Month: June 2021

Application of 70591-86-5,Some common heterocyclic compound, 70591-86-5, name is 3-Bromobenzoylacetonitrile, molecular formula is C9H6BrNO, 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.

3- (3-bromophenyl)-JH-pyrazol-5-amine: A mixture of 3 -(3 -bromophenyl)-3 – oxopropanenitrile (35 g, 156 mmol) and hydrazine hydrate (11.34 mL, 234 mmol) inethanol (600 mL) was refluxed for 16 h. Mixture was then cooled and concentratedin vacuuo. Crude product was diluted with dichloromethane and stirred for 5 mm.Solids were filtered and dried to afford 3-(3-bromophenyl)-1H-pyrazol-5-amine (30g, 126 mmol, 81 % yield) as off-white solid. ?H NMR (400 MHz, DMSO-d6) oe 12.02(br. s., 0.4H), 11.66 (br. s., 0.6H), 7.86 (t, J1 .6 Hz, 1H), 7.67 (d, J=7.5 Hz, 1H), 7.45(d,J=6.8 Hz, 1H), 7.37-7.18 (m, 1H), 5.78 (br. s., 1H), 5.08 (br. s., 1.2H), 4.68 (br.s., 0.8H). LCMS (M+H) = 240.1.

The synthetic route of 70591-86-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; NAIDU, B. Narasimhulu; PATEL, Manoj; D’ANDREA, Stanley; ZHENG, Zhizhen Barbara; CONNOLLY, Timothy P.; LANGLEY, David R.; PEESE, Kevin; WANG, Zhongyu; WALKER, Michael A.; KADOW, John F.; WO2015/126376; (2015); 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. 147754-12-9, name is 4-Fluoro-2-methylbenzonitrile, A new synthetic method of this compound is introduced below., COA of Formula: C8H6FN

A solution of compound 2 (20 g, 148 mmol), NBS (26.4 g, 150 mmol) and AIBN (1 g) in CCl4 under nitrogenThe mixture was refluxed for 2 hours and the reaction was cooled to room temperature. The solid was removed by filtration and the organic solution was concentrated to give the crude product as an oilWhich was used in the next step without further purification

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; Shanghai Institute of Pharmaceutical Industry; China Pharmaceutical Industry Research Institute; Chen, Wu; Liu, Xiangkui; Ji, Zhongde; Zhu, Xueyan; Yuan, Zhedong; (10 pag.)CN105418580; (2016); A;,
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Electric Literature of 1558-82-3,Some common heterocyclic compound, 1558-82-3, name is Ethyl N-cyanoacetimidate, molecular formula is C5H8N2O, 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.

the last step into the reactor material, heated to 75 ,Add 520kgCyanoethyl ester, Dropping 5 hours, dropping temperature at this temperature for 4 hours, and then cooled to room temperature, filtered to give acetamiprid, and then dried to obtain the finished product 995kg, content of 99%Yield 96%.

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

Reference:
Patent; Jiangsu Changqing Agrochemical Co., Ltd.; Lv Liangzhong; He Shuze; Ma Changqing; Ding Huaping; (5 pag.)CN107501172; (2017); A;,
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Electric Literature of 2469-99-0, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 2469-99-0 as follows.

To a stirring suspension of 5-hydrazinylisoqui- noline (prepared from Example 25 step a, 0.60 g, 3.8 mmol) and 3-oxobutanenitrile (0.31 g, 3.8 mmol) in ethanol (3 mE) was heated at 80 C. for 2 h. After cooling to room temperature, the reaction mixture was in vacuo and the resulting crude residue was purified by flash chromatography (Si02, 0-20% methanol in ethyl acetate) to give the desired product (0.067 g, 2.8 mmol, 73%)

According to the analysis of related databases, 2469-99-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ChemoCentryx, Inc.; Cappel, Markus; (83 pag.)US2018/9797; (2018); A1;,
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Application of 867366-91-4, 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. 867366-91-4, name is 3-Bromo-5-methoxybenzonitrile, This compound has unique chemical properties. The synthetic route is as follows.

3-bromo-5- methoxybenzonitrile (8.3 g, 39.1 mmol),dicyclohexyl(2′,6′-dimethoxy-[l, -biphenyl]-2- yl)phosphine (S-Phos) (1.286 g, 3.13 mmol), phenylboronic acid (5.84 g, 47.0 mmol), Pd2(dba)3 and 200 mL toluene were charged in a flask and refluxed overnight. The reaction was cooled down and 200 mL of ethyl acetate was added. The crude mixture was run though a silica gel plug, and the product was confirmed by GC. After distillation under vacuum, 7.5 g of a white product was obtained.

The chemical industry reduces the impact on the environment during synthesis 3-Bromo-5-methoxybenzonitrile. I believe this compound will play a more active role in future production and life.

Reference:
Patent; UNIVERSAL DISPLAY CORPORATION; XIA, Chuanjin; YEAGER, Walter; LI, David Zenan; FIORDELISIO, James; MA, Bin; ELSHENAWY, Zeinab; LAYEK, Suman; BARRON, Edward; KOTTAS, Gregg; BROOKS, Jason; WO2012/116231; (2012); 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, SDS of cas: 935-02-4

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%) 4.3.2 (Z)-3-(3-n-Butyl-2-thioxo-2,3-dihydro-1H-imidazol-1-yl)-3-phenyl-2-propenenitrile (3b) Analogously, from acetylene 2 (64.0 mg, 0.5 mmol), S (16.0 mg, 0.5 mmol), and 1-n-butylimidazole (1b; 62.0 mg, 0.5 mmol) (20-25 C, 24 h), thione 3b (31 mg, 39%) was obtained as a light-brown oil. Initial imidazole 1b was recovered (27 mg, conversion was 57%). 1H NMR (400.13 MHz, CDCl3): delta=7.50-7.30 [m, 5H, Ho,m,p from C(6)-Ph], 6.90 (s, 1H, 4-H), 6.79 (s, 1H, 5-H), 6.06 (s, 1H, 7-H), 4.08 [t, 3JH,H=7.7 Hz, 2H, CH2(CH2)2CH3 from N-n-Bu], 1.83-1.80 (m, 2H, CH2CH2CH2CH3 from N-n-Bu), 1.45-1.40 [m, 2H, (CH2)2CH2CH3 from N-n-Bu], 0.98 [t, 3JH,H=7.3 Hz, 3H, (CH2)3CH3, from N-n-Bu] ppm. 13C NMR (100.62 MHz, CDCl3): delta=164.0 (C-2), 154.4 (C-6), 132.6 [Ci from C(6)-Ph], 131.9 [Cp from C(6)-Ph], 129.2 [Cm from C(6)-Ph], 126.8 [Co from C(6)-Ph], 118.5 (C-4), 117.0 (C-5), 114.7 (CN), 97.2 (C-7), 47.9 [CH2(CH2)2CH3 from N-n-Bu], 30.7 (CH2CH2CH2CH3 from N-n-Bu), 19.8 [(CH2)2CH2CH3 from N-n-Bu], 13.7 [(CH2)3CH3 from N-n-Bu] ppm. IR (film): 2222 (CN), 1622 (C=C), 1402 (C=S) cm-1. Anal. Calcd for C16H17N3S (283.39): C, 67.81; H, 6.05; N, 14.83; S, 11.32. Found: C, 68.04; H, 5.96; N, 14.92; S, 11.03. 4.3.3 (Z)-3-(1-n-Butyl-1H-imidazol-2-yl)-3-phenyl-2-propenenitrile (5b) (0030) Brown oil (26 mg, 37%). 1H NMR (400.13 MHz, CDCl3): delta=7.50-7.26 [m, 5H, Ho,m,p from C(6)-Ph], 7.25 (s, 1H, 4-H), 7.06 (s, 1H, 5-H), 5.94 (s, 1H, 7-H), 3.61 [t, 3JH,H=7.2 Hz, 2H, CH2(CH2)2CH3 from N-n-Bu], 1.60-1.50 (m, 2H, CH2CH2CH2CH3 from N-n-Bu), 1.15-1.10 [m, 2H, (CH2)2CH2CH3 from N-n-Bu], 0.77 [t, 3JH,H=7.6 Hz, 3H, (CH2)3CH3 from N-nBu] ppm. 13C NMR (100.62 MHz, CDCl3): delta=151.6 (C-6), 142.3 (C-2), 136.2 [Ci from C(6)-Ph], 130.9 [Cp from C(6)-Ph], 129.7 (C-4), 129.0 [Cm from C(6)-Ph], 127.3 [Co from C(6)-Ph], 121.6 (C-5), 116.6 (CN), 99.5 (C-7), 46.7 [CH2(CH2)2CH3 from N-n-Bu], 32.6 (CH2CH2CH2CH3 from N-n-Bu), 19.4 [(CH2)2CH2CH3 from N-n-Bu], 13.2 [(CH2)3CH3 from N-n-Bu] ppm. IR (microlayer): 2216 (CN), 1650 (C=C) cm-1. Anal. Calcd for C16H17N3 (251.33): C, 76.46; H, 6.82; N, 16.72. Found: C, 76.15; H, 6.56; N, 16.39.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Phenylpropiolonitrile, and friends who are interested can also refer to 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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Adding a certain compound to certain chemical reactions, such as: 868-54-2, name is 2-Aminoprop-1-ene-1,1,3-tricarbonitrile, 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 868-54-2, Product Details of 868-54-2

General procedure: Heterocyclic ketene aminals (1 mmol), aryl aldehydes (1.2 mmol), malononitriledimer (1.5 mmol), acetic acid (1 mmol), piperidine (1 mmol) and ethanol (10 mL)were stirred at refluxing for 1 h. After completion of the reaction (confirmed by TLC),the reaction mixture was filtered to afford the crude product, which was furtherwashed with 95% ethanol to give pure product 4.

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, 2-Aminoprop-1-ene-1,1,3-tricarbonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Sun, Feilong; Zhu, Fengjuan; Shao, Xusheng; Li, Zhong; Synlett; vol. 26; 16; (2015); p. 2306 – 2312;,
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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. 64248-64-2, name is 2,5-Difluorobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C7H3F2N

Potassium carbonate (2.9Og, 21 mmol) was added to a solution of phenol (791 mg, 8.4mmol) in 30 ml of N,N-dimethylformamide. The reaction mixture was stirred for 15 minutes at room temperature, and then 2,5-difluorobenzonitrile (973mg, 7mmol) was added. The resulting mixture was heated to 1000C for 18 hours, after which time it was allowed to cool to room temperature. It was then concentrated in vacuo. The resulting residue was diluted with ethyl acetate (50ml), and then washed with water (2x100ml) and 1 M sodium hydroxide solution (100ml). The organic layer was dried over sodium sulfate, filtered and evaporated under reduced pressure to afford the title compound, as a yellow oil, 1.449g, 97%. 1HNMR(400MHz, CDCI3) delta: 6.87(q, 1 H), 7.05(d, 2H), 7.21(m, 2H), 7.33-7.43(m, 3H); LRMS APCI+ m/z 214 [MH]+

According to the analysis of related databases, 64248-64-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PFIZER LIMITED; WO2006/64336; (2006); A2;,
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Reference of 1187-42-4, These common heterocyclic compound, 1187-42-4, name is Diaminomaleonitrile, 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.

l,2-bis(4-chlorophenyl)ethane-l,2-dione, (20 g, 71.65 rnmol), diaminomaleonitrile (8.5 g,78.82 mmol) and acetic acid (6 ml) in ethanol (140 ml) and water (93 ml) were heated at75 °C overnight. The reaction mixture was cooled, and water was added. The precipitatewas filtered and washed with ethanol and then ether. The crude product was dissolved inDCM and treated with activated charcoal, then filtered through celite. After evaporation, asolid was formed and recrystallized from DCM/ethanol to give a pale yellow solid (17.3 g,69percent).1H NMR (400 MHz) 5 7.49 (d, 4H), 7.38 (d, 4H).

The synthetic route of 1187-42-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; WO2004/111034; (2004); A1;,
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Application of 139152-08-2, The chemical industry reduces the impact on the environment during synthesis 139152-08-2, name is 4,5-Dichlorophthalonitrile, I believe this compound will play a more active role in future production and life.

Compound 1 (2 g, 4.04 mmol), 4,5-dichloro-1,2-dicyanobenzene(1.6 g, 8.16 mmol) and 20 mL dry DMF were stirred under nitrogenatmosphere for 15 min at 25 C and dry K2CO3 (1.41 g, 10.1 mmol)was added portion-wise for 2 h. The reaction mixture was stirredunder nitrogen atmosphere at 70 C for about 3 days. Then, it wasemptied into ice-water and filtrated. The light brown product wasrecrystallized from ethanol. The raw product was refined by columnchromatography with silica gel, using chloroform/ethanol(98:2). Yield: 1.35 g (54%). m.p.:181-190 C. Anal. calcd. forC36H30O6SN2: C, 69.89; H, 4.89; N, 4.53%. Found: C, 69.93; H, 4.83;N, 4.82%. IR, nmax/cm1 : 3097 (Ar-H), 2920-2869 (Aliph., C-H), 2234(C^N), 1274 (Ar-O-C), 1129-1017 (-OCH2), 826.1H NMR (CDCl3),(delta:ppm): 7.72 (m, 4H, ArH), 7.46 (ddd, 4H, ArH), 7.15 (d, 2H, ArH),7.01 (d, 2H, ArH), 6.84 (d, 2H, ArH), 3.98 (d, 4H, O-CH2), 3.52 (m, 4H,O-CH2), 3.27 (d, 4H, O-CH2), 3.05 (m, 4H, O-CH2). 13C NMR(CDCl3), (delta:ppm): 155.89, 135.43, 129.48, 128.05, 125.92, 124.49,120.59, 118.85, 115.32(C^N), 112.55, 108.61, 72.28, 68.71, 61.32.MS(FAB) (m/z): 615 [M 3].

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, 4,5-Dichlorophthalonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Arucu, Sevinc; Sa?lam, Meltem Betuel; Oezkaya, Ali R?za; Journal of Molecular Structure; vol. 1198; (2019);,
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