Tag: M.W=100-200

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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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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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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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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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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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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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. 939-83-3, name is 2-Methyl-5-nitrobenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. HPLC of Formula: C8H6N2O2

EXAMPLE XV 3-Amino-6-methylbenzonitrile STR25 A suspension of 8.11 g (50 mmol) of 6-methyl-3-nitrobenzonitrile and 0.81 g of 10% of palladium-on-charcoal in 50 ml of ethanol and 50 ml of ethyl acetate is hydrogenated under 2.9 bar for 1 hour. The catalyst is filtered off, the filtrate is concentrated and the residue is crystallized from ether/petroleum ether. Yield: 59.6% of theory Melting point: 88 C.

The synthetic route of 939-83-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bayer Aktiengesellschaft; US5596006; (1997); A;,
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Application of 327-74-2,Some common heterocyclic compound, 327-74-2, name is 2-Amino-5-cyanobenzotrifluoride, molecular formula is C8H5F3N2, 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 solution of 2-amino-5-cyanobenzotrifluoride (1.0g, 5.37mmol, 1 eq) and benzyl bromide (2.55ml_, 21 .5mmol, 4.0eq) in dry DMF (10ml_) was added at rt NaH (970mg, 21.5mmol, 4eq) portion-wise under Ar(g). The reaction mixture was stirred at rt overnight, and was then partitioned with H20 (30ml_) and extracted with EtOAc (5 x 20ml_) and CH2CI2 (20ml_). The combined organic extracts were dried over MgS04 and the solvent was removed in vacuo. The residue was further purified by silica gel column chromatography with hexane/EtOAc (1 :0-9:1 ) to yield the product, 2, as a pale yellow solid (1 .66g, 85%).1H NMR (400MHz, CDCI3) deltaEta: 7.95 (d, J=2.0Hz, 1 H), 7.63 (dd, J=8.5, 1 .5Hz, 2H), 7.28-7.34 (m, 6H), 7.20 (d, J=6.5Hz, 4H), 7.12 (d, J=8.5Hz, 1 H), 4.23 (s, 4H).MS (ES+) 389.1 (100%, [M+Na]+).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Amino-5-cyanobenzotrifluoride, its application will become more common.

Reference:
Patent; KARUS THERAPEUTICS LIMITED; SHUTTLEWORTH, Stephen, Joseph; SILVA, Franck, Alexandre; WO2011/135351; (2011); A1;,
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Electric Literature 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.

A mixture of the product of step (a) (111 mg), Pd(OAc)2 (7 mg), BINAP (19 mg),cesium carbonate (120 mg) and 4-Amino-3-chloro-benzonitriIe (95 mg) in 15 ml toluene was reflaxed for 12 hours. The reaction mixture was eluted through a silica bed with Toluene and then with PE: EtOAc (1:1). The toluene fraction was discarded and the solvent of the PE:EtOAc fraction was removed under reduced pressure. The crude product was purified by Combiflash (linear gradient PE – THF). Yield 90 mg, 67 %. Finally, it was recrystallized from acetonitrile: water (1:1). Yield: 38 mg of colorless flakes.1H NMR (300 MHz3 CDC13, rt) delta 0.12 (m, 2H, CH2), 0.49 (m, 2H, CH2), 0.9 (m, IH, CH), 2.87 (dd, 2H, J= 5.7 Hz, J= 7.2 Hz, CH2) 4.735 (t, IH, J= 5.4 Hz, NH), 6.754 (s broad, IH, NH), 7.402 (d, IH, J= 8.7 Hz, ArH), 7.431 (dd, IH, J= 2.1 Hz, J= 8.6 Hz, ArH), 7.432 (dd, IH, J= 1.8 Hz, J= 8.7 Hz, ArH), 7.586 (d, IH, J= 1.8 Hz, ArH), 7.736 (d, IH, J= 1.8 Hz, ArH)3 and 8.21 (d, 2H, J= 8.7 Hz, ArH).MS: m/z 428.1 (M”)

The synthetic route of 21803-75-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PHARMOS CORPORATION; WO2008/75353; (2008); A1;,
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Application of 75279-55-9,Some common heterocyclic compound, 75279-55-9, name is 2-Chloro-6-fluorophenylacetonitrile, molecular formula is C8H5ClFN, 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: Typical procedure exemplified by the synthesis of 2-amino-4-chlorobenzo-1-thiophene-3-carbonitrile (Table 1, entry 5a): To a N2 flushed, 500 mL, three necked round bottomed flask were added 2-chloro-6-fluorophenylacetonitrile (1e) (8.48 g, 50 mmol) and DMSO (100 mL). To the solution was added 60% sodium hydride (2.10 g, 52.5 mmol) portion wise under N2 at rt (slightly exothermic). After 30 min, the reaction mixture was cooled to 15C with cold water bath and O-ethyl carbonisothiocyanatidate (2) (5.65 mL, 50.0 mmol) was added drop wise. After 1 h, the reaction mixture was heated at 100C for 2 h. A solution of 5 N NaOH (50 mL) was added and the reaction mixture was stirred at 100C for 2 h. The suspension was cooled to rt with stirring and 700 mL of water was added. The mixture was then cooled to 15C. The suspension was filtered and house vacuum air dried for 18 h to give the crude product as ayellow solid (6.5 g).

The synthetic route of 75279-55-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Krishnananthan, Subramaniam; Smith, Daniel; Traeger, Sarah C.; Mathur, Arvind; Li, Jianqing; Tetrahedron Letters; vol. 56; 24; (2015); p. 3766 – 3768;,
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