Month: February 2021

In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 796600-15-2 as follows. Quality Control of 2-Chloro-4-fluoro-3-methylbenzonitrile

Example 58; (R)-2-Chloro-4-(1-(5-(4-cyanophenyl)-1,3,4-oxadiazol-2-yl)-2-hydroxyethylamino)-3-methylbenzonitrile; Intermediate 58a; (R)-2-(3-Chloro-4-cyano-2-methylphenylamino)-3-hydroxypropanoic acid K2CO3 (5.71 g, 41.28 mol) was added to a solution of 2-chloro-4-fluoro-3-methylbenzonitrile (3.5 g, 20.64 mmol) and D-Serine (2.17 g, 20.096 mol) in DMSO (100 mL) at room temperature. The reaction mixture was heated to 75 C. and stirred for 19 h, then was allowed to cool to room temperature whereupon water (30 mL) was added followed by citric acid monohydrate (5g). After stirring for 10 min the mixture was partitioned between EtOAc (50 mL) and water. The organic phase was then washed with water (20 mL), brine (20 mL), dried (Na2SO4), filtered and concentrated to furnish a pale yellow solid (4.2 g). This crude product was then passed through a silica-plug [hexanes-EtOAc (95:5) as eluent] to furnish the title compound as a white solid (1.5 g, 29%) 1H NMR (500 MHz, acetone-d6, delta in ppm) 7.49 (d, J=9 Hz, 1H), 6.72 (d, J=9 Hz, 1H), 5.56 (d, J=8 Hz, 1H), 4.43-4.40 (m, 1H), 4.06 (dd, J=11, 18 Hz, 1H), 4.05 (dd, J=11, 18 Hz, 1H) and 2.31 (s, 3H).

According to the analysis of related databases, 796600-15-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Miller, Chris P.; US2009/253758; (2009); A1;,
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Synthetic Route of 1953-99-7, The chemical industry reduces the impact on the environment during synthesis 1953-99-7, name is 3,4,5,6-Tetrachlorobenzene-1,2-dicarbonitrile, I believe this compound will play a more active role in future production and life.

To a 100 mL flask was added the solid (4- (biphenyl-2-ylamino) -3,5,6-trichlorophthalonitrile) (1.0 g), 3,4,5,6-tetrachlorophthalonitrile (2.0 g), 1,8-Diazabicycloundec- -ene (3.0 g), and 1-pentanol (30 mL), and dissolve by heating. Then, zinc acetate (0.46 g) is added and refluxed with heating. After completion of the reaction, the solvent was removed, and the residue was purified by column chromatography. Dichloromethane was appropriately added to the obtained solid to dissolve the solid, and hexane was added to crystallize. At this time, the obtained solid was filtered and dried under vacuum to obtain a compound represented by the following general formula (7).

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, 3,4,5,6-Tetrachlorobenzene-1,2-dicarbonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Cheil Industries Co., Ltd.; Choe, Say Young; Kwon, JaeYoung; Park, Uhn B; Lee, Jong Son; Lee, Chang Ryul; Jong, Ju Ho; Choe, Mi Jin; Choe, Sung Gip; Hyung, Gyung Hee; (28 pag.)KR2015/130131; (2015); A;,
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Electric Literature of 2032-34-0,Some common heterocyclic compound, 2032-34-0, name is 3,3-Diethoxypropanenitrile, molecular formula is C7H13NO2, 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.

Preparation of cyanomalondialdehyde. To a dried flask was added sodium hydride (0.82 g, 50% suspended in mineral oil, 17 mmol). The sodium hydride was washed three times with 15 mL of ether, and then 15 mL of ether was added to the flask. After cooling the slurry to 0 C., ethyl formate (10.4 g, 140 mmol) was added. To this mixture was added 3,3-diethoxypropionitrile (2 g, 14 mmol) in 10 ml of ether over 2 hours (syringe pump). The mixture was stirred at room temperature for 20 hours, and then poured into 100 mL of ice water. This solution was extracted three times with ether, and then the ether extracts were discarded. The aqueous phase was acidified to pH 3 with concentrated HCl and extracted with dichloromethane. The organic phase was dried over MgSO4, filtered, and concentrated to yield 0.3 g of cyanomalondialdehyde as a yellow solid. Additional product was recovered from the pH 3 aqueous phase: the aqueous phase was concentrated to dryness, and then dissolved in 5 mL of methanol. The inorganic salt was removed by filtration, and the filtrate was concentrated to yield 1 g of cyanomalondialdehyde as a yellow solid. 1H NMR (300 MHz, DMSO-d6) delta8.94 (s, 2H), 4.95 (br s, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3,3-Diethoxypropanenitrile, its application will become more common.

Reference:
Patent; Bristol-Myers Squibb Company; US6420349; (2002); B1;,
Nitrile – Wikipedia,
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Related Products of 17626-40-3,Some common heterocyclic compound, 17626-40-3, name is 3,4-Diaminobenzonitrile, molecular formula is C7H7N3, 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: In a screw-cap vial, the diamine or aminothiophenol (1 mmol) was dissolved in fluorinated carboxylic acid (2 mL, 0.5 M) and the reaction was stirred at 70 C for 16 hours. The fluorinated carboxylic acid was then evaporated under reduced pressure and the crude product was purified by silica gel column chromatography to yield the corresponding product.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3,4-Diaminobenzonitrile, its application will become more common.

Reference:
Article; Rene, Olivier; Souverneva, Alexandra; Magnuson, Steven R.; Fauber, Benjamin P.; Tetrahedron Letters; vol. 54; 3; (2013); p. 201 – 204;,
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Some common heterocyclic compound, 55877-79-7, name is 5-Chloro-2-methoxybenzonitrile, molecular formula is C8H6ClNO, 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. Product Details of 55877-79-7

To a glass lined reactor were charged potassium tert-butoxide (1.5 kg/kg, 2.4 equiv) and THF (12.2 kg/kg) at 0 C. A mixture of Compound 4 (1.0 kg), L-methyl-N- formyl hydrazine (1.0 kg/kg, 2.30 equiv) and THF (5.3 kg/kg, 6.0 L/kg) was added slowly. The reactor line was r sed with THF (0.5 kg/kg). The reaction crude was aged at 0 C until reaction reached completion. Water (5.0 kg/kg) was added, and the resulting mixture was aged at 0 C for 30 min, heated to 40 C and aged for additional 30 min. The layers were separated and the aqueous layer was discarded. The organic layer was washed with brine (15 wt%, 5.7 kg/kg) before distilling under vacuum until total volume became approximately 5 L/kg. Four put/take distillations with ethyl acetate (4 x 10 L/kg) were undertaken for the purpose of azeotropic drying. The crude was cooled to 20 C. Sulfuric acid (0.66 kg/kg, 1.10 equiv.) was added, and the slurry was agitated for 2-3 h. Product was isolated by filtration. The cake was consecutively washed with ethyl acetate (2 c 6.5 L/kg) and heptane (8 L/kg), and dried under vacuum at 45 C. Compound 5 was isolated in 99 AP and 83% yield.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 55877-79-7, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; ROBERTS, Daniel Richard; (0 pag.)WO2019/232138; (2019); A1;,
Nitrile – Wikipedia,
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Reference of 57381-37-0, These common heterocyclic compound, 57381-37-0, name is 2-Bromo-5-chlorobenzonitrile, 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 stirred solution of 2-bromo-5-chloro-benzonitrile (10 g, 46 mmol) in THF (200 mL)at 0C, was added MeMgBr (77 mL, 230 mmol) dropwise. The reaction mixture wasallowed to warm up to room temperature and stuffed for 2 hours. Ti(Oi-Pr)4 (13 g, 46mmol) was added and the solution was stuffed for another 16 hours before it was quenchedwith aq. HC1 solution and washed with EtOAc. The aqueous phase was adjusted to pH 10 with aq. NaOH solution, and exacted with EtOAc (3 x 100 mL). The combined organic layers were concentrated to give a crude title product (3.8 g, yield 33%) as oil, which was used directly in the next step without further purification. MS: 249.30 (M+Hj

The synthetic route of 57381-37-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; AEBI, Johannes; AMREIN, Kurt; CHEN, Wenming; HORNSPERGER, Benoit; KUHN, Bernd; LIU, Yongfu; MAERKI, Hans P.; MARTIN, Rainer E.; MAYWEG, Alexander V.; TAN, Xuefei; WANG, Lisha; ZHOU, Mingwei; WO2014/191340; (2014); A1;,
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Application of 1009-35-4, 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. 1009-35-4, name is 4-Fluoro-3-nitrobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows.

4-fluoro-3-nitrobenzonitrile (5 g, 30 mmol) is first of all subjected to catalytic hydrogenation with 5% palladium on activated charcoal (0.4 g) in 300 mL methanol (2 h at 2 bar hydrogen pressure), whereupon the 3-amino-4-fluorobenzonitrile formed is obtained as a solid after filtration and evaporation of the solvent. Yield: 4.1 g.

The chemical industry reduces the impact on the environment during synthesis 4-Fluoro-3-nitrobenzonitrile. I believe this compound will play a more active role in future production and life.

Reference:
Patent; MCCONNELL, Darryl; BETZEMEIER, Bodo; GERSTBERGER, Thomas; IMPAGNATIELLO, Maria; STEURER, Steffen; van der VEEN, Lars; WEYER-CZERNILOFSKY, Ulrike; US2008/81802; (2008); A1;,
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Some common heterocyclic compound, 34667-88-4, name is 2-Fluoro-4-nitrobenzonitrile, molecular formula is C7H3FN2O2, 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. HPLC of Formula: C7H3FN2O2

2-fluoro-4-nitrobenzonitrile (0.125 g, 0.751 mmol) was hydrogenated at 50 psi in the presence of 10percent Pd/C (40 mg) in EtOH/EtOAc (15mL) for 1 h. Filtered through Celite? and concentrated to an orange solid that was carried onto next step. MS (ESI) m/z: 137 (M+H)+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 34667-88-4, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; ORWAT, Michael J.; PINTO, Donald J.P.; SMITH II, Leon M.; SRIVASTAVA, Shefali; CORTE, James R.; WO2013/55984; (2013); A1;,
Nitrile – Wikipedia,
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These common heterocyclic compound, 67515-59-7, name is 4-Fluoro-3-(trifluoromethyl)benzonitrile, 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. Recommanded Product: 67515-59-7

b. 3-Dimethoxymethyl-1-(2-trifluoromethyl-4-cyano-phenyl)-1,4,5,6-tetrahydro-cyclopentapyrazole 0.7 g (17.5 mmol) of sodium hydride are added at 0 C. to a solution of 3.2 g (17 mmol) of 4-fluoro-3-trifluoromethyl-benzonitrile and 3.1 g (17 mmol) of 3-dimethoxymethyl-1,4,5,6-tetrahydro-cyclopentapyrazole in 20 ml of dimethylformamide. After 3 hours at ambient temperature the reaction solution is poured onto ice water and extracted with ethyl acetate. The organic phase is washed with water and with saturated saline solution, dried and evaporated down. The crude product is recrystallized from diisopropylether/petroleum ether. Yield: 3.2 g (54% of theory) Rf value: 0.33 (silica gel; petroleum ether/ethyl acetate=7:3+1% conc. ammonia)

The synthetic route of 4-Fluoro-3-(trifluoromethyl)benzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Nar, Herbert; Priepke, Henning; Ries, Uwe; Stassen, Jean Marie; Wienen, Wolfgang; US2002/183519; (2002); A1;,
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Reference of 3939-09-1,Some common heterocyclic compound, 3939-09-1, name is 2,4-Difluorobenzonitrile, molecular formula is C7H3F2N, 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 2,4-difluorobenzonitrile (10 g, 72 mmol) dissolved in tetrahydrofuran (20 mL), and dimethylformamide (40 mL) was added the sodium salt of 1,2,4-triazole (6.3 g, 70 mmol) and the mixture was stirred at 90 C. for 3 h, filtered and concentrated. The residue was adsorbed onto Silica gel and purified by flash chromatography eluting with 0%-10%-30% ethylacetate/hexanes to give 4-fluoro-2-(1H-1,2,4-triazol-1-yl)benzonitrile as colorless needles (2.46 g, 18%) and 4-(1H-1,2,4-triazol-1-yl)-2-fluorobenzonitril as a white solid (0.746 g, 6%). 4-Fluoro-2-(1H-1,2,4-triazol-1-yl)benzonitrile. Colorless needles (2.46 g, 18% yield) 1H NMR (500 MHz, CDCl3) delta 8.89 (1H, s), 8.19 (1H, s), 7.85 (1H, dd, J=8.7, 5.6 Hz), 7.60 (1H, dd, J=8.8, 2.4 Hz), 7.28-7.24 (1H, m). LCMS (M+H) calcd for C9H6N4F: 189.05; found: 189.13. 4-(1H-1,2,4-Triazol-1-yl)-2-fluorobenzonitrile. White solid (0.746 g, 6% yield) 1H NMR (500 MHz, CDCl3) delta 8.66 (1H, s), 8.15 (1H, s), 7.79 (1H, dd, J=8.5, 6.7 Hz), 7.69 (1H, dd, J=9.5, 1.8 Hz), 7.65-7.63 (1H, m). LCMS (M+H) calcd for C9H6N4F: 189.05; found: 189.13.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2,4-Difluorobenzonitrile, its application will become more common.

Reference:
Patent; Bristol-Myers Squibb Company; US2007/111984; (2007); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts