Month: August 2021

Reference of 21803-75-8, A common heterocyclic compound, 21803-75-8, name is 4-Amino-3-chlorobenzonitrile, molecular formula is C7H5ClN2, 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.

An ethanolic solution (5 mL) of 4-amino-3-chlorobenzonitrile (L2, 1 mmol, 0.153 g) was added tothe saturated ethanolic solution (5 mL) of AgNO3. The test tube was covered with a perforated foil.After keeping the solution in air for 6 days, light yellow crystals of 2 suitable for structure determinationwere obtained. Yield 72%, m.p. 152-153 C. Anal. Calcd for C7H5AgClN3O3: C, 26.07; H, 1.56;N, 13.03%. Found: C, 26.04; H, 1.58; N, 13.01%. IR (KBr, cm-1): 3481 (m), 3361 (s), 3184 (w), 2360 (m),2206 (s), 1755 (w), 1645 (s), 1590 (m), 1525 (m), 1381 (s), 1206 (w), 887 (w), 810 (w), 666 (w), 578(w). 1H NMR (400 MHz, DMSO) delta/ppm: 7.69 (d, J = 1.9 Hz, 1H), 7.42 (dd, J = 8.5, 1.9 Hz, 1H), 6.82(d, J = 8.5 Hz, 1H), 6.42 (s, 2H).

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; Qian, Wei; Yuan, Hao-Kun; Zhang, Ran; Fang, Rui-Qin; Journal of Coordination Chemistry; vol. 69; 23; (2016); p. 3593 – 3602;,
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Electric Literature of 876-31-3, These common heterocyclic compound, 876-31-3, name is 4-(Cyanomethyl)benzonitrile, 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: Under N2 atmosphere, dinitrile 1 (0.2 mmol), potassium phenyltrifluoroborate 2 (147 mg, 0.8 mmol), Pd(OAc)2 (4.49 mg, 10 mol %), L4 (7.2 mg, 20 mol %), TFA/H2O (0.4 mL/0.4mL), and 2-MeTHF (2 mL) were successively added into a Schlenk reaction tube. The reaction mixture was stirred vigorously at 80 C for 48 h. After the completion of the reaction, the mixture was poured into ethyl acetate, which was washed with saturated NaHCO3 (2 × 10 mL) and then brine (1 × 10 mL). After the aqueous layer was extracted with ethyl acetate, the combined organic layers were dried over anhydrous Na2SO4 and evaporated under reduced pressure. The residue was purified by flash column chromatography (hexane/ethyl acetate) to afford the desired products 3. The physical and spectroscopic data of compounds 3a-h follow.

Statistics shows that 4-(Cyanomethyl)benzonitrile is playing an increasingly important role. we look forward to future research findings about 876-31-3.

Reference:
Article; Wang, Xingyong; Wang, Qingzong; Chen, Jiuxi; Liu, Miaochang; Ding, Jinchang; Wu, Huayue; Journal of Chemical Research; vol. 37; 8; (2013); p. 470 – 472;,
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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. 29509-06-6, name is 4-Methyl-3-oxopentanenitrile, This compound has unique chemical properties. The synthetic route is as follows., Formula: C6H9NO

General procedure: A mixture of 4-methyl-3-oxopentanenitrile 10i or 10ii (1.5eq), aldehyde 6(a-m) (1.0 eq), urea (1.5 eq) and CuCl (0.01eq) in MeOH containing concentrated H2SO4 (0.62 eq) wasstirred at reflux temperature for 3-5 days. After the reactionwas deemed complete by TLC, methanol was removed byconcentration in vacuo. The precipitated solid was extractedin dichloromethane. The dichloromethane layer was washedwithwater twice so as to removewater soluble impurities. Theorganic layerwas concentrated again to dryness in vacuo. Thecrude residue was purified by silica gel column chromatographyusing ethyl acetate: hexanes to give pyrimidine compound11(a-m).

According to the analysis of related databases, 29509-06-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Pachore, Sharad S; Ambhaikar, Narendra B; Siddaiah, Vidavalur; Khobare, Sandip R; Kumar, Sarvesh; Dahanukar, Vilas H; Kumar, U K Syam; Journal of Chemical Sciences; vol. 130; 6; (2018);,
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Related Products of 1953-99-7, A common heterocyclic compound, 1953-99-7, name is 3,4,5,6-Tetrachlorobenzene-1,2-dicarbonitrile, molecular formula is C8Cl4N2, 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.

(i) Preparation of 1,2-dicyano-3,4,5,6-tetra(2-naphthoxy)benzene 1,2-Dicyano-3,4,5,6-tetrachlorobenzene (30.5 parts), potassium carbonate (62.8 parts) and 2-naphthol (98.1 parts) were stirred in dimethylformamide (140 parts) at 70 C. for 3 hours. The mixture was poured into water (300 parts) and extracted with chloroform (3*300 parts). The combined chloroform extracts were washed with dilute aqueous sodium hydroxide solution (500 parts) and then with water (500 parts). The chloroform was dried over anhydrous magnesium sulphate before evaporating under reduced pressure to leave a brown liquid which crystallized on adding butan-1-ol, cooling and standing for 2 hours. The crystallized solid was filtered, washed with butan-1-ol until the filtrates were colourless. The solid was dried to give 1,2-dicyano-3,4,5,6-tetra(2-naphthoxy)benzene (40.6 parts), m.p. 188-190 C.

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; Zeneca, Limited; US5486274; (1996); A;,
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Related Products of 71825-51-9,Some common heterocyclic compound, 71825-51-9, name is 2-Methyl-2-(4-nitrophenyl)propanenitrile, molecular formula is C10H10N2O2, 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 cooled solution of 2-methyl-2-(4-nitrophenyl)propanenitrile (670 mg, 3.5 mmol) in THF (15 mL) was added BH3 (1M in THF, 14 mL, 14 mmol) dropwise at 0 C. The mixture was warmed to room temperature and heated at 70 C. for 2 h. 1N HCl solution (2 mL) was added, followed by the addition of NaOH until pH>7. The mixture was extracted with ether and ether extract was concentrated to give 2-methyl-2-(4-nitrophenyl)propan-1-amine (610 mg, 90%), which was used without further purification. 1H NMR (400 MHz, CDCl3) delta 8.20 (d, J=9.0 Hz, 2H), 7.54 (d, J=9.0 Hz, 2H), 2.89 (s, 2H), 1.38 (s, 6H).

The synthetic route of 71825-51-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Vertex Pharmaceuticals Incorporated; Van Goor, Fredrick F.; Burton, William Lawrence; US2015/231142; (2015); A1;,
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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. 330792-69-3, name is 2-(Methoxy(4-phenoxyphenyl)methylene)malononitrile, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C17H12N2O2

1,1-Dicyano-2-methoxy-2-(4-phenoxyphenyl)ethene (22.5 g) and 1,1-dicyano-2-methoxy-2-(4-phenoxyphenyl)ethene oil (15 g) are treated with a solution of hydrazine hydrate (18 mL) in ethanol (25 mL) and heated on the steambath for 1 hour. Ethanol (15 mL) is added followed by water (10 mL). The precipitated solid is collected and washed with ethanol:water (4:1) and then dried in air to give 3-amino-4-cyano-5-(4-phenoxyphenyl)pyrazole as a pale orange solid.

According to the analysis of related databases, 330792-69-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PHARMACYCLICS, INC.; US2008/76921; (2008); A1;,
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Reference of 6952-59-6, These common heterocyclic compound, 6952-59-6, name is 3-Bromobenzonitrile, 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: Aryl-halide (0.2 mmol, 1 equiv.), Ir(dtbbpy)(ppy)2PF6 (1.8 mg, 0.002 mmol, 1 mol %), NiCl2.glyme (4.4mg, 0.02 mmol, 10 mol %), DMSO (2.0 mL) was added to a 10 mL schlenk flask equipped with a magnetic stirrer bar. This resulting mixture was sealed and degassed via vacuum evacuation and subsequent backfill with ethylene for three times. Then, N,N,N?,N?-tetramethylethylenediamine, TMEDA(60 muL, 2 equiv.), N,N-diisopropylethylamine, DIPEA (70 muL, 2 equiv.) and H2O (7.2 muL, 2 equiv.) were subsequently added in this order. The mixture was then irradiated with blue LED (2 meter strip, 18 W)with ethylene balloon for 24 hours at 80oC (Figure S1). The reaction was added water (30 mL) and extracted with ethyl acetate (10 mL) three times. Combined organic layer was successively washed with brine three times and dried over Na2SO4 and concentrated under reduced pressure. The residue was then subjected to flash column chromatography (hexane or hexane/ethyl acetate) to yield theproduct

The synthetic route of 6952-59-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Li, Jiesheng; Luo, Yixin; Cheo, Han Wen; Lan, Yu; Wu, Jie; Chem; vol. 5; 1; (2019); p. 192 – 203;,
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Application of 42872-73-1,Some common heterocyclic compound, 42872-73-1, name is 2-Bromo-4-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.

A mixture of 2-bromo-4-methylbenzonitrile (2.00 g, 10.2 mmol), 5, 5, 5′, 5′- tetramethyl-2,2′-bi(l,3,2-dioxaborinane) (3.06 g, 13.6 mmol) and potassium acetate (3.00 g, 30.6 mmol) in anhydrous DMSO (10 mL), in a sealable flask, was purged with Argon for 20 min before PdChldppfj-Cl ECl? adduct (0.25 g, 0.34 mmol) was added, the flask was sealed and the reaction heated at 80 C. After 17 hrs, the reaction was cooled to RT before being partitioned between EtOAc and brine. The layers were separated and the aqueous layer was extracted once more with EtOAc. The organic layers were combined, washed with brine, dried (MgS04), filtered and concentrated in vacuo to afford a brown oil which solidified upon standing. Purification by Isco chromatography afforded 301 A as an off-white solid (1.96 g; 84% yield). NMR (400MHz, DMSO-d6) d 7.72 – 7.63 (m, 2H), 7.43 (dd, 7=7.9, 1.1 Hz, 1H), 3.79 (s, 4H), 2.38 (s, 3H), 0.98 (s, 6H).

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

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; BALOG, James Aaron; MARKWALDER, Jay A.; SHAN, Weifang; WILLIAMS, David K.; NARA, Susheel Jethanand; ROY, Saumya; THANGAVEL, Soodamani; CHERUKU, Srinivas; SISTLA, Ramesh Kumar; (230 pag.)WO2020/23355; (2020); A1;,
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Application of 3556-60-3, 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. 3556-60-3, name is 3-Methoxy-4-methylbenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Under an inert atmosphere, to a solution of 3-methoxy-4-methylbenzonitrile (2.00 g, 13.6 mmol) in tetrahydrofuran (50 mL), a methylmagnesium chloride solution (5 mL, 3M in tetrahydrofuran) was added dropwise during cooling with ice at 0-2 C, and the mixture was stirred at 40 C for 12 hours. (0195) The reaction mixture was quenched by dropwise addition of 6 M HC1 solution (3.4 mL), and was stirred stirred at 40 C for another hour. The mixture was extracted with ethyl acetate, the combined organic layer was washed with brine, dried over Na?.S04, evaporated, and the crude residue was purified with column chromatography on silica gel with gradient elution, using a mixture of dichlorom ethane and cyclohexane as eluent. Yield: 356 mg (16 %).

The synthetic route of 3-Methoxy-4-methylbenzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; RICHTER GEDEON NYRT.; LEDNECZKI, Istvan; ELES, Janos; TAPOLCSANYI, Pal; JABLONKAI, Erszebet; GABOR, Eszter; VISEGRADI, Andras; NEMETHY, Zsolt; LEVAY, Gyoergy Istvan; PETRO, Jozsef Levente; SELENYI, Gyoergy; (0 pag.)WO2020/12423; (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. 179898-34-1, name is 3-Bromo-5-fluorobenzonitrile, A new synthetic method of this compound is introduced below., Safety of 3-Bromo-5-fluorobenzonitrile

Step 1 (0915) A solution of 3-bromo-5-fluorobenzonitrile (CXVIII) (44.0 g, 220.0 mmol, 1.0 eq) was dissolved in THF (30 mL). BH3-Me2S (33.43 g, 440.0 mmol, 2.0 eq) was added to the solution at 20 C. Then it was stirred at 80 C. for 2 h, HCl (6 N, 100 mL) was added to the mixture slowly at 20 C. The mixture was stirred at 80 C. for 1 h, then it was washed with EtOAc (300 ml). The water phase was basified with 50% aqueous NaOH and it was extracted with EtOAc (300 mL×3). The combined organic layers were dried over anhydrous Na2SO4 and concentrated in vacuo to produce (3-bromo-5-fluoro-phenyl)methanamine (CXIX) (24.0 g, 117.62 mmol, 53.5% yield). 1H NMR (CDCl3, 300 MHz) 3.86 (s, 2H), 7.01 (d, J=8 Hz, 1H), 7.12 (d, J=8 Hz, 1H), 7.28 (s, 1H); ESIMS found C7H7BrFN m/z 203.9 (Br79M+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; Samumed, LLC; KC, Sunil Kumar; Wallace, David Mark; Cao, Jianguo; Chiruta, Chandramouli; Hood, John; (390 pag.)US2016/90380; (2016); A1;,
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