Month: September 2021

Application of 143879-77-0, 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. 143879-77-0, name is 2,6-Difluoro-3-nitrobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows.

a) 2-Amino-6-fluoro-3-nitrobenzonitrileA solution of NH3 in EtOH (19 mL, 8.6 M, 160 mmol) was added dropwise to a solution of 2,6-difluoro-3-nitrobenzonitrile (10 g, 54 mmol) in THF (50 mL) at 0 C under Ar and the resulting mixture was stirred at 0 C for 1 h. The mixture was concentrated and the residue washed with brine and extracted with EtOAc. The organic layer was dried over Na2S04, filtered and concentrated.Yield: 9.59 g (98%).

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

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; PRIEPKE, Henning; KUELZER, Raimund; MACK, Juergen; PFAU, Roland; STENKAMP, Dirk; PELCMAN, Benjamin; ROENN, Robert; LUBRIKS, Dimitrijs; SUNA, Edgars; WO2012/76672; (2012); A1;,
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Electric Literature of 935-02-4, A common heterocyclic compound, 935-02-4, name is 3-Phenylpropiolonitrile, molecular formula is C9H5N, 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.

Dissolve 0.5 mmol of acetylene nitrile (1) in 2 mL of acetic acid,After addition of 0.75 mmol (62.3 mg) of lithium bromide, the reaction mixture was obtained;The reaction mixture was heated to 110C and stirred for 12 hours to give the first product;After the first product was cooled, 10 mL of water was added thereto to obtain a second product.Ethyl acetate is added to the second product and extracted twiceEach time 10 mL was added, the first organic phase product was obtained after extraction with the ethyl acetate;After washing the first organic phase product with brine for 1 time,After drying the first organic phase product over anhydrous sodium sulfate for 2 hours, a second organic phase product is obtained.The second organic phase product is distilled under reduced pressure to remove ethyl acetate to obtain a third organic phase product;Silica gel chromatography column (silicon gel particle size 200-300 mesh, eluent is a mixed solvent of petroleum ether and ethyl acetate,The volume ratio of the petroleum ether and the ethyl acetate is 200:1) to separate the third organic phase product,The product (3) is obtained,The product (3) is 3-bromo-3-aryl acrylonitrile, and the chemical reaction formula of acetylene nitrile and lithium bromide is as follows:

The synthetic route of 935-02-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Huazhong Agricultural University; Shi Wei; Guan Zhipeng; Tang Jiahao; Chen Hao; (13 pag.)CN107814752; (2018); A;,
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3759-28-2, name is 2-(Cyanomethyl)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. Recommanded Product: 3759-28-2

General procedure: To a solution of homophthalonitrile 2 (129 mg, 0.82 mmol) in PriOH (4 ml), salicylaldehyde 1 (2.46 mmol) and NH4OAc (143 mg, 1.64 mmol) were added. The mixture was placed into a microwave reactor and heated at 150 C for 10 min. The vessel was opened, MeNO2 (0.439 ml, 8.2 mmol) and Et3N (0.114 ml, 0.82 mmol) were added, the mixture was heated again in the microwave reactor at 150 C for 10 min. The solvent was evaporated under reduced pressure, the residue was chromatographed on silica gel (EtOAc-hexane, 1:5-1:1) (method A) or was dissolved in asmall volume of Et2O or CH2Cl2 and extracted with HCl aqueous solution(0.6 m, 3 30 ml). The aqueous layer was neutralized with Na2CO3. The precipitate was filtered off and washed with H2O several times and once with a small amount (1.5 ml) of PriOH and dried in air (method B).

The synthetic route of 3759-28-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Festa, Alexey A.; Storozhenko, Olga A.; Bella Ndoutoume, Delphine R.; Varlamov, Alexey V.; Voskressensky, Leonid G.; Mendeleev Communications; vol. 27; 5; (2017); p. 451 – 453;,
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Synthetic Route of 94087-40-8, These common heterocyclic compound, 94087-40-8, name is 3-Chloro-2-fluorobenzonitrile, 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.

3L bottle take four reflux means of 2-fluoro-3-chlorobenzonitrile 437g, water 500g, concentrated sulfuric acid, 1248g, acetic acid 21g, slowly warmed to reflux and reflux temperature of about 155 , heat the reaction 5h, the control sample, the raw material ?1%, the reaction was stopped, cooled to 50 , dropping water 750g, stirred for 1h and then cooled to 10 , filtration, the filter cake with the amount of water rinsed, drained, dried was 458.5g, content ?99%, yield 93.5%.

The synthetic route of 94087-40-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Zhejiang Yongtai Technology Co ., Ltd; Zhang, xing; Shu, zhujin; (10 pag.)CN104529729; (2016); B;,
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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. 76469-88-0, name is Methyl 4-(cyanomethyl)benzoate, A new synthetic method of this compound is introduced below., Application In Synthesis of Methyl 4-(cyanomethyl)benzoate

General procedure: To a solution of potassium tert-butoxide (8.0 g, 0.08 mmol,2.5 equiv) in THF (25 ml) at 30 C was added a solution of methyliodide (5.35 ml, 0.09 mmol, 3.0 equiv) and methyl 4-(cyanomethyl)benzoate (5.0 g, 0.03 mmol,1.0 equiv) in THF (25 ml) under nitrogen atmosphere over 20 min. The cooling bath was removed and the reaction mixture was allowed to warm to rt and stirred for 2 h.Following this the reaction was quenched with water (10 ml) and ethyl acetate was added and the organic and aqueous layers were separated. The organic layer was washed with water, brine, anddried over sodium sulfate. The organic solvent was removed under vacuum to obtain a violet residue that was purified by column chromatography using 20:80 EtOAc:Pet ether to obtain an off white solid that was crystallized in CHCl3:Pet ether to afford the title compound (4.0 g, 69%) as a white solid.

The synthetic route of 76469-88-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Kadam, Kishorkumar S.; Jadhav, Ravindra D.; Kandre, Shivaji; Guha, Tandra; Reddy, M. Mahesh Kumar; Brahma, Manoja K.; Deshmukh, Nitin J.; Dixit, Amol; Doshi, Lalit; Srinivasan, Shaila; Devle, Jayendra; Damre, Anagha; Nemmani, Kumar V. S.; Gupte, Amol; Sharma, Rajiv; European Journal of Medicinal Chemistry; vol. 65; (2013); p. 337 – 347;,
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Reference of 41963-20-6,Some common heterocyclic compound, 41963-20-6, name is 4-Bromo-3-methylbenzonitrile, molecular formula is C8H6BrN, 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 17 (10.0 g, 49.5 mmol) in carbon tetrachloride (200 mL) were added N-bromosuccinimide (8.81 g, 49.5 mmol) and 2,2′-azobis(isobutyronitrile) (414 mg, 5 mol %), and the mixture was refluxed for 3 h. Water was added, and the mixture was extracted with chloroform. The organic layer was washed with brine and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure. To the residue were added dimethylformamide (150 mL) and sodium acetate (20.5 g, 250 mmol), and the mixture was stirred at 80 C. overnight. Water was added, and the mixture was extracted with ether. The organic layer was washed with water and brine, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure. To the residue was added methanol (150 mL) and 1 mol/L sodium hydroxide (50 mL), and the mixture was stirred at room temperature for 1 h. The reaction mixture was concentrated to about a third of volume under reduced pressure. Water and hydrochloric acid were added, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the residue was purified by silica gel column chromatography (3:1 hexane/ethyl acetate) followed by trituration with dichloromethane to give 2-bromo-5-cyanobenzyl alcohol (4.63 g, overall 44%): 1H NMR (300 MHz, DMSO-d6) delta (ppm) 4.51 (d, J=5.9 hz, 2H), 5.67 (t, J=5.6 Hz, 1H), 7.67 (dd, J=8.2, 2.0 Hz, 1H), 7.80 (s, J=8.2 Hz, 1H), 7.83 (d, J=2.0 Hz, 1H).

The synthetic route of 41963-20-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Anacor Pharmaceuticals; US2007/265226; (2007); A1;,
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Adding a certain compound to certain chemical reactions, such as: 1835-49-0, name is Tetrafluoroterephthalonitrile, 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 1835-49-0, name: Tetrafluoroterephthalonitrile

[Comparative Example 1]; The same operations as in Example 1 were carried out, except that the amount of the catalyst used was changed from 0.25 g to 0.05 g on a dry weight basis. After a lapse of 7.0 hours, absorption of hydrogen ceased. The quantity of hydrogen absorbed was 83% of the theoretical quantity of hydrogen absorbed. Treatment of the reaction solution was carried out in the same manner as in Example 1. EPO From the toluene extract, a small amount of a sample was withdrawn, and it was subjected to GC analysis. As a result of the analysis, the tetrafluoroterephthalonitrile as a raw material remained in an amount of 21.0 mol%, and tetrafluoroterephthalaldehyde was obtained in an amount of only 5.0 mol%. The amount of 2, 3, 5, 6-tetrafluorobenzene was 0.65 mol%, the amount of 2,3,5,6- tetrafluorobenzonitrile was 0.53 mol%, and 1-cyano- 2, 3, 5, 6-tetrafluorobenzaldehyde wherein a nitrile group on only one side had reacted was obtained in an amount of 63.1 mol%. On the other hand, the aqueous phase was neutralized and then subjected to GC analysis. As a result of the analysis, presence of 2.88 mol% of 2,3,5,6- tetrafluorobenzylamine was confirmed. The results are set forth in Table 2.; [Comparative Example 3]; The same operations as in Example 1 were carried out, except that the amount of sulfuric acid used was changed from 20.6 g to 5.15 g (50 mmol). After a lapse of 4.2 hours, absorption of hydrogen ceased. The quantity of hydrogen absorbed was 47% of the theoretical quantity of hydrogen absorbed. Treatment of the reaction solution was carried out in the same manner as in Example 1.From the toluene extract, a small amount of a sample was withdrawn, and it was subjected to GC analysis. As a result of the analysis, a peak of the tetrafluoroterephthalonitrile as a raw material was below EPO the detection limit, and tetrafluoroterephthalaldehyde was obtained in an amount of only 14.5 mol%. The amount of 2, 3, 5, 6-tetrafluorobenzene was 0.81 mol%, the amount of 2, 3, 5, 6-tetrafluorobenzonitrile was 0.67 mol%, and 1- cyano-2, 3, 5, 6-tetrafluorobenzaldehyde wherein a nitrile group on only one side had reacted was obtained in an amount of 54.0 mol%. On the other hand, the aqueous phase was neutralized and then subjected to GC analysis. As a result of the analysis, presence of 0.04 mol% of 2,3,5,6- tetrafluorobenzylamine was confirmed. The results are set forth in Table 2.

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

Reference:
Patent; SHOWA DENKO K.K.; WO2006/137347; (2006); A2;,
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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. 3598-14-9, name is Phenoxyacetonitrile, A new synthetic method of this compound is introduced below., Quality Control of Phenoxyacetonitrile

(a) 5 millimoles (0.665 g) of phenoxy-acetonitrile are dissolved in 8 ml of anhydrous toluene at 0 C., under an argon atmosphere 7.5 millimoles of a toluenic solution 1.5 M of diisobutylaluminum hydride (5 ml) are added dropwise, at this temperature. The stirring is maintained for 1 hour at 0 C., then 5.9 ml (1.3 eq) of diethylaluminum cyanide are added. The reaction mixture is stirred for 3 hours at room temperature, then hydrolyzed with 4 ml of methanol and pasty sodium sulfate. After purification by high pressure liquid chromatography on silica, there are obtained 0.182 g of 2-amino-3-phenoxy-propionitrile, in form of a cream-colored solid-state product; M.P. 65 C., yield: 22%.

The synthetic route of 3598-14-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Albert Rolland S.A.; US4942221; (1990); A;,
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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. 630-18-2, name is Pivalonitrile, A new synthetic method of this compound is introduced below., Product Details of 630-18-2

General procedure: To a solution of 4-bromobiphenyl 1a (3.0 mmol, 699.3 mg) in THF (3.0 mL) was added n-BuLi (4.5 mmol, 1.55 M in hexane, 2.87 mL) at 50 C. The obtained mixture was stirred for 30 min at 50 C under an argon atmosphere. Pivalonitrile (6.0 mmol, 498.8 mg) in THF (2.0 mL) was added to the mixture at 50 C and the obtained mixture was stirred for 30 min in the temperature range of 50 C to room temperature. MeOH (2.0 mL) was added to the mixture. Then, I2 (12.0 mmol, 3045.6 mg) and K2CO3 (12.0 mmol, 1658.4 mg) were added to the mixture at room temperature, and the obtained mixture was stirred for 6 h at 70 C. Sat. aq. Na2SO3 solution (20.0 mL) was added to the reaction mixture, and the product was extracted with AcOEt (10.0 mL x 3). The organic layer was dried over Na2SO4. After filtration and removal of the solvent, the residue was purified by silica-gel column chromatography (chloroform: n-hexane 1:1) to give 4-cyanobiphenyl 2a (451.6 mg, 84%).

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:
Article; Uchida, Ko; Togo, Hideo; Tetrahedron; vol. 75; 39; (2019);,
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654-70-6, name is 4-Cyano-3-trifluoromethylaniline, 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

General procedure: A solution of NaHCO3 (0.82 g) in distilled water (4 mL) wasstirred for 10 min and to it was added DCM (4 mL) followed by thedifferent aniline 7e12 (2.4 mmol). The reaction mixture was cooledto 0 C, thiophosgene (0.3 mL, 3.7 mmol) was added dropwise over10 min and the reaction was then stirred at r.t. overnight. Themixture was then diluted with DCM (20 mL), washed with brine(20 mL), the organic layer was dried over Na2SO4 and concentratedto dryness.

The synthetic route of 654-70-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Pertusati, Fabrizio; Ferla, Salvatore; Bassetto, Marcella; Brancale, Andrea; Khandil; Westwell, Andrew D.; McGuigan, Christopher; European Journal of Medicinal Chemistry; vol. 180; (2019); p. 1 – 14;,
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