Month: March 2021

Reference of 1187-42-4,Some common heterocyclic compound, 1187-42-4, name is Diaminomaleonitrile, molecular formula is C4H4N4, 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.

Under N2 atmosphere, bi-indole (420 mg, 1.4 mmol), diaminomaleonitrile (240 mg, 2.2 mmol) and sulfamic acid (1200 mg, 12.0 mmol) were refluxed in 30 mL of methanol for 3 h. The residual methanol was removed by vacuum distillation, then the resulting precipitate was washed by saturated aq. NaHCO3 and dried in vacuo to afford a yellow solid. The solid was subjected to chromatography over silica gel (ethyl acetate:petroleum ether, 1:1) to give 1 as yellow powder in about 80percent yield. 1H NMR (400 MHz, DMSO-d6, TMS): delta 7.10 (t, 2H, J = 7.3 Hz), 7.20 (t, 2H, J = 7.5 Hz), 7.48 (d, 2H, J = 8.0 Hz), 7.75 (d, 2H, J = 8.2 Hz), 7.81 (d, 2H, J = 2.4 Hz), 11.85 (s, 2H); ESI-MS (m/z): 359.2 [M?H]?, 394.6 [M+Cl]?, 754.5 [2M+Cl]?; HRMS (ESI) (m/z): 359.1047 [M?H]?, calcd. for C22H12N6 360.3709.

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

Reference:
Article; Liu, Xiu-Ming; Zhao, Qiang; Li, Yue; Song, Wei-Chao; Li, Ya-Ping; Chang, Ze; Bu, Xian-He; Chinese Chemical Letters; vol. 24; 11; (2013); p. 962 – 966;,
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Electric Literature of 57418-97-0, The chemical industry reduces the impact on the environment during synthesis 57418-97-0, name is 4-Bromo-3-chlorobenzonitrile, I believe this compound will play a more active role in future production and life.

Next, into a 50-mL round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed dioxane (5 mL), water (1 mL), 6-chloro-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)-2-(trifluoromethyl)-1H-indole (100 mg, 0.29 mmol, 1.00 equiv), 4-bromo-3-chlorobenzonitrile (62.6 mg, 0.29 mmol, 1.00 equiv), (phosphoperoxy)potassium; dipotassium (184 mg, 0.866 mmol, 3.00 equiv), Pd(dppf)Cl2.CH2Cl2 (21 mg, 0.10 equiv). The resulting solution was stirred overnight at 80 C. in an oil bath. The reaction mixture was cooled. The crude product was purified by Prep-HPLC product was obtained. This resulted in 23.9 mg (23%) of 3-chloro-4-[6-chloro-2-(trifluoromethyl)-1H-indol-5-yl]benzonitrile as a off-white solid. (ES, m/z): 353 [M-H]-; (300 MHz, DMSO-d6, ppm): delta 12.64 (brs, 1H), 8.20 (s, 1H), 7.95-7.92 (m, 1H), 7.69 (s, 2H), 7.63-7.60 (d, J=8.1 Hz, 1H), 7.12 (s, 1H).

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-Bromo-3-chlorobenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERIAL, INC.; Meng, Charles; Le Hir de Fallois, Loic; (40 pag.)US2015/366198; (2015); A1;,
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69395-13-7, name is 4-(2-Hydroxyethyl)benzonitrile, belongs to nitriles-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. COA of Formula: C9H9NO

PREPARATION 13 Preparation of 4-carbamoylphenethyl bromide and 4-cyanophenethyl bromide STR36 A solution of phosphorus tribromide (5 g) in carbon tetrachloride (10 ml) was added, dropwise, to a solution of 4-cyanophenethyl alcohol (8.06 g) in carbon tetrachloride (60 ml). The mixture was heated under reflux for 4 hours. On cooling to room temperature, the mixture was poured onto ice (200 g). The layers were separated and the organic layer was washed with 10% aqueous sodium carbonate (50 ml) and brine (50 ml), dried (MgSO4) and concentrated in vacuo to give a colourless oil which solidified on standing. The solid was chromatographed on silica eluding with ethyl acetate containing hexane (20%). The fractions containing the less polar (higher Rf) product were combined and concentrated in vacuo to give 4-cyanophenethyl bromide as a yellow oil which solidified on standing, yield 8.9 g. The fractions containing the more polar (lower Rf) product were combined and concentrated in vacuo to give 4-carbamoylphenethyl bromide as a colourless solid, yield 0.47 g, m.p. 152-153.

The synthetic route of 69395-13-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Pfizer Inc.; US5340831; (1994); A;,
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Electric Literature of 873-74-5, 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. 873-74-5, name is 4-Aminobenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: Alcohol, phenol, and/or amine (1 mmol) were added to amixture of the ZnAl2O4SiO2 nanocomposite (100 mg) andacetic anhydride (1 mmol). The mixture was stirred at 75 C(for alcohols and phenols) or at room temperature (for amines)for a time. The progress of the reaction was monitored by TLCand/or GC-MS. When the reaction was completed, ethyl acetate(10 mL) was added and the mixture was filtered to separate offthe catalyst. The catalyst was washed twice with 7.5 mL ethylacetate. The combined organic phases were washed with a10% solution of NaHCO3 and then dried over MgSO4. The solventwas removed to yield the product. If further purificationwas needed, the product was passed through a short column ofsilica gel. All products were characterized on the basis ofGC-MS, FT-IR, and 1H-NMR spectral data by comparing thesespectra with those of standard samples or literature data.

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

Reference:
Article; Farhadi, Saeed; Jahanara, Kosar; Cuihua Xuebao/Chinese Journal of Catalysis; vol. 35; 3; (2014); p. 368 – 375;,
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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. 60710-80-7, name is 3-Amino-4-methylbenzonitrile, A new synthetic method of this compound is introduced below., COA of Formula: C8H8N2

To a solution of intermediate 7R (231 g, 0.556 mol) in 1,4-dioxane (2.3 L), ptoluenesulfonic acid monohydrate (179 g, 0.95 mol) and 3-amino-4-methylbenzonitrile (110 g, 0.83 mol) were added, purged three times with N2 and stirred at 95 C for 12 h. Then, the reaction mixture was cooled down to 20 C, and a solution of NaHCO3 was added to neutralize the mixture. The precipitated solid formed was filtrated andcombined with another precipitate coming from a reaction performed on 179 g of intermediate 7R. The resulting solid was dissolved in Me-THF (5 L), washed with water three times (3 x 5 L). A silanethiol resin [from Shanghai Meryer CO.,LTD] (60 g) was added to the mixture and reflux for 1.5 h. Then, the resulting mixture was filtered through a pad of celite and concentrated under vacuum. The residue wassuspended in EtOH (5L) overnight, filtered and dissolved in THF (3L). Methyl ten?butylether (6 L) was added to THF and the solid was precipitated, filtered and dried to afford 243g of compound 1.

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; JANSSEN PHARMACEUTICA NV; STANSFIELD, Ian; QUEROLLE, Olivier Alexis Georges; PONCELET, Virginie Sophie; GROSS, Gerhard Max; JACOBY, Edgar; MEERPOEL, Lieven; KULAGOWSKI, Janusz Jozef; MACLEOD, Calum; MANN, Samuel Edward; GREEN, Simon Richard; HYND, George; (477 pag.)WO2017/125530; (2017); A1;,
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Synthetic Route of 85068-32-2,Some common heterocyclic compound, 85068-32-2, name is 2-(3,5-Bis(trifluoromethyl)phenyl)acetonitrile, molecular formula is C10H5F6N, 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 ethanol (10 mL) solution of 3,5-bis(trifluoromethyl)phenylacetonitrile (3.59 g, 14.2 mmol) and 2-ethylsulfanylaniline (2.54 g, 14.2 mmol) was cooled on ice, and an ethanol (10 mL) solution of sodium methoxide (1.2 g, 21.3 mmol) was sequentially added dropwise, followed by stirring under ice cooling for 72 hours. Water was poured in the reaction solution, and the resulting solution was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over sodium sulfate, filtered to remove the white precipitate, and concentrated under reduced pressure, and the obtained crude product was purified by silica gel column chromatography (eluting solvent: ethyl acetate/hexane=1:6) to afford the title compound (yielded 5.3 g, yield: 87%) as a red-tan oily product. 1HNMR Spectrum (CDCl3) sigma: 8.29 (2H, s), 7.79 (1H, s), 7.58-7.52 (2H, m), 7.44-7.39 (2H, m), 4.00 (2H, br), 2.87 (2H, q, J=7.3 Hz), 1.27 (3H, t, J=7.3 Hz).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-(3,5-Bis(trifluoromethyl)phenyl)acetonitrile, its application will become more common.

Reference:
Patent; HOKKO CHEMICAL INDUSTRY CO., LTD.; HIROKI, Hidekatsu; KOBAYASHI, Yuta; SUZUKI, Jun; ONOUE, Shinji; IWASAKI, Katsuhiko; OOTAKA, Akihito; DOI, Hayato; MATSUO, Eiko; ONOUE, Miwa; OKIMOTO, Asako; (68 pag.)US2018/290986; (2018); 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. 16588-02-6, name is 2-Chloro-5-nitrobenzonitrile, A new synthetic method of this compound is introduced below., Application In Synthesis of 2-Chloro-5-nitrobenzonitrile

A solution of 2-chloro-5-nitrobenzonitrile (19.5 g, 106.81 mmol), HMDS (43.7 mL, 213.62 mmol), Pd2(dba)3(2.93 g, 3.20 mmol), 2′-(di-tert-butylphosphino)-N,N-dimethyl-[1,1′-biphenyl]-2-amine (3.28 g, 9.61 mmol), water (3.85 g, 213.62 mmol) and lithium acetate (35.2 g, 534.06 mmol) in DMF (400 mL) was stirred under argon gas atmosphere at 100C for 5 hr. To the reaction mixture were added water and ethyl acetate, and the organic layer was separated. The organic layer was dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (solvent gradient; 0?5% ethyl acetate/hexane) to give 5-nitro-2-(trimethylsilyl)benzonitrile (13.2 g, 59.9 mmol, 56.1%) as a white solid.

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; TAKEDA PHARMACEUTICAL COMPANY LIMITED; YAMAMOTO, SATOSHI; SHIRAI, JUNYA; WATANABE, HIROYUKI; FUKUMOTO, SHOJI; ODA, TSUNEO; TOKUHARA, HIDEKAZU; TOMATA, YOSHIHIDE; ISHII, NAOKI; TAWADA, MICHIKO; KOUNO, MITSUNORI; OCHIDA, ATSUKO; IMADA, TAKASHI; FUKASE, YOSHIYUKI; YUKAWA, TOMOYA; (719 pag.)TW2016/2105; (2016); A;,
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Synthetic Route of 1250444-23-5,Some common heterocyclic compound, 1250444-23-5, name is 3-Bromo-2,6-difluorobenzonitrile, molecular formula is C7H2BrF2N, 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 3- bromo-2,6-difluorobenzonitrile (4.4 g, 20 mmol), potassium ethanethioate (2.88 g, 25 mmol), Pd2(dba)3 (0.555 g, 0.61 mmol) and Xantphos (0.70 g, 1.2 mmol) in p-dioxane (30 mL) was stirred at 102 C for 15 hours. After cooling to ambient temperature, 28% aqueous ammonium hydroxide (12.3 g, 202 mmol) was added. The mixture was stirred at ambient temperature for 1 hour. Water (50 mL) and 2: 1 MTBE/hexanes (200 mL) were added. The aqueous layer was separated, acidified with 1 N HC1 to pH~5 and extracted with MTBE (50 mL). The organic layer was separated, washed with brine, dried (sodium sulfate), filtered and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel eluting with 3: 1 hexane/CH2Cl2 to give 2,6-difluorG-3-mercaptobenzonitrie (0.74 g, 21 %) as solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Bromo-2,6-difluorobenzonitrile, its application will become more common.

Reference:
Patent; PELOTON THERAPEUTICS, INC.; DIXON, Darryl, David; GRINA, Jonas; JOSEY, John, A.; RIZZI, James, P.; SCHLACHTER, Stephen, T.; WALLACE, Eli, M.; WANG, Bin; WEHN, Paul; XU, Rui; YANG, Hanbiao; WO2015/35223; (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. 6011-14-9, name is 2-Aminoacetonitrile hydrochloride, A new synthetic method of this compound is introduced below., Computed Properties of C2H5ClN2

A. 2-tert-Butyloxycarbonylamino-3-methyl-pentanoic acid cyanomethyl-amide N-Tertbutyloxycarbonyl-isoleucine semihydrate (3 g, 12.5 mmol), HOBt (3.71 g, 27.5 mmol, 2.2 eq.) and aminoacetonitrile hydrochloride (1.27 g, 13.7 mmol, 1.1 eq.) are dissolved in dimethylformamide (36 ml) and WSCD (2.5 ml, 13.7 mmol, 1.1 eq.) is added.. After stiring for 1 hour at rt, 4% sodium bicarbonate solution is added and the mixture is extracted with ethyl acetate.. The organic layer is washed with sodium bicarbonate and dilute hydrochloric acid, dried over magnesium sulfate and evaporated, to give the product in quantitative yield. mp. 125-133.5 C., Rf=0.44 (hexanes:ethyl acetate=1:1)

The synthetic route of 6011-14-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Novartis AG; US6353017; (2002); B1;,
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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. 4640-66-8, name is 4-Chlorophenacylcyanide belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. COA of Formula: C9H6ClNO

In a 25 mL reaction tube with a Teflon magnetic stir bar,Add 0.5 mmol of 3-(4-chlorophenyl)-3-oxopropanenitrile, 0.5 mmol of 3-bromo-1,1,1-trifluoroacetone, 0.5 mmol of sodium acetate,Finally, 58 mmol of 1,4 dioxane was added, and the reaction was stirred at room temperature for 8 hours.Add 15 mL of water, extract three times with 10 mL of ether, and combine the organic phases.Washing with saturated sodium chloride solution, drying over anhydrous magnesium sulfate, and then removing the organic solvent by rotary evaporation;The obtained crude product was eluted with n-pentane and ethyl acetate (10:1, v/v).5-Hydroxy-2-(4-chlorophenyl)-5-(trifluoromethyl)-4,5-dihydrofuran-3-carbonitrile (isolated yield 60%) was obtained by silica gel column chromatography.

The synthetic route of 4640-66-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Fuzhou University; Weng Zhiqiang; Wang Junwen; (29 pag.)CN110272400; (2019); A;,
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