Month: September 2021

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,
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. 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

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. 20249-16-5, name is 3-Oxocyclobutanecarbonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. category: nitriles-buliding-blocks

Step 2. 3-Hydroxycyclobutane-l-carbonitrile. Sodium borohydride (597 mg, 15.8 mmol) was added in portions into a cold (0 C) mixture of 3-oxocyclobutane-l- carbonitrile (1.0 g, 10.52 mmol) and anhydrous methanol (10 mL). After the addition the mixture stirred for 30 minutes, and then it was carefully poured into ice water. The mixture was extracted with ethyl acetate and the organic extracts washed with water and brine and dried over anhydrous MsS04. The solvents were removed under vacuum and the residue was purified on silica gel (Biotage; eluting solvents hexanes: EtOAc 2/1 ratio) to afford 3- hydroxycyclobutane-l-carbonitrile, 8: 1 isomeric mixture, as oil (920 mg, 92% yield): XH NMR (500MHz, CDCh) delta ppm [4.62 (m), 4.26 (m), 1H], [3.06 (m), 2.75 (m), 2H], [5.65 (m), 2.33 (m), 2H], 2.6 (m, 1), 2.31 (m, 1H).

The synthetic route of 20249-16-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NORTHEASTERN UNIVERSITY; MALAMAS, Michael; MAKRIYANNIS, Alexandros; SUBRAMANIAN, Kumara Vadivel; WHITTEN, Kyle M.; ZVONOK, Nikolai M.; WEST, Jay Matthew; MCCORMACK, Michael; PAVLOPOULOS, Spiro; WO2015/179190; (2015); 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. 72291-30-6, name is Methyl 2-cyano-2-methylpropanoate, A new synthetic method of this compound is introduced below., Safety of Methyl 2-cyano-2-methylpropanoate

At -10C, hydrogen chloride gas was bubbled into an ethanol (50 ml) solution of 8.00 g of the mixture of cyano-dimethylacetic acid ethyl ester and cyano-dimethylacetic acid methyl ester (I-69), while stirring for 6 hours. After concentration of the reaction solution, ether was added to the thus obtained residue and stirred for 30 minutes, and the precipitated crystals were collected by filtration and dried to obtain 8.2 g of the title compound as a colorless solid. This was directly used in the subsequent reaction.

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; DAIICHI PHARMACEUTICAL CO., LTD.; EP1717238; (2006); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 214623-57-1,Some common heterocyclic compound, 214623-57-1, name is 5-Amino-2-methoxybenzonitrile, molecular formula is C8H8N2O, 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.

a 2-Methoxyl-5-N-[[4-morpholino]carbonyl]amino benzonitrile To a stirred mixture of 2-methoxyl-5-aminobenzonitrile (2 g, 12.34 mmol), and pyridine (1.28 g, 16.2 mmol) in dried CH2Cl2 (20 mL) was added 4-morpholinecarbonyl chloride (2.42 g, 16.2 mmol). After stirring at RT for 24 h, the mixture was diluted with CH2Cl2 and washed with H2O, brine, dried over MgSO4, concentrated to give an orange solid (3.04 g, 86%) 1H NMR: (400MHz, DMSO-d6): d 3.23 (t, J=4.9 Hz, 4H), 3.47 (t, J=4.9 Hz, 4H), 3.9 (s, 3H), 6.89 (d, J=9 Hz, 1H), 7.3 (d, J=9 Hz, 1H), 8.01 (s, 1H).

The synthetic route of 214623-57-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SmithKline Beecham Corporation; US6294531; (2001); B1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Related Products of 53312-78-0,Some common heterocyclic compound, 53312-78-0, name is 3-Amino-5-chlorobenzonitrile, molecular formula is C7H5ClN2, 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.

Representative of synthesis of ( N-(3-(3-aminopropanamido)-5-chlorobenzyl)-6 – chloro-1, 3, 4,9-tetrahydro-2H-pyrido[ 3, 4-b lindole-2-carboxamide : To a solution of 3-amino-5- chlorobenzonitrile (1.0 g, 6.55 mmol,1.0 eq), 3-((tert-butoxycarbonyl) amino) propanoic acid (1.24 g, 6.55 mmol,1.0 eq) and HATU (2.98 g, 7.86 mmol,1.2 eq) in DMF (15 mL) was added DIEA (2.5 g,19.65 mmol, 3.0 eq) at 25 C. Then the reaction mixture was stirred at 25 C for 1 hr. TLC showed 3 -amino-5 -chlorobenzonitrile was consumed completely and one new spot formed. The reaction mixture was diluted with water (100 mL) and extracted with ethyl acetate (100 mL x 3). The combined organic phase was concentrated in vacuo. The residue was purified by silica gel column chromatography (eluent: PE/EA = 5/1 to 3/1) to give tert-butyl (3 -((3- chloro-5-cyanophenyl) amino)-3-oxopropyl) carbamate (1.5 g, yield: 70.8%) as a yellow solid. NMR (400 MHz, DMSO-^) d 10.42 (s,1 H), 7.98 (d, J = 1.6 Hz,1 H), 7.92 (s,1H), 7.71 -7.67 (m,1 H), 6.90 (t, J = 5.2 Hz,1 H), 3.32 (s, 2 H), 3.22 (dd, J = 12.8, 6.8 Hz, 2 H),1.37 (s, 9 H). [0234] To a solution of tert-butyl (3-((3-chloro-5-cyanophenyl) amino)-3-oxopropyl) carbamate (500 mg,1.54 mmol,1.0 eq) in methanol (10.0 mL) was added Raney-Ni (180 mg, 3.08 mmol, 2.0 eq) and NH3·H20 (0.1 mL). The reaction was stirred at 25 C for 4 hrs under . LCMS showed the complete consumption of the starting material, and the desired product mass was detected. The reaction mixture was filtered and concentrated in vacuo to give tert-butyl (3- ((3-(aminomethyl)-5-chlorophenyl) amino)-3-oxopropyl) carbamate (460 mg, yield: 90.9%) as a yellow oil. LCMS: [M+H] + = 328.1

The synthetic route of 53312-78-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; RECREO PHARMACEUTICALS LLC; ZHANG, Jing; WANG, Xiang; PODOLL, Jessica, D.; (207 pag.)WO2020/37155; (2020); A1;,
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. 20249-16-5, name is 3-Oxocyclobutanecarbonitrile, This compound has unique chemical properties. The synthetic route is as follows., name: 3-Oxocyclobutanecarbonitrile

3,3-difluorocyclobutanecarbonitrile[1268] Example 125 A (8.21 g, 86 mmol) in dichloromethane (135 mL) was stirred at room temperature, cooled to <10 C, added DAST (1 1.41 mL, 86 mmol), warmed to room temperature, and stirred for 2 hours. The mixture was poured into saturated aqeuous NaHCC (200 mL) and partitioned. The aqueous phase was extracted with 2 x 50 mL dichloromethane. The combined organic phase was dried (Na2S04), filtered, and concentrated to give Example 125B (9.14 g, 78 mmol, 90 % yield) as a brown oil. XH NMR (400 MHz, CDC13) ? 3.06 - 2.91 (m, 5H). According to the analysis of related databases, 20249-16-5, the application of this compound in the production field has become more and more popular. 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; WO2013/62964; (2013); A2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Application of 874-89-5, A common heterocyclic compound, 874-89-5, name is 4-(Hydroxymethyl)benzonitrile, molecular formula is C8H7NO, 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.

A solution of 25.0 g (150 mmol) of 4- (hydroxymethyl) benzonitrile, 20.8 g (300 mmol) of hydroxyamine hydrochloride and 50.4 g (600 mmol) of sodium bicarbonate in 250 [ML] of methanol was heated to reflux and stirred for 20 h. The reaction mixture was cooled to rt and filtered. The solid was washed with 100 mL of methanol. The combined methanol solution was concentrated to dryness to afford [31.] 0 g (99 %) of the title compound: 1H NMR (400 Mhz, CD30D) [8] 4.63 (s, 2H), 7.39 (d, J= 8.0, 2H), 7.62 (d, J= 8.0, 2H).

The synthetic route of 874-89-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Merck & Co., Inc.; WO2003/105771; (2003); A2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts