Tag: M.W=100-200

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. 120351-94-2, name is 3-(2-Aminoethoxy)benzonitrile, A new synthetic method of this compound is introduced below., COA of Formula: C9H10N2O

Step 1 Synthesis of N-[2-(3-cyanophenoxy)ethyl]-(1S)-10-camphorsulfonamide: 700 mg (4.32 mmol) of 3-(2-aminoethoxy)benzonitrile was dissolved in 20 ml of DMF. 0.75 ml (4.32 mmol) of diisopropylethylamine and a solution of 1.08 g (4.32 mmol) of (1S)-(+)-10-camphorsulfonyl chloride in 5 ml of DMF were added to the solution at 0C, and they were stirred for 4 hours. The crude product was obtained by the same isolation process as that of step 1 in Example 1 with ethyl acetate as the extractant. After the purification by the silica gel column chromatography, the title compound was obtained. Yield: 1.41 g (3.75 mmol) (87 %) MS (ESI, m/z) 377 (MH+) H-NMR (CDCl3) delta 0.88 (3H, s), 1.04 (3H, s) 1.47 (1H, ddd), 1.89-2.15(5H, m), 2.33 (1H, td), 2.98 (1H, d), 3.46 (1H, d), 3.59 (2H, dt), 4.14 (2H, t), 6.00(1H, t), 7.15 (1H, d), 7.18(1H, s), 7.26 (1H, d), 7.39 (1H,t)

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; Ajinomoto Co., Inc.; EP976722; (2000); A1;,
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Application of 1897-52-5, 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. 1897-52-5, name is 2,6-Difluorobenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a piperidine (5 mL, 50.6 mmol) solution in toluene (20 mL) was added MeMgCI (3.0 M in THF, 16.9 mL, 50.6 mmol). The solution was heated to 50 C, for two hours before allowing to cool to room temperature and transferring using a cannula to a solution of 2,6-difluorobenzonitrile (7.03 g, 50.6 mmol) in toluene (20 mL). The solution was stirred for 16 h at room temperature after which time the reaction was quenched by addition of water (1 mL). After stirring for an hour, anhydrous sodium sulfate was added and the solution was then filtered to remove salts. The clear solution was then washed with brine (2 x 40 mL) before removal of the volatiles under reduced pressure to yield a viscous yellow oil. This was then diluted with another portion of hexanes (15 mL) and placed at -20 C for two days resulting in crystallization of the desired product. Yield = 8.7 g (77 %). 1H NMR (300 MHz) (CDCb) delta (ppm): 7.24 (m, 1 H, Ar); 6.86 (m, 2 H, Ar); 6.06 (m, 1 H, NH), 3.33 (br m, 4 H, NCH2), 1.53 (br m, 6 H, CH2CH2CH2) ppm. 19F- NMR (282 MHz, CDCI3) delta: -1 13.30 ppm.

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, 2,6-Difluorobenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; LANXESS ELASTOMERS B.V.; KARBAUM, Peter; SCOTT, Richard, Thomas, William; VAN DE MOOSDIJK, John; (39 pag.)WO2016/41818; (2016); A1;,
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Synthetic Route of 35704-19-9, 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. 35704-19-9, name is N-(4-Cyanophenyl)acetamide belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

The R-N02 or R-CN (1 mmol), G-NiPd catalyst (4mg), and water:methanol (3:7) were stirred 5 mm in a 100 mL thermolysis tube at room temperature. Next, AS (3 mmol) was added to the reaction mixture and the vessel was closed. Reaction was then continued under vigorous stirring at room temperature. The progress of the catalytic reaction was monitored by thin layered chromatography (TLC). Most reactions completed over the time period of 5-30 mi Afier completion of the reaction, the catalysts were removed by centrifugation at 7000 rpm and washed three times with water or methanol. Then, the catalysts were allowed to dry for further uses. The solvent was removed by using a rotary evaporatot Finally, the crude residue was directly purified by colunm chromatography on silica gel using acetone. The yields of the reduced compounds were determined by ?H and ?3C NMR with D20, DM50, CD3OD or CDC13 as the solvent depending on the product separated.

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-(4-Cyanophenyl)acetamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BROWN UNIVERSITY; Sun, Shouheng; Ho, Sally Fae; Mendoza-Garcia, Adriana; (10 pag.)US2016/279619; (2016); A1;,
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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 654-70-6 as follows. Formula: C8H5F3N2

Example 43 (General Procedure (D)) 3-Tert-Butyl-5-Chloro-N-(4-Cyano-3-Trifluoromethyl-Phenyl)-2-Hydroxy-6-Methyl-Benzamide. The title compound was prepared from 5-chloro-3-tert-butyl-6-methylsalicylic acid and 4-cyano-3-trifluoromethylanilin. 1H-NMR: (CDCl3, 400 MHz): delta ppm 1.40 (s, 9 H) 2.53 (s, 3 H) 7.39 (s, 1 H) 7.66 (s, 1 H) 7.86 (d, J=8,3 Hz, 1 H) 8.97 (d, J=8,3 Hz, 1 H) 8.05 (s, 1 H) 9.05 (s, 1H).

According to the analysis of related databases, 654-70-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Hansen, Birgit Sehested; Hansen, Thomas Kruse; Tullin, Soren; Colding-Jorgensen, Morten; US2004/138301; (2004); A1;,
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Electric Literature of 40497-11-8, 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. 40497-11-8, name is Ethyl 2,3-dicyanopropanoate belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

300L glass lined kettle add 80.142kg of absolute ethanol, stir,Then add 30.1% hydrogen chloride ethanol 45.579kg (containing hydrogen chloride 376.273mol), Configured to about 11% hydrogen chloride ethanol,Then add 98.0% 2,6-dichloro-4-trifluoromethylaniline 47.060kg (200.504mol),Control temperature 30 40 , after stirring and dissolving,Add 98.0% ethyl 2,3-dicyanopropionate 31.026kg (199.838mol), stir well,It is prepared as a raw material liquid and stored at about 20 .Add 25.136 kg of absolute ethanol to the axial-flow stirring tank, stir, and add 16.523 kg (234.704 mol) of 98.0% sodium nitrite, keeping the stirring configuration as a suspension.Pass the frozen brine at about 0 C into the reactor casing described in Example 1 above, and adjust the flow rate of the frozen brine after normal circulation. Then, the raw material liquid described in this example was pumped into the reactor described in Example 1 with a diaphragm metering pump at a flow rate of 5.00 l / min, and the suspension liquid in this example was pumped using a diaphragm metering pump at a flow rate of 1.00 l / min. Into the reactor described in Example 1, the reactor outlet was connected to a 500L glass-lined kettle. The flow rate of frozen brine is adjusted to control the temperature of the first stage of the reactor at 10-15 C, the temperature of the second stage at 15-20 C, and the temperature of the third stage at 20-25 C. Monitor the pH value and nitrite concentration, fine-tune the suspension flow, control the nitrite concentration at the outlet of the reactor to 0.1 to 0.5%, and the pH value to 1 to 5, after starting the discharge,Sampling HPLC to detect 2,6-dichloro-4-trifluoromethylaniline content of 0.169% (Figure 1, 12.329min is the raw material peak).After continuing to feed until the material is pumped, add 50 liters of 10% hydrogen chloride ethanol to the 300L mentioned in this example, add 10 liters of absolute ethanol to the stirring tank, and continue to use 5.00 liters / min and 1.00 liters / min. The partial flow rate is pumped into the reactor. After the pumping is completed, the contents of the reactor are purged with nitrogen.

The synthetic route of Ethyl 2,3-dicyanopropanoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Jiangsu Youpu Biochemical Technology Co., Ltd.; Zhang Jiqian; Shi Yunyun; Ma Chenglong; Jiang Fei; Gu Jialin; (10 pag.)CN111018786; (2020); A;,
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Adding a certain compound to certain chemical reactions, such as: 6575-00-4, name is 3,5-Dichlorobenzonitrile, 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 6575-00-4, COA of Formula: C7H3Cl2N

To a 250 mL round bottom flask charged with 3,5-dichlorobenzonitrile (42; 7.31 g; 34.90 mmol) and maintained under an argon atmosphere was added DMF (70 mL). The flask was cooled to 0 C. and powdered sodium methoxide (1.88 g; 34.90 mmol) was added in two portions 15 min apart. The homogeneous mixture was allowed to warm to room temperature and stirred for 24 h. The solution was cooled to 0 C. and aqueous 10% HCl (20 mL) was added dropwise via an addition funnel after which the reaction was warmed to RT. The mixture was extracted with EtOAc and the combined extracts washed sequentially with water and brine. The organic phase was dried (Na2SO4), filtered, and volatile solvents were removed in vacuo. The resulting solid was recrystallized from hexanes to afford 3-chloro-5-methoxybenzonitrile (43, 4.2 g; 72%).

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, 3,5-Dichlorobenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Roche Palo Alto LLC; US2005/234236; (2005); A1;,
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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. 621-50-1, name is 2-(3-Nitrophenyl)acetonitrile, A new synthetic method of this compound is introduced below., name: 2-(3-Nitrophenyl)acetonitrile

Step a: Synthesis of 2-methyl-2-(3-nitrophenyl)propanenitrile To an ice-cold slurry of 50% NaH (6.84 g, 171 mmol) in anhydrous THF (30.0 ml) was slowly added a solution of 2-(3-nitrophenyl)acetonitrile (4.2 g, 25.9 mmol) in anhydrous THF (30 ml). After 30 min, methyl iodide (12.63 ml, 202 mmol) was slowly added. The reaction mixture was allowed to warm to room temperature and stirred overnight. It was then quenched with ice-water. The reaction mixture was then extracted with ethyl acetate, the organic layer was separated and washed with water, dried over anhydrous sodium sulphate; filtered and concentrated to get crude oil. The crude oil was purified by column chromatography over silica gel by eluting with ethyl acetate/hexane (5:95) gave 2-methyl-2-(3-nitrophenyl) propanenitrile (2.1 g). 1HNMR (400 MHz, CDCl3), delta 8.33-8.32 (m, 1H), 8.24-8.21 (m, 1H), 7.92-7.89 (m, 1H), 7.63 (t, J=8.00 Hz, 1H), 1.82 (s, 6H). GCMS:190.11[M+]

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; Dave, Bhavesh; Banerjee, Rakesh Kumar; Phukan, Samiron; Khoje, Abhijit Datta; Hangarge, Rajkumar; Jadhav, Jitendra Sambhaji; Palle, Venkata P.; Kamboj, Rajender Kumar; US2015/133424; (2015); A1;,
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Reference of 6283-71-2, 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. 6283-71-2 name is Dimethyl 2-cyanosuccinate, 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.

To a solution of dimethyl 2-cyanobutanedioate (CAS 6283-71-2, 10.0 g, 58.4 mmol, 1.00 eq) in methanol (60.0 niL) and water (60.0 mL) was added triethylamine (8.87 g, 87.6 mmol, 12.1 mL, 1 50 eq) at 0- 5 C. After stirring for 30 minutes, ten- butyl prop-2-enoate (CAS 1663-39-4, 8.99 g, 70.1 mmol, 10.2 mL, 1.20 eq) was added to the reaction mixture. The mixture was stirred at 0- 5 C for 1.5 hours and was allowed to warm to 25 C and stirred for a further 2 hours TLC showed that starting material was consumed and one new spot was detected. The reaction mixture was acidified with 2 N aq HC1 to pH = 4 and extracted with EtOAc (3 x 50 mL). The combined organic layers were washed with brine (50 mL), dried over NaiSCX filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by chromatography (SiC , petrol ether: ethyl acetate = 20: 1 to 4: 1) to afford 4-0-tert-butyl 1-6), 2-O-dimethyl 2-cyanobutane- 1,2, 4- tricarboxylate (10.0 g, 33.4 mmol, 57.2%) as a yellow gum. NMR: 400 MHz, CDCh: d 3.82- 3 87 (m, 3H), 3.73 (s, 3H), 3.09 (d, ./ 17.07 Hz, 11 1 ), 2.83 id, J = 17 32 Hz, i l l), 2 47- 2 61 ( n, (1198) 1H), 2.31- 2.43 (m, 1H), 2.10- 2.25 (m, 2H), 2.03 (s, 1H), 1.43 (s, 9H)

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

Reference:
Patent; C4 THERAPEUTICS, INC.; NASVESCHUK, Christopher, G.; DEY, Fabian; GOERGLER, Annick; KUHN, Bernd; NORCROSS, Roger; ROEVER, Stephan; SCHMID, Philipp; (270 pag.)WO2019/204354; (2019); A1;,
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Adding a certain compound to certain chemical reactions, such as: 108168-88-3, name is N-(tert-Butyl)-2-cyanoacetamide, 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 108168-88-3, COA of Formula: C7H12N2O

Into a 8-mL sealed tube, was placed 3-(2-fluoro-5-formylphenoxy)propanoic acid (20 mg, 0.09 mmol, 1.00 eq.), methanol (0.25 mL), N-tert-butyl-2-cyanoacetamide (13.2 mg, 0.09 mmol, 1.00 eq.), CH3COONH4 (36.3 mg, 0.47 mmol, 5.00 eq.). The resulting solution was stirred for 30 min at 60 C. The reaction was then quenched by the addition of 10 mL of water. The resulting solution was extracted with 3×10 mL of ethyl acetate and the organic layers combined and dried over anhydrous sodium sulfate and concentrated under vacuum. The crude product was purified by Flash-Prep-HPLC with the following conditions (CombiFlash-l): Column, C18 silica gel; mobile phase, FbC):ACN=99: l increasing to FLO: ACN= 1 :99 within 100 min; Detector, UV 254 nm. This resulted in 5 mg (16%) of 3-[5- [2-(tert-butylcarbamoyl)-2- cyanoeth-l-en-l-yl]-2-fluorophenoxy]propanoic acid as a white solid.

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; PRINCIPIA BIOPHARMA INC.; LOU, Yan; OWENS, Timothy Duncan; BRAMELD, Kenneth Albert; GOLDSTEIN, David Michael; (171 pag.)WO2019/99576; (2019); A1;,
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621-50-1, name is 2-(3-Nitrophenyl)acetonitrile, 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. Computed Properties of C8H6N2O2

To a solution of 4-(methylamino)-2-(methylsulfanyl)pyrirnidine-5-carbaldehyde (10.0 g, 55 mmol) and (3-nitrophenyl)acetonitrile (10.5 g, 65 mmol) in DMF (150 mL) was added K2CO3 (38 g, 275 mmol) at RT. The mixture was stirred at 100 C for 18h. After cooling, the reaction was diluted with DMF (50 mL) and filtered. The filtrate was concentrated to give crude 8-methyl-2-(methylsulfanyl)-6-(3-nitrophenyl)-8H-pyrido[2,3-d]pyrimidin-7- ylideneamine (9.0 g, 50% yield) which was used in the next reaction without further purification.

The synthetic route of 621-50-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DECIPHERA PHARMACEUTICALS, LLC; WO2006/71940; (2006); A2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts