Month: June 2021

Synthetic Route of 29509-06-6,Some common heterocyclic compound, 29509-06-6, name is 4-Methyl-3-oxopentanenitrile, molecular formula is C6H9NO, 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 solution of 4-methyl-3-oxo-pentanenitrile (Method 30; 0.42 g, 3. 78 mmol) and hydrazine monohydrate (0.183 ml, 3.78 mmol) inEtOH (20 ml) was heated to reflux for 1 hour, cooled, and then concentrated under reduced pressure. The resulted oil was dissolved with DCM, washed with brine, dried over anhydrousNa2S04, concentrated, and purification by column chromatography (EtOAc:MeOH = 20: 1) to the title compound as an orange solid (0.26 g,56%). 1H NMR (400 MHz,CDC13) 8 1.21-1. 23 (d, J= 7.0 Hz, 6 H), 2.82-2. 89 (q, 1 H), 5.42 (s, 1 H). MS: Calcd.: 125; Found:[M+H] + 126.

The synthetic route of 29509-06-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2005/49033; (2005); A1;,
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Reference of 64248-64-2,Some common heterocyclic compound, 64248-64-2, name is 2,5-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.

To a stirred solution of NaH (2.58 g, 60% in mineral oil, 64.74 mmol) in DMSO (30 mL) ethyl cyanoacetate (7.3 g, 64.7 mmol) was added slowly at 0 C and stirred at the same temperature for 20 min. Then 2,5-difluoro benzonitrile (3 g, 21 .5 mmol) in DMSO (10 mL) was added. The mixture was heated at 95 C overnight then water (20 mL) was added and the solution was heated to 1 20 for 1 2 h. Completion of the reaction was monitored by LCMS. 0.1 N HCI (30 mL) was added to the reaction mixture at 0C, after stirring 10 min the solid was filtered and washed with water and petroleum ether. The crude was purified by flash chromatography (24% EtOAc in petroleum ether) to give the title compound (1 .8 g, 53.0%) as an off-white solid. LCMS m/z: 159.2 (M-1 ). 1 HNMR (DMSO d6): delta ppm 4.2 (s, 2H), 7.64- 7.73 (m, 2H), 7.96 (dd, J = 8.5, 2.5 Hz, 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 2,5-Difluorobenzonitrile, its application will become more common.

Reference:
Patent; AZIENDE CHIMICHE RIUNITE ANGELINI FRANCESCO A.C.R.A.F. S.P.A.; OMBRATO, Rosella; GAROFALO, Barbara; MANGANO, Giorgina; CAPEZZONE DE JOANNON, Alessandra; CORSO, Gaia; CAVARISCHIA, Claudia; FURLOTTI, Guido; IACOANGELI, Tommaso; (161 pag.)WO2016/96686; (2016); A1;,
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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 21423-84-7 as follows. Computed Properties of C8H6ClN

To a solution of 2-chloro-4-methylbenzonitrile (1 .06 g, 7 mmol) and /V-bromosuccinimide (1 .37 g, 7.7 mmol) in acetonitrile (70 ml_) was added 2,2-azob/s(2-methylpropionitrile (0.230 g, 1 .4 mmol) under argon. The mixture was stirred at 80 C for 20 h. The reaction mixture was filtered and washed with ethyl acetate (80 ml_). The filtrate was concentrated, and the resulting crude material was purified by column chromatography (silica gel, petroleum ether/ethyl acetate = 10/1 ) to give 4-(bromomethyl)-2-chlorobenzonitrile as a light-yellow solid (0.661 g, 2.87 mmol, 41 %). 1 H NMR (400 MHz, Chloroform-d) d 7.67-7.69 (m, 1 H), 7.57-7.58 (m, 1 H), 7.41 (dd, J/ = 1 .5 Hz, J2= 8.0 Hz, 1 H), 4.454 (s, 2H).

According to the analysis of related databases, 21423-84-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; YUMANITY THERAPEUTICS, INC.; LE BOURDONNEC, Bertrand; LUCAS, Matthew; OZBOYA, Kerem; PANDYA, Bhaumik; TARDIFF, Daniel; TIVITMAHAISOON, Parcharee; WRONA, Iwona; (475 pag.)WO2019/183587; (2019); A1;,
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Related Products of 170230-29-2, A common heterocyclic compound, 170230-29-2, name is 4-Bromo-3-ethylbenzonitrile, molecular formula is C9H8BrN, 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.

Description 27; 2-ethyl-2′-fluoro-4-biphenylcarboxylic acid (D27); A mixture of 4-bromo-3-ethylbenzonitrile (D25) (651 mg, 3.10 mmol), 2- fluorophenylboronic acid (867 mg, 6.20 mmol), palladiumtetrakistriphenylphosphine (359 mg, 0.31 mmol) and potassium carbonate (1.29 g, 9.30 mmol) in dimethylformamide (10 ml.) was heated to 170 0C in the microwave for 30 minutes. The mixture was allowed to stand at room temperature over a weekend before it was poured into a mixture of ice and saturated aqueous ammonium chloride. The mixture was extracted with ethyl acetate (3 x 20 ml.) and the combined organics washed with brine, dried (phase separator) and evaporated. The residue was purified by silica chromatography, eluting 0-5 % EtOAc in hexane to give a colourless oil (655 mg). This material was added to ethanol (26 ml.) and water (6 ml.) followed by potassium hydroxide (1.62 g, 28.9 mmol) and the mixture heated to 90 0C for 17 h. The solvent was evaporated and the residue partitioned between ethyl acetate and 2M HCI. The organic layer was washed with further HCI before it was dried (phase separator) and concentrated in vacuo to give the title compound as a white solid (648 mg, 2.66 mmol). MS (ES”): Ci5H13FO2 requires 244; found 243 (M-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; GLAXO GROUP LIMITED; WO2008/74820; (2008); 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. 57381-34-7, name is 5-Chloro-2-fluorobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 5-Chloro-2-fluorobenzonitrile

To a stirred [0C] solution of 1,1, 1,3, 3, [3-HEXAMETHYLDISILAZANE] (63 mL, 0.3 mmol) in dry diethyl ether was added dropwise n-Butyl lithium (2M in hexanes, 119 mL, 0.3 [MMOL).] A white suspension formed, to which was added [2-FLUORO-5-CHLOROBENZONITRILE (21.] 0 g, 0.14 mmol) over 5 min. The resultant orange mixture was allowed to warm to r. t. and stirred for 2h. The mixture was cooled to 0C and the reaction quenched by the addition [OF 3M HCI] (aq. ) (240 mL). The mixture was stirred for [0.] 5h before water (600 mL) was added. The purple organic layer was discarded and the aqueous layer basified to pH 14 with satd. NaOH (aq. ). The aqueous layer was extracted with [CHC13] [(5X100] mL) and the organic extracts dried over [NA2SO4.] Evaporation yielded the desired product as a yellow solid (16.2g, 73% yield).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 57381-34-7.

Reference:
Patent; SCIOS INC.; WO2004/24159; (2004); A1;,
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Reference of 1897-52-5, 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. 1897-52-5, name is 2,6-Difluorobenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

EXAMPLE 1 2-Amino-6-fluoro-benzonitrile 50 parts of 2,6-difluorobenzonitrile and 40 parts by volume of ammonia are stirred for 10 hours at 100 C. in a closed vessel. The reaction mixture is taken up in methylene chloride, the solid is filtered off, the organic phase is extracted three times by shaking with water and is dried over sodium sulfate, the solvent is stripped off and the residue is dried under reduced pressure. 48 parts (98.1% of theory) of 2-amino-6-fluoro-benzonitrile, of solidification point 125-128 C., are obtained.

The synthetic route of 2,6-Difluorobenzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BASF Aktiengesellschaft; US4359428; (1982); A;,
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Adding a certain compound to certain chemical reactions, such as: 654-70-6, name is 4-Cyano-3-trifluoromethylaniline, 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 654-70-6, Quality Control of 4-Cyano-3-trifluoromethylaniline

[003 19j Thionyl chloride (46.02 g, 0.39 mol) was added dropwise to a cooled solution (less than 4C) of (R)-3-bromo-2-hydroxy-2-methylpropanoic acid (51.13 g, 0.28 mol) in 300 mL of THF under an argon atmosphere. The resulting mixture was stirred for 3 h under the same condition. To this was added Et3N (39.14 g, 0.39 mol) and stirred for 20 mm under the same condition. After 20mm, 5-amino-2-cyanobenzotrifluoride (40.0 g, 0.21 mol), 400 mL of THF were added and then the mixture was allowed to stir overnight at RT. The solvent was removed under reduced pressure to give a solid which was treated with 300 mL of H20, extracted with EtOAc (2 x400 mL). The combined organic extracts were washed with saturated NaHCO3 solution (2 x 300 mL) and brine (300 mL). The organic layer was dried over MgSO4 and concentrated under reduced pressure togive a solid which was purified from column chromatography using CH2CWEtOAc (80:20) to give a solid. This solid was recrystallized from CH2CWhexane to give 55.8 g (73.9%) of (2R)-3-bromo- N-[4-cyano-3 -(trifluoromethyl)phenylj -2-hydroxy-2-methylpropanamide as a light-yellow solid. Mp 134.0-136.5C;[00320j ?H NMR (CDC13fFMS) oe 1.66 (s, 3H, CH3), 3.11 (s, 1H, OH), 3.63 (d, J= 10.8 Hz, 1H,CH2), 4.05 (d, J= 10.8 Hz, 1H, CH2), 7.85 (d, J= 8.4 Hz, 1H, Ar]), 7.99 (dd, J=2.1, 8.4 Hz, 1H,ArH), 8.12 (d, J = 2.1 Hz, 1H, ArH), 9.04 (bs, 1H, NH). MS (ESI) 349.0 [M – Hj M.p.: 124- 126C.

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-Cyano-3-trifluoromethylaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GTX, INC.; UNIVERSITY OF TENNESSEE RESEARCH FOUNDATION; NARAYANAN, Ramesh; MILLER, Duane D.; PONNUSAMY, Thamarai; HWANG, Dong-Jin; DUKE, Charles B.; COSS, Christopher C.; JONES, Amanda; DALTON, James T.; (159 pag.)WO2016/172330; (2016); 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. 628-20-6, name is 4-Chlorobutyronitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Quality Control of 4-Chlorobutyronitrile

A solution of 4-chlorobutyronitrile (2.5 mmol) in dimethylformamide (1 mL) was added during 1.5h to a mixture of the arylamine (2.5 mmol), Cs2CO3 (2.5 mmol) and KI (5 mmol) in dimethylformamide (4 mL). The mixture was stirred at the indicated temperature and time. After completion of the reaction, as indicated by TLC, the mixture was treated with ethyl ether (50 mL) and water (10 mL). The aqueous phase was separated and extracted with ethyl ether (30 mL). The combined organic layers were dried over anhydrous sodium sulphate and filtered. The solvent was evaporated in vacuo. The crude product was purified by column chromatography (Silica gel, hexane:DCM).

The synthetic route of 628-20-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Diaz, Jimena E.; Bisceglia, Juan A.; Mollo, Ma. Cruz; Orelli, Liliana R.; Tetrahedron Letters; vol. 52; 16; (2011); p. 1895 – 1897;,
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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., COA of Formula: C3H4N2S

Example 1 2-Amino-6-({[2-(4-chlorophenyl)-1,3-thiazol-4-yl]methyl}sulphanyl)-4-[4-(2-hydroxyethoxy)phenyl]pyridine-3,5-dicarbonitrile (II) 5.334 kg (24.90 mol) of 2-[4-(2-hydroxyethoxy)benzylidene]malononitrile (XI) and 1.309 kg (13.07 mol) of 2-cyanothioacetamide (XII) were suspended in 27.4 kg (34.8 l) of methanol. The suspension was warmed to 40 C., and 3.779 kg (37.35 mol) of triethylamine were metered in at at most 40 C. The mixture was stirred at 40 C. for another 3 h and cooled to room temperature. 3.147 kg (12.45 mol) of 4-(chloromethyl)-2-(4-chlorophenyl)-1,3-thiazole (XIV) were added to the dark-brown solution, and the content of the tank was stirred at room temperature overnight. The suspension now present was cooled to 5 C., isolated by filtration and washed with 11.7 kg (14.85 l) of methanol in total. The moist product was dried at 50 C. in a vacuum drying cabinet. This gave 4862 g or 75.1% of theory of 2-amino-6-({[2-(4-chlorophenyl)-1,3-thiazol-4-yl]methyl}sulphanyl)-4-[4-(2-hydroxyethoxy)phenyl]pyridine-3,5-dicarbonitrile as a beige-greenish solid (content 95.5%, ESTD).

The synthetic route of 7357-70-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; MAIS, Franz-Josef; HEILMAN, Werner; OLENIK, Britta; KEIL, Birgit; BECKER, Guido; MEIBOM, Daniel; KUHLMANN, Thomas; (42 pag.)US2018/155336; (2018); A1;,
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Adding a certain compound to certain chemical reactions, such as: 455-18-5, name is 4-(Trifluoromethyl)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 455-18-5, name: 4-(Trifluoromethyl)benzonitrile

Take a 250 mL three-necked flask and add 100 mL of dry tert-amyl alcohol.Sodium (4.0 g, 100 mmol), 10 mg of ferric chloride, heated to 100 C,The mixture was heated and stirred under a nitrogen atmosphere for about 30 minutes, and the sodium particles were completely dissolved. Cool down to around 50 CThen, 4-trifluoromethylbenzonitrile, Compound 1-1 (11.8 g, 68.6 mmol) was added to the system, and the temperature was raised to 100 C. Diisopropyl succinate, Compound 2 (8 mL, 39.6 mmol), was diluted with 30 mL of tert-amyl alcohol, and the mixture was slowly dropped (2-3 h) into a three-necked flask using a constant pressure dropping funnel. After the addition was completed, the reaction was continued for 3 hours.After the reaction is completed, the reaction mixture is poured into a clean 500 mL beaker and naturally cooled to room temperature. Slowly add glacial acetic acid to the beaker to adjust the pH to neutrality.Out. Filter through a Buchner funnel and wash the filter cake with methanol and water until the filtrate is colorless and transparent.After drying the filter cake, a brick red solid powder, Compound 3-1, is obtained.The yield was 81%.

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-(Trifluoromethyl)benzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; East China University of Science and Technology; Wang Limin; Yang Qingying; Xu Jie; Li Jun; Han Jianwei; Tian He; (18 pag.)CN109897045; (2019); A;,
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