzonitrile A solution of diisopropylamine (0.046 mL, 0.47 mmol) in tetrahydrofuran (2.7 mL) was chilled to -78 C. and butyllithium (0.13 mL, 0.32 mmol, 2.5 N in hexanes) was added dropwise. The solution was stirred 10 minutes and then a solution 6-fluoro-2-methyl-3-(2-methyl-pyridin-3-yl)-3H-quinazolin-4-one (0.10 g, 0.37 mmol) in tetrahydrofuran (0.7 mL) was added dropwise. The solution became intense red and was stirred 30 minutes. In a separate vessel a solution of methyl 2-cyanobenzoate (0.50 g, 3.1 mmol) in tetrahydrofuran (10 mL) was prepared and chilled to -78 C. The cold red anion solution was added to the cold methyl 2-cyanobenzoate solution via canula over 30 seconds. The resulting mixture was stirred 30 minutes at -78 C. and then quenched with saturated aqueous bicarbonate and warmed to ambient temperature. The mixture was diluted with water and repeatedly extracted with ethyl acetate. The combined extracts were washed with water and brine, dried over magnesium sulfate and concentrated. The residue was flash chromatographed on silica gel (20*100 mm) with elution proceeding as follows: 10% ethyl acetate/hexane (50 mL), nil; 20% ethyl acetate/hexane (50 mL), unweighedrecovered 3-(2-methyl-pyridin-3-yl)-6-fluoro-2-methyl-3H-quinazolin-4-one; 30% ethyl acetate/hexane (50 mL), nil; 40% ethyl acetate/hexane (50 mL), unweighed recovered methyl 2-cyanobenzoate; 50% ethyl acetate/hexane (50 mL), unweighed impurity; 60% ethyl acetate/hexane (50 mL), mixture of impurity and desired product; 70% ethyl acetate/hexane (50 mL), product. The product containing fractions were combined and concentrated. The residue was triturated with 1% ethyl acetate/ether and the yellow solid which formed was collected and dried to yield 0.017 g (10%) of 2-{2-[6-fluoro-3-(2-methyl-pyridin-3-yl)-4-oxo-3,4-dihydro-quinazolin-2-yl]-1-hydroxy-vinyl}-benzonitrile which had: mp 213-215 C.; 1 H NMR delta8.70 (d, J=4 Hz, 1 H), 7.85 (dd, J=3, 8 Hz, 1 H), 7.67 (d, J=7 Hz, 1 H), 7.60 (d, J=9 Hz, 1 H), 7.58-7.38 (m, 6 H), 4.94 (s, 1 H), 2.44 (s, 3 H). Analysis calculated for C23 H15 FN4 O2.0.25 H2 O: C, 68.57; H, 3.88; N, 13.91. Found: C, 68.52, 68,91; H, 4.13, 4.21; N, 13.25, 13.28.

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

Reference:
Patent; Pfizer Inc; US6060479; (2000); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Application of 3759-28-2, These common heterocyclic compound, 3759-28-2, name is 2-(Cyanomethyl)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.

General procedure: A mixture of 1-aryl/alkyl-3,3-bis-methylsulfanyl-propenone (1.0 mmol), 2-cyanomethyl-benzonitrile (1 mmol, 142.0 mg), and powdered KOH (2 mmol, 112.0 mg) in dry DMSO (5 mL) was stirred at room temperature for 2 h. Completion of reaction was monitored by TLC. After completion, reaction mixture was poured onto ice-water with constant stirring and then neutralized with 10% HCl. The precipitate obtained was filtered, washed with water and dried over dry sodium sulfate. Many compounds were purified by recrystallization in dry methanol. Some compounds were purified through column chromatography using 15% ethylacetate in hexane as an eluent. Characterization data for some of the synthesized compounds are reported earlier.17

Statistics shows that 2-(Cyanomethyl)benzonitrile is playing an increasingly important role. we look forward to future research findings about 3759-28-2.

Reference:
Article; Singh, Surjeet; Althagafi, Ismail; Yadav, Pratik; Panwar, Rahul; Kumar, Abhinav; Pratap, Ramendra; Tetrahedron; vol. 70; 46; (2014); p. 8879 – 8884;,
Nitrile – Wikipedia,
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Related Products of 499983-13-0, 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 499983-13-0 as follows.

Ethylene carbonate (370.2 g, 4.204 mol, 30.0 eq.) was loaded in a 500 ml reactor at room temperature and heated to an internal temperature of 40C till all the solid melted. Then 1.4 g of PEG-200 (0.007 mol, 0.05 eq.) and 30.0 g of 4-bromo-3-fluorophenylacetonitrile (0.140 mol, 1.0 eq.) were charged in the reactor. Potassium tert-butoxide (31.4 g, 0.280 mol, 2.0 eq.) was added portion-wise, under stirring, to the resulting clear colorless solution. The internal temperature rose up to 60C. Then, the mixture was heated to 130C and kept under stirring for 8 hours. The mixture was cooled to 40C and then 105 g of toluene and 240 g of deionised water were added. The mixture was kept under stirring for 15 minutes at 40C and then stirring was stopped. After 15 minutes two layers were separated: a lower organic clear red phase and an upper aqueous colorless phase. The organic solution was reloaded into the reactor and heated to an internal temperature of 40C. 240 g of deionised water were added. The mixture was kept under stirring for 15 minutes at 40C and then stirring was stopped. After 30 minutes the yellowish opalescent aqueous layer (lower) was discarded and the organic phase was washed again two times with 240 g of deionised water. After 30 minutes, the yellowish opalescent aqueous layer was discarded. The organic solution was warmed to 80C and the volatile solvents were removed under reduced pressure until 36 ml as the final volume. A solution 9.6 g of isopropyl alcohol was added. The solution was cooled from 80C to 50C in 30 minutes and a small amount of seed was added. The crystallization mixture was cooled from 50C to 0C in 60 minutes. The suspension was stirred for at least 60 minutes then filtered washing three times with 9.0 g of a toluene/isopropyl alcohol mixture (1/1.25 w/w). The wet product was dried under vacuum at 40C for 15-18 hours. 22.7 g of a pale yellow solid were obtained (purity = 99,94%; molar yield = 68%).

According to the analysis of related databases, 499983-13-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ZaCh System S.p.A.; Verzini, Massimo; Cotarca, Livius; Guidi, Alberto; Melloni, Alfonso; Maragni, Paolo; EP2818460; (2014); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

These common heterocyclic compound, 154607-01-9, name is 4-Bromo-2-chlorobenzonitrile, 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. COA of Formula: C7H3BrClN

Preparation of Intermediate 4-Bromo-2-chloro-benzaldehvde (l-3a):The 4-Bromo-2-chloro-benzaldehyde was prepared using procedures described in J. Med. Chem. 1981, 24, 1155-1161.4-bromo-2-chloro-benzonitrile (7.05g, 32.5 mmol) was dissolved in toluene (60 mL) and dichloromethane (1OmL) and cooled to -600C as a 1.5M solution of diisobutylaluminum hydride in toluene (33.4 ml, 49.8 mmol) was added dropwise over 30 minutes keeping the temperature between -60 and – 500C. The reaction was allowed to warm slowly to room temperature and stirred for an additional 3 hours. The reaction was quenched using ethyl acetate and stirred for 20 minutes before the addition of 1 N hydrochloric acid at O0C. The reaction was then allowed to warm slowly to room temperature. The reaction was extracted using ethyl acetate (2 times). Removal of the solvent provided the title compound (l-3a). 1H NMR (CDCI3): delta 7.52 (dd, 1H), 7.64 (d, 1H), 7.77 (d, 1H), 10.4 (s, 1 H)

The synthetic route of 4-Bromo-2-chlorobenzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER PRODUCTS INC.; WO2008/59335; (2008); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts