Month: March 2021

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. 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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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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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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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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Adding a certain compound to certain chemical reactions, such as: 288251-96-7, name is 2-Isobutyl-5-nitrobenzonitrile, 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 288251-96-7, name: 2-Isobutyl-5-nitrobenzonitrile

To a solution of 2-isobutyl-5-nitrobenzonitrile (D56) (7.5 g) in methanol (80 mL) and water (80 mL) was added ammonium formate (51.9 g) and zinc (26.9 g). The reaction mixture was stirred at 80 C for 4 h. After cooling the reaction, the solid was filtered, the filtrate was concentrated under reduced pressure, the residue was extracted with EtOAc(300mL*2), the combined organic layers were washed with water (30mL*2), dried and concentrated to give 5-amino-2-(2- methylpropyl)benzonitrile (D57) (17.5 g) as a colorless solid. MS (ES): CnH14N2 requires 174; found 175.1 (M+H+).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; GLAXO GROUP LIMITED; DENG, Guanghui; LIN, Xichen; REN, Feng; ZHAO, Baowei; WO2011/134280; (2011); A1;,
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These common heterocyclic compound, 2338-75-2, name is 4-(Trifluoromethyl)phenylacetonitrile, 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. HPLC of Formula: C9H6F3N

In a first Schlenk vessel 2,5-difluoro-1,4-benzenedicarbaldehyde 1 (680 mg, 0.40 mmol) and (4-trifluoromethyl)phenylacetonitrile 2 (1.48 g, 0.80 mmol) were taken in absolute ethanol (50 mL). In a second Schlenk vessel, sodium ethoxide (0.400 g, 5.76 mmol) and freshly distilled dry pyridine (4.96 mmol, 0.40 mL) were taken in absolute ethanol (50 mL). Under protection from air, the two solutions were mixed and heated to reflux for 3 h.;Then, pyridine and volatiles were removed under reduced pressure. Under protection from air, the residue was repeatedly extracted with small portions (15 mL) of dichloromethane. The organic layer was washed with water, dried over anhydrous MgSO4, and then, filtered through a syringe filter. The extract was evaporated under reduced pressure to leave the residue affording 2,5-difluoro-1,4-phenylene-3,3′-bis{2-[(4-trifluoromethyl)phenyl]acrylonitrile} 3 in 90% yield. Pale-green solid, M.p: 259-261 C; 1H NMR (400 MHz, CDCl3) 7.76 (d, phenyl, 4 H, J = 8.2 Hz), 7.83 (s, 2 H, ethenyl-H), 7.85 (d, 4 H, phenyl, J = 8.2 Hz), 8.21 (t, 2H, phenyl, J = 8.4 Hz). EI-MS (MH+): 503. Elemental analysis calculated for C26H12F8N2: C, 61.91%; H, 2.40%; N, 5.55%. Found: C, 61.80%; H, 2.55%; N, 5.64%.

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

Reference:
Article; Moriguchi, Tetsuji; Kitou, Naoya; Jalli, Venkataprasad; Yoza, Kenji; Nagamatsu, Shuichi; Okauchi, Tatsuo; Tsuge, Akihiko; Takashima, Wataru; Journal of Molecular Structure; vol. 1118; (2016); p. 372 – 377;,
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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. 591769-05-0, name is 3-Cyclopentylacrylonitrile, A new synthetic method of this compound is introduced below., Application In Synthesis of 3-Cyclopentylacrylonitrile

To a solution of 4-(1H-pyrazol- 4-yl)-7-[2-(trimethylsilyl)ethoxy]methyl-7H-pyrrolo[2,3-d]-pyrimidine (15.0 g, 0.0476 mol) in ACN (300 mL) was added 3-cyclopentylacrylonitrile (15 g, 0.12 mol) (as a mixture of cis and trans isomers), followed by DBU (15 mL, 0.10 mol). The resulting mixture was stirred at room temperature overnight. The ACN was evaporated. The mixture was diluted with ethyl acetate, and the solution was washed with 1.0 N HCl. The aqueous layer was back-extracted with three portions of ethyl acetate. The combined organic extracts were washed with brine, dried over sodium sulfate, filtered and concentrated. The crude product was purified by silica gel chromatography (gradient of ethyl acetate/hexanes) to yield a viscous clear syrup, which was dissolved in ethanol and evaporated several times to remove ethyl acetate, to afford 19.4 g of racemic adduct (93percent). The enantiomers were separated by preparative-HPLC, (OD-H column, 15percent ethanol/hexanes) and used separately in the next step to generate their corresponding final product. The final products (see Step 3) stemming from each of the separated enantiomers were found to be active JAK inhibitors; however, the final product stemming from the second peak to elute from the preparative-HPLC was more active than its enantiomer. The products may be isolated by preparative HPLC or other means known to those of skill in the art for use in Step 3 below. 1H NMR (300 MHz, CDCl3): delta 8.85 (s, 1H), 8.32 (s, 2H), 7.39 (d, 1H), 6.80 (d, 1H), 5.68 (s, 2H), 4.26 (dt, 1H), 3.54 (t, 2H), 3.14 (dd, 1H), 2.95 (dd, 1H), 2.67-2.50 (m, 1H), 2.03- 1.88 (m, 1H), 1.80-1.15 (m, 7H), 0.92 (t, 2H),?0.06 (s, 9H); MS(ES): 437 (M+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; ACERTA PHARMA B.V.; HAMDY, Ahmed; ROTHBAUM, Wayne; IZUMI, Raquel; LANNUTTI, Brian; COVEY, Todd; ULRICH, Roger; JOHNSON, Dave; BARF, Tjeerd; KAPTEIN, Allard; (637 pag.)WO2015/193740; (2015); A2;,
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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. 21423-84-7, name is 2-Chloro-4-methylbenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 2-Chloro-4-methylbenzonitrile

4-(Bromomethyl)-2-chlorobenzonitrile (Intermediate h) [00161] To a solution of 44 (160 mg, 1.05 mmol) in CCLI (5 mL) was added NBS (224 mg, 1.26 mmol), AIBN (183 mg, 1.05 mmol). The mixture was stirred at 70 C for 6 h. The mixture was concentrated under reduced pressure. The residue was purified by preparative TLC (petroleum ether / ethyl acetate = 10:1) to give intermediate h (110 mg, 45%) as a white solid.

According to the analysis of related databases, 21423-84-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; VITAE PHARMACEUTICALS, INC.; CLAREMON, David, A.; DILLARD, Lawrence, Wayne; DONG, Chengguo; FAN, Yi; JIA, Lanqi; LOTESTA, Stephen, D.; MARCUS, Andrew; SINGH, Suresh, B.; TICE, Colin, M.; YUAN, Jing; ZHAO, Wei; ZHENG, Yajun; ZHUANG, Linghang; WO2014/179564; (2014); A1;,
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1223434-15-8, name is Methyl 4-bromo-2-cyanobenzoate, 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: C9H6BrNO2

Methyl 4-bromo-2-cyanobenzoate (800.0 mg; 3.33 mmol; 1.00 eq.) was combined with titanium(IV) isopropoxide (1.10 mL; 3.67 mmol; 1.10 eq.) in dry diethyl ether (16 mL) under argon atmosphere and ethylmagnesium bromide (2.22 mL; 3 M solution in diethyl ether; 6.67 mmol; 2.00 eq.) was added at rt. After 2h stirring, the reaction was quenched with 1N HCI (2 mL) and extracted with DCM. The organic extract was washed with brine, dried over MgSO4 and concentrated under reduced pressure. The residue was recrystallized from a mixture of diethyl ether and n-heptane giving 5′-bromospiro[cyclopropane-1,3′-isoindoline]-1′-one (385.0 mg; 49 %).

The synthetic route of 1223434-15-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Eng Bang Tiba; Ba Seu-ma-tin; Kon Tal-sil-bi-e; Ju Ni-en-jang—ru-i-seu; Ma Sa-reu-di-e-reu-keu-ri-seu-tin; Mon Tal-be-ti-keu-ri-seu-chan; Su Deu-an-ne; (111 pag.)KR2019/137803; (2019); A;,
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