Tag: M.W=100-200

Related Products of 939-79-7, These common heterocyclic compound, 939-79-7, name is 4-Methyl-3-nitrobenzonitrile, 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: To a stirred solution of 18(166.51 mmol), 23 (166.51 mmol) or 27 (166.51 mmol) in CCl4 (350 mL) were added NBS (199.82 mmol) and benzoyl peroxide (16.65 mmol) under nitrogen atmosphere. The mixture was heated at reflux temperature for 13 h and then cooled to room temperature. The reaction mixture was filtered and then washed with CH2Cl2 (2 × 400 mL). The combined organic layers waswashed with water (200 mL), dried over anhydrous Na2SO4, and then evaporated to dryness under reduce pressure. The residue was purified by MPLC on silica gel to afford the titled compounds.

The synthetic route of 939-79-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Jin, Cheng Hua; Krishnaiah, Maddeboina; Sreenu, Domalapally; Subrahmanyam, Vura Bala; Park, Hyun-Ju; Park, So-Jung; Sheen, Yhun Yhong; Kim, Dae-Kee; Bioorganic and Medicinal Chemistry; vol. 22; 9; (2014); p. 2724 – 2732;,
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Adding a certain compound to certain chemical reactions, such as: 5332-06-9, name is 4-Bromobutanenitrile, 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 5332-06-9, Quality Control of 4-Bromobutanenitrile

To a solution of 4-bromobutanenitrile (1.50 g, 10.17 mmol) in dimethylformamide (20 ml) were added 1-(4-chlorophenyl)piperazine (2.0 g, 10.17 mmol)and potassium carbonate (2.81 g, 20.34 mmol) at room temperature and the reaction mixture was stirred for 3 h at same temperature. The progress of the reaction was monitored by TLC. The reaction mixture was diluted with water (50 ml) and the aqueous layer was extracted with ethyl acetate (3 x 50 ml). Thecombined organic layer was dried over anhydrous sodium sulphate. The solvent in the organic layer was removed under reduced pressure to obtain a crude product, which was purified by column chromatography over silica gel (100-200 mesh) using 10% ethyl acetate in hexane to yield the title compound (2.32 g, 86% yield).

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

Reference:
Patent; LUPIN LIMITED; JANA, Gourhari; KURHADE, Sanjay, Pralhad; JAGDALE, Arun, Rangnath; KUKREJA, Gagan; SINHA, Neelima; PALLE, Venkata, P.; KAMBOJ, Rajender, Kumar; WO2014/9872; (2014); A1;,
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Application of 654-70-6,Some common heterocyclic compound, 654-70-6, name is 4-Cyano-3-trifluoromethylaniline, 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.

Thionyl chloride (46.02 g, 0.39 mol) was added dropwise to a cooled solution (less than 4 C) of (/?)-3-bromo-2-hydroxy-2-methylpropanoic acid (51.13 g, 0.28 mol) in 300 mL of THF under an argon atmosphere. The resulting mixture was stirred for 3 h under the same condition. To this was added Et3N (39.14 g, 0.39 mol) and stirred for 20 min under the same condition. After 20 min, 5-amino-2- cyanobenzotrifluoride (40.0 g, 0.21 mol), 400 mL of THF were added and then the mixture was allowed to stir overnight at rt. The solvent was removed under reduced pressure to give P-75003-PC a solid which was treated with 300 mL of H20, extracted with EtOAc (2 X 400 mL). The combined organic extracts were washed with saturated NaHCC>3 solution (2 X 300 mL) and brine (300 mL). The organic layer was dried over MgS04 and concentrated under reduced pressure to give a solid which was purified from column chromatography using CH2Cl2/EtOAc (80:20) to give a solid. This solid was recrystallized from CH2Cl2/hexane to give 55.8 g (73.9%) of (2/?)-3-bromo-N-[4-cyano-3-(trifluoromethyl)phenyl]-2-hydroxy-2- methylpropanamide as a light-yellow solid. *H NMR (CDC13/TMS) delta 1.66 (s, 3H, CH3), 3.11 (s, 1H, OH), 3.63 (d, / = 10.8 Hz, 1H, CH2), 4.05 (d, / = 10.8 Hz, 1H, CH2), 7.85 (d, / = 8.4 Hz, 1H, ArH), 7.99 (dd, / = 2.1, 8.4 Hz, 1H, ArH), 8.12 (d, / = 2.1 Hz, 1H, ArH), 9.04 (bs, 1Eta, NH). Calculated Mass: 349.99, [Mu-Eta]” 349.0. M.p.: 124-126 C.

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

Reference:
Patent; GTX, INC.; DALTON, James, T.; GOSNELL, Matthew; WO2013/67170; (2013); A1;,
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Electric Literature of 1897-52-5, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 1897-52-5 name is 2,6-Difluorobenzonitrile, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Cyano-(2-cyano-3-fluoro-phenyl)-acetic acid ethyl ester.A mixture of cyanoacetic acid ethyl ester (26.7 mL, 251 mmol), 2,6-difluorobenzonitrile (33.2 g, 239 mmol) and potassium carbonate (82.5 g, 597 mmol) in dimethyl sulfoxide (120 mL) was stirred at +55C for 16 hours and poured into ice-water mixture (ca. 400 mL). It was acidified with cone. aq. HCl with caution (CO2 evolution) and extracted with ethyl acetate (600 ml). The organic phase was washed with brine (100 mL) and evaporated to give 55.1 g of a pale yellow solid that was used in the next step without further purification. 1H NMR (500 MHz, CDCl3): 1.35 (t, J=7.0 Hz, 3H), 4.34 (m, 2H), 5.13 (s, IH), 7.33 (t, J=8.4 Hz, IH), 7.57 (d, J=7.9 Hz, IH), 7.33 (dd, J=7.9 Hz, J=13.9 Hz, IH).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2,6-Difluorobenzonitrile, and friends who are interested can also refer to it.

Reference:
Patent; H. LUNDBECK A/S; WO2009/156339; (2009); 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. 15666-97-4, name is Octyl 2-cyanoacetate, A new synthetic method of this compound is introduced below., Computed Properties of C11H19NO2

d) In a 20 mL one-necked flask,Compound 2 (0.15 g, 0.1 mmol)And n-octyl cyanoacetate (0.2 g, 1 mmol) were dissolved in 20 mL of dry chloroform,Piperidine (0.1 mL) was added under argon,Followed by heating to 60 C for 24 h.After the reaction is over,The mixture was poured into water,Extracted with dichloromethane,The organic phase was collected and dried to give the crude product,And the product was separated by silica gel column using petroleum ether: dichloromethane (2: 1 by volume)Recrystallization from chloroform and methanol gave the dark red solid product NDFP-CNCOO (30 mg, yield: 14.6%),The synthetic compound NDFP-CNCOO is characterized as follows:

The synthetic route of 15666-97-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Central South University; Peng Hongjian; Luan Xiangfeng; Feng Liuliu; Li Hang; Zou Yingping; (11 pag.)CN106939013; (2017); A;,
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Electric Literature of 939-80-0, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 939-80-0 name is 4-Chloro-3-nitrobenzonitrile, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Step A 3-nitro-4-vinylbenzonitrile To N,N-dimethylformamide (50 ml) were added 4-chloro-3-nitrobenzonitrile (2.81 g, 15.39 mmol), tri-n-butylvinyltin (5.23 g, 16.49 mmol) and bis(triphenylphosphine)palladium(II) dichloride (701 mg, 0.999 mmol), and the mixture was stirred with heating at 100 C. for 160 min. The reaction mixture was cooled, diluted with an ethyl acetate-hexane=1:1 mixed solvent, washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The insoluble material was filtered off, and the solution was concentrated under reduced pressure. The obtained oil was purified by silica gel column chromatography (ethyl acetate-hexane) to give the title compound (2.21 g, yield 82%) as a yellow solid. 1H-NMR (300 MHz, CDCl3); delta(ppm) 5.69 (d, J=11.3, 1H), 5.90 (d, J=17.3, 1H), 7.20 (dd, J=11.3, 17.3, 1H), 7.78 (d, J=8.1, 1H), 7.85 (dd, J=1.5, 8.1, 1H), 8.24 (d, J=1.5, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Chloro-3-nitrobenzonitrile, and friends who are interested can also refer to it.

Reference:
Patent; MITSUBISHI TANABE PHARMA CORPORATION; US2012/196824; (2012); A1;,
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Related Products of 327-74-2,Some common heterocyclic compound, 327-74-2, name is 2-Amino-5-cyanobenzotrifluoride, 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.

4-Amino-3-trifluoromethylbenzonitrile (100mg, 0.54mmol) and lCl(1.1eq, 0.58mmol, 96.00mg) were added to methylene chloride. The mixture was stirred for 12hrs. The reaction mixture was purified accoding to step 2 of Example 8 to give the title compound (30.5mg, 18.10%). mp: 86~88 C; IR(KBr pellet, cm-1): 3371, 3080, 2924, 2226, 1125, 701; 1H NMR(400MHz, CDCl3): delta 8.02 (d, 1 H, J=1.6Hz), 7.35 (dd, 1 H, J=133.2, 1.6Hz), 7.65 (dd, 1H, J=10.0, 1.6Hz), 5.20 (d, 2H, J=22.0Hz).

The synthetic route of 327-74-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Amorepacific Corporation; EP1862454; (2007); 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. 2941-29-9, name is Cyclopentanone-2-carbonitrile, A new synthetic method of this compound is introduced below., Computed Properties of C6H7NO

1006801 Step B: Preparation of 2-(1-methyl-1H-pyrazol-4-yl)-2,4,5,6-tetrahydrocyclopenta- [clpyrazol-3-amine: To a solution of di-tert-butyl 1 -(i-methyl- 1H- pyrazol-4-yl)hydrazine- 1 ,2-dicarboxylate (103 mg, 0.330 mmol) in EtOH (1.65 mL, 0.330 mmol) was added concentrated HC1 (137 iL, 1.65 mmol). The mixture was stirred at ambient temperature for 5 minutes, then cooled in an ice bath followed by addition of 2- oxocyclopentanecarbonitrile (36.0 mg, 0.330 mmol). After stirring for 5 minutes, the reaction mixture was warmed to ambient temperature overnight. The reaction mixture was concentrated and partitioned in water and DCM. After phase-separation, the aqueous layer was basified (pH 10) and then extracted with DCM (3 x 10 mL). The combined organic extracts were dried with MgSO4, filtered and concentrated in vacuo. The crude material was purified by reverse-phase column chromatography, eluting with 0-100percent acetonitrile/water to afford the product as a yellow solid (4.5 mg, 6.7percent yield). MS (apci) mlz = 204.1 (M+H).

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; ARRAY BIOPHARMA INC.; BLAKE, James F.; BRANDHUBER, Barbara J.; HAAS, Julia; NEWHOUSE, Brad; THOMAS, Allen A.; WINSKI, Shannon L.; WO2014/78331; (2014); 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. 876-31-3, name is 4-(Cyanomethyl)benzonitrile, A new synthetic method of this compound is introduced below., Application In Synthesis of 4-(Cyanomethyl)benzonitrile

General procedure: To a solution of alpha,beta-unsaturated ketones 3 (0.30 mmol) in CH2Cl2 (0.6 mL) at room temperature was added pyrrolidine (0.060 mmol) followed by addition of 2-arylacetate or 2-arylacetonitrile 2 (0.45 mmol). The resulting solution was stirred at room temperature until complete consumption of alpha,beta-unsaturated ketones 3 was observed as determined by TLC. The resulting mixture was direct purified by silica gel chromatography to afford desired compounds 4 and 5.

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; Do, Jungho; Kim, Sung-Gon; Tetrahedron Letters; vol. 52; 18; (2011); p. 2353 – 2355;,
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Reference of 2338-75-2, 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. 2338-75-2, name is 4-(Trifluoromethyl)phenylacetonitrile, This compound has unique chemical properties. The synthetic route is as follows.

Intermediate (51 .1 ) tert-butyl 4-(cyano(4- (trifluoromethyl)phenyl)methylene)piperidine- 1 -carboxylateTo the solution of 4-(trifluoromethyl)phenylacetonitrile (2560.9 mg; 1 3.83 mmol; 1 .06 eq.) in ethanol (50 mL), 21 % sodium ethoxide (5.70 ml; 15.27 mmol; 1 .17 eq.) in ethanol was added dropwise at RT. After stirred for 30 min, a solution of 1 -boc-4- piperidone (2600.00 mg; 13.05 mmol; 1 .00 eq.) in ethanol (10 mL) was added slowly. The reaction mixture was stirred at room teperature for 4h. The reaction was quenched with 50mL of saturated aqueous NH4CI and concentrated to half volume. The aqueous solution was extracted with ether three times. The combined organic extracts were washed with brine, dried and then concentrated to give the crude product, which was purified by Biotage chromatography with EtOAc/Hexane (5-30%) to yield the desired product as light yellow solid (3200.00 mg, yield 66.9%).

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

Reference:
Patent; MERCK PATENT GMBH; LAN, Rouxi; HUCK, Bayard R.; CHEN, Xiaoling; DESELM, Lizbeth Celeste; XIAO, Yufang; QIU, Hui; NEAGU, Constantin; MOCHALKIN, Igor; JOHNSON, Theresa L.; WO2013/40044; (2013); A1;,
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