Month: February 2021

Reference of 4426-11-3, 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. 4426-11-3, name is Cyclobutanecarbonitrile, This compound has unique chemical properties. The synthetic route is as follows.

1 -[4-(trifluoromethyl)pyridin-2-yl]cyclobutanecarbonitrile[194] 2-Fluoro-4-(trifluoromethyl)pyridine (0.731 mL, 6 mmol) and cyclobutane- carbonitrile (0.841 mL, 9.00 mmol) were dissolved in toluene (10 mL). 0.5M KHMDS (18.00 mL, 9.00 mmol) in toluene was added, and the reaction stirred at ambient temperature for 3 days. The reaction mixture was quenched with water and extracted three times with diethyl ether. The combined organic layers were washed with brine, dried with MgS04, filtered, and concentrated. The residue was chromatographed on an AnaLogix SF25-60g column and eluted with 10% EtOAc in hexanes to give Example 116A (0.88 g, 3.89 mmol, 64.8% yield). MS (DCI+): m/z 227.2 (M+H), 244.1 (M+NH4). XH NMR (300 MHz, DMSO-d6) ? 8.93 (d, J= 5.0 Hz, 1H), 7.96 – 7.90 (m, 1H), 7.82 (ddd, J= 5.1, 1.5, 0.7 Hz, 1H), 2.90 – 2.68 (m, 4H), 2.35 – 2.21 (m, 1H), 2.13 – 2.00 (m, 1H).

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

Reference:
Patent; ABBVIE INC.; BAYBURT, Erol K.; CLAPHAM, Bruce; COX, Phil B.; DAANEN, Jerome F.; GOMTSYAN, Arthur; KORT, Michael E.; KYM, Philip R.; VOIGHT, Eric A.; SCHMIDT, Robert G.; DART, Michael J.; GFESSER, Gregory; WO2013/62966; (2013); A2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthetic Route of 19853-10-2, 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. 19853-10-2 name is 2-([1,1′-Biphenyl]-2-yl)acetonitrile, 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.

A 1M solution of hydroxylamine hydrochloride in MeOH (15 ml) and 1M KOH solution in MeOH (15 ml) was combined at 0 C. After 10 minutes, the salt was removed by filtration and the filtrate was directly added to a flask containing 2-(biphenyl-2-yl)acetonitrile (0.50 g, 2.58 mmol) and was heated at 60 C. overnight. The cooled mixture was evaporated to dryness under reduced pressure and the residue was dissolve in EtOAc, washed with water, and brine, dried (MgSO4) and evaporated to dryness. The residue was dissolved in chloroform (10 ml) and treated with dimethyl but-2-ynedioate (0.403 g, 2.84 mmol). The mixture was stirred at 60 C. for 1 h and then evaporated to dryness. The residue was diluted with xylenes (10 ml) and heated at 130 C. for 90 min. The cooled filtrate was filtered, triturated with EtOAc and dried under vacuum to give the title product as an off-white solid (0.161 g; 18%). LCMS: m/z=337 (MH+).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-([1,1′-Biphenyl]-2-yl)acetonitrile, and friends who are interested can also refer to it.

Reference:
Patent; SAVIRA PHARMACEUTICALS GMBH; EUROPEAN MOLECULAR BIOLOGY LABORATORY; F. HOFFMANN-LA ROCHE AG; BUSCHMANN, Helmut; WOLKERSTORFER, Andrea; SZOLAR, Oliver; HANDLER, Norbert; CUSACK, Stephen; SMITH, Mark; SO, Sung-Sau; US2014/38990; (2014); A1;,
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Application of 7357-70-2, A common heterocyclic compound, 7357-70-2, name is 2-Cyanothioacetamide, molecular formula is C3H4N2S, 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.

2-(4-phenylthiazol-2-yl)acetonitrile A mixture of 2-bromoacetophenone (1 .0 g, 5 mmol) and 2- cyanothioacetamide (0.5 g, 10 mmol) in ethanol (25 mL) was heated to 80C for 4 h. The reaction mixture was cooled to room temperature and poured into an aqueous ammonia solution (final pH was >7). The mixture was then extracted with ethyl acetate (100 mL x 3) and the organic layers were washed with H2O and brine. The organic layers were dried over anhydrous magnesium sulfate, filtered, and concentrate in vacuo. The crude product was purified by flash column chromatography, eluting with 0-30% ethyl acetate and petroleum benzene, afforded 2-(4-phenylthiazol-2-yl)acetonitrile (0.69 g, yield 70%) as a yellow 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; MONASH UNIVERSITY; THE UNIVERSITY OF WESTERN AUSTRALIA; BAELL, Jonathan; PIGGOTT, Matthew; RUSSELL, Stephanie; TOYNTON, Arthur; RAHMANI, Raphael; FERRINS, Lori; NGUYEN, Nghi; (178 pag.)WO2015/172196; (2015); A1;,
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Application of 185147-08-4, A common heterocyclic compound, 185147-08-4, name is 4-Fluoro-3-methylbenzonitrile, molecular formula is C8H6FN, 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.

Example 804-{3-Isopropyl-4-(quinolin-3-yl)-1H-pyrazolo[3,4-b]pyridin-1-yl}-3-methylbenzamide (80)4-Fluoro-3-methylbenzonitrile (0.077 g) and cesium carbonate (0.203 g) were added to a solution of compound (6c) (0.150 g) in DMF (1.73 mL), followed by stirring at 80¡ã C. for 18 hr. The reaction solution was distributed between ethyl acetate and water. The organic layer was washed with saturated saline and then dried over anhydrous sodium sulfate. The solvent was distilled away, and the residue was purified by neutral silica gel column chromatography (hexane/ethyl acetate) to obtain 4-{3-isopropyl-4-(quinolin-3-yl)-1H-pyrazolo[3,4-b]pyridin-1-yl}-3-methylbenzonitrile (0.154 g, 73percent). This 4-{3-isopropyl-4-(quinolin-3-yl)-1H-pyrazolo[3,4-b]pyridin-1-yl}-3-methylbenzonitrile was dissolved in DMSO (5.0 mL) and ethanol (5.0 mL). A 4 N aqueous sodium hydroxide solution (0.195 mL) and a 30percent hydrogen peroxide solution (0.088 mL) were added to the resulting solution, followed by stirring at room temperature for 30 min. Water was added to the reaction solution, and the precipitate was collected by filtration, washed with diethyl ether, and dried under reduced pressure to obtain compound (80) (0.135 g, 83percent) as a white solid.1H-NMR (DMSO-d6) delta: 9.88 (1H, d, J=2.20 Hz), 9.43 (1H, d, J=2.20 Hz), 9.35 (1H, d, J=4.63 Hz), 8.87 (2H, t, J=9.03 Hz), 8.81 (1H, brs), 8.70 (1H, d, J=1.46 Hz), 8.63-8.59 (2H, m), 8.46 (1H, td, J=7.56, 0.73 Hz), 8.30 (1H, d, J=8.05 Hz), 8.20 (1H, brs), 8.09 (1H, d, J=4.63 Hz), 3.72 (1H, tt, J=6.83, 6.83 Hz), 2.94 (3H, s), 1.76 (6H, d, J=6.83 Hz); LRMS (ESI) m/z 422 [M+H]+.

The synthetic route of 185147-08-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TAIHO PHARMACEUTICAL CO., LTD.; US2012/108589; (2012); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 3672-47-7, name is 3-(4-Methoxyphenyl)-3-oxopropanenitrile, 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 3672-47-7, SDS of cas: 3672-47-7

3-(4-methoxyphenyl)-3-oxopropanenitrile (2) (2.8571 mmol, 1 equiv.) and hydroxylamine hydrochloride (H2NOH.HCI) (2.8856 mmol, 1.05 equiv.) were added to solution of sodium hydroxide (NaOH) (5.8570 mmol, 2.05 equiv.) in water. The reaction mixture was refluxed for 4 h. After the resulting mixture cooled down to RT, it was diluted with water and extracted with dichloromethane (DCM). The organic layer was dried, filtered and evaporated to give the crude product, which was purified by automated -flash chromatography on silica gel (24 g) eluting with a gradient of 0-60% ethyl acetate (EtOAc) in hexane. Yield 59%. MP: 135.4-137.2C. HRMS (m/z): [M+H]+ calculated for C H N O : 191.0821; found: 191.0812

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, 3-(4-Methoxyphenyl)-3-oxopropanenitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BANO?LU, Erden; CALI?KAN, Burcu; ?AH?N, Oezguer; LENGERL?, Deniz; AKBULUT, Oezge; (39 pag.)WO2020/18039; (2020); A2;,
Nitrile – Wikipedia,
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Reference of 127946-77-4, 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. 127946-77-4, name is 1-Amino-1-cyclopropanecarbonitrile hydrochloride belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

The carboxylic acid 5A (195 mg, 0.5 mmol), 1-aminocyclopropanecarbonitrile hydrochloride (65.2 mg, 550 muiotaetaomicron), HATU (380 mg, 1.00 mmol) and ethyldiisopropyl amine (262 mu, 1.5 mmol) were dissolved in acetonitrile (10 mL) and stirred at room temperature over night. The reaction was concentrated under reduced pressure. The residue was diluted with 5% aquous sodium carbonate solution and extracted twice with ethyl acetate. The combined organic layers were washed withlM aqueous hydrogen chloride solution and with saturated aqueous sodium chloride solution, dried over Na2S04, filtered and concentrated under reduced pressure to yield (2S,4R)-iert-butyl 4-(2- chlorophenylsulfonyl)-2-( 1 -cyanocyclopropylcarbamoyl)-pyrrolidine- 1 -carboxylate 6H as a yellow oil (66 %). MS ISP (m/e): 354.2 (100) [(M-BOC+H)]+, 398.1 (25) [(M- Isobutylene+H)]+, 454.1 (12) [(M+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, 1-Amino-1-cyclopropanecarbonitrile hydrochloride, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; BANNER, David; HAAP, Wolfgang; LUEBBERS, Thomas; PETERS, Jens-Uwe; WO2013/120921; (2013); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 19924-43-7, 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 19924-43-7 as follows.

GP 8b was applied in the synthesis of the following nitriles; General Procedure 8b (GP 8b): Cyclopropanation conditions B; To a stirred mixture of the respective benzyl cyanide (1.0 eq.), triethylbenzylammonium chloride (2 to 4 mol%) and 1 -bromo-2-chloroethane (2 to 5 eq.) was added dropwise 50% aq. NaOH solution (6-8 eq.). After complete addition the reaction is stirred at 40-50 0C until complete turnover. The reaction mixture was then diluted with water, the organic products extracted with benzene, the combined organic extracts were washed with 5% aq. HCl and subsequently with water, dried and concentrated in vacuo. The crude products were in general used for the subsequent nitrile hydrolysis without further purification.

According to the analysis of related databases, 19924-43-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BAYER SCHERING PHARMA AKTIENGESELLSCHAFT; WO2007/144203; (2007); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Application of 2920-38-9,Some common heterocyclic compound, 2920-38-9, name is [1,1′-Biphenyl]-4-carbonitrile, molecular formula is C13H9N, 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 solution of 4-cyanobiphenyl 2a (1.0 mmol, 179.2 mg) in THF (8.0 mL) were added aq. NH3 (28%, 10.0 mL) and KI (3.0 mmol, 498.0 mg) at 0 C. Aq. H2O2 (30%, 10.0 mL) was added dropwise to the mixture. The obtained mixture was stirred for 2 h at room temperature. Sat. aq. Na2SO3 solution (20.0 mL) was added to the reaction mixture and the product was extracted with AcOEt (10.0 mL x 3). The organic layer was dried over Na2SO4 and filtered. The solvent was removed under reduced pressure to give 4-biphenylcarboxamide 4a (183.4 mg, 93%). 4.5.1. 4-Biphenylcarboxamide (4a) Yield: 183.4 mg (93%); white solid; Mp 223 C: IR (neat) 3404, 3170, 1644, 1614, 1407 cm-1; 1H NMR (400 MHz, DMSO-d6): delta = 6.51-5.54 (m, 2H), 6.61 (dd, 2H, J = 6.8, 7.7 Hz), 6.84-6.89 (m, 4H), 7.10 (d, 2H, J = 6.8 Hz), 7.17 (s, 1H); 13C{1H}NMR (100 MHz, DMSO-d6): delta = 126.5, 126.9, 128.0, 128.2, 129.0, 133.1, 139.2, 142.8, 167.6; HRMS (ESI) Calcd for C13H12ON [M+H]+ = 198.0913, Found = 198.0915.

The synthetic route of 2920-38-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Uchida, Ko; Togo, Hideo; Tetrahedron; vol. 75; 39; (2019);,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Application of 3759-28-2,Some common heterocyclic compound, 3759-28-2, name is 2-(Cyanomethyl)benzonitrile, molecular formula is C9H6N2, 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: A mixture of 1-aryl/alkyl-3,3-bis-methylsulfanyl-propenone (1.0 mmol), 2-cyanomethyl-benzonitrile (1 mmol, 142.0 mg), and powdered KOH (2 mmol, 112.0 mg) in dry DMSO (5 mL) was stirred at room temperature for 2 h. Completion of reaction was monitored by TLC. After completion, reaction mixture was poured onto ice-water with constant stirring and then neutralized with 10% HCl. The precipitate obtained was filtered, washed with water and dried over dry sodium sulfate. Many compounds were purified by recrystallization in dry methanol. Some compounds were purified through column chromatography using 15% ethylacetate in hexane as an eluent. Characterization data for some of the synthesized compounds are reported earlier.17

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

Reference:
Article; Singh, Surjeet; Althagafi, Ismail; Yadav, Pratik; Panwar, Rahul; Kumar, Abhinav; Pratap, Ramendra; Tetrahedron; vol. 70; 46; (2014); p. 8879 – 8884;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 103146-25-4, name is 4-(4-(Dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl)-3-(hydroxymethyl)benzonitrile, 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 103146-25-4, Safety of 4-(4-(Dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl)-3-(hydroxymethyl)benzonitrile

Experiment 4: The general procedure of Experiment 2 was applied. To the 4-[4-(dimethylamino)- l-(4′-fluorophenyl)-l-hydroxybutyl]-3-(hydroxymethyl)-benzonitrile free base solution in 1-propanol was added 0.05 V of water. No toluene or acetic acid was present in the system. An exemplary batch gave molar yield: 29.3%; enantiomeric purity: 99.3% S.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-(4-(Dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl)-3-(hydroxymethyl)benzonitrile, and friends who are interested can also refer to it.

Reference:
Patent; H. LUNDBECK A/S; WO2009/33488; (2009); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts