Month: September 2021

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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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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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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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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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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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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67515-59-7, name is 4-Fluoro-3-(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. SDS of cas: 67515-59-7

A mixture of 4-fluoro-3-trifluoromethylbenzonitrile (75 mg, 0.40 mmol), sodium sulfinate (44.5 mg, 0.44 mmol) in N,N-dimethylformamide (1.5 mL) was heated at 100 C. for 2 h. The reaction mixture was cooled to room temperature, quenched with water. The resulting white solid was collected via filtration, washed with cold water, dried in a vacuum oven to give 4-methanesulfonyl-3-trifluoromethyl-benzonitrile (90 mg, 90% yield). This benzonitrile was hydrogenated in 2N NH3 in methanol with 35 mg of Raney Ni under a hydrogen balloon for 2 h. The reaction mixture was filtered through a celite plug, washed with methanol, evaporated in vacuo to give the titled compound.

The synthetic route of 67515-59-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Liu, Gang; Sham, Hing L.; Szczepankiewicz, Bruce G.; Xin, Zhili; Zhao, Hongyu; Serby, Michael D.; Liu, Bo; Liu, Mei; US2006/173050; (2006); A1;,
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Application of 874-97-5, These common heterocyclic compound, 874-97-5, name is 3-Cyanobenzyl alcohol, 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.

3-[(5-Amino-2H-pyrazol-3-yl)oxymethyl]benzonitrile, used as starting material, was prepared as follows: a) 3-Amino-5-hydroxypyrazole (2 g, 20.18 mmol, 1 eq) and triphenylphosphine (6.36 g, 24.22 mmol, 1.2 eq) were stirred in DCM (20 ml) for 30 mins. After this time, DIAD (4.77 ml, 24.22 mmol, 1.2 eq) was slowly added, keeping the temp below 20 C. with a water bath, and the resulting mixture stirred for a further 45 mins. A solution of 3-cyanobenzyl alcohol (3.23 g, 24.22 mmol, 1.2 eq) in DCM (10 ml) was added slowly and the reaction left to stir at RT for 24 hours. After this time the solid was filtered off and the solution extracted with 2M HCl solution (3×30 ml). The aqueous layer was back-washed with diethyl ether (2×30 ml), then basified to pH 9 using ammonium hydroxide, cooling the mixture to avoid a strong exotherm. The solution was extracted with DCM (3×30 ml) and the organic fractions combined, dried over magnesium sulphate and concentrated to give 3-[(5-amino-2H-pyrazol-3-yl)oxymethyl]benzonitrile as a colourless gum (321 mg, 7%). MS: m/z 215 (MH+)

Statistics shows that 3-Cyanobenzyl alcohol is playing an increasingly important role. we look forward to future research findings about 874-97-5.

Reference:
Patent; ASTRAZENECA AB; US2008/4302; (2008); 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. 25808-30-4, name is 2-(Methylamino)acetonitrile hydrochloride, A new synthetic method of this compound is introduced below., Application In Synthesis of 2-(Methylamino)acetonitrile hydrochloride

REFERENCE SYNTHETIC EXAMPLE 41 2-(Methyl{[trans-4-(3-methyl-4-oxo-7-{[2-(trimethylsilyl)ethoxy]methyl}-2,3,4,7-tetrahvdro-1H-pyrrolo[3′,2′:5,6]pyrido[4,3-d]pyrimidin-1-yl)cyclohexyl]methyl}amino)acetonitrile To a solution of trans-4-(3-methyl-4-oxo-7-{[2-(trimethylsilyl)ethoxy]methyl}-2,3,4,7-tetrahydro-1H-pyrrolo[3′,2′:5,6]pyrido[4,3-d]pyrimidin-1-yl)cyclohexanecarbaldehyde (25 mg, 0.056 mmol) obtained in Reference Synthetic Example 29 in methanol (0.5 mL), methylaminoacetonitrile hydrochloride (7.8 mg, 0.073 mmol) and 2-picoline borane (8.1 mg, 0.073 mmol) were added, and the mixture was stirred at room temperature for 3 hours. The reaction mixture was mixed with 1 M aqueous sodium hydroxide and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel thin-layer chromatography (ethyl acetate/2-propanol=9/1 (v/v)) to obtain the title compound as a colorless oil (27.5 mg, yield: 99percent).

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; Nissan Chemical Industries, Ltd.; TAKAHASHI, Keiji; WATANABE, Tsuneo; HAYASHI, Keishi; KURIHARA, Kazunori; NAKAMURA, Takanori; YAMAMOTO, Akio; NISHIMURA, Takuya; KAMIYAMA, Toshihiko; HIDAKA, Yuuki; EP2955181; (2015); A1;,
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Some common heterocyclic compound, 1080-74-6, name is 2-(3-Oxo-2,3-dihydro-1H-inden-1-ylidene)malononitrile, molecular formula is C12H6N2O, 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. Formula: C12H6N2O

To a three-necked round bottom flask were added 5,5′-(9,9′-spirobi[fluorene]-20,7-diyl)bis(4-(2-ethylhexyl)thiophene-2-carbaldehyde) (205 mg, 0.27 mmol), 1,1-dicyanomethylene-3-indanone (430 mg, 2.2 mmol), chloroform (50 mL), and 0.9 mLpyridine. The mixture was deoxygenated with nitrogen for 30 minand then refluxed for 12 h. After cooling down to room temperature,the mixture was poured into methanol (200 mL) and filtered.The residue was purified by column chromatography on silica gelusing petroleum ether/dichloromethane (1:1) as eluent yield anorange solid (207 mg, 69%). 1H NMR (400 MHz, CDCl3): delta 8.77 (s,2H), 8.68 (d, J 6.9 Hz, 2H), 7.96 (s, 1H), 7.93 (d, J 2.7 Hz, 2H), 7.89(d, J 4.8 Hz, 2H), 7.86 (d, J 1.8 Hz, 1H), 7.76 (m, 4H), 7.61 (d,J 5.4 Hz, 4H), 7.45 (t, J 7.5 Hz, 2H), 7.21 (t, J 7.5 Hz, 2H), 6.92 (s,2H), 6.82 (d, J 7.5 Hz, 2H), 2.39 (d, J 6.9 Hz, 4H),1.42 (m, 2H),1.09(m, 16H), 0.75 (m, 6H), 0.59 (t, J 6.9 Hz, 6H). 13C NMR (100 MHz,CDCl3): delta 188.63, 161.13, 157.22, 149.46, 149.27, 148.30, 143.36,141.49, 141.22, 140.47, 138.67, 137.35, 135.67, 135.47, 135.10, 133.58,130.17, 129.32, 128.84, 125.88, 125.17, 124.72, 124.37, 123.20, 121.23,121.15, 115.08, 114.99, 70.28, 66.57, 40.64, 32.95, 32.60, 28.90, 25.88,23.49, 14.65, 10.92. MS (MALDI): m/z calcd for C75H60N4O2S2 H:1114.4; found: 1114.1. Anal. Calcd for C75H60N4O2S2: C, 80.90; H,5.43; N, 5.03. Found: C, 80.77; H, 5.58; N, 5.33.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1080-74-6, its application will become more common.

Reference:
Article; Wang, Jiayu; Dai, Shuixing; Yao, Yuehan; Cheng, Pei; Lin, Yuze; Zhan, Xiaowei; Dyes and Pigments; vol. 123; (2015); p. 16 – 25;,
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