Month: September 2021

Electric Literature of 138642-47-4, These common heterocyclic compound, 138642-47-4, name is 2-Bromo-5-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.

General procedure: To a mixture of substituted alcohol 1 (1 mmol) and substituted nitrile 2 (1 mmol), T3P 50 wt% in ethyl acetate (50 mol%) was added and stirred at 90 C. After the reactant disappeared (monitored by TLC), the reaction mixture was cooled to room temperature, excess of water was added and extracted with ethyl acetate and combined organic layer was washed with brine, dried over Na2SO4 and concentrated under reduced pressure. The crude product was purified by recrystallization using DCM: pet ether (1:9) mixture to get pure compound 3.

The synthetic route of 138642-47-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Chaithra, Nagaraju; Mantelingu, Kempegowda; Rangappa, Kanchugarakoppal S.; Rangappa, Shobith; Sandhya, Nagarakere C.; Swarup, Hassan A.; Synthetic Communications; vol. 49; 16; (2019); p. 2106 – 2116;,
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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. 7357-70-2, name is 2-Cyanothioacetamide, A new synthetic method of this compound is introduced below., Recommanded Product: 7357-70-2

12.46 g (75 mmol) of 4-(2-hydroxyethoxy)benzaldehyde, 15.02 g (150 mmol) of cyanothioacetamide and 15.15 g (150 mmol) of N-methylmorpholine are initially charged in 75 ml of ethanol and heated under reflux for 3 h. After cooling, the reaction solution is concentrated under reduced pressure. The residue is dissolved in IN aqueous sodium hydroxide solution and washed twice with ethyl acetate. The aqueous sodium hydroxide phase is acidified with IN hydrochloric acid and the precipitated crystals are filtered off with suction and dried under reduced pressure at 450C. This gives 12.05 g (51% of theory) of product.MS (ESIpos): m/z = 313 (M+H)+, 330 (M+NH^1H=NMR (300 MHz, DMSO-d*): delta = 3.7 (t, 2H); 4.1 (t, 2H); 7.1 (d, 2H); 7.4 (d, 2H); 8.0 (br s, 2H).

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; BAYER HEALTHCARE AG; WO2007/73855; (2007); A1;,
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Reference of 64248-62-0,Some common heterocyclic compound, 64248-62-0, name is 3,4-Difluorobenzonitrile, molecular formula is C7H3F2N, 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 1: 3,4-Difluorobenzonitrile (30 g, 0 · 22 mol) was placed in a 500 mL autoclave, and an ammonia gas of 37 · 4 g (2.2 mol) was introduced. Then, the temperature was raised to 110 C for 24 hours, sampled, and the reaction was monitored by liquid chromatography to a normalized content of 0.5%. After cooling to room temperature, pressure was added, toluene (120 mL) was added, the temperature was raised to 60 C for 0.5 h, then the temperature was lowered to 0 C, filtered, and the filter cake was mixed with water (150 mL X 3 ), filtered, and filtered cake 40. (: Vacuum drying to give 2- fluoro-4-aminobenzonitrile 27.9 g (yield 95%; purity >99%, off-white solid, melting point 70-72 C). It is 3-fluoro-4-aminobenzonitrile.

The synthetic route of 64248-62-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Jinkai (Liaoning) Chemical Co., Ltd.; Yang Xiaoge; Wang Yongcan; Wang Xiuying; Jiang Zhipeng; Zhang Jinxin; Song Tongji; (13 pag.)CN109678741; (2019); A;,
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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 52798-01-3 as follows. Computed Properties of C10H9NO2

To a solution of methyl (4-cyanophenyl)acetate (4.00 g, 27.8 mmol) in MeOH (20 mL), hydroxylamine hydrochloride (3.17 g, 45.7 mmol) and NaHCO3 (3.84 g, 45.7 mmol) is added. The suspension is stirred at 60 C. for 18 h before it is filtered and the filtrate is concentrated. The residue is dissolved in DCM, washed with water followed by brine, dried over MgSO4, filtered, concentrated and dried to give methyl [4-(N-hydroxycarbamimidoyl)-phenyl]-acetate (3.67 g) as a colourless oil; LC-MS: tR=0.50 min, [M+1]+=209.05.

According to the analysis of related databases, 52798-01-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Actelion Pharmaceuticals Ltd.; US2010/63108; (2010); 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. 623-26-7, name is Terephthalonitrile, A new synthetic method of this compound is introduced below., Recommanded Product: 623-26-7

Crude p-cyanobenzylamine was synthesized in accordance with the process described in Japanese Unexamined Patent Publication (kokai) No. 9-40630 as follows. Into a 100 ml autoclave, methanol (30 ml) and sponge nickel (R-2400, product of W.R. Grace & Co.) (1.0 g) were placed, and the internal pressure of the autoclave was elevated to 1.0 MPa by introducing hydrogen. The mixture contained in the autoclave was stirred while heating at 150 C. for one hour. Terephthalonitrile (5.0 g) and sodium hydroxide (0.1 g) were introduced into the reactor, and the internal pressure was elevated to 0.5 MPa at ambient temperature while introducing hydrogen. Under monitoring of the hydrogen absorbing rate, when the hydrogen pressure was dropped to 0.1 MPa, the pressure was elevated again to 0.5 MPa. This pressure control operation was repeated. Reaction was terminated when the hydrogen absorption ratio reached 115% of the theoretical value. From the thus-obtained reaction mixture, methanol was removed through distillation. The resultant mixture was subjected to a further distillation at a high temperature under a reduced pressure, thereby removing crude p-cyanobenzylamine. Through high-performance liquid chromatographic analysis of the distillate, the p-cyanobenzylamine content and the p-xylylenediamine content were found to be 93 mass % and 7 mass %, respectively.

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; Showa Denko K.K.; US6392083; (2002); B1;,
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Adding a certain compound to certain chemical reactions, such as: 6011-14-9, name is 2-Aminoacetonitrile hydrochloride, 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 6011-14-9, 6011-14-9

A solution of 4-(2-((6-carboxy-2-(3,4-dichloro-5-methyl-1H-pyrrole-2-carboxamido)benzo[d]thiazol-4- yl)oxy)ethyl)morpholin-4-ium chloride (Example 10) (19 mg, 0.035 mmol) in N,N-dimethylformamide (4 mL) was cooled to 0 C and then EDC (8 mg, 0.042 mmol), HOBt (6 mg, 0.046 mmol) and N- methylmorpholine (12 muL, 0.106 mmol) were added and the reaction mixture stirred for 20 min at 0 C. Then aminoacetonitrile hydrochloride (5 mg, 0.053 mmol) was added and reaction mixture stirred overnight at room temperature. The solvent was evaporated in vacuo, to the residue ethyl acetate (10 mL) and 1M HCl (10 mL) were added after which the precipitate formed. The solid was filtered off and dried. Yield: 14 mg (68.0%); beige solid. (0686) 1H NMR (400 MHz, DMSO-d6) d 2.29 (s, 3H), 3.25-3.34 (m, 2H), 3.62-3.73 (m, 4H), 3.76-3.88 (m, 2H), 4.01-4.10 (m, 2H), 4.36 (d, J = 5.4 Hz, 2H), 4.71 (t, 2H), 7.62 (d, J = 1.5 Hz, 1H), 8.21 (d, J = 0.5 Hz, 1H), 9.40 (t, J = 5.5 Hz, 1H), 10.93 (s, 1H), 12.20 (s, 1H), 12.78 (s, 1H). (0687) HRMS (ESI+) m/z for C22H23Cl2N6O4S ([M+H]+): calculated 537.0873, found 537.0861.HPLC: tr 4.313 min (96.9 % at 254 nm, 97.7 % at 280 nm), method A

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-Aminoacetonitrile hydrochloride, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; UNIVERZA V LJUBLJANI; MTA SZEGEDI BIOLOGIAI KUTATOKOeZPONT; HELSINGIN YLIOPISTO; TOMA?IC, Tihomir; ZIDAR, Nace; DURCIK, Martina; ILA?, Janez; ZEGA, Anamarija; DURANTE CRUZ, Cristina; TAMMELA, Paeivi; PAL, Csaba; NYERGES, Akos Jozsef; KIKELJ, Danijel; MA?IC, Lucija Peterlin; (116 pag.)WO2020/48949; (2020); A1;,
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Related Products of 60702-69-4, 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. 60702-69-4, name is 2-Chloro-4-fluorobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows.

EXAMPLE 23A; 2-chloro-4-fluoro-5-nitrobenzonitrile; To a solution of 2-chloro-4-fluorobenzonitrile (10.1 g, 64.9 mmol) in concentrated sulfuric acid (20 mL) was added fuming nitric acid (5.80 ml, 130 mmol) at room temperature slowly and the mixture was stirred for 60 minutes. The solution was then poured into ice-water and stirred for 20 minutes. The precipitate was filtered, washed with more water and air-dried to afford the crude material, which was purified by sublimation to afford the title compound. .H NMR (300 MHz, dimethylsulfoxide-d6) delta ppm 8.97 (d, J = 8.09 Hz, 1 H) 8.30 (d, J = 11.03 Hz, 1 H).

The chemical industry reduces the impact on the environment during synthesis 2-Chloro-4-fluorobenzonitrile. I believe this compound will play a more active role in future production and life.

Reference:
Patent; ABBOTT LABORATORIES; ABBOTT LABORATORIES TRADING (SHANGHAI) COMPANY, LTD.; XU, Xiangdong; DINGES, Jurgent; HASVOLD, Lisa; LONGENECKER, Kenton, L.; WO2012/45196; (2012); 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. 935-02-4, name is 3-Phenylpropiolonitrile, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 935-02-4

4.4.1 (Z+E)-3-(3-Methyl-2-selenoxo-2,3-dihydro-1H-imidazol-1-yl)-3-phenyl-2-propenenitrile (4a) To a mixture of acetylene 2 (64.0 mg, 0.5 mmol) and Se (40.0 mg, 0.5 mmol) in MeCN (1 mL) was added 1-methylimidazole (1a; 41.0 mg, 0.5 mmol) in MeCN (1 mL). The mixture was stirred at 82 C for 5 h. After cooling to 20-25 C, the solvent was removed and column chromatography afforded selone (Z)-4a (46 mg, 39%) as a yellow microcrystalline powder, mp 208-209 C (ethanol). Initial imidazole 1a was recovered (7 mg, conversion was 83%). Initial Se was recovered (20 mg, conversion was 50%). Z:E-isomers ratio was 5:1 [(E)-isomer, 5%, data 1H NMR]. (Z)-Isomer: 1H NMR (400.13 MHz, CDCl3): delta=7.50-7.27 [m, 5H, Ho,m,p from C(6)-Ph], 7.07 (s, 1H, 4-H), 6.98 (s, 1H, 5-H), 6.12 (s, 1H, 7-H), 3.76 (s, 3H, N-CH3) ppm. 13C NMR (100.62 MHz, CDCl3): delta=159.2 (C-2), 154.9 (C-6), 132.4 [Ci from C(6)-Ph], 132.0 [Cp from C(6)-Ph], 129.3 [Cm from C(6)-Ph], 127.0 [Co from C(6)-Ph], 121.7 (C-4), 119.3 (C-5), 114.5 (CN), 97.7 (C-7), 37.5 (N-CH3) ppm. (E)-Isomer: 1H NMR (400.13 MHz, CDCl3): delta=7.50-7.45 [m, 5H, Ho,m,p from C(6)-Ph], 6.94 (s, 1H, 7-H), 6.90 (s, 1H, 4-H), 6.65 (s, 1H, 5-H), 3.73 (s, 3H, N-CH3) ppm. IR (KBr): 2222 (CN), 1622 (C=C), 1368 (C=Se) cm-1. Anal. Calcd for C13H11N3Se (288.21): C, 54.18; H, 3.85; N, 14.58; Se, 27.40. Found: C, 54.50; H, 3.99; N, 14.52; Se, 27.07.

According to the analysis of related databases, 935-02-4, the application of this compound in the production field has become more and more popular.

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 4640-66-8, 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.

General procedure: To a 0.5-2.0ml vial with 1 mmol ketone (1 eq) issolved in 2-pentanol (1.66 M) was added 1.1 eq of aromatic aldehyde and catalytic piperidine (0.08 eq), stirring vigorously. After heating under muWave for 15min at 120 C, the reaction was cooled to r.t. and precipitate was vacuum filtered and washed with minimal, cold hexanes. After drying under vacuum, solid was analyzed via NMR, IR, and mp.

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

Reference:
Article; Deshpande, Shyam J.; Leger, Paul R.; Sieck, Stephen R.; Tetrahedron Letters; vol. 53; 14; (2012); p. 1772 – 1775;,
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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. 362527-61-5, name is Ethyl 3-bromo-4-cyanobenzoate, A new synthetic method of this compound is introduced below., Application In Synthesis of Ethyl 3-bromo-4-cyanobenzoate

STEP 1 : To a pressure vessel were added ethyl 3-bromo-4-cyanobenzoate (500 mg, 1.97 mmol), cesium carbonate (1.28 g, 3.94 mmol), pentan-3 -amine (688 uL, 5.90 mmol), XANTPHOS (1 14 mg, 0.20 mmol), tris(dibenzylideneacetone)dipalladium(0) (90 mg, 0.10 mmol), and dioxane (3 mL). The vessel was sealed and heated to 95 C for 15 h. After cooling to room temperature, the mixture was filtered through celite and the filter cake rinsed with ethyl acetate. The filtrate was then concentrated and the residue was purified by column chromatography (10% ethyl acetate in hexanes) to provide ethyl 4-cyano-3- (pentan-3-ylamino)benzoate (315 mg, 1.21 mmol, 61% yield) as a yellow syrup. 1H NMR (400 MHz, CDCl3): 7.43 (d, IH), 7.33 (s, I H), 7.25 (dd, IH), 4.44-4.35 (m, 3H), 3.48-3.40 (m ,1H), 1..72-1.48 (m ,4H), 1.40 (t, 3H), 0.96 (t, 6H); MS (EI) for Ci5H20N2O2: 261 (MH+).

The synthetic route of 362527-61-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; EXELIXIS, INC.; WO2009/55077; (2009); A1;,
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