Month: September 2021

Electric Literature of 67515-59-7,Some common heterocyclic compound, 67515-59-7, name is 4-Fluoro-3-(trifluoromethyl)benzonitrile, molecular formula is C8H3F4N, 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.

14) l-[4-[(l-Methylpiperidin-4-yl)oxy]-3-(trifluoromethyl)phenyl]ethanamineA.4-[(l -Methylpiperidin-4-yl)oxy]-3-(trifluoromethyl)benzonitrile A mixture of 4-hydroxy-iV-methylpiperidine (133 mg, 1.15 mmol) and potassium tert-bu- toxide (150 mg, 1.27 mmol) in tetrahydrofuran (2.5 mL) was stirred under nitrogen for 10 min. 4-Fluoro-3-(trifluoromethyl)benzonitrile (218 mg, 1.15 mmol) was added, and the 5 reaction mixture was stirred at ambient temperature for 1 h. The solvent was removed in vacuo, and the residue was partitioned between a 1 M NaOH solution and ethyl acetate. The organic layer was dried (Na2SO4) and evaporated. The residue was purified by column chromatography on silica gel (eluent: CHCl3/MeOH/conc. NH3, 95:5:0.5) affording 0.18 g (54% yield) of the pure product as a colourless solid. MS (APCI) m/z 285 [M+H]. 1H NMR o (400 MHz, DMSO-D6) delta ppm 1.67-1.74 (m, 2 H), 1.89-1.95 (m, 2 H), 2.16 (s, 3 H), 2.26- 2.31 (m, 2 H), 2.44-2.48 (m, 2 H), 4.78-4.82 (m, 1 H), 7.51 (d, J = 8.8 Hz, 1 H), 8.08 (dd, J = 8.8, 2.0 Hz, 1 H), 8.14 (d, J = 2.0 Hz, 1 H).

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

Reference:
Patent; ASTRAZENECA AB; WO2007/73303; (2007); A2;,
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Related Products of 53312-80-4, 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. 53312-80-4, name is 4-Amino-2-fluorobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows.

A solution of 4-amino-2-fluorobenzonitrile(2 g, 14.7 mmol, 1 equiv) and NBS (2.6 g, 14.7 mmol, 1 equiv) in MeCN (100 rnL) was stirred for 4 h at 65 C under nitrogen atmosphere. The resulting mixture was concentrated under vacuum. The residue was purified by silica gel column chromatography, eluted with PE/EtOAc (13: 1) to afford 4-amino-5-bromo-2- fluorohenzonitrile(3.1 g, 97 2%) as a yellow solid.

The chemical industry reduces the impact on the environment during synthesis 4-Amino-2-fluorobenzonitrile. I believe this compound will play a more active role in future production and life.

Reference:
Patent; NOVARTIS INFLAMMASOME RESEARCH, INC.; FRANCH, Luigi; GHOSH, Shomir; GLICK, Gary; KATZ, Jason; OPIPARI, Anthony William, Jr.; ROUSH, William R.; SEIDEL, Hans Martin; SHEN, Dong-Ming; VENKATRAMAN, Shankar; WINKLER, David Guenther; (479 pag.)WO2020/10143; (2020); 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. 179897-89-3, name is 5-Bromo-2-fluorobenzonitrile, A new synthetic method of this compound is introduced below., Safety of 5-Bromo-2-fluorobenzonitrile

II1 (1.0 g, 5 mmol) was dissolved in DMF (15 mL)K2CO3 (2.0 g, 15 mmol), tetrahydropyrrole (1.0 g, 15 mmol)The response was complete at 6C for 6 h at 86 C. Add 80 mL of water to dilute,Ethyl acetate (80 mL x 3), washed with saturated brine, dried over anhydrous magnesium sulfate,The solvent was evaporated under reduced pressure to give 1.1 g of an orange solid, 5-bromo-2-tetrahydropyrrole-benzonitrile (III7) in a yield of 97.3%.

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; South China University of Technology; Zhang Lei; Wu Fangping; Li Jing; Zou Yake; (15 pag.)CN106632245; (2017); A;,
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Related Products of 179897-89-3, A common heterocyclic compound, 179897-89-3, name is 5-Bromo-2-fluorobenzonitrile, molecular formula is C7H3BrFN, 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.

General procedure: Into an oven-dried flask equipped with a magnetic stir bar was added aryl fluoride (1.00 g, 1.0 eq.), Na2S (1.1 eq.) and DMF (5 mL) under argon. The reaction mixture was stirred at room temperature for 1 h. Then 1 M NaOH (50 mL) was added and was washed with CH2Cl2 (2 x 25 mL). The aqueous layer was acidified to pH ~ 1-2 with 6 N HCl and extracted with CH2Cl2 (2 x 50 mL). The combined organic layer was washed with brine (50 mL), dried over MgSO4, filtered and concentrated under reduced pressure to provide a crude residue. To the residue was added 10% HCl (40 mL) and cooled with an ice-water bath. Then zinc dust (4 g) was added and the mixture was stirred for 1 h. Then EtOAc (100 mL) was added and the mixture was stirred for an additional 30 minutes. The organic layer was separated and washed with water (40 mL) and brine (40 mL), dried over MgSO4, filtered and concentrated to provide the desired product with satisfactory purity.

The synthetic route of 179897-89-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Taldone, Tony; Patel, Pallav D.; Patel, Hardik J.; Chiosis, Gabriela; Tetrahedron Letters; vol. 53; 20; (2012); p. 2548 – 2551;,
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Related Products of 2469-99-0, The chemical industry reduces the impact on the environment during synthesis 2469-99-0, name is 3-Oxobutanenitrile, I believe this compound will play a more active role in future production and life.

General procedure: In a 250 mL RBF, 3-aminobut-2-enenitrile (2.0 g, 0.24 mole) was added to a stirred solution of cyclohexyl hydrazine hydrochloride (4.0 g, 0.026 mole) and acetic acid (0.1 mL) in ethanol (60 mL). The reaction was refluxed for 6 h. Crude was evaporated and loaded on column to elute out product at 40% ethyl acetate in hexane. (1.74 g, 40%)

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-Oxobutanenitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Sharma, Swagat; Kozek, Krystian A.; Abney, Kristopher K.; Kumar, Sushil; Gautam, Nagsen; Alnouti, Yazen; David Weaver; Hopkins, Corey R.; Bioorganic and Medicinal Chemistry Letters; vol. 29; 6; (2019); p. 791 – 796;,
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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. 1885-38-7, name is (E)-Cinnamonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. category: nitriles-buliding-blocks

In accordance with Scheme la, hydrogen chloride is bubbled through a solution ofcinnamonitrile 1 in methanol at room temperature. The volatiles are removed under reduced pressureand the resulting residue is triturated with ether and filtered to yield the intermediate imidate 2. Imidate2 is dissolved in methanol at ambient temperature, treated with amine 4 (commercially available fromAcros Chemicals) at ambient temperature and stirred under argon. The volatiles are removed underreduced pressure and the residue purified by preparative HPLC or trituration with ether to afford amidine3.

The synthetic route of 1885-38-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK & CO., INC.; WO2004/108705; (2004); A1;,
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Application of 15760-35-7, A common heterocyclic compound, 15760-35-7, name is 3-Methylenecyclobutanecarbonitrile, molecular formula is C6H7N, 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.

Step 1 (0730) To a solution of compound 21-1 (5 g, 62 mmol) and RuCl3 (0.25 g, 1.4 mmol) in CH3CN/DCM/H2O (100 mL/100 mL/150 mL) at 0 C. was added NaIO4 (47.3 g, 250 mmol). The mixture was stirred at RT overnight, quenched with water, and extracted with DCM. The combined extracts were washed with brine, dried over Na2SO4, concentrated and purified by silica gel chromatography (PE: EA=5:1) to give 4.5 g of compound 21-2. 1H NMR (400 MHz, CDCl3): delta 3.53-3.55 (m, 4H), 3.23-3.29 (m, 1H).

The synthetic route of 15760-35-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Merck Sharp & Dohme Corp.; Wu, Wen-Lian; Burnett, Duane A.; Stamford, Andrew W.; Cumming, Jared N.; Asberom, Theodros; Bennett, Chad; Sasiskumar, Thavalakulamgara K.; Scott, Jack D.; US9181236; (2015); B2;,
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85363-04-8, name is N-(tert-Butoxycarbonyl)-2-aminoacetonitrile, 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 85363-04-8

Description 22: (N-Hvdroxvcarbamimidovlmethvl) carbamic acid ter-butyl ester To a solution of N- (tert-butoxycarbonyl)-2-aminoacetonitrile (20. 0g) in absolute ethanol (200moi) was added a solution of hydroxylamine (9. 0g) and potassium carbonate (17. 6g) in water (50ml). The solution was heated to reflux for 2 days. The absolute ethanol was removed in vacuo and the aqueous residue extracted with ethyl acetate. The solvent was partially removed in vacuo until a precipitate formed. The suspension was cooled and filtered. The residue was washed with ethyl acetate to give the title compound as a white solid (12. 84g). Thermospray Mass Spectrum m/z 190 [MH+].

The synthetic route of 85363-04-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; WO2003/82861; (2003); A2;,
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Reference of 1483-54-1,Some common heterocyclic compound, 1483-54-1, name is 2-Amino-4-(trifluoromethyl)benzonitrile, molecular formula is C8H5F3N2, 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.

EXAMPLE 4 9-Amino-1,4-methano-1,2,3,4-tetrahydro-6-trifluoromethylacridine To a solution of 2-amino-4-trifluoromethylbenzonitrile (12.8 g) in 50 ml of nitrobenzene was added freshly fused and pulverized ZnCl2 (14.1 g). This was heated at 50 C. fo 1 hour and to this mixture was added norcamphor (11.4 g). The reaction mixture was heated at 130 C. for 3 hours, after which it was cooled, diluted with ethyl ether and filtered. The resulting solid was partitioned between 2-butanone (MEK) and aqueous NH4 OH and the aqueous portion was extracted with MEK. The combined organics were washed with water, dried (satureatd NaCl, MgSO4) and concentrated to a solid which was triturated with ether/hexane to give 10.3 g of a white powder, m.p. 174-179 C. A 4.0 g portion was recrystallized from methanol/water to give 3.5 g of an analytically pure white powder, m.p. 175-178 C.

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

Reference:
Patent; Hoechst-Roussel Pharmaceuticals Inc.; US5401749; (1995); A;,
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Some common heterocyclic compound, 59997-51-2, name is 4,4-Dimethyl-3-oxopentanenitrile, molecular formula is C7H11NO, 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. Quality Control of 4,4-Dimethyl-3-oxopentanenitrile

(4) Synthesis of Intermediate (d)Water (128 mL) was added to 50 g (357 mmol) of Intermediate (c), and the mixture was stirred at room temperature. To this suspension, 98.2 g (785 mmol) of pivaloylacetonitrile was added, and aqueous 12 M hydrochloric acid was added dropwise at the same temperature to adjust the pH to 3. Thereafter, the resulting mixture was heated until the interior temperature became 50 C., and stirred at the same temperature for 6 hours. After the completion of reaction, the reaction solution was neutralized by adding an aqueous 8N potassium hydroxide solution to a pH of 6.4 and then cooled by ice cooling until the internal temperature became 10 C. The precipitated crystal was collected by filtration and spray-washed with water, and the obtained crystal was dried at 60 C. under reduced pressure. To the obtained crude product, 30 mL of toluene was added, and the mixture was dissolved under heating at 60 C. The resulting solution was left standing still at room temperature for 12 hours, and the precipitated crystal was collected by filtration, spray-washed with cooled toluene and dried at 60 C. under reduced pressure to obtain 87.7 g of Intermediate (d) (white powder, yield: 69.3%). The NMR measurement results of Intermediate (d) obtained are as follows. 1H NMR (300 MHz, d-DMSO) 8.74 (s, 1H), 7.99 (s, 1H), 6.87 (s, 4H), 5.35 (s, 2H), 1.24 (s, 18H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 59997-51-2, its application will become more common.

Reference:
Patent; FUJIFILM CORPORATION; US2011/17099; (2011); A1;,
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