Month: June 2021

Synthetic Route of 555-21-5,Some common heterocyclic compound, 555-21-5, name is 4-Nitrophenylacetonitrile, molecular formula is C8H6N2O2, 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-4 The following example illustrates the hydrogenation of various nitroaromatics as mentioned in Table 4. The hydrogenation of exemplary nitroaromatics was conducted under the following conditions. The procedure was similar to that for biphasic reactions [reaction numbers 7- 10, Table 2] Reaction conditions: Pressure: 400 psi; Temperature: 423K; Aqueous phase: 9×10-5 m3 ; Organic phase consists of neat substrate; catalyst FeS04. 7H20 : 7. 2×10-5 mol ; Fe: EDTANa2 1: 5; conversion in all cases was complete ; TOF calculated as mols of nitro compound converted per mol of Fe, § based on GC analysis. Table 4 Reaction No Substrate Substrate Yield of TOF (mols) corresponding hr~’ amine % 16 Nitrobenzelle 0. 090 98. 5 529 17 2-nitrotoluene 0. 0849 98. 75 457 18 2, 4-dinitrotoluene 0. 056 84. 63 134 19 4-nitrochlorobenzene 0.0635 96. 2 434 20 3-nitrochlorobenzene 0. 0635 99 400 21 2-nitrotoluene 0. 0849 98. 75 462 22 2-nitroanisole 0. 0820 89. 19 450 23 2-nitroaniline 0.0725 98. 2 116 24 4-nitrobenzoic acid 0.0598 85.8 393 25 4-nitro acetophenone 0.06 99 208 26 4-nitro benzylnitrile 0. 061 90 99

The synthetic route of 555-21-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; COUNCIL OF SCIENTIFIC & INDUSTRIAL RESEARCH; WO2005/70869; (2005); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Reference of 69395-13-7, 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. 69395-13-7 name is 4-(2-Hydroxyethyl)benzonitrile, 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.

Intermediate 33: N’-hvdroxy-4-(2-hvdroxyethyl)benzenecarboximidamide; Hydroxylamine (5 mL) was added to a solution of 4-(2-hydroxyethyl)benzonitrile (2.43 g; 16.5 mmol) in ethanol (30 mL) and the mixture was heated to 80 C in a sealed tube for 3 hours. The solvent was removed in vacuo and the residue triturated with water to yield Intermediate 33 (2.95 g; 99 %) as a white solid which was used without further purification.20 1H NMR (DMSO-d6, 400MHz) delta 9.58 (1 H, s), 7.60 (2 H, d, J = 7.9 Hz), 7.24 (2 H, d, J = 7.9 Hz), 5.75 (2 H, s), 4.75-4.69 (1 H, m), 3.64 (2 H, d, J = 6.6 Hz), 2.80-2.72 (2 H, m).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-(2-Hydroxyethyl)benzonitrile, and friends who are interested can also refer to it.

Reference:
Patent; MERCK SERONO S.A.; QUATTROPANI, Anna; BAKER-GLENN, Charles; BLACKABY, Wesley; KNIGHT, Chris; WO2010/142628; (2010); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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 68119-31-3 as follows. HPLC of Formula: C9H5F2NO2

A mixture of (2,2-difluoro-l,3-benzodioxol-5-yl)-acetonitrile (1.0 eq), 50 wt % aqueous KOH (5.0 eq) l-bromo-2-chloroethane (1.5 eq), and OCt4NBr (0.02 eq) is heated at 70 0C for 1 h. The reaction mixture is cooled then worked up with MTBE and water. The organic phase is washed with water and brine then the solvent is removed to afford (2,2-difluoro-l,3-benzodioxol-5-yl)-cyclopropanecarbonitrile.

According to the analysis of related databases, 68119-31-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; YOUNG, Christopher; WO2010/37066; (2010); A2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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. 4426-11-3, name is Cyclobutanecarbonitrile, This compound has unique chemical properties. The synthetic route is as follows., Safety of Cyclobutanecarbonitrile

1 -cyclopentylcyclobutanecarbonitrile[291] To a solution of cyclobutanecarbonitrile (405 mg, 5 mmol) in THF (7 mL) was added dropwise LDA (2.0 M, 2.5 mL, 5 mmol) at -78 C over 10 minutes. After stirring for 30 minutes, a solution of bromocyclopentane (888 mg, 6.0 mmol) in HMPA (268 mg, 1.5 mmol) was added and the mixture was stirred at room temperature for 3 hours. The reaction mixture was quenched with the addition of IN aqueous HC1 (10 mL) and extracted with EtOAc (20 mL x 3). The combined organic phases were washed with brine, dried over Na2S04, filtered and concentrated. The residue was purified by column chromatography (petroleum ether/EtOAc =20/1) to give Example 163A (0.46 g, yield 62.3%) as a colorless oil. ? NMR (400 MHz, CDC13): ? 2.53-2.44 (m, 2H), 2.25-2.07 (m, 4H), 2.03-1.95 (m, 1H), 1.86-1.69 (m, 4H), 1.62-1.54 (m, 2H).

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 4426-11-3.

Reference:
Patent; ABBVIE INC.; BAYBURT, Erol K.; CLAPHAM, Bruce; COX, Phil B.; DAANEN, Jerome F.; GOMTSYAN, Arthur; KORT, Michael E.; KYM, Philip R.; VOIGHT, Eric A.; SCHMIDT, Robert G.; DART, Michael J.; GFESSER, Gregory; WO2013/62966; (2013); A2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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. 191014-55-8, name is 4-Fluoro-2-methoxybenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Product Details of 191014-55-8

4-Fluoro-2-hydroxyben?onitrile. A mixture of intermediate 127, 4-fluoro-2- methoxybenzonitrile, (4.53 g, 30 mmol;) and AlCl3 (5.0 g, 37.6 mmol; Aldrich) in anhydrous toluene (30 mL) was stirred at approximately 130 C for 18 hrs. After cooling, ice water (~50 mL)was added and the resulting mixture extracted with ether (20 mL x 2). The combined extracts were washed sequentially with water and brine, then dried (MgSO4), and concentrated in vacuo to provide the title compound (3.90 g, 28.5 mmol, Yield 95%) as a white solid: 1H NMR (DMSO-d6, 300 MHz) delta ppm: 6.74-6.84 (2H, m, Ar-Hs), 7.71 (IH, dd, J = 7 Hz, J = 8.5 Hz, Ar-H), 11.64 (IH, s, OH); 13C NMR (DMSO-d6, 75.5 Hz) delta ppm: 95.13 102.45, 102.78, 106.53, 106.83 115.53, 134.68, 134.84, 161.41, 161.58, 163.00, 166.35.HRMS (ESI-) calcd for C7H3NOF (M-H) 136.0199, found 136.0199.

The synthetic route of 191014-55-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2007/64316; (2007); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthetic Route of 50397-74-5, These common heterocyclic compound, 50397-74-5, name is 4-Amino-3-bromobenzonitrile, 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.

In another example of a dye compound according to Formula 1, the dye compound has the following formula: This compound is (E)-N-(5-(bis(2-ethylhexyl)amino)-2-((2,4-dicyanophenyl)diazenyl)-4-ethoxyphenyl)-2-ethylhexanamide may be synthesised as follows: A suspension of 4-Amino-3-bromobenzonitrile (15.0 g, 76.1 mmol) in a mixture of AcOH (120 mL) and EtCO2H (80 mL) was warmed until a clear solution was obtained and then cooled to 8 C. with an ice bath. 40% nitrosyl sulfuric acid (14.3 mL, 83.7 mmol) was added drop wise. The mixture was stirred 1 h at 7 C. and then added slowly to a solution of N-{3-[bis(2-ethylhexyl)amino]-4-ethoxyphenyl}-2-ethylhexanamide (35.0 g, 69.6 mmol) in 1,4-dioxane (120 mL) and acetic acid (30 mL) cooled in an ice bath. The mixture was stirred at 7 C. during 1 h and then hydrolyzed by drop wise addition of 33% NaOH (75 mL) while cooling in an ice bath. After 30 minutes, the mixture was poured into water and extracted with toluene. The combined organic layers were washed with water and the solvent evaporated. Purification by column chromatography (silicagel, heptane/EtOAc 60/1) afforded (E)-N-(5-(bis(2-ethylhexyl)amino)-2-((2-bromo-4-cyanophenyl)diazenyl)-4-ethoxyphenyl)-2-ethylhexanamide (35 g). This was dissolved in dimethylformamide DMF (400 mL) and copper(I) cyanide (17.6 g, 196.9 mmol) was added while the mixture was cooled in a water bath. After 20 h of stirring at RT, the reaction mixture was poured into 15% ammonia and extracted with toluene (3*). The combined organic layers were washed with ammonia, water and dried with Na2SO4. After evaporation of the solvent the residue was purified by column chromatography (silicagel, heptane/EtOAc 80/1 to 30/1) to obtain (E)-N-(5-(bis(2-ethylhexyl)amino)-2-((2,4-dicyanophenyl)diazenyl)-4-ethoxyphenyl)-2-ethylhexanamide (19.8 g, 39% yield) as a purple oil.

Statistics shows that 4-Amino-3-bromobenzonitrile is playing an increasingly important role. we look forward to future research findings about 50397-74-5.

Reference:
Patent; Amazon Technologies, Inc.; Leguijt, Robin; Mans, Jurrinn; Sandhu, Sukhdip; US2015/370062; (2015); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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 1813-33-8 as follows. name: 2-Chloro-4-(trifluoromethyl)benzonitrile

General procedure: A mixture of 2-chloro-4-(trifluoromethyl)-benzonitrile (1.00 mmol), appropriate amine (NR2, 2.00 mmol),and DBU (2.5 mmol) were dissolved in 1,4-dioxane (8 ml). Themixture was stirred for 12 h at 50 C. The reaction was quenched with water and extracted with EtOAc twice. The combined organicextracts were dried over MgSO4, filtered, and concentrated invacuo. The residue was purified by flash column chromatographyon silica gel using EtOAc/hexane (1:7-1:10) eluant condition.(NR2 = 4-(4-fluorophenyl)-1,2,3,6-tetrahydropyridine hydrochloridefor 17).

According to the analysis of related databases, 1813-33-8, the application of this compound in the production field has become more and more popular.

Reference:
Article; Ann, Jihyae; Jung, Aeran; Kim, Mi-Yeon; Kim, Hyuk-Min; Ryu, Hyungchul; Kim, Sunjoo; Kang, Dong Wook; Hong, Sunhye; Cui, Minghua; Choi, Sun; Blumberg, Peter M.; Frank-Foltyn, Robert; Bahrenberg, Gregor; Stockhausen, Hannelore; Christoph, Thomas; Lee, Jeewoo; Bioorganic and Medicinal Chemistry; vol. 23; 21; (2015); p. 6844 – 6854;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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. 22364-68-7, name is 2-(o-Tolyl)acetonitrile, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 22364-68-7

General procedure: To a stirred solution of compound 4a (700 mg, 5.18 mmol) in THF (10 mL) was added LiHMDS (6.2 ml, 1 M sol. in THF, 6.2 mmol) at 0 C and the reaction mixture was stirred at this temperature for 30 min. Ethyl-1-imidazole carboxylate 2 (870 mg, 6.22 mmol) in dry THF (3 ml) was added drop wise to the reaction mixture at 0 C and stirred at rt for 4 h. The reaction mixture was quenched with saturated ammonium chloride solution and extracted with ethyl acetate. The combined organic layer was washed with water, saturated brine solution and dried over Na2SO4. The solvent was evaporated under reduced pressure and the crude product was chromatographed on a silica gel column. Elution with 10% ethyl acetate/pet ether gave the pure compound 5a (720 mg, 68% yield) as a colorless liquid.

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 22364-68-7.

Reference:
Article; Behera, Manoranjan; Venkat Ragavan; Sambaiah; Erugu, Balaiah; Rama Krishna Reddy; Mukkanti; Yennam, Satyanarayana; Tetrahedron Letters; vol. 53; 9; (2012); p. 1060 – 1062;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 50712-68-0, name is 4-Chloro-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 50712-68-0, Computed Properties of C8H6ClN

A mixture of the oxathiazolone compound (170 mg, 1 mmol) and 4-chloro-2-methylbenzonitrile (3.03 g, 20 mmol) was heated in the microwave at 190 C. for 20 mm. A second reaction was performed and the mixtures were combined. Excess of the nitrile by-product (furonitrile) were removed in vacuo (120 C., 0.3 mbar). The residual brown solid (100 mg) was taken in hot MeOH (10 mE) and decanted from insoluble material (presumably sulphur). The MeOH solution was left at room temperature overnight. The precipitated solid was collected and dried to give compound 5-(2-chioro-4-methylphenyl)-3-(furan-2-yl)-1 ,2,4-thiadiaz- ole as brown solid, 40 mg (7%). NMR conform structure. Chemical Formula: C13R9C1N2OS; MW: 278.7; RPLC-ESMS: tj6.36 mm and mlz 277.01 (M+1); RPLC purity: 93.5 (216 nm) 91% (324 nm); ?R-NMR (300 MHz, CDC13): 7.87 (dd, J=8.1, 1H), 7.5 1-7.60 (m, 1H), 7.24-7.32 (m, 2H), 7.15-7.20 (m, 1H), 6.50-6.56 (m, 1H), 2.58 (s, 3H)

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; Monsanto Technology LLC; Shortt, Barry J.; South, Michael S.; Wideman, Al S.; Williams, Deryck Jeremy; (34 pag.)US2018/228158; (2018); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

85363-04-8, name is N-(tert-Butoxycarbonyl)-2-aminoacetonitrile, 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. Application In Synthesis of N-(tert-Butoxycarbonyl)-2-aminoacetonitrile

Description 22: (N-Hvdroxvcarbamimidovlmethvl) carbamic acid ter-butyl ester To a solution of N- (tert-butoxycarbonyl)-2-aminoacetonitrile (20. 0g) in absolute ethanol (200moi) was added a solution of hydroxylamine (9. 0g) and potassium carbonate (17. 6g) in water (50ml). The solution was heated to reflux for 2 days. The absolute ethanol was removed in vacuo and the aqueous residue extracted with ethyl acetate. The solvent was partially removed in vacuo until a precipitate formed. The suspension was cooled and filtered. The residue was washed with ethyl acetate to give the title compound as a white solid (12. 84g). Thermospray Mass Spectrum m/z 190 [MH+].

The synthetic route of 85363-04-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; WO2003/82861; (2003); A2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts