Month: December 2020

These common heterocyclic compound, 1813-33-8, name is 2-Chloro-4-(trifluoromethyl)benzonitrile, 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. HPLC of Formula: C8H3ClF3N

General procedure: Appropriate ROH (3.00 mmol) was added topotassium tert-butoxide (3.00 mmol) solution in toluene (7 ml).1,3-Dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (DMPU, 3ml)was added to the mixture and stirred for 30 min at 80 C. Aftercooled down to ambient temperature of the reaction mixture,2-chloro-4-(trifluoromethyl)-benzonitrile (1.00 mmol) in toluenewas dropwise and stirred for 3 h at 80 C. The reaction wasquenched by adding water and extracted with EtOAc twice. Thecombined organic extracts were dried over MgSO4, filtered, andconcentrated in vacuo. The residue was purified by flash columnchromatography on silica gel using EtOAc/hexane (1:7) eluantcondition.

The synthetic route of 2-Chloro-4-(trifluoromethyl)benzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Article; Ann, Jihyae; Jung, Aeran; Kim, Mi-Yeon; Kim, Hyuk-Min; Ryu, Hyungchul; Kim, Sunjoo; Kang, Dong Wook; Hong, Sunhye; Cui, Minghua; Choi, Sun; Blumberg, Peter M.; Frank-Foltyn, Robert; Bahrenberg, Gregor; Stockhausen, Hannelore; Christoph, Thomas; Lee, Jeewoo; Bioorganic and Medicinal Chemistry; vol. 23; 21; (2015); p. 6844 – 6854;,
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Synthetic Route of 6575-00-4, These common heterocyclic compound, 6575-00-4, name is 3,5-Dichlorobenzonitrile, 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.

step 1-A 100 ml round bottom flask was charged under a stream of nitrogen with 3,5-dichlorobenzonitrile (R-3a, 7.0 g, 40.69 mmol) and anhydrous DMF (75 mL). To the solution was added sodium methoxide (2.26 g, 44.76 mmol) and resulting solution was stirred further at RT for 24 h. When the reaction was complete, aqueous 10% HCl added dropwise to the reaction vessel. The crude mixture was extracted with EtOAc and sequentially washed with aqueous acid, water and brine. The EtOAc extracts were dried (Na2SO4), filtered and the solvent was removed in vacuo to afford a crude solid which was recrystallized from hexane/acetone to afford 5.9 g (86%) of R-3b.

The synthetic route of 6575-00-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Billedeau, Roland Joseph; Sweeney, Zachary Kevin; US2009/170856; (2009); A1;,
Nitrile – Wikipedia,
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Related Products of 330793-38-9,Some common heterocyclic compound, 330793-38-9, name is 4-Bromo-2-methoxybenzonitrile, molecular formula is C8H6BrNO, 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: Following general procedure Q, 4-bromo-2-methoxybenzonitrile (108 mg, 0.51 mmol) gave (4-bromo- 2-methoxy-phenyl)methanamine (67.2 mg, 0.31 mmol, 61 percent yield). NMR (500 MHz, CDCI3, delta): 7.12-7.02 (m, 2H), 7.00-6.96 (m, 1 H), 3.84 (s, 3H), 3.77 (s, 2H). To a solution of cobalt (II) chloride (1 eq.) and nitrile derivative (1 eq.) in anhydrous MeOH (0.05 M), cooled to 0 ¡ãC under a nitrogen atmosphere, was added sodium borohydride (10 eq) portion wise over 10 min. The reaction mixture was then stirred for 20 min at 0 ¡ãC and then stirred for a further 60 min at room temperature, quenched with an aqueous solution of ammonium chloride, and allowed to stand overnight. Most of methanol was removed under reduced pressure and the remaining aqueous mixture was diluted with water and washed with Epsilon2theta (x 2). The aqueous layer was basified to pH = 12 with 1 M NaOH and extracted with CHC (* 3). The combined organics were dried (phase separator) and concentrated to give the desired amine.

The synthetic route of 330793-38-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; REDX PHARMA PLC; GUISOT, Nicolas; (191 pag.)WO2017/46604; (2017); A1;,
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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. 148932-68-7, name is 2-Amino-3-methoxybenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Safety of 2-Amino-3-methoxybenzonitrile

To a solution of sodium thiocyanate (4.06 g) in methanol(70 mL) was added bromine (1.35 mL) at -700C. The reaction mixture was stirred for 10 min, and 2-amino-3- methoxybenzonitrile (3.71 g) was added. The temperature was risen to room temperature, and the mixture was stirred for 2 hr. The reaction mixture was poured into ice water, and the precipitated crystals were collected by filtration, washed with water and dried to give the title compound (4.28 g, yield 84%) as colorless crystals. Melting point 121-122C.

The synthetic route of 148932-68-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; TAKEDA SAN DIEGO, INC.; WO2008/156757; (2008); A1;,
Nitrile – Wikipedia,
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Reference of 4592-94-3, These common heterocyclic compound, 4592-94-3, name is 3-(4-Bromophenyl)-3-oxopropanenitrile, 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 stirred solution of 3-oxo-3-aryl-propionitriles 2 and Et3N (0.101 g, 1 mmol) inCH3OH:H2O (2:1, 6 mL) was added adducts of acenaphthoquinone and malononitrile or ethylcycnoacetate 1 (1 mmol) at room temperature. After completion of the reaction [about 30-120min, TLC (n-hexan/EtOAc, 2:1) monitoring], the solvent was evaporated under vacuum and thecrude product was purified by flash column chromatography on silica gel using EtOAc/n-hexane(1:2) as eluent (for compound 3a-d) and or was washed by methanol (for compounds 3e-h) toafford the pure product 3.

Statistics shows that 3-(4-Bromophenyl)-3-oxopropanenitrile is playing an increasingly important role. we look forward to future research findings about 4592-94-3.

Reference:
Article; Yavari, Issa; Khajeh-Khezri, Aliyeh; Bahemmat, Samira; Halvagar, Mohammad Reza; Synlett; vol. 28; 14; (2017); p. 1785 – 1788;,
Nitrile – Wikipedia,
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Related Products of 7357-70-2, 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. 7357-70-2, name is 2-Cyanothioacetamide, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: A mixture of the required acetophenones (0.001 mol),the appropriate aromatic aldehydes (0.001 mol), cyanothioacetamide(0.1 g, 0.001 mol) and ammonium acetate (0.62 g,0.008 mol) in n-butanol (10 mL) is irradiated at 150C for20 min in the microwave oven. After the reaction mixture iscooled to room temperature, the reaction mixture is dilutedwith 10 mL diethyl ether and the separated solid is filtered,dried and crystallized from ethanol to afford compounds 4-10.1,2-Dihydro-6-(3,4,5-trimethoxyphenyl)-4-(4-methoxyphenyl)-2-thioxopyridine-3-carbonitrile (4)Yellow powder, yield: 0.35g (87%), mp: 294-296C. IR(KBr, cm-1): 3421 (NH), 3066 (CH-aromatic), 2843 (CHaliphatic),2222 (CN), 1136 (C=S). 1H-NMR (400 MHz, dimethylsulfoxide (DMSO)-d6), delta ppm: 3.73 (s, 3H, OCH3),3.85 (s, 3H, OCH3), 3.88 (s, 6H, 2OCH3), 6.88 (s, 1H, Ar-H),7.13 (d, 2H, J=7.5 Hz, Ar-H), 7.20 (s, 2H, Ar-H), 7.72 (d, 2H,J=7.7 Hz, Ar-H), 12.53 (s, 1H, NH, D2O exchangeable).13CNMR(100 MHz, DMSO-d6), delta ppm: 55.9, 56.2 (2C), 56.7,97.7, 102.3, 105.8 (2C), 114.6 (2C), 117.4, 128.6, 129.5, 130.5(2C), 140.4, 153.5 (2C), 155.9, 161.5, 167, 169. Anal. Calcd for:C22H20N2O4S (408.47): C, 64.69; H, 4.94; N, 6.86. Found: C,64.93; H, 5.07; N, 7.04.

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

Reference:
Article; Elhameid, Mohammed K. Abd; Ryad, Noha; My, Al-Shorbagy; Mohammed, Manal R.; Ismail, Mohammed M.; El Meligie, Salwa; Chemical and Pharmaceutical Bulletin; vol. 66; 10; (2018); p. 939 – 952;,
Nitrile – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 1009-35-4, name is 4-Fluoro-3-nitrobenzonitrile, 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 1009-35-4, COA of Formula: C7H3FN2O2

N-(4-Cvano-2-nitrophenyl)-N-methylglycineA mixture of 4-fluoro-3-nitrobenzonitrile (3.0 g) and sarcosine (2.53 g) with sodium hydrogen carbonate (2.39 g) in water (15 mL) and ethanol (15 mL) was heated at 8O0C. After 2 hours, the reaction was concentrated to half its volume and poured into IM HCl (50 mL). The aqueous solution was extracted with ethyl acetate and then with chloroform. The combined organic phases were dried over sodium sulfate and concentrated under reduced pressure. The residue was suspended in a minimum of dichloromethane and filtered yielding 3.74 g of product.MS TES): 236 (MH+) for Ci0H9N3O41H NMR (DMSO-D^ delta: 2.87 (s, 3H); 4.19 (s, 2H); 7.13 (d, IH); 7.82 (dd, IH); 8.29 (d,IH); 13.03 (s,lH).

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

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2008/71981; (2008); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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. 53312-79-1, name is 3-Amino-4-chlorobenzonitrile, A new synthetic method of this compound is introduced below., name: 3-Amino-4-chlorobenzonitrile

Step A:2-Th ioxo-2 , 3-d ihyd robenzoth iazole-5-carbon itrile; A mixture of 3-amino-4-chlorobenzonitrile (200 mg, 1.32 mmol) and potassium o-ethyl- xanthate (422 mg, 2.64 mmol) in lambda/-methyl-2-pyrrolidone (1.5 ml.) was heated at 140 0C for 2 h. After cooling, the mixture was poured into ice-water. Then concentrated hydrochloric acid(0.2 ml.) was added. The solid was collected, washed with water and dried to give 2-thioxo-2,3-dihydrobenzothiazole-5-carbonitrile 250 mg (99 %).1H NMR (400 MHz, CDCI3): delta 7.53-7.50 (m, 2 H); 7.49 (s, 1 H).

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; NOVO NORDISK A/S; WO2007/110364; (2007); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Related Products of 103146-25-4, 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. 103146-25-4, name is 4-(4-(Dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl)-3-(hydroxymethyl)benzonitrile, This compound has unique chemical properties. The synthetic route is as follows.

Oxalate [(+-)-Diol Oxalate Salt] (+-)-Diol compound (VI) (12 g, 0.035 mol) and oxalic acid dihydrate (4.64 g, 0.0368, 1.05 mol) were added to methanol (36 ml) and heated the contents to 55-60 C. to obtain a clear solution. The obtained solution was cooled to 25-30 C. and stirred for 3 h to complete the crystallization. Product was filtered and thereafter, dried at 50-60 C. under reduced pressure to yield 11 g of diol oxalate salt (VIa) with HPLC purity 99.93%.

The chemical industry reduces the impact on the environment during synthesis 4-(4-(Dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl)-3-(hydroxymethyl)benzonitrile. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Kaushik, Vipin Kumar; Mohammed, Umar Khan; Meenakshisunderam, Sivakumaran; US2009/99375; (2009); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 123-06-8, These common heterocyclic compound, 123-06-8, name is Ethoxymethylenemalononitrile, 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.

To a mixture of Et3N (1.39 mL, 10 mmol) and cyclohexylhydrazine hydrochloride (1.51 g, 10 mmol) in EtOH (35 mL) was added ethoxymethylenemalononitrile (1.22 g, 10 mmol) portion wise. The reaction mixture was heated at reflux for 5 h, then cooled to room temperature and concentrated in vacuo. The residue was taken up in EtOAc (50 mL) and washed with water (2 x 25 mL). The organic phase was dried over Mg504, filtered and concentrated in vacuo to return 5-amino-1-cyclohexyl-pyrazole-4-carbonitrile (1.95 g, 103%) as an orange solid which was used without further purification. 1H NMR (300 MHz, CDCI3) O 7.49 (5, 1H), 4.45 (5, 2H), 3.77 (tt, =J= 11.2, 4.2 Hz, 1H), 1.88 (ddt, =J= 17.4, 11.4, 5.4 Hz, 6H), 1.83-1.65 (m, 1H), 1.49-1.32 (m, 1H), 1.38-1.15 (m, 2H).

The synthetic route of 123-06-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CANCER RESEARCH TECHNOLOGY LIMITED; JORDAN, Allan; NEWTON, Rebecca; (145 pag.)WO2017/178845; (2017); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts