Month: June 2021

Synthetic Route of 7251-09-4, These common heterocyclic compound, 7251-09-4, name is 4-Amino-2-methoxybenzonitrile, 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 2) A solution of the compound obtained in Step 1 (670 mg, 4.52 mmol) and 3-methylglutaric anhydride (579 mg, 4.52 mmol) in THF (20 mL) was heated with reflux for 14 hr. The reaction solution was concentrated under reduced pressure to give 5-((4-cyano-3-methoxyphenyl)amino)-3-methyl-5-oxopentanoic acid (1.35 g, 4.89 mmol, quantitative) as a brownish-red oil. 1H-NMR(300MHz,DMSO-d6): delta0.75-1.12(3H,m), 1.58-1.91(1H,m), 2.08-2.19(1H,m), 2.22-2.46(2H,m), 2.48-2.55(1H,m), 2.65-2.94(1H,m), 3.36(1H,brs), 3.60(1H,t,J=6.4Hz), 7.25(1H,dd,J=8.3,1.5Hz), 7.45-7.76(2H,m), 10.34(1H,s), 12.11(1H,brs).

Statistics shows that 4-Amino-2-methoxybenzonitrile is playing an increasingly important role. we look forward to future research findings about 7251-09-4.

Reference:
Patent; Takeda Pharmaceutical Company Limited; YAMAMOTO, Satoshi; SHIRAI, Junya; FUKASE, Yoshiyuki; TOMATA, Yoshihide; SATO, Ayumu; OCHIDA, Atsuko; YONEMORI, Kazuko; NAKAGAWA, Hideyuki; EP2759533; (2014); A1;,
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Related Products of 20099-89-2, A common heterocyclic compound, 20099-89-2, name is 4-(2-Bromoacetyl)benzonitrile, molecular formula is C9H6BrNO, 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.

Preparation 4; 4-(2-Methylamino-thiazol-4-yl)-benzylamine; 4-(2-Methylamino-thiazol-4-yl)-benzonitrile; Slurry 4-cyanophenacyl bromide (1.12 g, 5 mmol) in absolute ethanol (25 mL). Heat to 40C to dissolve, then add N-methyl-thiourea (0.45 g, 5 mmol) and sodium bicarbonate (0.42 g, 5 mmol), and heat to reflux for 5 h. Cool to room temperature, filter the resulting off-white solid and wash with hexane (10 mL). Partition aqueous/ethanolic filtrate between water/EtOAc (4: 1) and extract aqueous phase with EtOAc (2×25 mL). Dry the combined organic extracts over Na2SO4, concentrate in vacuo and combine with filtered solid from crude reaction mixture to obtain the desired intermediate (1.1 g, 99%) as an off- white solid suitable for use without additional purification. MS (ES+) m/z: 216 (M+H)+.

The synthetic route of 20099-89-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ELI LILLY AND COMPANY; WO2007/28083; (2007); A2;,
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Adding a certain compound to certain chemical reactions, such as: 935-02-4, name is 3-Phenylpropiolonitrile, 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 935-02-4, Quality Control of 3-Phenylpropiolonitrile

General procedure: To a mixture of acetylene 2 (127 mg, 1 mmol) and S (32 mg, 1 mmol) was added 1-methylimidazole (1a; 82 mg, 1 mmol). The mixture was stirred at 20-25 C for 24 h. Column chromatography afforded thione 3a (132 mg, 67%), 4.3.7 (Z)-3-(3-Benzyl-2-thioxo-2,3-dihydro-1H-imidazol-1-yl)-3-phenyl-2-propenenitrile (3e) Analogously, from acetylene 2 (64.0 mg, 0.5 mmol), S (16.0 mg, 0.5 mmol), and 1-benzylimidazole (1e; 79.0 mg, 0.5 mmol) in MeCN (1 mL) (20-25 C, 24 h) thione 3e (27 mg, 96%) was obtained as a light-yellow microcrystalline powder, mp 129-131 C (washed with ether). Initial imidazole 1e was recovered (65 mg, conversion was 18%). 1H NMR (400.13 MHz, CDCl3): delta=7.50-7.30 [m, 10H, Ho,m,p from C(6)-Ph and Ph from N-Bn], 6.74 (s, 2H, 4-H, 5-H), 6.06 (s, 1H, 7-H), 5.27 (s, 2H, CH2 from N-Bn) ppm. 13C NMR (100.62 MHz, CDCl3): delta=164.7 (C-2), 154.1 (C-6), 135.2 (Ci, Ph from N-Bn), 132.4 [Ci from C(6)-Ph], 131.8 [Cp from C(6)-Ph], 129.1 [Cm from C(6)-Ph], 128.9 (Cm, Ph from N-Bn), 128.2 (Cp, Ph from N-Bn), 128.1 (Co, Ph from N-Bn), 126.7 [Co from C(6)-Ph], 118.3 (C-4), 117.1 (C-5), 114.5 (CN), 97.2 (C-7), 51.3 (CH2 from N-Bn) ppm. IR (KBr): 2221 (CN), 1621 (C=C), 1398 (C=S) cm-1. Anal. Calcd for C19H15N3S (317.41): C, 71.90; H, 4.76; N, 13.24; S, 10.10. Found: C, 71.67; H, 4.85; N, 12.92; S, 9.84.

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:
Article; Belyaeva, Kseniya V.; Andriyankova, Ludmila V.; Nikitina, Lina P.; Mal’Kina, Anastasiya G.; Afonin, Andrei V.; Ushakov, Igor A.; Bagryanskaya, Irina Yu.; Trofimov, Boris A.; Tetrahedron; vol. 70; 5; (2014); p. 1091 – 1098;,
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Synthetic Route of 6574-97-6, A common heterocyclic compound, 6574-97-6, name is 2,3-Dichlorobenzonitrile, molecular formula is C7H3Cl2N, 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: A mixture of a benzonitrile, 3a (310mg, 3mmol), 28 sodium azide (586mg, 9 mmol), and 29 triethylamine hydrochloride (1.24 g, 9 mmol) in 30 toluene (80 mL) was heated to 100°C for 24h with stirring. After cooling, the reaction mixture was extracted with water. Then, 36percent 31 HCl was added dropwise to the aqueous layer. Precipitation occurred, which was filtered off and washed with water to provide 32 4a as white solid (395mg, 90percent). Mp: 214?216°C. 1H NMR (500MHz, DMSO-d6): delta 8.04?7.02 (m, 2H), 7.62?7.57 (m, 3H)

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; Paudel, Suresh; Min, Xiao; Acharya, Srijan; Khadka, Daulat Bikram; Yoon, Goo; Kim, Kyeong-Man; Cheon, Seung Hoon; Bioorganic and Medicinal Chemistry; vol. 25; 20; (2017); p. 5278 – 5289;,
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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, category: nitriles-buliding-blocks

Step 1: tert-butyl 4-(3-cyanopropyl)-3-methylpiperazine-1-carboxylate To the stirred solution of tert-butyl 3-methylpiperazine-1-carboxylate (prepared according to procedure reported in US200876758A1, 2008, 5 g, 24.97 mmol) in N,N-dimethylformamide (50 ml) were added potassium carbonate (17.25 g, 125 mmol) and 4-bromobutanenitrile (2.98 ml, 30.0 mmol) at 25 C. The resulting solution was stirred at 25 C. for 16 h. The progress of the reaction was monitored by TLC. After completion of the reaction water (100 ml) was added and extracted with dichloromethane (3*60 ml). The combined extract was washed with brine (25 ml) and dried over sodium sulphate, filtered and concentrated to give crude compound. The crude compound was purified by column chromatography over silica gel (100-200) using 15% ethyl acetate in hexane to obtain the title compound (5 g, 75%). 1H NMR (400 MHz, CDCl3) delta 3.66-3.62 (m, 2H), 3.16-3.13 (m, 1H), 2.85-2.66 (m, 3H), 2.41-2.14 (m, 5H), 1.81-1.74 (m, 2H), 1.72 (s, 9H), 1.00 (d, J=6.4 Hz, 3H).

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

Reference:
Patent; LUPIN LIMITED; Jana, Gourhari; Kurhade, Sanjay Pralhad; Jagdale, Arun Rangnath; Kukreja, Gagan; Sinha, Neelima; Palle, Venkata P.; Kamboj, Rajender Kumar; US2015/152118; (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. 17354-04-0, name is 2-(4,5-Dimethoxy-2-nitrophenyl)acetonitrile, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 17354-04-0

General procedure: Piperidine (0.03 ml, 5 mol %) was added to a warm solution of the appropriate salicylaldehyde 5 (5 mmol) and 2-(4,5-dimethoxy-2-nitrophenyl)acetonitrile (1.12 g, 5 mmol) in EtOH (10 ml). The resulting solution was refluxed with stirring for 5 h. The mixture was treated with a solution of concentrated H2SO4 (0.55 ml) in EtOH (2 ml) and refluxed with stirring for 2 h. The obtained precipitate was filtered, washed with EtOH (10 ml), hot H2O (40 ml) and finally with EtOH (10 ml), and dried at 100 C.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 17354-04-0.

Reference:
Article; Irgashev, Roman A.; Karmatsky, Arseny A.; Slepukhin, Pavel A.; Rusinov, Gennady L.; Charushin, Valery N.; Tetrahedron Letters; vol. 54; 42; (2013); p. 5734 – 5738;,
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Reference of 327056-73-5, 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. 327056-73-5, name is 3-Chloro-5-fluorobenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Step 3: 3-chloro-5-(2-chloro-3-fluoro-5-methoxyphenoxy)benzonitrile (50-4); Under a nitrogen atmosphere, 2-chloro-3-fluoro-5-methoxyphenol (50-2) (6.7 g, 37.9 mmol) was diluted in NMP (40 mL, 0.95 M). To this solution Cs2CO3 (24.73 g, 76 mmol) was added and the reaction was allowed to stir at room temperature for 5 minutes. Then, 3-chloro-5-fluorobenzonitrile (11.81 g, 76 mmol) was added to the reaction and it was then heated to 120 C. After 2 hours the reaction was cooled to room temperature and then diluted with EtOAc (40 mL). It was partitioned with water (20 mL) and then extracted with EtOAc (3×30 mL). The organic extracts were then washed with water (3×20 mL) and brine (1×20 mL), dried over sodium sulfate and concentrated. Silica gel chromatography (1%-15% EtOAc/Hexanes) gave 3-chloro-5-(2-chloro-3-fluoro-5-methoxyphenoxy)-benzonitrile (50-4) (10.4 g, 88%).

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-Chloro-5-fluorobenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Saggar, Sandeep A.; Sisko, John T.; Tucker, Thomas J.; Tynebor, Robert M.; Su, Dai-Shi; Anthony, Neville J.; US2007/21442; (2007); 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. 3695-84-9, name is Methyl 2-cyano-3-phenylacrylate, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C11H9NO2

General procedure: A mixture of pyrazoline-5-one 1 (5 mmol), activated olefin 2 (5 mmol) and sodium bromide (0.31 g, 3 mmol) in methanol (20 mL) was electrolyzed in undivided cellequipped with a magnetic stirrer, a graphite anode and an iron cathode at 20 C under a constant current density of 100 mA cm-2 (I = 500 mA, electrodes square5 cm2) until the quantity of electricity 2.5 Fmol-1 of charge was passed. After the electrolysis was finished, spirocyclopropylpyrazolone 3 was filtered out and dried under reduced pressure. An additional amount of spirocyclopropylpyrazolone was isolated as follows. The reaction mixture was concentrated to 5 mL and cooled to -10 C overnight and filtered.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 3695-84-9.

Reference:
Article; Elinson, Michail N.; Dorofeeva, Evgeniya O.; Vereshchagin, Anatoly N.; Korshunov, Alexander D.; Egorov, Mikhail P.; Research on Chemical Intermediates; vol. 42; 3; (2016); p. 2191 – 2200;,
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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. 127946-77-4, name is 1-Amino-1-cyclopropanecarbonitrile hydrochloride, A new synthetic method of this compound is introduced below., Safety of 1-Amino-1-cyclopropanecarbonitrile hydrochloride

In a 10 mL round-bottomed flask, example 7G) (35 mg, 89.8 mumol, Eq: 1.00) was combined with DMF (1 mL) to give a light brown solution. HATU (68.3 mg, 180 mumol, Eq: 2.00), 1-aminocyclo-propanecarbonitrile hydrochloride (13.0 mg, 108 mumol, Eq: 1.20) and Hunig’s base (40.6 mg, 54.9 muL, 314 mumol, Eq: 3.50) were added. The reaction mixture was stirred at 22 C. for 20 h. The reaction mixture was poured into saturated aqueous NaHCO3 solution and extracted with DCM (2*). The organic layers were combined, washed with water (3*) and brine (1*). The organic layers were dried over Na2SO4 and concentrated in vacuo. The crude material was purified by flash chromatography (silica gel, 10 g, n-heptane/AcOEt 1/1) and preparative HPLC to yield a light brown powder (11 mg; 27%). m/z=454.2 [M+H]+.

The synthetic route of 127946-77-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; HOFFMANN-LA ROCHE INC.; Anselm, Lilli; Banner, David; Blanc, Jean-Baptiste; Gaufreteau, Delphine; Haap, Wolfgang; Hartmann, Guido; Kuhn, Bernd; Luebbers, Thomas; Peters, Jens-Uwe; Spinnler, Beat; US2013/196965; (2013); 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. 2469-99-0, name is 3-Oxobutanenitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. COA of Formula: C4H5NO

3-Oxobutyronitrile (5.04, 1.05 eq) and potassium t-butoxide (7 g, 1.05 eq) were added to DMSO (80 mL).Stir at room temperature for 10 minutes, add (E)-3-penten-2-one (5 g, 1 eq), stir at room temperature for half an hour.Further potassium t-butoxide (7 g, 1.05 eq) was added, and after 1 hour, it was stirred with air overnight. The reaction solution was cooled to 0 C.Diluted with 20 ml of water, 4N HCl (15 ml) was added dropwise, stirred for 15 minutes, filtered to give a solid, which was washed with 100 ml of water to give product g (3.8 g).No further purification is required.

The synthetic route of 2469-99-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chinese Academy Of Sciences Hefei Matter Sciences Institute; Liu Qingsong; Liu Jing; Lv Fengchao; Hu Chen; Wang Wenliang; Wang Aoli; Qi Ziping; Liang Xiaofei; Wang Wenchao; Ren Tao; Wang Beilei; Wang Li; (56 pag.)CN108314677; (2018); A;,
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