Tag: M.W=100-200

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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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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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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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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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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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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Related Products of 14447-18-8, The chemical industry reduces the impact on the environment during synthesis 14447-18-8, name is Benzyl cyanoacetate, I believe this compound will play a more active role in future production and life.

General procedure: A 100-mL round-bottom flask equipped with a stir bar is charged with dimethyl malonate (2.0 g, 15.0 mmol), crotonaldehyde (1.3 mL, 15.0 mmol), piperidine (0.2 mL, 3.0 mmol), benzoic acid (0.4 g, 3.0 mmol) and toluene (50 mL). The reaction mixture is heated at reflux using a Dean-Stark apparatus for 2 h. The toluene solution is washed with water, dried over Na2SO4 and concentrated in vacuo. The crude product is purified by silica gel column chromatography eluting with hexanes/ethyl acetate (20/1) to afford 1a (1.7 g, 60% yield) as a red liquid.

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, Benzyl cyanoacetate, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Zhang, Wei; Ghiviriga, Ion; Grenning, Alexander J.; Tetrahedron; vol. 73; 29; (2017); p. 4076 – 4083;,
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3441-01-8, name is 3-Cyanobenzamide, belongs to nitriles-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Safety of 3-Cyanobenzamide

To a vial were added methyl l-(4-bromophenyl)-3- hydroxycyclobutanecarboxylate (335.8 mg, 1.178 mmol), 3-cyanobenzamide (258 mg, 1.77 mmol), copper(I) iodide (40.4 mg, 0.212 mmol), (lS,2S)-Nl,N2-dimethylcyclohexane-l,2- diamine (80 mg, 0.56 mmol), K2CO3 (331 mg, 2.39 mmol) and dioxane (6 mL). The mixture was evacuated and backfilled with N2 for 4 times, then heated at 120 °C for 17 h. The mixture was diluted with water and EtOAc. After extraction, the combined organic layers were washed with brine, dried over Na2S04i filtered and concentrated in vacuo to afford a residue, which was purified by column chromatography on silica gel (EtOAc in hexane : 0-100percent gradient) to afford the title compound. MS (EI) m/z 373 [M+Na]+.

The synthetic route of 3441-01-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; ZHOU, Hua; ACHAB, Abdelghani; FRADERA, Xavier; HAN, Yongxin; LI, Derun; MCGOWAN, Meredeth, A.; SCIAMMETTA, Nunzio; SLOMAN, David, L.; YU, Wensheng; (98 pag.)WO2019/27855; (2019); 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 5922-60-1 as follows. name: 2-Amino-5-chlorobenzonitrile

General procedure: 2-aminobenzonitrile (1mmol), and KCC-1/IL NPs (0.0007g) were added. The autoclave was closed, purged twice with CO2 gas, pressurized with 0.8MPa of CO2 and then heated at 70C for 60min. Then the reactor was cooled to ambient temperature, and the resulting mixture was transferred to a 50mL round bottom flask. Upon completion, the progress of the reaction was monitored by TLC when the reaction was completed, EtOH was added to the reaction mixture and the KCC-1/IL NPs were separated by distillation under vacuum. Then the solvent was removed from solution under reduced pressure and the resulting product purified by recrystallization using n-hexane/ethyl acetate.

According to the analysis of related databases, 5922-60-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Sadeghzadeh, Seyed Mohsen; Catalysis Communications; vol. 72; (2015); p. 91 – 96;,
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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. 610-66-2, name is 2-(2-Nitrophenyl)acetonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Quality Control of 2-(2-Nitrophenyl)acetonitrile

Absolute ethanol (2,250 ml) and 1,500 g (9.25 moles) of o-nitrophenylacetonitrile is charged into a 22 liter flask. The suspension is cooled to 5-10 and hydrogen chloride is bubbled into the mixture for 2.5 hours. The reaction mixture is stirred at 10 under nitrogen atmosphere overnight. It is then diluted with 16,000 ml of ether and stirred for 1 hour; the solid is collected by filtration, washed with 4*1,000 ml of ether and dried (5 mm Hg/40) to give ethyl 2-(o-nitrophenyl)-acetimidate hydrochloride, m.p. 122-123 (dec).

The synthetic route of 610-66-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Ciba-Geigy Corporation; US4595535; (1986); A;,
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