Month: February 2021

Adding a certain compound to certain chemical reactions, such as: 846023-24-3, name is 2-Cyano-N-(2,4-dichloro-5-methoxyphenyl)acetamide, 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 846023-24-3, Product Details of 846023-24-3

EXAMPLE 20 2-Cyano-N-(2,4-dichloro-5-methoxyphenyl)-3-[(3-iodo-4-methoxyphenyl)amino]prop-2-enamide To a suspension of 2-cyano-N-(2,4-dichloro-5-methoxyphenyl)acetamide (5.00 g, 19.30 mol) in 400 mL of iso-propanol, under N2, was added 3-iodo-p-anisidine (5.80 g, 23.16 mmol). This mixture was heated to reflux to give a clear yellow solution. To this solution, triethylorthoformate (8.60 mL, 52.11 mmol) was added dropwise and the reaction mixture was heated at reflux overnight. An additional 10 mL of triethylorthoformate was added and the mixture was heated at reflux overnight. The mixture was allowed to cool to room temperature and the white solid was collected by filtration, washed with isopropanol, and dried overnight at ~40 C. under reduced pressure. Purification by suspension in hot ethyl acetate followed by addition of cold hexanes gave 8.50 g (85%) of 2-cyano-N-(2,4-dichloro-5-methoxyphenyl)-3-[(3-iodo-4-methoxyphenyl)amino]prop-2-enamide as a yellow solid, mp 289-290 C.; MS (ES) m/z 516.7 (M-H)- Analysis for C18H14Cl2IN3O3; Calcd: C, 41.73; H, 2.72; N, 8.11. Found: C, 40.66; H, 2.94; N, 7.90.

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-Cyano-N-(2,4-dichloro-5-methoxyphenyl)acetamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Wyeth Holdings Corporation; US2005/43537; (2005); A1;,
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630-18-2, name is Pivalonitrile, 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. Product Details of 630-18-2

A solution of 2-bromobenzo[h]quinoline (1.52 g, 5.89 mmol) in THF (36 ml) was cooled to -78 oC and after 10 minutes a solution of 2.5 M of n-butyllithium in n-hexane (2.47 ml, 6.18 mmol) was added slowly. The resulting dark red solution was stirred at this temperature for 1 hour and then a solution of 2,2-dimethylpropanonitrile (0.78 ml, 7.04 mmol) in THF (5 ml) was added drop-wise. The solution was stirred for a further hour at -78 oC and finally allowed to warm slowly to ambient temperature. A solution of 1 M H2SO4 (25 ml, 25 mmol) was then added and the mixture was heated under reflux for 3 hours: After cooling, the organic phase was separated and the aqueous phase was extracted with Et2O (3 x 15 ml). The organic phases were combined, dried over anhydrous Na2SO4 and the solvent evaporated under reduced pressure. The residue was purified by flash chromatography (eluent: petroleum ether /acetate = 9/1) to give 1.24 g (80% yield) of 1-(benzo[h]quinolin-2-yl)-2,2-dimethylpropanone in the form of a yellow solid; melting point: 88-90 oC. Elemental analysis (%) calculated for C18H17NO: C, 82.10; H, 6.51; N, 5.32. Found: C, 82.10; H, 6.51; N, 5.32. 1H NMR (CDCl3): delta 9.20 (d, J= 7.8 Hz, 1H), 8.13 (s, 2H), 7. 84 (d, J= 7. 8 Hz, 1H), 7.80-7.73 (m, 2H), 7. 73-7. 62 (m, 1H), 7.56 (d, J= 9 Hz, 1H), 1.67 (s, 9H). 13C{1H} NMR (CDCl3): delta 206.7, 152.1, 144.5, 136.3, 133.7, 131.8, 129.5, 128.4, 127.9, 127.5, 124.9, 124.5, 121.2, 44.3, 28.0.

The synthetic route of 630-18-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Universita’ Degli Studi di Udine; RIGO, Pierluigi; BARATTA, Walter; SIEGA, Katia; CHELUCCI, Giorgio Adolfo; BALLICO, Maurizio; MAGNOLIA, Santo; EP2178843; (2013); B1;,
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Related Products of 13544-06-4, 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. 13544-06-4, name is 2-(2-Nitro-4-(trifluoromethyl)phenyl)acetonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

EXAMPLE 155 Methyl-[2-(6-trifluoromethyl-1H-indol-3-yl)-cyclopropylmethyl]-amine The commercially available (2-nitro-4-trifluoromethylphenyl) acetonitrile (14.0 g, 60.8 mmol) was dissolved in 9:1 EtOH:H2O (50 mL) and glacial acetic acid (1.4 mL). This mixture was hydrogenated over 10% Pd/C (5.0 g) at 50 psi for 16 h at room temperature. The reaction was filtered over celite and evaporated in vacuo. The residue was partitioned between saturated aqueous sodium carbonate and dichloromethane (2*200 mL) and the combined organic extract was dried over sodium sulfate, filtered, and concentrated in vacuo. The crude material was purified by silica gel column chromatography (hexanes/ethyl acetate, 20:1, 9:1, 5:1) to afford 12.9 g (65% yield) of 6-trifluoromethyl-1H-indole as a yellow solid: 1H NMR (400 MHz, CDCl3) 8.36, (1H, br s), 7.72 (2 H, m), 7.37 (2 H, m), 6.63 (1 H, m); MS m/e 184 (M-H)-. Anal calcd. for C9H6F3N: C, 58.38; H, 3.26; N, 7.56. Found: C, 58.30; H, 2.92; N, 7.49.

The synthetic route of 2-(2-Nitro-4-(trifluoromethyl)phenyl)acetonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Mattson, Ronald J.; Denhart, Derek John; Deskus, Jeffrey A.; Ditta, Jonathan L.; Marcin, Lawrence R.; Epperson, James R.; Catt, John D.; King, Dalton; Higgins, Mendi A.; US2003/73849; (2003); A1;,
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Related Products of 77668-42-9, These common heterocyclic compound, 77668-42-9, name is 2,3-Dichlorobenzoyl cyanide, 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.

5. Synthesis of lamotrigine via the tetrafluoroborate saltA solution of aminoguanidinium tetrafluoroborate was freshly prepared from aminoguani- dinium bicarbonate (2.42 g, 17.8 mmol) and anhydrous tetrafluoroboric acid, 53% (v/v) in diethylether (6.18 g), and diluted with acetonitrile (8 mL). 2,3-dichlorobenzoyl cyanide (1.50 g, 7.50 mmol) was added and the reaction mixture was heated to 45 C for 4 hours.In analogy to example 2 the reaction mixture was poured into ice water, yielding the tetrafluoroborate salt of compound II as a suspension which was cooled down to 10 C and filtrated. The filter cake was directly dissolved from the filter at room temperature using essentially pure acetonitrile without any additional solvent. The subsequent cyclization step was performed as described in example 2.

Statistics shows that 2,3-Dichlorobenzoyl cyanide is playing an increasingly important role. we look forward to future research findings about 77668-42-9.

Reference:
Patent; LONZA AG; WO2008/19798; (2008); A1;,
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Electric Literature of 159847-81-1, These common heterocyclic compound, 159847-81-1, name is Methyl 2-amino-5-cyanobenzoate, 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 mixture of A [(2. 0] g, 7.37 [MMOL),] oxalyl chloride (10 mL), and [CH2CL2] (4 mL) was treated with DMF (ca. [2GEL).] The mixture was stirred at room temperature for 1 hr and then heated to reflux for 5 h. The yellow solution was cooled and concentrated in vacuo to give crude acid chloride that was redissolved in [CH2C12] (2 mL) and added slowly to a mixture of methyl [2-amino-5-cyanobenzoate] (1.28 g, 7.37 mmol) in dry pyridine (10 mL). The red mixture was stirred at room temperature for lh and then heated to reflux for 3 h under N2. The reaction mixture was cooled to room temperature, diluted with H20 (2 mL), and concentrated in vacuo to a slurry mixture that was diluted with ethyl acetate. The mixture was filtered. The solids were washed with H20 and dried in a vacuum oven to give 2.02 g (64 % yield) of product: mp 184- [185 C] : MS (ESI+) for [C2OH19N306S] [M/Z] 429.9 [(M+H) +.] IR (diffuse reflectance) 3457,3362, 2224,1642, 1551,1485, 1401,1306, 1261,1178, 1156,900, 858, [821,] 634 [CM~L.] MS (CI) m/z [(REL.] intensity) 244 (M+, 0), 245 (12), 244 (99), 127 (9), 118 (9), 117 (72), 90 (75), 84 (11), 64 (14), 63 (42), 62 (13). Anal. Calcd for [C7HSIN2] : C, 34.45 ; H, 2.07 ; N, 11.48.Found: C, 34.57 ; H, 2.08 ; N, 11. 48.

Statistics shows that Methyl 2-amino-5-cyanobenzoate is playing an increasingly important role. we look forward to future research findings about 159847-81-1.

Reference:
Patent; PHARMACIA & UPJOHN COMPANY; WO2004/18461; (2004); A2;,
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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. 34667-88-4, name is 2-Fluoro-4-nitrobenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. COA of Formula: C7H3FN2O2

Production Example 6-1 2-(6-bromo-2-naphthyloxy)-4-nitrobenzonitrile After heating to reflux 2-fluoro-4-nitrobenzonitrile (1 g), 6-bromo-2-naphthol (1.41 g), potassium fluoride/alumina (0.7 g) and 18-crown-6 (0.16 g) in acetonitrile, the mixture was reacted for 12 hours. It was then cooled to room temperature, the insoluble portion was filtered using celite, the ethyl acetate layer was washed with water and saturated saline and then dried over magnesium sulfate, and the solvent was distilled off. Methanol was added to the residue for crystallization to obtain 1.43 g of 2-(6-bromo-2-naphthyloxy)-4-nitrobenzonitrile. 1H-NMR (CDCl3) delta:7.31 (1H, dd, J=2.4, 8.8 Hz), 7.54 (1H, d, J=2.0 Hz), 7.62-7.70 (3H, m), 7.88 (1H, s), 7.90 (1H, s), 8.01 (1H, dd, J=2.0, 8.4 Hz), 8.08 (1H, s).

The synthetic route of 34667-88-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Satoh, Takashi; Okamoto, Yasushi; Asano, Osamu; Watanabe, Nobuhisa; Nagakura, Tadashi; Saeki, Takao; Inoue, Atsushi; Sakurai, Masahiro; US2003/181766; (2003); A1;,
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Related Products of 26830-95-5, 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. 26830-95-5 name is 4-Methyl-2-nitrobenzonitrile, 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.

4-methyl-2-nitrobenzonitrile (0 ¡¤ 2mmol, 32 ¡¤ 4mg) ,tetrahydroxydiboron (0.6mmol, 53.8 mg), glacial acetic acid (0.24mmol, 14.5mg), cuprous chloride (0.04mmol, 4.0mg), Benzaldehyde (0¡¤24mmol, 25¡¤4mg), methanol (1ml), water (1ml) were added to the test tube, reacted at 60 C for 3h, after the completion of reaction, the reaction solution was extracted with ethyl acetate three times, the combined organic phases are concentrated to dryness, separated through column chromatography (petroleum ether: ethyl acetate =4:1), Yield:(34.8mg,73%)

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

Reference:
Patent; China Three Gorges University; Zhou Haifeng; Sui Yuebo; Jiang Xiaolan; Yang Bing; Yu Tao; (16 pag.)CN108558778; (2018); A;,
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Some common heterocyclic compound, 6136-93-2, name is 2,2-Diethoxyacetonitrile, molecular formula is C6H11NO2, 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. Computed Properties of C6H11NO2

In a 2 L, three-neck round bottom flask (equipped with magnetic stir bar, thermometer, and addition funnel), charged diethoxyacetonitrile (111.1 g, 860 mmol) and methanol (620 mL, anhydrous) while under a steady nitrogen flow. Via an addition funnel, slowly charged 25 wt % solution of sodium methoxide (4.64 g, 86 mmol, 19.7 mL) in methanol. (Note: addition is slightly exothermic). The mixture was stirred for 15 h, at which point, the solvent was removed under vacuum (Note: starting material had not been completely converted according to NMR). The residue was dissolved in methanol and charged with a fresh sodium methoxide solution- same concentration/equivalents- and stirred another 15 h). The solvent was removed under vacuum and the residue was dissolved in diethyl ether (1.0 L), with the organic phase washed with water (3 x 500 mL), then brine (1 x 300 mL). The organic layer was dried over magnesium sulfate, the salts filtered and the solvent reduced under vacuum to give 89.9 g of a crude mixture of methyl 2,2-diethoxyethanimidoate and un-reacted starting material (10-12 mol % by NMR) as a thin oil. Note that best yields of the imidate are obtained when the organic layer is stripped of at 400 mbar and 45 0C because of its volatility.The oil was dissolved in methanol (300 mL,) and placed into a 2 L round bottom flask (equipped with magnetic stir bar, reflux condenser) along with 1-(4-bromophenyl)methanamine (100.0 g, 537 mmol) and the mixture subjected to heating in a pre-heated oil bath. The mixture was stirred at 700C for 18 h and then allowed to cool. The solvent was removed to give 158.8 g of the desired intermediate (1) in 93.8% yield (based on 1-(4-bromophenyl)methanamine as limiting reagent).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6136-93-2, its application will become more common.

Reference:
Patent; PFIZER PRODUCTS INC.; WO2007/125405; (2007); A2;,
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Synthetic Route of 5866-98-8, 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. 5866-98-8, name is 2,6-Dichloro-3-nitrobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows.

To a stirred solution of 2,6-dichloro-3-nitrobenzonitrile (750.0 g, 3.45 mol, 1.0 equiv.) in ethanol (7.5 L, 10.0 V) at 15-20 oC. was slowly added hydrazine hydrate (519.0 g, 10.36 mol, 3.0 equiv.) while maintaining the reaction mass below 25 C (Observation: Addition is slightly exothermic and solid formation will begin upon addition). The reaction mixture temperature was slowly raised to room temperature and then the mixture was stirred for 3 h (Observation: the quantity of solids will increase during this time). After completion of the reaction (monitored by TLC), the mixture was diluted with water (7.5 L, 10.0 V) and further stirred for 1 h at room temperature. The solids were isolated via filtration and then were washed with water (2.25 L, 3.0 V). The wet solid was washed with a 1:1 ratio mixture of acetone (1.875 L, 2.5 V) and hexanes (1.875 L, 2.5 V). Bulk residual water was removed from the solids by maintaining vacuum filtration for 60-90 min. The wet solid was finally dried in a hot air oven for 7-8 h at 50 oC (until moisture content reaches below 1.5%) to get the dried product, 4-chloro-7-nitro-1H-indazol-3-amine (549.0 g, 75% yield) as a brick red-colored solid.1H NMR (400 MHz, CDCl3): d 10.36 (bs, 1H), 8.20 (d, J = 8.4 Hz, 1H), 7.07 (d, J = 8.40 Hz, 1H), 4.73 (bs, 2H).

The chemical industry reduces the impact on the environment during synthesis 2,6-Dichloro-3-nitrobenzonitrile. I believe this compound will play a more active role in future production and life.

Reference:
Patent; VIIV HEALTHCARE UK (NO.5) LIMITED; GILLIS, Eric P; PARCELLA, Kyle E.; PATEL, Manoj; PEESE, Kevin M; (277 pag.)WO2020/84492; (2020); A1;,
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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. 78881-21-7, name is 4-Amino-3-methylbenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 78881-21-7

To the ice-cold trifluoroacetic anhydride (60 mL) was added 4-amino-3-methyl-benzonitrile (14.33 g, 0.108 mol) in portion. The resulting white slurry was stirred at 0 C. for 30 min. Then ammonium nitrate (17.28 g, 0.216 mol) was added. The reaction mixture was allowed to stir at 0 C. for 1 h and at room temperature for 14 h. After removal of most solvent, the reaction mixture was cooled with ice and quenched with ice. The yellow precipitate was filtered, washed with cold water, and dried under vacuum. The crude product (15.5 g, 52% yield, and ca. 80% pure) was used for the next step without purification. 1H NMR (300 MHz, CD3OD) delta 8.05 (1H, s), 7.74 (1H, s), 2.30 (3H, s). LRMS (neg. ESI, (M-H)-) m/z 272.

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 78881-21-7.

Reference:
Patent; Wittman, Mark D.; Balasubramanian, Neelakantan; Velaparthi, Upender; Zimmermann, Kurt; Saulnier, Mark G.; Liu, Peiying; Sang, Xiaopeng; Frennesson, David B.; Stoffan, Karen M.; Tarrant, James G.; Marinier, Anne; Roy, Stephan; US2004/44203; (2004); A1;,
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