Month: January 2021

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. 60702-69-4, name is 2-Chloro-4-fluorobenzonitrile, A new synthetic method of this compound is introduced below., Computed Properties of C7H3ClFN

General procedure: To an ice-cooled solution of 12 (0.200 g, 0.979 mmol) in DMF (2.0 mL) was added NaH (60% in mineral oil, 0.047 g, 1.18 mmol), and the mixture was stirred at 0 C for 30 min. To the mixture was added 4-fluorobenzonitrile (0.237 g, 1.96 mmol), and the mixture was stirred at 0 C for 2 h and room temperature for 18 h. The mixture was acidified with saturated aqueous solution of NH4Cl and extracted twice with EtOAc. The organic layers were combined, washed with brine, dried over anhydrous MgSO4, and concentrated in vacuo. The residue was purified by silica gel column chromatography (hexane-EtOAc). The product was recrystallized from hexane-EtOAc to give 3 (0.131 g, 44%) as white crystals.

The synthetic route of 60702-69-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Yamamoto, Satoshi; Tomita, Naoki; Suzuki, Yuri; Suzaki, Tomohiko; Kaku, Tomohiro; Hara, Takahito; Yamaoka, Masuo; Kanzaki, Naoyuki; Hasuoka, Atsushi; Baba, Atsuo; Ito, Mitsuhiro; Bioorganic and Medicinal Chemistry; vol. 20; 7; (2012); p. 2338 – 2352;,
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Synthetic Route of 332-25-2,Some common heterocyclic compound, 332-25-2, name is 4-(Trifluoromethoxy)benzonitrile, molecular formula is C8H4F3NO, 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.

In the same manner as in Reference Example 1, the title compound was obtained. Melting point: 222-225¡ã C. NMR (CDCl3( delta: 5.19(2H,s), 5.92(2H,s), 7.25-7.45(5H,m), 7.73(1H,d,J=8.8 Hz), 8.46 (1H,s). Elemental analysis for C20H11F3O5 Calcd: C, 61.86percent; H, 2.86percent Found: C, 64.79percent; H, 2.79percent

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-(Trifluoromethoxy)benzonitrile, its application will become more common.

Reference:
Patent; Takeda Chemical Industries, Ltd.; US6340704; (2002); B1;,
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Synthetic Route of 103146-25-4,Some common heterocyclic compound, 103146-25-4, name is 4-(4-(Dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl)-3-(hydroxymethyl)benzonitrile, molecular formula is C20H23FN2O2, 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 test tube equipped with a stopper was charged with 10 mg (0.029 m mol) of [(=T :)-4-] [4-dimethylamino-1- (4′-fluorophenyl)-1-hydroxybutyl]-3-hydroxymethylbenzonitrile, 10 mg of Novozym 435 (product of NOvozymes), 33 mg (0.29 [M MOL)] of vinyl butyrate and 1 ml of various kinds of solvents, and stirred at [30C] for 16 hours. After the reaction, converted ratios and optical purities were analyzed and E-values were calculated. The results are shown in Table 9.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-(4-(Dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl)-3-(hydroxymethyl)benzonitrile, its application will become more common.

Reference:
Patent; H. LUNDBECK A/S; WO2004/14821; (2004); A1;,
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Reference of 628-20-6, The chemical industry reduces the impact on the environment during synthesis 628-20-6, name is 4-Chlorobutyronitrile, I believe this compound will play a more active role in future production and life.

Boron trichloride -methyl sulfide complex (6.353 g, 35.43 mmol) was diluted with dichloroethane (70 mL) and cooled to 0 0C. Aniline (24, 3.000 g, 32.21 mmol) was added dropwise and the solution was allowed to stir at 0 0C for 10 min. 4-Chlorobutyronitrile (4.170 g, 40.27 mmol) was added, followed by aluminum chloride (4.724 g, 35.43 mmol), and the solution was allowed to gradually warm to room temperature. After 10 min, the reaction mixture was heated at reflux for 2.5 h. The solution was allowed to cool to room temperature, 10% aq HCl (70 mL) was added, and the reaction mixture was heated at reflux for 30 min. The reaction mixture was allowed to stir at room temperature for 24 h and the organic layer was separated. The aqueous layer was extracted with CH2Cl2 (3 x 50 mL). The combined organic layers were washed with sat NaCl (50 mL) and dried over sodium sulfate. Concentration provided a crude yellow-brown oil that was purified by flash column chromatography (SiO2), eluting with a gradient of hexanes to 50% EtOAc-hexanes. The solvent was evaporated and the resulting product was diluted with Et2O (50 mL) and treated with 3 M HCl in MeOH (10 mL) and allowed to stir at room temperature for 20 min. The salt was filtered and washed with Et2O (50 mL) to provide a white solid. The solid was dissolved in sat NaHCO3 (150 mL) and extracted with CHCl3 (3 x 50 mL). The combined organic layers were washed with sat NaCl (50 mL), dried over sodium sulfate, filtered, and concentrated to provide a yellow oil (2.022 g, 32%) that solidified upon standing: mp 51-55 0C. 1H NMR (300 MHz, CDCl3) delta 7.79 (dd, J= 8.5 Hz and 1.6 Hz, 1 H), 7.31-7.25 (m, 1 H), 6.70-6.65 (m, 2 H), 3.70 (t, J= 6.3 Hz, 2 H), 3.18 (t, J= 7.1 Hz, 2 H), 2.25 (pent, J = 6.9 Hz, 2 H).

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

Reference:
Patent; PURDUE RESEARCH FOUNDATION; THE GOVERNMENT OF THE UNITED STATES OF AMERICA, as represented by THE SECRETARY OF THE DEPARTENT OF HEALTH & HUMAN SERVICES; WO2009/140467; (2009); A1;,
Nitrile – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 64248-62-0, name is 3,4-Difluorobenzonitrile, 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 64248-62-0, Recommanded Product: 3,4-Difluorobenzonitrile

Into a 1000 mL four-necked flask, 500 g of DMF was charged and 100 g of Compound A, 1 was charged13.6 g of potassium carbonate and 5 g of tetrabutylammonium bromide, warmed to 60 C.,A mixed solution of 83.9 g of compound B in 50 g of DMF was added dropwise thereto at a controlled temperature of 65 to 70 C,The addition was complete, the reaction for about 2 hours, the reaction was completed, added to 1000g of water,With hydrochloric acid to adjust the pH to 7 ~ 8, stirred for 1 hour, filtered,The solid is etherified, dried.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3,4-Difluorobenzonitrile, and friends who are interested can also refer to it.

Reference:
Patent; Jiangsu Fuding Chemical Co., Ltd.; Liu, Dongwei; Cheng, Lizhong; Chang, Qing; Dong, Hailong; Zhu, Ruiyu; Gu, Junkun; (11 pag.)CN106631896; (2017); A;,
Nitrile – Wikipedia,
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Reference of 6575-05-9,Some common heterocyclic compound, 6575-05-9, name is 2,4,6-Trichlorobenzonitrile, molecular formula is C7H2Cl3N, 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.

EXAMPLE 57; N-{[1-{[4-(1,1-Dimethylethyl)phenyl]methyl}-4-hydroxy-6-oxo-2-(2,4,6-trichlorophenyl)-1,6-dihydro-5-pyrimidinyl]carbonyl}glycine; 57a) 3-{[4-(1,1-Dimethylethyl)phenyl]methyl}-6-hydroxy-2-(2,4,6-trichlorophenyl)-4(3H)-pyrimidinone; A 1 M solution of dimethylaluminium chloride in hexane (2.75 mL, 2.75 mmol) was added to a stirred mixture of 4-tert-butylbenzylamine (0.408 g, 2.50 mmol), 2,4,6-trichlorobenzonitrile (0.619 g, 3.00 mmol) and toluene (3 mL) at room temperature. After 2 min at room temperature, the mixture was stirred in a microwave reactor at 150 C. for 0.5 h, then cooled and the solvent removed under reduced pressure. Diethyl malonate (1.60 g, 10.0 mmol), 2-methoxyethanol (15 mL) and 4.37 M sodium methoxide in methanol (2.30 mL, 10.0 mmol) were added and the mixture refluxed under nitrogen for 8 h. After cooling, the mixture was poured into water (150 mL), washed with ether, acidified to pH 1 with 6 M aqueous hydrochloric acid, and extracted with ethyl acetate. The extracts were washed with water and brine, dried (MgSO4) and evaporated under reduced pressure. The residue was triturated with ether and the solid collected, washed with ether and dried to give the title compound (0.551 g, 50%) as a solid. 1H NMR (400 MHz, DMSO-d6) delta ppm 1.23 (s, 9 H) 4.88 (s, 2 H) 5.59 (s, 1 H) 6.79-6.85 (m, 2 H) 7.18-7.25 (m, 2 H) 7.84 (s, 2 H) 11.94 (br. s., 1 H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2,4,6-Trichlorobenzonitrile, its application will become more common.

Reference:
Patent; Shaw, Antony N.; Duffy, Kevin J.; Tedesco, Rosanna; Wiggall, Kenneth; US2008/171756; (2008); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Related Products of 16588-02-6,Some common heterocyclic compound, 16588-02-6, name is 2-Chloro-5-nitrobenzonitrile, molecular formula is C7H3ClN2O2, 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) 5-nitro-2-phenylaminobenzonitrile 2-Chloro-5-nitrobenzonitrile (Aldrich) (3.64grams (hereinafter ‘g’), 20 millimoles (hereinafter ‘mmol’), aniline (2 milliliter (hereinafter ‘mL’), 22 mmol), N-methylpyrollidine (10 mL) and diisopropylethylamine (4 mL) were combined and heated to 120 under Ar for 18 hours (hereinafter ‘h’), cooled, poured into EtOAc (150 mL), washed with H2O (3X 50 mL) and saturated aqueous (hereinafter ‘satd. aq.) NaCl (50 mL), dried (Na2SO4), concentrated, and the residue was triturated with hexane, filtered and the solid was washed with hexane and dried in vacuo to afford 4.23 g (88%) of the title compound as a light green solid. 1H NMR (400) MHz, delta: 8.45 (finely split doublet, 1), 8.19 (dd, 1), 7.48 (m,3), 7.28 (d,2), 7.06 (d,1), 6.96 (br s,1).

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

Reference:
Patent; SmithKline Beecham Corporation; EP1233951; (2005); B1;,
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Application of 22364-68-7, A common heterocyclic compound, 22364-68-7, name is 2-(o-Tolyl)acetonitrile, molecular formula is C9H9N, 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.

Part A: Preparation of ethyl 2-(alpha-cyano-2′-methylphenylacetyl)cyclohexyl carboxylate Using the procedure described in Example I, Part A, and starting with 159.80 g (0.700 mol) of diethyl 1,2-cyclohexanedicarboxylate, 61.65 g (0.47 mol) of 2-methylbenzyl cyanide, 14.06 g (0.61 mol) of sodium, and 250 ml of ethanol, 87.74 g (60% yield) of the desired cyano keto ester was obtained as a red, viscous oil.

The synthetic route of 22364-68-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Union Carbide Corporation; US4283348; (1981); 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 69395-13-7 as follows. Safety of 4-(2-Hydroxyethyl)benzonitrile

To a stirred solution of 4-(2-hydroxyethyl)benzonitrile (1.0g ,6.8mmol,1eq.) in DCM (20 mL) was added CBr4 (4.5016g, 13.6mmol, 2.0 eq) and TPP (3.835g, 13.6mmol, 2.0 eq). The resulting solution was stirred at RT for 5h. Reaction was monitored TLC. Reaction was diluted with water and extracted with EtOAc. Organic layer was dried over sodium sulfate, filtered and the filtrated concentrated. The crude compound was isolated by column chromatography to get pure 4-(2-bromoethyl)benzonitrile (1.3 g, 91%). LC-MS (method 23): Rt = 2.01 min; m/z = 210.05 (M+H+).

According to the analysis of related databases, 69395-13-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ORYZON GENOMICS, S.A.; SALAS SOLANA, Jorge; CARCELLER GONZALEZ, Elena; ORTEGA MUNOZ, Alberto; (195 pag.)WO2018/149986; (2018); A1;,
Nitrile – Wikipedia,
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Reference of 98730-77-9,Some common heterocyclic compound, 98730-77-9, name is 1-(Hydroxymethyl)cyclopropanecarbonitrile, molecular formula is C5H7NO, 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 stirred mixture of 1-(hydroxymethyl)cyclopropanecarbonitrile (24.30mmoi, 2.36g) in dichioromethane (3OmL) was treated with triethylamine (48.deltammol, 6.83mL, 4.92g) and portiortwise with methanesuifonyl chloride (31.deltammol, 2.445mL, 3.62g) keeping the reaction mixture at O0C. The solution was allowed to stir for 1 hour then diluted with saturated sodium hydrogencarbonate and extracted with 10% methanol/dichloromethane (x3). The organic layers were combined and concentrated under reduced pressure to give the intermediate (i-cyanocydopropyl)methyl methanesutfonate (3.77g).1H NMR (CDCI3, 400 MHz): delta 1.18 (2H, m), 1.46 (2H, m), 3,14 (3H, s), 4.18 (2H, s)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-(Hydroxymethyl)cyclopropanecarbonitrile, its application will become more common.

Reference:
Patent; N.V. ORGANON; PHARMACOPEIA, LLC; COOKE, Andrew, John; BENNETT, David, Jonathan; EDWARDS, Andrew Stanley; ROUGHTON, Andrew Laird; NEAGU, Irina; CHAN, Jui-Hsiang; HO, Koc-Kan; ANSARI, Nasrin; MORRIS, Michelle Lee; RONG, Yajing; OHLMEYER, Michael; WO2010/25179; (2010); A1;,
Nitrile – Wikipedia,
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