Tag: M.W=100-200

Application of 64248-64-2, The chemical industry reduces the impact on the environment during synthesis 64248-64-2, name is 2,5-Difluorobenzonitrile, I believe this compound will play a more active role in future production and life.

Step A: 5-Fluoro-2-hydroxybenzonitrile (23t): 2,5-Difluorobenzonitrile (14.9 g, 107 mmol) and benzyl alcohol (11.1 mL, 11.6 g, 107 mmol) were dissolved in DMF (330 mL) and cooled to 0 C. Sodium hydride (60% in oil, 6.40 g, 161 mmol) was added to the solution at 0 C. and the reaction mixture was allowed to warm to room temperature. After stirring for 1 hour at room temperature, the reaction solution was cooled to 0 C. and water (330 mL) was gradually added to the solution. The mixture was transferred to a separatory funnel and extracted 3 times with 500 mL of Et2O. The combined organic layer was washed with 100 mL of water twice, brine once, then dried over MgSO4. After filtration, the solution was concentrated under reduced pressure to obtain a crude pale yellow solid. The crude solid was dissolved in MeOH (500 mL). To the solution was added 10% palladium on activated carbon under a nitrogen atmosphere. Replacing nitrogen gas with hydrogen gas, reaction mixture was stirred at room temperature (if the reaction did not proceed in 30 minutes, the palladium on carbon was filtered off and set up again). After 2 hours of stirring, the palladium on carbon was filtrated off and washed with MeOH. The solution was concentrated under reduced pressure to obtain a pale yellow solid. The solid was recrystallized from hot toluene (100 mL) by addition of hexane (10 mL) followed by cooling to 0 C. The obtained white needles were washed with 1:1 mixture of toluene and hexane (7.23 g, 49% yield). The mother liquor was concentrated and purified on silica gel with Et2O/hexane (2:3-1:1) to afford desired compound (23t) (6.94 g, 47% yield). Total 14.2 g (96% yield) over 2 steps. 1H-NMR (400 MHz, d6-DMSO) delta 11.09 (s, 1H), 7.58 (dd, J=8.4, 3.2 Hz, 1H), 7.40 (td, J=8.6, 3.2 Hz, 1H), 7.03 (dd, J=9.2, 4.4 Hz, 1H) ppm.

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, 2,5-Difluorobenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Munson, Mark; Kim, Youngboo; Groneberg, Robert D.; Rizzi, James; Rodriguez, Martha; Kim, Ganghyeok; Vigers, Guy; Rao, Chang; Balachari, Devan; US2004/180896; (2004); A1;; ; Patent; Munson, Mark; Mareska, David A.; Kim, Youngboo; Groneberg, Robert D.; Rizzi, James; Rodriguez, Martha; Kim, Ganghyeok; Vigers, Guy; Rao, Chang; Balachari, Devan; Harvey, Darren; US2004/192653; (2004); A1;,
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Synthetic Route of 143879-78-1, These common heterocyclic compound, 143879-78-1, name is 3-Amino-2,6-difluorobenzonitrile, 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.

Methyl (3 S)-3 ,7-dimethyl- 1,1 -dioxo-2,3 ,4,5 -tetrahydropyrrolo [3 ,4-f]thiazepine-6- carboxylate (200 mg, 0.73 mmol) and 3-amino-2,6-difluoro-benzonitrile (0.16 g, 0.88 mmol) in dry THF (5 mL) was treated with lithium bis(trimethylsilyl)amide (2.2 mL, 1 M in THF, 2.2 mmol) and this was stirred overnight at room temperature. Theresulting mixture was quenched with NH4C1 (aq., sat., 5 mL). Then 5 mL of brine wasadded and the layers were separated. The water layer was extracted using EtOAc (2 X30 mL). The combined extracts were concentrated in vacuo and the obtained crude waspurified using silica gel column chromatography (gradient elution: EtOAc:heptane0:100 to 100:0). The desired fractions were concentrated in vacuo and the obtainedresidue was purified via preparative HPLC (Stationary phase: RP XBridge Prep C18 OBD-l0jim, 3OxlSOmm, Mobile phase: 0.25% NH4HCO3 solution in water, ACN). The desired fractions were concentrated under reduced pressure, co-evaporated with methanol (2 X 25 mL) and dried in a vacuum oven at 55C for 18 hours yielding compound 157 (7.6 mg). ?H NMR (400 MHz, DMSO-d6) oe ppm 1.14 (d, J=6.82 Hz,3H)1.31-1.45(m,1H)1.81-1.91(m,1H)2.77-2.89(m,1H)3.07-3.18(m,1H)3.58 – 3.67 (m, 1 H) 3.70 (s, 3 H) 7.03 (d, J=9.68 Hz, 1 H) 7.40 – 7.51 (m, 2 H) 8.06(td,J=8.97, 6.05 Hz, 1 H) 10.31 (s, 1 H); Method B; Rt: 0.85 mi mlz :393 (M-H)Exact mass: 394.1, MP: 247.5 C.

The synthetic route of 143879-78-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN SCIENCES IRELAND UC; VENDEVILLE, Sandrine, Marie, Helene; LAST, Stefaan, Julien; DEMIN, Samuel, Dominique; GROSSE, Sandrine, Celine; HACHE, Geerwin, Yvonne, Paul; HU, Lili; PIETERS, Serge, Maria, Aloysius; ROMBOUTS, Geert; VANDYCK, Koen; VERSCHUEREN, Wim, Gaston; RABOISSON, Pierre, Jean-Marie, Bernard; (244 pag.)WO2017/1655; (2017); A1;,
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Electric Literature of 1187-42-4,Some common heterocyclic compound, 1187-42-4, name is Diaminomaleonitrile, molecular formula is C4H4N4, 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.

The compound J (0.70 g, 1.56 mmol), diaminomaleonitrile (0.20 g, 1.85 mmol), 40 mL of ethanol, 20 mL of THF, and 0.24 mL of a 12M hydrochloric acid were charged in a three-necked flask having a capacity of 300 mL, and the mixture was stirred while heating at 40 C. for 24 hours. Water was added to the resultant solution, the resultant mixture was subjected to extraction with chloroform, and then the resultant extract was dried by adding sodium sulfate thereto. Sodium sulfate hydrate was removed by conducting filtration, and the solvent was distilled off from the filtrate using an evaporator. The resultant solid was purified by silica gel column chromatography (developing solvent: toluene) to obtain a yellow solid (yield amount: 0.40 g, yield: 49%). Chemical shift values (delta) of the compound measured by 1H NMR (400 MHz, CDCl3) were as follows: delta 9.32 (d, J=8.4 Hz, 1H), 9.25 (dd, J=10.8, 2.8 Hz, 1H), 8.94 (d, J=2.0 Hz, 1H), 8.80 (d, J=8.8 Hz, 1H), 8.20-8.16 (m, 3H), 8.07 (dd, J=8.8, 2.4 Hz, 2H), 8.01 (td, J=8.8, 1.6 Hz, 1H), 7.89 (td, J=7.2, 1.2 Hz, 1H), 7.81 (dd, J=8.4, 2.0 Hz, 2H), 7.55-7.52 (m, 2H), 7.47 (dd, J=7.2, 1.2 Hz, 2H), 7.36-7.31 (m, 2H). It was confirmed by 1H NMR measurement that the obtained compound was a compound 4 (Cz-CNBQx).

The synthetic route of 1187-42-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KYUSHU UNIVERSITY, NATIONAL UNIVERSITY CORPORATION; Nippon Soda Co., Ltd.; YASUDA, Takuma; FURUE, Ryuhei; ISHIHARA, Hiroyuki; FUKUSHIMA, Yukio; (61 pag.)US2019/330162; (2019); A1;,
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6587-24-2, name is Methyl 2-cyanobenzoate, 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 Methyl 2-cyanobenzoate

From methyl 2-cyanobenzoate (1). To a freshly prepared solution of sodium methoxide obtained by dissolving sodium metal (0.69 g, 30 mmol) in dry MeOH (25 mL), methyl 2-cyanobenzoate (1) (1.61 g, 10 mmol) and malononitrile (1.98 g, 30 mmol) were added with stirring. The obtained yellow-orange solution was refluxed for 8 h till the TLC showed the absence of starting ester 1. Then the resulting suspension was cooled, fine pale yellow precipitate of compound 10a was filtered off, washed with MeOH (10 mL) and dried in air. Pale yellow powder. Yield: 2.00 g (68 %); mp 262-263 C.

The synthetic route of 6587-24-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Tkachuk, Volodymyr; Merkulova, Vladyslava; Omelchenko; Arrault, Axelle; Hordiyenko, Olga; Tetrahedron Letters; vol. 60; 30; (2019); p. 1959 – 1963;,
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Adding a certain compound to certain chemical reactions, such as: 19924-43-7, name is 2-(3-Methoxyphenyl)acetonitrile, 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 19924-43-7, Quality Control of 2-(3-Methoxyphenyl)acetonitrile

To a solution of sodium hydride (1.79 g, 44.8 mmol) in dimethylsulfoxide (DMSO, 60 ml) is added a solution of (3-methoxyphenyl)acetonitrile (2.50 ml, 17.9 mmol) and 2-bromoethyl tert-butyldimethylsilyl ether (9.22 ml, 43.0 mmol) in ether (20 ml) at room temperature, and the mixture is stirred overnight. To the mixture is added water, and the mixture is extracted twice with ether. The organic layer is washed three times with water, dried over anhydrous magnesium sulfate, and the solvent is evaporated under reduced pressure. Then, the reaction mixture is dissolved in tetrahydrofuran (THF, 100 ml), and thereto is added tetrabutylammonium fluoride (TBAF, 12.2 g, 46.5 mmol), and the mixture is stirred at room temperature overnight. Water is added to the mixture, and the mixture is extracted twice with ethyl acetate. The organic layer is washed twice with water, dried over anhydrous magnesium sulfate, and the solvent is evaporated under reduced pressure. The residue is purified by silica gel chromatography to give the title compound (2.91 g) as colorless oil.1H-NMR delta (DMSO-d6): 1.97-2.02 (4H, m), 3.12-3.22 (2H, m), 3.32-3.45 (2H, m), 3.76 (3H, s), 4.59 (2H, t, J = 5.13), 6.87-7.03 (3H, m), 7.31-7.36 (1H, m).

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; Sumitomo Pharmaceuticals Company, Limited; EP1500648; (2005); A1;,
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455-18-5, name is 4-(Trifluoromethyl)benzonitrile, 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. category: nitriles-buliding-blocks

Step A (4-Trifluoromethylphenyl)thiocarboxamide To a stirred solution of 25.0 grams (0.146 mole) of 4-(trifluoromethyl)benzonitrile in 190 ml of pyridine was added 14.8 grams (0.146 mole) of triethylamine. During a two hour period, hydrogen sulfide gas was bubbled into the reaction mixture. The reaction mixture was stirred under a dry nitrogen atmosphere for 15 minutes and then was poured into ice-water. The aqueous mixture was extracted with three portions of diethyl ether. The organic extracts were combined and washed in succession with 10% hydrochloric acid, water, and an aqueous, saturated sodium chloride solution. The washed extract was dried over anhydrous sodium sulfate and was filtered. The filtrate was evaporated under reduced pressure to yield 28.3 grams of (4-trifluoromethylphenyl)thiocarboxamide as a solid.

The synthetic route of 455-18-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FMC Corporation; US4889867; (1989); A;,
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Application of 6136-68-1, These common heterocyclic compound, 6136-68-1, name is 3-Acetylbenzonitrile, 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.

Part A. Preparation of ethyl 3-(3-cyanophenyl)-3-oxopropionate. To a suspension of sodium hydride (1.2 g of 60% suspension in mineral oil, hexane-washed, 30.3 mmol) in 40 mL of tetrahydrofuran was added diethyl carbonate (3.7 mL, 30.3 mmol) and 3-acetyl benzonitrile (2.2 g, 15.2 mmol). The resulting suspension was stirred at 65 C for 1 h and then was cooled to room temperature. There was added 40 mL of 10% aqueous HCl and the reaction mixture was diluted with ethyl acetate and the layers were separated. The organic layer was washed with brine, dried (MgSO4) and concentrated in vacuo to afford 3.2 g (96%) of the title compound, which was sufficiently pure to be used without purification. MS (NH3-CI) 218.3 (M+H)+.

The synthetic route of 6136-68-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bristol-Myers Squibb Pharma Company; EP946528; (2003); B1;,
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Electric Literature of 115661-37-5, A common heterocyclic compound, 115661-37-5, name is 2-Amino-3-fluorobenzonitrile, molecular formula is C7H5FN2, 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-amino-3-fluorobenzonitrile (17.07 g, 0.125 mol) in 1,4-dioxane (20 ml) was added 48% aqueous hydrobromic acid (200 ml) and the solution was cooled to 0C before adding dropwise a solution of sodium nitrite (9.95 g, 0.144 mol) in water (22 ml) over 35 min so that the temperature did not rise above 3C. The resulting mixture was stirred at 2-3C for 2 h then poured onto a cooled (5C) solution of copper (I) bromide (26.98 g, 0.188 mol) in 48% hydrobromic acid (100 ml). The mixture was stirred for 10 min then heated to 50C over 1 h. The mixture was cooled to ambient temperature, diluted with water (11) and extracted with diethyl ether (2 x 500 ml). The combined organic extracts were washed with 1 M aqueous Na2SO3 (500 ml), then saturated aqueous NH4C1 (200 ml), dried (MgSO4), and evaporated to give a brown oil/solid. Purification by chromatography (silica gel, 10% EtOAc/isohexane) and trituration of a mixed fraction with isohexane afforded 13.22 g (53%) of 2-bromo-3- fluorobenzonitrile as a pale yellow solid : 1H NMR (360 MHz, CDCl3) 5 7.62-7. 68 (1H, m), 7.74-7. 85 (1H, ddd, J 9, 9,1), 7.74-7. 85 (1H, ddd, J 8, 1, 1).

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; MERCK SHARP & DOHME LIMITED; WO2003/93272; (2003); 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. 623-00-7, name is 4-Bromobenzonitrile, A new synthetic method of this compound is introduced below., COA of Formula: C7H4BrN

To a solution of 4-bromobenzonitrile (4.0 g, 22 mmol) in conc. H2SO4 (10 mL) was added dropwise at 0 C. nitric acid (6 mL). The reaction mixture was stirred at 0 C. for 30 min, and then at room temperature for 2.5 h. The resulting solution was poured into ice-water. The white precipitate was collected via filtration and washed with water until the washings were neutral. The solid was recrystallized from an ethanol/water mixture (1:1, 20 mL) twice to afford 4-bromo-3-nitrobenzonitrile as a white crystalline solid (2.8 g, 56%). 1H NMR (300 MHz, DMSO-d6) delta 8.54 (s, 1H), 8.06 (d, J=8.4 Hz, 1H), 7.99 (d, J=8.4 Hz, 1H); 13C NMR (75 MHz, DMSO-d6) delta 150.4, 137.4, 136.6, 129.6, 119.6, 117.0, 112.6; HPLC ret. time 1.96 min, 10-100% CH3CN, 5 min gradient; ESI-MS 227.1 Ink (MH+).

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; Vertex Pharmaceuticals Incorporated; Van Goor, Fredrick F.; Burton, William Lawrence; US2015/231142; (2015); A1;,
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17417-09-3, name is 2-Fluoro-5-nitrobenzonitrile, 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. name: 2-Fluoro-5-nitrobenzonitrile

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.

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

Reference:
Patent; Bristol-Myers Squibb Pharma Company; EP946508; (2009); B1;,
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