Month: June 2021

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 3672-47-7 as follows. Quality Control of 3-(4-Methoxyphenyl)-3-oxopropanenitrile

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.

According to the analysis of related databases, 3672-47-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Deshpande, Shyam J.; Leger, Paul R.; Sieck, Stephen R.; Tetrahedron Letters; vol. 53; 14; (2012); p. 1772 – 1775;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Application of 51762-67-5, A common heterocyclic compound, 51762-67-5, name is 3-Nitrophthalonitrile, molecular formula is C8H3N3O2, 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.

3-nitrophthalonitrile (0.99 g, 5.90 mmol) was dissolved in 15.0 ml DMF under argon atmosphere and 3,4-dimethoxythiophenol (1.00 g, 5.90 mmol) was added at room temperature. After stirring for 30 min at room temperature, finely ground anhydrous potassium carbonate (3.94 g, 28.4 mmol) was added portion wise for over 1 h and the reaction mixture was stirred at room temperature for 24 h. Then the mixture was poured into 100.0 ml ice water, and the precipitate was filtered off, washed with water and methanol, and then dried. The crude product was recrystallized from ethanol. Finally the pure product was dried in vacuum. Yield: 3.12 g (90%). FT-IR (cm-1) (KBr): 3070, 3004 (Ar-CH), 2960, 2934, 2840 (CH), 2230 (C?N), 1583, 1567, 1505 (C=C), 1461, 1439, 1417, 1401, 1328, 1259 (C-O-C), 765 (C-S-C). 1H NMR (CDCl3): delta = 7.65-7.06 (6H, m, Ar-H), 3.92 (3H, s, C-H), 3.82 (3H, s, C-H). Calcd for C16H12N2O2S: C, 64.90; H, 4.10; N, 9.45; S, 10.80; Found: C, 64.85; H, 4.14; N, 9.52; S, 10.85. MS (GC-MS) m/z: Calc.: 296.35, Found: 296 [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:
Article; Arican, Duygu; Arici, Muersel; Ugur, Ahmet Luetfi; Erdo?mu?, Ali; Koca, Atif; Electrochimica Acta; vol. 106; (2013); p. 541 – 555;,
Nitrile – Wikipedia,
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Related Products of 69395-13-7, 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. 69395-13-7, name is 4-(2-Hydroxyethyl)benzonitrile, This compound has unique chemical properties. The synthetic route is as follows.

Reference Example 76 4-Cyanophenylacetic acid A catalytic amount of ruthenium chloride (28 mg) and sodium periodate (5.80 g) were added to a carbon tetrachloride-acetonitrile-water (2:2:3) solvent solution (20 ml) of 4-(2-hydroxyethyl)benzonitrile (1.00 g), followed by stirring overnight at room temperature. The reaction solution was extracted with dichloromethane and dried over sodium sulfate to obtain the title compound (755 mg) as a colorless oil. 1H-NMR (400 MHz, CDCl3) delta: 3.73 (2H, s), 7.40 (2H, d, J=8.3 Hz), 7.63 (2H, d, J=8.3 Hz).

The chemical industry reduces the impact on the environment during synthesis 4-(2-Hydroxyethyl)benzonitrile. I believe this compound will play a more active role in future production and life.

Reference:
Patent; DAIICHI PHARMACEUTICAL CO., LTD.; EP1612204; (2006); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Application of 68119-31-3,Some common heterocyclic compound, 68119-31-3, name is 2-(2,2-Difluorobenzo[d][1,3]dioxol-5-yl)acetonitrile, molecular formula is C9H5F2NO2, 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.

Step e: 1-(2,2-Difluoro-benzo[1,3]dioxol-5-yl)-cyclopropanecarbonitrileSodium hydroxide (50% aqueous solution, 10 mL) was slowly added to a mixture of crude (2,2-difluoro-benzo[1,3]dioxol-5-yl)-acetonitrile, benzyltriethylammonium chloride (3.00 g, 15.3 mmol), and 1-bromo-2-chloroethane (4.9 g, 38 mmol) at 70 C. The mixture was stirred overnight at 70 C. before the reaction mixture was diluted with water (30 mL) and extracted with ethyl acetate. The combined organic layers were dried over sodium sulfate and evaporated to dryness to give crude 1-(2,2-difluoro-benzo[1,3]dioxol-5-yl)-cyclopropanecarbonitrile, which was used directly in the next step.

The synthetic route of 68119-31-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Ruah, Sara Hadida; Miller, Mark; Zhou, Jinglan; Bear, Brian; US2009/221597; (2009); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 76469-88-0, name is Methyl 4-(cyanomethyl)benzoate, 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 76469-88-0, SDS of cas: 76469-88-0

A solution of methyl 4- (cyanomethyl) benzoate 24, (2.0 g, 11.4 mmol) in 6M Sodium hydroxide (15 mi) and methanol (15 mL) was heated at 90 C. overnight. After concentrating the reaction mixture, the aqueous layer was washed with dichloromethane (30 mL chi 2), then acidified to pH~3 with 12 HC1. The aqueous solution was extracted with ethyl acetate (20 ml 2). Organics was combined, dried over Na2S< and evaporated in vacuo to give titled compound. (1.45 mg, 70%). [M+H]* = 181.4 (APCI+) . 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:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthetic Route of 139152-08-2, 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 139152-08-2 as follows.

The mixture of 1-(2-hydroxyethyl)-4-(4-methoxybenzylamino)-3-p-tolyl-1H-1,2,4-triazol-5(4H)-one (1)(1.00 g, 2.82 mmol) and 4,5-dichlorophthalonitrile (2) (0.28 g, 1.41 mmol) were dissolved in dry DMF(15 mL) under a nitrogen atmosphere and this mixture was stirred at 50 C for 10 min. After stirring,finely ground anhydrous K2CO3 (0.58 g, 4.23 mmol) was added portionwise over a period of 2 h and thereaction mixture was stirred under nitrogen at this temperature for 5 days. At the end of this time, themixture was poured into ice water (100 mL) and stirred for 30 min. The reaction mixture was extractedwith chloroform (50 mL × 3) and the organic layer was dried over anhydrous magnesium sulfate andthen solvent was removed under reduced pressure. The oily green product was dried in vacuo (P2O5).Yield: 1.00 g (85%). Calcd for C46H44N10O6: % C 66.33, % H 5.32, % N 16.82. Found: % C 66.28, % H 5.30, %N 16.85. FT-IR numax cm-1 (NaCl disk): 3259 (N-H), 3033 (Ar-H), 2935-2837 (Aliph. C-H), 2233 (C?N), and1699 (C=O), 1613, 1513, 1422, 1250, 1176, 1035, 822 and 739. 1H NMR (CDCl3) (delta: ppm): 7.79 (ArH, 4H,d), 7.28 (ArH, 4H, d), 7.18 (ArH, 4H, d), 6.79 (ArH, 4H, d), 6.75 (ArH, 2H, d), 4.93 (NH, 2H, s), 4.43 (O-CH2,4H, t), 4.11 (CH2, 8H, m), 3.78 (O-CH3, 6H, s), 2.42 (CH3, 6H, s). 13C NMR (CDCl3) (delta: ppm): 159.63, 158.24,153.75, 153.41, 144.95, 140.95, 140.80, 135.15, 130.90, 129.32, 127.46, 123.41, 117.09, 115.84, 114.08,107.89, 67.12, 61.57, 55.49, 54.48, 49.39, 44.48, and 21.77. MS (ES+), m/z: Calcd: 832.92; Found: 832.37 [M]+.

According to the analysis of related databases, 139152-08-2, the application of this compound in the production field has become more and more popular.

Reference:
Article; Nas, Asiye; Journal of Coordination Chemistry; vol. 69; 8; (2016); p. 1326 – 1336;,
Nitrile – Wikipedia,
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Electric Literature of 29509-06-6, 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. 29509-06-6 name is 4-Methyl-3-oxopentanenitrile, 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.

2B. Preparation of 3-isopropyl-1H-pyrazol-5-amine To a mixture of 4-methyl-3-oxopentanenitrile (0.9 g, 0.008 mole) in ethyl alcohol (5 mL) was added hydrazine (0.25 mL, 0.008 mole). The reaction mixture was refluxed for 1 hour and then cooled to room temperature. The reaction mixture was concentrated and the residue was dissolved in MeOH (2 mL). The crude product was loaded on a sulfuric acid bound resin (AG 50W-X2, hydrogen form, 100-200 mesh, BioRad), washed with MeOH (50 mL), then washed with 2N NH3 in methanol (10 mL). The ammonia washes were combined and concentrated to afford the desired product (700 mg, 68%). 1H-NMR (400 MHz, MeOD) delta 5.44 (s, 1H), 2.84-2.90 (m, 1H), 1.24 (d, J=6.4 Hz).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Methyl-3-oxopentanenitrile, and friends who are interested can also refer to it.

Reference:
Patent; Bristol-Myers Squibb Company; US2008/45496; (2008); A1;,
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. 6283-71-2, name is Dimethyl 2-cyanosuccinate, A new synthetic method of this compound is introduced below., Product Details of 6283-71-2

To a solution of dimethyl 2-cyanobutanedioate (compound 62a, 513 mg, 3 mmol) in acetone (5 mL) was added iodomethane (639 mg, 4.5 mmol) and potassium carbonate (829 mg, 6 mmol). The reaction mixture was stirred at room temperature for 2 hours. The reaction mixture was extracted with EtOAc twice, washed with water. The combined organic phase was dried over Na2SO4, filtrated and concentrated to give compound 62b (556 mg, crude). LCMS (M+H+): 186.

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; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; HU, Taishan; KOU, Buyu; LIN, Xianfeng; LIU, Haixia; ZHANG, Zhisen; (152 pag.)WO2018/11160; (2018); A1;,
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. 53312-80-4, name is 4-Amino-2-fluorobenzonitrile, A new synthetic method of this compound is introduced below., Computed Properties of C7H5FN2

To a stirred solution of 4-amino-2-fluorobenzonitrile (5 g, 36.8 mmol, 1 eq) in H2O (200 mL) chloroform (50 mL) mixture was added thiophosgene (3 mL, 40.4 mmol, 1.1 eq) slowly and the mixture was stirred at RT for 5 h. The reaction was monitored by TLC. After completion, the reaction mixture was diluted with water (300 mL) and extracted with DCM (200 mL c 3). The combined organic layers were washed with water (200 mL), brine (200 mL), dried over NaaSCfi, filtered and concentrated under reduced pressure to afford the title compound. Analytical data: ‘H NMR (400 MHz, DMSO-c/r,) d 8.02 (t, J = 7.9 Hz, 1H), 7.76 (dd, J= 10.3, 1.5 Hz, 1H), 7.44-7.53 (m, 1H).

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; NUVATION BIO INC.; PETTIGREW, Jeremy D.; CHAKRAVARTY, Sarvajit; PHAM, Son Minh; CHEN, Jiyun; KANKANALA, Jayakanth; NAYAK, Anjan Kumar; BARDE, Anup; PUJALA, Brahmam; (108 pag.)WO2020/113088; (2020); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 17417-09-3, name is 2-Fluoro-5-nitrobenzonitrile, 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 17417-09-3, Computed Properties of C7H3FN2O2

Part A: Preparation of 2-fluoro-5-aminobenzonitrile. To a solution of 2-fluoro-5-nitrobenzonitrile(2.0 g, 12 mmol) in ethyl acetate(50 mL) was added stannous chloride(27.0 g, 120 mmol). The reaction-mixture was stirred at reflux 1.5 h, then cooled to room temperature. Partitioned between ethyl acetate(150 mL) and saturated sodium bicarbonate(150 mL). Organic phase was separated and washed with water(5×75 mL), brine(75 mL); dried over sodium sulfate(anhy.); filtered and concentrated to give 2-fluoro-5-aminobenzonitrile (1.4 g) as pure compound.

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; Bristol-Myers Squibb Pharma Company; EP946508; (2009); B1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts