Author: Jessica.F

Electric Literature of 79463-77-7, The chemical industry reduces the impact on the environment during synthesis 79463-77-7, name is Diphenyl N-cyanocarbonimidate, I believe this compound will play a more active role in future production and life.

Diphenyl N-cyanocarbonimidate [79463-77-7] (200 mg, 0.81 mmol) and 3,4-dimethoxyaniline [6315- 89-5] (137 mg, 0.89 mmol) were dissolved in DCM (2 mL) and 2-propanol (2 mL) and DIPEA (159 mg, 1.22 mmol) were added and the reaction mixture was stirred at r.t. for ~1 h. The mixture was concentrated in vacuo and the residue was purified by flash column chromatography on silica (gradient elution with 15 – 100% EtOAc/hexane) to afford the title compound (198 mg, 82%) as a white solid. dH (300 MHz, DMSO -d6) 10.65 (s, 1H), 7.51 – 7.37 (m, 2H), 7.36 – 7.22 (m, 3H), 7.09 (d, J 1.8 Hz, 1H), 7.03 – 6.91 (m, 2H), 3.75 (s, 6H).

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, Diphenyl N-cyanocarbonimidate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; UCB BIOPHARMA SRL; CHOVATIA, Prafulkumar Tulshibhai; CONNELLY, Rickki Lee; FRANKLIN, Richard Jeremy; HASLETT, Gregory William; HENRY, Alistair James; MADDEN, James; NEUSS, Judi Charlotte; NORMAN, Timothy John; PHILPS, Oliver; PITT, William Ross; RAMPALAKOS, Konstantinos; SELBY, Matthew Duncan; SELVARATNAM, Suganthan; TRANI, Giancarlo; ZHU, Zhaoning; (768 pag.)WO2019/243550; (2019); A1;,
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Related Products of 16588-02-6, 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. 16588-02-6 name is 2-Chloro-5-nitrobenzonitrile, 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.

Reference Example 1 1-(2,6-Dichlorophenyl)-2-oxo-3,4-dihydro-6-(4-fluorophenyl)thioquinazolinea) 2-(2,6-dichlorophenylamino)-5-nitrobenzonitrile 2,6-Dichloroaniline (2.84 g, 17.5 mmol) was dissolved in DMSO (5 mL) and 60% NaH (0.60 g, 15 mmol) was added. The mixture was stirred 30 min and then 2-chloro-5-nitrobenzonitrile (0.91 g, 5.0 mmol) in DMSO (5 mL) was added. The reaction darkened and warmed to 50. After cooling to 23 the reaction was diluted with EtOAc (200 mL) and washed with H2O (3X), satd. aq. NaCl, and dried (Na2SO4), and concentrated to afford 1.45 g (94%) of the title compound as an ivory colored powder. 1H NMR (400) MHz, delta: 8.49 (finely split doublet, 1), 8.20 (dd, 1), 7.51 (d,2), 7.34 (d, 2), 6.41 (d,1).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Chloro-5-nitrobenzonitrile, and friends who are interested can also refer to it.

Reference:
Patent; SmithKline Beecham Corporation; EP1233951; (2005); B1;,
Nitrile – Wikipedia,
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Electric Literature of 7357-70-2,Some common heterocyclic compound, 7357-70-2, name is 2-Cyanothioacetamide, molecular formula is C3H4N2S, 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.

2-(Bis(methylthio)methylene)malononitrile (10 g, 58.7 mmol) and cyanothioacetamide (7.06 g, 70.5 mmol) were added to a round-bottom flask and dissolved in N,N-dimethylformamide (21 mL). Triethylamine (16.37 mL, 117 mmol) was added dropwise at room temperature and the mixture was stirred for 18 hours. The reaction mixture was added to 300 mL of 3 N hydrochloric acid. The resulting precipitate was filtered off, washed with water and dried with suction to afford 2-amino-6-mercapto-4-(methylthio)pyridine-3,5-dicarbonitrile (13.5 g, 54.7 mmol, 93% yield). LCMS m/z = 222.9 [M+H]+.

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

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; ADAMS, Nicholas David; BENOWITZ, Andrew B.; RUEDA BENEDE, Maria Lourdes; EVANS, Karen Anderson; FOSBENNER, David T.; KING, Bryan Wayne; LI, Mei; MILLER, William Henry; REIF, Alexander Joseph; ROMERIL, Stuart Paul; SCHMIDT, Stanley J.; WIGGALL, Kenneth; (1283 pag.)WO2017/216726; (2017); A1;,
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Synthetic Route of 14618-78-1, These common heterocyclic compound, 14618-78-1, name is 4,4-Dimethoxybutanenitrile, 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.

SYNTHESIS EXAMPLE 4 Production of methyl 4,5,7-trichloroindole-3-acetate: 10.0 Grams (0.047 mole) of 2,4,5-trichlorophenylhydrazine, 9.2 g (0.07 mole) of beta-cyanopropionaldehyde dimethylacetal and 7.1 g (0.052 mole) of zinc chloride were mixed and then heated in a nitrogen stream at 140 C. for 2 hours. The reaction mixture was cooled to room temperature and dissolved in an acetic acid-water (2:1) solution, and the resulting solution was extracted with ethyl acetate. The ethyl acetate phase was washed with a saturated aqueous sodium bicarbonate solution, water and then a saturated aqueous sodium chloride solution, and then dried over anhydrous sodium sulfate. The ethyl acetate was removed by distillation under reduced pressure to obtain a black oily substance, which was then purified by a silica gel column chromatography to obtained 0.86 g of the desired compound represented by the formula: STR15 The analysis result of NMR of this compound is shown below. 1 H NMR (200 MHz) (CD3)2 CO, TMS) ppm: 7.48 (1H, s).. C2 –H 7.34 (1H, s).. C6 –H 3.99 (2H, s).. CH2 — 3.66 (3H, s).. OCH3 MS (75 ev) (relative intensity, %) m/z 295 (M+ +4, 10), 293 (M+ +2, 23), 291 (M+, 24), 260 (6), 259 (5), 258 (7), 236 (30), 234 (91), 232 (100), 199 (7), 198 (9), 197 (11), 162 (12), 161 (13), 118 (7), 116 (8), 97 (9), 98 (9).

The synthetic route of 14618-78-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Nippon Kayaku Kabushiki Kaisha; US4806143; (1989); A;,
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Application of 154607-01-9,Some common heterocyclic compound, 154607-01-9, name is 4-Bromo-2-chlorobenzonitrile, molecular formula is C7H3BrClN, 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.

1-(Benzo[d][1,3]dioxol-5-yl)-N-(4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)cyclopropanecarboxamide (0.084 g, 0.20 mmol), 4-bromo-2-chlorobenzonitrile (0.043 g, 0.20 mmol), aqueous potassium carbonate (520 muL, 1M), FibreCat 1007 (7 mg), and DMF (1 mL) were combined. The mixture was heated at 80 C. for 18 hours. After cooling, the mixture was filtered and purified by preparative HPLC to provide 1-(benzo[d][1,3]dioxol-5-yl)-N-(3′-chloro-4′-cyano-6-methylbiphenyl-3-yl)cyclopropanecarboxamide.

The synthetic route of 154607-01-9 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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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. 115279-57-7, name is 2-(4-Aminophenyl)-2-methylpropanenitrile, A new synthetic method of this compound is introduced below., Product Details of 115279-57-7

N-Chloro-succinimide (91.0 mg; 0.68 mmol) was added to a solution of 2-(4-amino- phenyl)-2-methyl-propionitrile (100 mg; 0.62 mmol), prepared as described in 1(B), in isopropanol (3 mL). The resulting solution was stirred at reflux for Ih. Then the solvent was evaporated under vacuum and the crude was portioned between EtOAc and H2O. The layers were separated and the organic phase was washed with brine, dried over Na2SO4, filtrated and concentrated under reduced pressure. The crude was purified by chromatography [SiO2, DCM] to afford the title compound as an orange oil (58.0 mg; 48% yield).1H NMR (300 MHz, CDC13) delta(ppm): 7.34 (d, 1 H), 7.18 (dd, 1 H), 6.78 (d, 1 H), 3.73(br. s., 2 H), 1.68 (s, 6 H).LCMS (RT): 4.63 min (Method B); MS (ES+) gave m/z: 195.05 (MH+).

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; ADDEX PHARMA SA; WO2008/117175; (2008); 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. 950596-58-4, name is 2-Amino-4,5-bis(2-methoxyethoxy)benzonitrile, This compound has unique chemical properties. The synthetic route is as follows., category: nitriles-buliding-blocks

(12.2 g, 50 mmol) (E)-N,N’-bis(3-ethynylphenyl)methyl ether (Compound B) and (13.3 g, 50 mmol) 2-Amino-4,5-bis(2-methoxyethoxy)benzonitrile (Compound C3), 0.5 g of p-toluenesulfonic acid was added to 50 mL of toluene,After heating to 110 C in an oil bath for 5 h, after TLC monitoring reaction, after cooling to room temperature, concentrated, add ice water and stir for 1 h.The brown solid product erlotinib 17.34 g was obtained in a yield of 88.2%, HPLC: 99.24%.

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 950596-58-4.

Reference:
Patent; Yancheng Normal College; Nanjing University Of Technology Dafeng Ocean Industrial Institute; Sun Yaquan; Chen Zhiyuan; Gu Huiwen; Zhang Lijie; Yang Kang; Zong Chaoyang; (11 pag.)CN108503596; (2018); A;,
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Related Products of 38487-86-4, These common heterocyclic compound, 38487-86-4, name is 2-Amino-4-chlorobenzonitrile, 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.

5-Chloro-2-(lH-tetrazol-5-yl)aniline: 2-Amino-4-chlorobenzonitrile (1000 mg, 6.6 mmol), sodium azide (555 mg, 8.5 mmol) and triethylamine hydrochloride (1175 mg, 8.5 mmol) were taken up in 15 mL of toluene. The suspension was heated to 100 0C overnight. After cooling, the reaction mixture was washed 3 times with 5 mL portions of water. The combined aqueous fractions were acidified with concentrated hydrochloric acid. The desired 5-Chloro-2-(lH-tetrazol-5-yl)aniline precipitated from aqueous solution and was isolated by filtration (1090 mg, 85% yield). 1H NMR (500 MHz, DMSO-d6) delta 7.73 (d, IH), 6.97 (d, IH), 6.74 (dd, IH); MS (electrospray) m/z 196 (M+H).

Statistics shows that 2-Amino-4-chlorobenzonitrile is playing an increasingly important role. we look forward to future research findings about 38487-86-4.

Reference:
Patent; EXELIXIS, INC.; WO2007/44724; (2007); A2;,
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Some common heterocyclic compound, 916792-13-7, name is 4-Bromo-2-fluoro-5-methylbenzonitrile, molecular formula is C8H5BrFN, 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. Formula: C8H5BrFN

To a solution of 4-bromo-2-fluoro-5-methylbenzonitrile (10.0 g, 46.7 mmol) in N,N-dimethylacetamide (30 mL) was added Pd(dppf)Cl2 (5.1 g, 7.0 mmol) and MeOH (10 mL), followed by TEA (14.3g, 140.1 mmol). The mixture was heated at 90 C overnight under carbon monoxide (5 MPa). The mixture was cooled to RT and the mixture was diluted with water, extracted with EA. The combined organic layers were concentrated to give the crude product, which was purified by silica gel chromatography eluting with EA/petroleum ether from 5% to 10% to give methyl 4-cyano-5-fluoro-2-methylbenzoate (7.33 g, 81%) as a white solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 916792-13-7, its application will become more common.

Reference:
Patent; BIOTHERYX, INC.; MERCURIO, Frank; CHAN, Kyle, W.H.; SULLIVAN, Robert; ERDMAN, Paul, E.; FUNG, Leah; (105 pag.)WO2018/169777; (2018); A1;,
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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 17354-04-0 as follows. name: 2-(4,5-Dimethoxy-2-nitrophenyl)acetonitrile

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.

According to the analysis of related databases, 17354-04-0, the application of this compound in the production field has become more and more popular.

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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