Tag: M.W=100-200

Electric Literature of 143879-80-5, These common heterocyclic compound, 143879-80-5, name is 2,3,4-Trifluorobenzonitrile, 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.

Example 4 1-(4-Amino-8-fluoro-quinazolin-7-yl)-3,6,6-trimethyl-1,5,6,7-tetrahydro-indol-4-one (Compound 4); 2,3,4-Trifluoro-benzonitrile (3.00 g, 19.1 mmol) is mixed with dimethylacetamide (30 mL). Formamidine acetate (1.99 g, 19.1 mmol) and diisopropylethyl amine (10 mL, 57.3 mmol) are added, and the resulting reaction mixture is slowly heated. Upon heating, the starting heterogeneous mixture slowly turns into a homogeneous solution. At 80 C., precipitates start to form. The reaction mixture proceeds at 80 C. for 30 minutes before it is cooled and filtered. The collected solid is further washed with DCM to afford 1.50 g of 7,8-Difluoro-quinazolin-4-ylamine (43% yield) as white solid. LC/MS found m/z=182 [M+H]+.

The synthetic route of 143879-80-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Huang, Kenneth He; Veal, James; Barta, Thomas; Smith, Emilie D.; Ma, Wei; Ommen, Andy; US2008/70935; (2008); A1;,
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These common heterocyclic compound, 53312-80-4, name is 4-Amino-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. Product Details of 53312-80-4

A mixture of 4-amino-2-fluorobenzonitrile (2.0 g, 14.7 mmol) in water (4 ml_), ACN (32 ml_), and concentrated HCI (10 ml.) was stirred at RT under N2 overnight. NaNO2 (2.0 g, 29.4 mmol) was then added portion-wise and stirring was continued at RT for 2 h. The mixture was cooled to 0 C, NaN3 (1.9 g, 29.4 mmol) was added portion-wise and stirring was continued at RT for 2 h. Water (50 ml.) was added and most of the organic solvent was removed under reduced pressure. The remaining aqueous mixture was then extracted with DCM (50 ml. x 4) and the combined organic extracts were washed with water, brine, dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography (Pet. ether/EtOAc = 100/0 to 20/1) to give the title compound (1.5 g, 62%) as a yellow solid, which was used directly in the next step.

The synthetic route of 4-Amino-2-fluorobenzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CTXT PTY LIMITED; STUPPLE, Paul, Anthony; LAGIAKOS, Helen, Rachel; MORROW, Benjamin, Joseph; FOITZIK, Richard, Charles; HEMLEY, Catherine, Fae; CAMERINO, Michelle, Ang; BOZIKIS, Ylva, Elisabet, Bergman; WALKER, Scott, Raymond; (321 pag.)WO2019/243491; (2019); A1;,
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Related Products of 95-11-4, 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. 95-11-4 name is 5-Norbornene-2-carbonitrile, 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.

72 g (0.604 mol, 1 equivalent) of 5-norbornenecarbono-2-nitrile, 39.4 g (0.604 mol, 1 equivalent) of potassium cyanide, nickel chloride (II) 6 in a 1 L reactor equipped with a mechanical stirrer, thermometer and dropping funnel 7.2 g (0.03 mol, 0.05 equivalent) of hydrate, 15.84 g (0.06 mol, 0.1 equivalent) of triphenylphosphine, 20.66 g (0.3 mol, 0.5 equivalent) of zinc powder were added and acetone (100 ml), methanol (200 ml), distilled water (100 ml) was added. 36.3 g (0.604 mol, 1 equivalent) of acetic acid was added over 2 hours while maintaining the reaction internal temperature at 5 to 10 C.After the addition, the reaction internal temperature was raised to 70 C. and stirred for 2 hours. Gas chromatography analysis confirmed that the reaction was completed, and the reaction internal temperature was cooled to 25 . 300 ml of toluene was added to the reaction mixture to extract the dicyanobornane produced. The organic layer was washed three times with 300 ml of a 2N hydrochloric acid solution, and the organic layer was passed through a silica pad and concentrated to obtain 77 g of dicyanobornane having a purity of 99%. Yield was 98%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Norbornene-2-carbonitrile, and friends who are interested can also refer to it.

Reference:
Patent; Kes Optics Co., Ltd.; Kim Geun-sik; Kwon O-jun; (9 pag.)KR2019/102853; (2019); A;,
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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. 6629-04-5, name is N-Cyanoacetylurethane belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: N-Cyanoacetylurethane

Take aniline (compound c) 0.08mol, concentrated hydrochloric acid 45mL, 120mL water to make it dissolve,The solution was cooled to below 0C, and a 60 mL aqueous solution containing 0.11 mol of sodium nitrite was added dropwise.During the dropwise addition, the temperature was maintained below 0 C., and the mixture was stirred dropwise for 0.5 h. Ethyl 2-cyano-2-acetylcarbamate (compound d) dissolved in 400 mL of ethanol was added dropwise and 0.09 molA mixture of 0.27 mol sodium acetate was incubated for 3 h.The solid precipitated from the reaction mixture is filtered and the cake is washed with water.The pale yellow product was dried to give intermediate e(ethyl ((Z)-[2-cyano-2-(2-phenylhydrazono)acetyl]carbamate).

The synthetic route of 6629-04-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Liaoning University; Liu Ju; Chen Ye; Wang Yang; Li Jun; Zhou Ziyun; (22 pag.)CN107652300; (2018); A;,
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Reference of 64248-64-2, 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. 64248-64-2, name is 2,5-Difluorobenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Reference Example 69 2-(2-Cyano-4-fluorophenoxy)ethylpiperazine Under nitrogen atmosphere, potassium tert-butoxide (869 mg) was added to a tetrahydrofuran solution (10 ml) of benzyl 4- (2-hydroxyethyl)-1-piperazinecarboxylate (1.86 g) in an ice bath. After stirring for one hour, the reaction system was transferred to a dry ice-methanol bath, and after 10 minutes, a 2,5-difluorobenzonitrile (1.09 g)/tetrahydrofuran solution (5 ml) was added thereto. After stirring for 2 hours while the temperature of the reaction system was naturally returned to a room temperature, an aqueous saturated ammonium chloride and diethyl ether were added thereto, to separate the organic layer. The resulting organic layer was washed with water and brine, and dried over anhydrous magnesium sulfate. After filtering off the drying agent, the filtrate was evaporated. The residue was purified by silica gel column chromatography (hexane: ethyl acetate system), to give a colorless oil as an intermediate (1.10 g, 46%). The intermediate (1.10 g) was dissolved in methanol (10 mL), 10% palladium carbon (100 mg) was added, andthe mixture was stirred at room temperature under hydrogen atmosphere. After 1.5 hours, the reaction catalyst was filtered through Celite, and the filtrate was evaporated. The resulting title compound (647 mg, 80%) obtained was used for the next reaction as it was. Free body; 1H-NMR (400MHz, CDCl3) delta 2.55-2.63 (m, 4H), 2.87 (t, J = 5.7Hz, 2H), 2.89-2.92 (m, 4H), 4.19 (t, J = 5.7Hz, 2H), 6.93 (dd, J = 4Hz, 8.8Hz, 1H), 7.21-7.29 (m, 2H).

The synthetic route of 2,5-Difluorobenzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Eisai Co., Ltd.; EP1254895; (2002); A1;,
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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. 4640-66-8, name is 4-Chlorophenacylcyanide belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. COA of Formula: C9H6ClNO

In a 25 mL reaction tube with a Teflon magnetic stir bar,Add 0.5 mmol of 3-(4-chlorophenyl)-3-oxopropanenitrile, 0.5 mmol of 3-bromo-1,1,1-trifluoroacetone, 0.5 mmol of sodium acetate,Finally, 58 mmol of 1,4 dioxane was added, and the reaction was stirred at room temperature for 8 hours.Add 15 mL of water, extract three times with 10 mL of ether, and combine the organic phases.Washing with saturated sodium chloride solution, drying over anhydrous magnesium sulfate, and then removing the organic solvent by rotary evaporation;The obtained crude product was eluted with n-pentane and ethyl acetate (10:1, v/v).5-Hydroxy-2-(4-chlorophenyl)-5-(trifluoromethyl)-4,5-dihydrofuran-3-carbonitrile (isolated yield 60%) was obtained by silica gel column chromatography.

The synthetic route of 4640-66-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Fuzhou University; Weng Zhiqiang; Wang Junwen; (29 pag.)CN110272400; (2019); 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. 16588-02-6, name is 2-Chloro-5-nitrobenzonitrile, A new synthetic method of this compound is introduced below., Application In Synthesis of 2-Chloro-5-nitrobenzonitrile

A solution of 2-chloro-5-nitrobenzonitrile (19.5 g, 106.81 mmol), HMDS (43.7 mL, 213.62 mmol), Pd2(dba)3(2.93 g, 3.20 mmol), 2′-(di-tert-butylphosphino)-N,N-dimethyl-[1,1′-biphenyl]-2-amine (3.28 g, 9.61 mmol), water (3.85 g, 213.62 mmol) and lithium acetate (35.2 g, 534.06 mmol) in DMF (400 mL) was stirred under argon gas atmosphere at 100C for 5 hr. To the reaction mixture were added water and ethyl acetate, and the organic layer was separated. The organic layer was dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (solvent gradient; 0?5% ethyl acetate/hexane) to give 5-nitro-2-(trimethylsilyl)benzonitrile (13.2 g, 59.9 mmol, 56.1%) as a white solid.

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; TAKEDA PHARMACEUTICAL COMPANY LIMITED; YAMAMOTO, SATOSHI; SHIRAI, JUNYA; WATANABE, HIROYUKI; FUKUMOTO, SHOJI; ODA, TSUNEO; TOKUHARA, HIDEKAZU; TOMATA, YOSHIHIDE; ISHII, NAOKI; TAWADA, MICHIKO; KOUNO, MITSUNORI; OCHIDA, ATSUKO; IMADA, TAKASHI; FUKASE, YOSHIYUKI; YUKAWA, TOMOYA; (719 pag.)TW2016/2105; (2016); 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. 60710-80-7, name is 3-Amino-4-methylbenzonitrile, A new synthetic method of this compound is introduced below., COA of Formula: C8H8N2

To a solution of intermediate 7R (231 g, 0.556 mol) in 1,4-dioxane (2.3 L), ptoluenesulfonic acid monohydrate (179 g, 0.95 mol) and 3-amino-4-methylbenzonitrile (110 g, 0.83 mol) were added, purged three times with N2 and stirred at 95 C for 12 h. Then, the reaction mixture was cooled down to 20 C, and a solution of NaHCO3 was added to neutralize the mixture. The precipitated solid formed was filtrated andcombined with another precipitate coming from a reaction performed on 179 g of intermediate 7R. The resulting solid was dissolved in Me-THF (5 L), washed with water three times (3 x 5 L). A silanethiol resin [from Shanghai Meryer CO.,LTD] (60 g) was added to the mixture and reflux for 1.5 h. Then, the resulting mixture was filtered through a pad of celite and concentrated under vacuum. The residue wassuspended in EtOH (5L) overnight, filtered and dissolved in THF (3L). Methyl ten?butylether (6 L) was added to THF and the solid was precipitated, filtered and dried to afford 243g of compound 1.

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; JANSSEN PHARMACEUTICA NV; STANSFIELD, Ian; QUEROLLE, Olivier Alexis Georges; PONCELET, Virginie Sophie; GROSS, Gerhard Max; JACOBY, Edgar; MEERPOEL, Lieven; KULAGOWSKI, Janusz Jozef; MACLEOD, Calum; MANN, Samuel Edward; GREEN, Simon Richard; HYND, George; (477 pag.)WO2017/125530; (2017); A1;,
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Electric Literature of 873-74-5, 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. 873-74-5, name is 4-Aminobenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: Alcohol, phenol, and/or amine (1 mmol) were added to amixture of the ZnAl2O4SiO2 nanocomposite (100 mg) andacetic anhydride (1 mmol). The mixture was stirred at 75 C(for alcohols and phenols) or at room temperature (for amines)for a time. The progress of the reaction was monitored by TLCand/or GC-MS. When the reaction was completed, ethyl acetate(10 mL) was added and the mixture was filtered to separate offthe catalyst. The catalyst was washed twice with 7.5 mL ethylacetate. The combined organic phases were washed with a10% solution of NaHCO3 and then dried over MgSO4. The solventwas removed to yield the product. If further purificationwas needed, the product was passed through a short column ofsilica gel. All products were characterized on the basis ofGC-MS, FT-IR, and 1H-NMR spectral data by comparing thesespectra with those of standard samples or literature data.

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

Reference:
Article; Farhadi, Saeed; Jahanara, Kosar; Cuihua Xuebao/Chinese Journal of Catalysis; vol. 35; 3; (2014); p. 368 – 375;,
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69395-13-7, name is 4-(2-Hydroxyethyl)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. COA of Formula: C9H9NO

PREPARATION 13 Preparation of 4-carbamoylphenethyl bromide and 4-cyanophenethyl bromide STR36 A solution of phosphorus tribromide (5 g) in carbon tetrachloride (10 ml) was added, dropwise, to a solution of 4-cyanophenethyl alcohol (8.06 g) in carbon tetrachloride (60 ml). The mixture was heated under reflux for 4 hours. On cooling to room temperature, the mixture was poured onto ice (200 g). The layers were separated and the organic layer was washed with 10% aqueous sodium carbonate (50 ml) and brine (50 ml), dried (MgSO4) and concentrated in vacuo to give a colourless oil which solidified on standing. The solid was chromatographed on silica eluding with ethyl acetate containing hexane (20%). The fractions containing the less polar (higher Rf) product were combined and concentrated in vacuo to give 4-cyanophenethyl bromide as a yellow oil which solidified on standing, yield 8.9 g. The fractions containing the more polar (lower Rf) product were combined and concentrated in vacuo to give 4-carbamoylphenethyl bromide as a colourless solid, yield 0.47 g, m.p. 152-153.

The synthetic route of 69395-13-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Pfizer Inc.; US5340831; (1994); A;,
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