Author: Jessica.F

Reference of 6136-93-2, These common heterocyclic compound, 6136-93-2, name is 2,2-Diethoxyacetonitrile, 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.

Sodium methylate (54 g, 1 mol) was added to a solution of diethoxyacetonitrile (139 ml_, 1 mol) in methanol (500 ml_). The reaction mixture was kept at room temperature for 24 g, then the reaction mixture was evaporated, treated with water (500 mL), and the product was extracted with ether (2×300 mL). The combined organic extracts were dried over anhydrous K2CO3 and evaporated to give 114.62 g (60% purity) of methyl 2,2- diethoxyethanimidoate. The obtained crude product was used for the next stage without additional purification.10% Pd/C (2 g) was added to a solution of 4,5-difluoro-2-nitroaniline (40 g, 0.229 mol) in methanol (500 mL). The reaction mixture was hydrogenated at room temperature for 3 h and treated with the mixture of compound methyl 2,2-diethoxyethanimidoate (71 g, 0.23 mol) with acetic acid (60 g). After 16 h at room temperature, the reaction mixture was evaporated, washed with the 10% K2CO3 solution (1 L), and the product was extracted with ether (300 mL). The organic extract was evaporated, and the residue was purified on silica gel (ethyl acetate/hexane 1 :5) to give 48 g of 2-(diethoxymethyl)-5,6-difluoro-1H-benzimidazole. Cs2CO3 (67.21 g, 0.206 mol) and methyl iodide (27 g, 0.19 mol) were added to a solution of 2-(DiethoxymethyI)-5,6-difluoro-1H-benzimidazoIe (48 g, 0.1875 mol) in DMF (250 mL). The reaction mixture was stirred at room temperature for 16 h and evaporated. Ethyl acetate (300 mL) was added to the residue, and the reaction mixture was washed with water (1 L). The organic layer was separated, dried, and evaporated. The residue was purified on silica gel (ethyl acetate/hexane 1 :5) to give 40.8 g of 2-(diethoxymethyl)-5,6-difluoro-1-methyl- 1 /-/-benzimidazole. 2-(Diethoxymethyl)-5,6-difluoro-1-methyl-1W-benzimidazole was treated with 5 M HCI (300 ml_), and the reaction mixture was kept at 60 0C for 6 h. Then the reaction mixture was evaporated to a volume of 100 ml_ and treated with acetone (200 mL). Then the mixture was kept in a refrigerator, and white crystals precipitated. The crystals were separated by filtration and dried under a reduced pressure to give 5,6-Difluoro-1-methyl-1H-benzimidazole-2- carbaldehyde Hydrochloride Hydrate in 72% (26.77 g, 21.4 g of free base) yield. Satisfactory C, H, lambda/-analysis was obtained.

The synthetic route of 6136-93-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER PRODUCTS INC.; WO2007/135527; (2007); A2;,
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Electric Literature of 17417-09-3, A common heterocyclic compound, 17417-09-3, name is 2-Fluoro-5-nitrobenzonitrile, molecular formula is C7H3FN2O2, 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.

To a solution of 2-fluoro-5-nitrobenzonitrile (5.00 g, 30.1 ?unol) and 3-aminophenol (3.28 g, 30.1 itimol) in N, N- dimethylformamide (30 itiL) was added potassium carbonate (6.23 g, 45.2 itunol) , and the mixture was stirred at 600C for 2 hr. The reaction mixture was cooled to room temperature, insoluble material was filtered off and washed with ethyl acetate (150 mL) . The filtrate and washings were combined and the mixture was concentrated under reduced pressure. The obtained residue was diluted with ethyl acetate (200 mL) , washed with 5% aqueous sodium hydrogen carbonate solution (100 mL) and saturated brine (100 mL) , successively, and dried over anhydrous sodium sulfate. Insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by basic silica gel column chromatography (ethyl acetate/n-hexane=20/80-»70/30) and the obtained solution was concentrated under reduced pressure. The residue was crystallized from ethyl acetate/n-hexane to give the title compound (5.09 g, 66%) as a yellow powder. 1H-NMR (DMSO-de, 300 MHz) delta 5.48 (2H, s) , 6.31 – 6.37 (IH, m) , 6.38 (IH, t, J = 2.2 Hz), 6.51 – 6.58 (IH, m) , 7.03 (IH, d, J = 9.4 Hz), 7.11 – 7.20 (IH, m) , 8.45 (IH, dd, J = 9.4, 2.8 Hz), 8.82 (IH, d, J = 2.8 Hz)

The synthetic route of 17417-09-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; OKANIWA, Masanori; TAKAGI, Terufumi; WO2010/64722; (2010); 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. 6609-57-0, name is 2-Ethoxybenzonitrile, A new synthetic method of this compound is introduced below., Safety of 2-Ethoxybenzonitrile

To a 250 mL three-necked flask, 100 mL of ethanol, 13.8 g (0.2 mol) of hydroxylamine hydrochloride and 20 g (0.2 mol) of triethylamine were added, and the mixture was heated to 50-60 C for 1 h, and free hydroxylamine hydrochloride. After 1 h, 18 g of compound 4 (o-ethoxybenzonitrile) was added to the flask, and the mixture was refluxed for 2 h. The compound 4 disappeared by TLC. Ethanol was distilled off, and 150 mL of water was added to the flask to dissolve the triethylamine hydrochloride. The mixture was filtered under suction, and the cake was compound 3, which was dried to give a white solid.

The synthetic route of 6609-57-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Qingdao University of Science and Technology; Xu Liangzhong; Sun Jianxin; Zhang Mingming; Cui Huanqi; Hu Rao; Wang Minghui; (6 pag.)CN108912106; (2018); A;,
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Related Products of 63069-50-1, The chemical industry reduces the impact on the environment during synthesis 63069-50-1, name is 4-Amino-3-fluorobenzonitrile, I believe this compound will play a more active role in future production and life.

To a solution of 4-amino-3-fluoro-benzonitrile (5.0 g, 36.7 mmol) in ethanol (61 mL) was added a hydroxylamine hydrochloride solution (5.16 g, 73.5 mmol) in 50 mL of water followed by potassium carbonate (8.12 g, 58.8 mmol) in 75 mL of water. To the cloudy solution was then introduced quinolin15 8-01 (0.07 g, 0.48 mmol). The reaction mixture was stirred for 5 hours at 100C. The reaction mixturewas then cooled to 25C, the ethanol was removed under reduced pressure, and the resulting mixture was then extracted with ethyl acetate. The total combined organic layer was washed with brine, dried over sodium sulfate, filtered and concentrated under reduced pressure to give 5.83 g of 4-amino-3- fluoro-N-hydroxy-benzamidine as a yellow solid. The crude residue was used in the following stepwithout further purification. LC/MS (Method A) retention time = 0.20 mm; 166 [M+H].(brs, 2H).1H NMR (400 MHz, CDCI3) oe ppm: 9.30 (s, 1H), 7.25 (m, 2H), 6.70 (t, 1H), 5.60 (brs, 2H), 5.30

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, 4-Amino-3-fluorobenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; HOFFMAN, Thomas, James; STIERLI, Daniel; BEAUDEGNIES, Renaud; POULIOT, Martin; (65 pag.)WO2018/15458; (2018); 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. 5922-60-1, name is 2-Amino-5-chlorobenzonitrile, A new synthetic method of this compound is introduced below., SDS of cas: 5922-60-1

Step A: (2-Amino-5-chloro-phenyl)-(3-chloro-phenyl)-methanone To the stirred solution of 2-amino-5-chloro-benzonitrile (500 mg, 3.28 mmol) in diethyl ether (10 ml) was added 3-chloro phenyl magnesium bromide (freshly prepared 1M solution in ether, 10 ml, 9.83 mmol) drop wise at 0° C. and the resulting reaction mixture was refluxed for 1 h. Then the mixture was stirred for 16 h at 25° C., cooled to 5° C. and quenched with water followed by 2 N HCl solution (20 ml). The reaction mixture was stirred at 45° C. for 5 h and then the pH of the reaction mixture was adjusted to 8-9 with 2N aqueous NaOH solution. The mixture was extracted with diethyl ether (3*30 ml) and the combined organic extracts were washed with brine (25 ml), dried over sodium sulfate and concentrated in vacuo to give a crude residue which was purified by flash column chromatography (5percent ethyl acetate in hexane) to yield (2-amino-5-chloro-phenyl)-(3-chloro-phenyl)-methanone (550 mg, 63percent) as a yellow solid. LC-MS (ESI): 266 (M+H)+.

The synthetic route of 5922-60-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hoffmann-La Roche Inc.; Ceccarelli, Simona M.; Conte, Aurelia; Kuehne, Holger; Kuhn, Bernd; Neidhart, Werner; Obst Sander, Ulrike; Rudolph, Markus; US2013/116234; (2013); A1;,
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Adding a certain compound to certain chemical reactions, such as: 26391-06-0, name is 2-Cyano-N,N-diethylacetamide, 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 26391-06-0, HPLC of Formula: C7H12N2O

Example 1; A mixture of 3,4-dihydroxy-5-nitro benzaldehyde (50Og), N,N-diethyl cyano acetamide(575ml), acetic acid (375ml) and piperidine (500ml) in ethanol (4.51) were refluxed for 6 hrs. Ethanol was distilled off under vacuum and 1.5 1 of formic acid was added to the residue at65 C and stirred for 30 mins at 65 C. The reaction mixture was cooled to R T and charged with methylene dichloride. The organic layer was separated and washed twice with 2 x 3.5 1 water. Methylene dichloride was distilled off under vacuum from the organic layer and the residue was treated with ethyl acetate 1.25 1. The yellow solid was filtered out from the solvent, washed with 1.25 1 ethyl acetate and dried in an electric oven at 60-70 C to obtain crude N,N-diethyl-2-cyano-3-(3,4-dihydroxy-5-nitro phenyl) acrylamide.Yield of crude entacapone 495g (59.63 %), Purity 99.2++Z- isomer 0.5%

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

Reference:
Patent; USV LIMITED; WO2007/54950; (2007); 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. 67515-59-7, name is 4-Fluoro-3-(trifluoromethyl)benzonitrile, A new synthetic method of this compound is introduced below., HPLC of Formula: C8H3F4N

A solution of 4-Fluoro-3-trifluoromethyl-benzonitrile (10 g, 52.9 mmol) sodium methoxide (10.6 mL of a 0.5 M solution in methanol, 5.3 mmol; 0.1 eq) in methanol (40 mL) was allowed to stir 12-36 h at room temperature. Acetic acid (0.32 g, 5.3 mmol) was added followed by NH4Cl (2.8 g, 52.9 mmol). The reaction was stirred at 50 C. for 24 h. The reaction was cooled, the unreacted ammonium chloride removed by filtration and the resultant white solid was used without purification 9 g (82%).

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; Reiter, Lawrence A.; Linde, Robert G.; US2008/76771; (2008); A1;,
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Related Products of 1572-52-7, These common heterocyclic compound, 1572-52-7, name is 2-Methylenepentanedinitrile, 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.

Reference example 14 3-(3,4-Dimethylphenylthio)-2-(2-methoxycarbonylethyl)propionic acid A mixture of 3,4-dimethylbenzenethiol (0.59 ml), 2-methyleneglutaronitrile (0.48 ml), ethanol (10 ml), and triton B (40% ethanol solution, 5 drops) was refluxed for 5 hours. After the reaction mixture was concentrated in vacuo, the resulting residue was dissolved in chloroform, washed with water, and dried over MgSO4. The solvent was evaporated at reduced pressure, and the residue was purified by flash column chromatography on silica eluding with benzene/ethyl acetate (7:1) to give 1.18 g of 2-(3,4-dimethylphenylthiomethyl)glutaronitrile as oil. IR (neat): nuCN2230 cmmin1 NMR (CDCl3)

Statistics shows that 2-Methylenepentanedinitrile is playing an increasingly important role. we look forward to future research findings about 1572-52-7.

Reference:
Patent; Kissei Pharmaceutical Co., Ltd.; EP508004; (1992); A1;,
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Synthetic Route of 658-99-1, 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. 658-99-1, name is 2-(3,4-Difluorophenyl)acetonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Preparation 10 4-Cyano-4-(3,4-difluorophenyl)-5-(1,3-dioxolan-2-yl)pentanoic acid A solution of 3,4-difluorobenzyl cyanide (20g, 0.13mol) in tetrahydrofuran (20ml) was added dropwise to a solution of lithium bis(trimethylsilyl)amide (1.0M, 144ml, 0,14mol) in tetrahydrofuran at 0C under nitrogen. The reaction mixture was allowed to warm to room temperature and stirred for 2 hours, after which time it was cooled to 0C and a solution of 2-bromomethyl-1,3-dioxolane (15ml, 0.14mol) in tetrahydrofuran (15ml) was added followed by tetra-n-butylammonium iodide (2g, 5.4mmol). The reaction mixture was warmed to room temperature and stirred for 18 hours. A further portion of solution of lithium bis(trimethylsilyl)amide in tetrahydrofuran (1M, 144ml, 0.14mol) was added dropwise to the reaction mixture at 0C and then the mixture was allowed to warm to room temperature over 5 hours. The reaction mixture was cooled to 0C and a solution of ethyl 3-bromopropionate (18ml, 0.14mol) in tetrahydrofuran (20ml) was added dropwise. The reaction mixture was allowed to warm to room temperature and stirred for 18 hours. A solution of sodium hydroxide (7.8g, 0.20mol) in water (50ml) was added to the crude reaction mixture at 0C and the mixture then allowed to warm to room temperature. The reaction mixture was stirred for 36 hours. The reaction mixture was partitioned between water and diethyl ether, the organic layer re-extracted with water and the combined aqueous layers were acidified to pH 1.0 with aqueous hydrochloric acid (2N). The aqueous layer was extracted with ethyl acetate (x2), dried over Na2SO4and the solvent removed under reduced pressure. The residue was purified by column chromatography on silica gel eluding with a gradient system of dichloromethane gradually changing to dichloromethane: methanol: acetic acid (95: 5: 1, by volume) to afford the title compound as a brown oil (15.0g, 37%) which solidified on standing. 1H-NMR (CDCl3): delta = 7.30 (1H, m), 7.20 (2H, m), 4.80 (1H, m), 3.95 (2H, m), 3.80 (2H, m), 2.50 (2H, m), 2.30 (2H, m), 2.20 (2H, m). m/z: 312 (MH+).

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-(3,4-Difluorophenyl)acetonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PFIZER INC.; Pfizer Limited; EP992493; (2000); A1;,
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Reference of 185147-07-3, These common heterocyclic compound, 185147-07-3, name is 2-Fluoro-3-methylbenzonitrile, 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.

Intermediate 81 : 3-Methyl-2-(2H-1 ,2,3-triazol-2-yl)benzonitrile.To a mixture of 2-fluoro-3-methylbenzonitrile (4.0 g, 29.6 mmol) and 2H-1 ,2,3- triazole (2.04 g, 29.6 mmol) in DMF (80 mL) was added potassium carbonate (8.26 g, 59.2 mmol). The resulting mixture was heated to 120 C for 2h. The mixture was cooled, diluted with water and extracted with EtOAc. The organic layers were combined, dried over Na2S04, filtered and concentrated. The residue was purified by FCC (Si02, ethyl acetate/hexanes, gradient 0-50%) to yield the title compound (1 .5 g, 26%). MS (ESI) mass calcd. for Ci0H8N4, 184.2; m/z found, 185.1 [M+H]+. 1H NMR (500 MHz, CDCI3): 7.95 (s, 2H), 7.66 (d, J = 7.7, 0.7 Hz, 1 H), 7.59 (d, J = 7.8, 0.6 Hz, 1 H), 7.50 (dd, J = 9.8, 5.7 Hz, 1 H), 2.20 (s, 3H).

The synthetic route of 185147-07-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; LETAVIC, Michael; RUDOLPH, Dale, A.; SAVALL, Brad, M.; SHIREMAN, Brock, T.; SWANSON, Devin; WO2012/145581; (2012); A1;,
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