Tag: M.W=100-200

Adding a certain compound to certain chemical reactions, such as: 17417-09-3, name is 2-Fluoro-5-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 17417-09-3, Recommanded Product: 17417-09-3

Ethyl 3-amino-5-nitrobenzothiophene-2-carboxylate. 2-Fluoro-5-nitrobenzonitrile (1.664 g, 10 mmol), ethyl thioglycollate (1.21 g, 10 mmol) and NEt3 (3.06 g, 30 mmol) are stirred in DMSO (5 mL) at 100 C. under N2 for h h. The deep orange-red reaction mixture is poured onto ice-water (50 mL), and the solid is collected by suction filtration, rinsed with water, and dried in a vacuum oven at 60 C. to give ethyl 3-amino-5-nitrobenzothiophene-2-carboxylate (2.675 g, 100%) as a bright orange solid. 1 H NMR (DMSO) delta9.23 (1H, d, J=2.1 Hz), 8.28 (1H, dd, J=2.3, 8.9 Hz), 8.10 (1H, d, J=9.0 Hz), 7.45 (2H, brs), 4.29 (2H, q, J=7.1 Hz), 1.30 (3H, t, J=7.1 Hz).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Fluoro-5-nitrobenzonitrile, and friends who are interested can also refer to it.

Reference:
Patent; Warner-Lambert Company; US5679683; (1997); A;,
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Reference of 53312-81-5, These common heterocyclic compound, 53312-81-5, name is 5-Amino-2-fluorobenzonitrile, 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.

Lithium bis(trimethylsilyl)amide in toluene (0.59 mL, 1 M, 0.59 mmol) was added to ethyl 3 -fluoro- 1 -methyl-4-[ [1 -(trifluoromethyl)cyclopentyl]sulfamoyl] pyrrole-2-carboxylate (57 mg, 0.148 mmol) and 5-amino-2-fluoro-benzonitrile (26.1 mg, 0.19 mmol) in THF (10 mL) at room temperature under nitrogen. The reaction mixture was stirred 1 hour, quenched with NH4C1(25 mL) solution, diluted with brine (25 mL) and extracted with EtOAc (50 mL). The organic layer was dried over magnesium sulphate, filtered and concentrated. The residue was purified by silica gel column chromatography using a gradient from 10 to 100% EtOAc in heptane. The product fractions were concentrated. The residue was dissolved in hot methanol (10 mL). The product crystallised upon addition of water. Compound 281 (30.5 mg) was filtered off and driedovernight in vacuo at 50C. Method D: Rt: 2.02 mm mlz: 475.3 (M-H) Exact mass: 476.1. ?HNMR (400 MHz, DMSO-d6) oe ppm 1.42 – 1.54 (m, 2 H), 1.58 – 1.71 (m, 2 H), 1.72 – 1.85 (m, 2H), 2.21 – 2.32 (m, 2 H), 3.81 (s, 3 H), 7.50 – 7.57 (m, 2 H), 7.97 (ddd, J=9.2, 4.8, 2.9 Hz, 1 H),8.17 (dd, J=5.8, 2.8 Hz, 1 H), 8.32 (s, 1 H), 10.33 (s, 1 H). Differential scanning calorimetry:From 30 to 300 C at 10C/mm: peak at 187.0 C.

The synthetic route of 53312-81-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN R&D IRELAND; VANDYCK, Koen; HACHE, Geerwin, Yvonne, Paul; LAST, Stefaan, Julien; MC GOWAN, David, Craig; ROMBOUTS, Geert; VERSCHUEREN, Wim, Gaston; RABOISSON, Pierre, Jean-Marie, Bernard; WO2014/184350; (2014); 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. 10406-25-4, name is 4-(Aminomethyl)benzonitrile, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C8H8N2

Synthesis of intermediate 13: 4~(4-Cyano- benzylcarbamoyl) -piperidine-1-carboxylic acid tert- butyl esterA solution of HOBt (1.54 g; 10 mmol) and TBTU (3.22 g; 10 mmol) in DMF (10ml) was added to a solution of N- Boc-piperidine-1-carboxylic acid (2 g; 8.72 mmol) and 4-cyanobenzylamine (8.72 mmol) in DMF (10 ml) followed by TEA (4.85 ml; 35 mmol). After 16h, water was added to the reaction mixture and the mixture was extracted with DCM (3 times) . The combined organics were washed with an aqueous solution of NaHCO3 and water and dried (MgSO4) . The residue was purified by silica gel chromatography (eluent:DCM and MeOH/DCM: 5/95) to afford after dry evaporation the title intermediate as an oil (2.4g; Y:80%) .MS: (M+H)+ = 344.

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 10406-25-4.

Reference:
Patent; EUROSCREEN S.A.; WO2009/10480; (2009); A1;,
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These common heterocyclic compound, 21667-62-9, name is 3-(3-Chlorophenyl)-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. name: 3-(3-Chlorophenyl)-3-oxopropanenitrile

To 3-chlorobenzoylacetonitrile (24,360 mg, 2 mmol) and sulfur (76 mg) in DMF (4 [N-IL),] triethylamine (0.25mL) is added under stirring. To this solution tetrahydro-4H-pyran-4-one (1,200 mg, 2 mmol) is added dropwise. The mixture is stirred for 16 hours and it is poured into water (30 [ML),] which is extracted with diethyl ether (30 [ML).] The ethereal solution is dried with sodium sulfate and concentrated to give the desired compound as an orange solid (253 mg, 43%). Physical characteristics: MS [(ES+)] for [M/Z] 294,296 (M+H).

The synthetic route of 3-(3-Chlorophenyl)-3-oxopropanenitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PHARMACIA & UPJOHN COMPANY; WO2004/35591; (2004); A1;,
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Electric Literature of 42872-73-1, 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. 42872-73-1, name is 2-Bromo-4-methylbenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

{4-methyl-2-[(propan-2-yl)amino]phenyl}(phenyl)methanaminium chloride – The titled compound was obtained following the modified procedure described in WO2006035157 (Protocol A). The starting material 2-(isopropylamino)-4- methylbenzonitrile was prepared from 2-bromo-4-methylbenzonitrile using a Ex.77 Buchwald-Hartwig reaction (2-bromo-4-methylbenzonitrile (1 eq.), isopropylamine (1 .5 eq.), BINAP (0.05 eq.), Pd2(dba)3 (0.03 eq.), Cs2C03 (2 eq.) in toluene at 90C for 6h) – Yield: 43% ; appearance: pale yellow solid ; 1 H NMR, d (ppm) (Methanol d4) : 1 .06 (d, 3H, J=6.2Hz); 1.15 (d, 3H, J=6.2Hz); 2.25 (s, 3H); 3.51 -3.58 (m, 1 H); 5.88 (s, 1 H); 6.61 (s, 2H); 7.25-7.47 (m, 6H); 8.94 (br s, 3H)

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, 2-Bromo-4-methylbenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GENFIT; DELHOMEL, Jean-Francois; WALCZAK, Robert; MAJD, Zouher; PIHAN, Emilie; BONNET, Pascal; PERSPICACE, Enrico; (198 pag.)WO2016/102633; (2016); A1;,
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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, Recommanded Product: 4-Fluoro-3-nitrobenzonitrile

General procedure: Before each run, the system (see Fig.4) was allowed to equilibrate by pumping solvent through for 30min with the Tube-in-Tube device at 16bar of hydrogen. An omnifit cartridge (20.0mm OD, 15.0mm ID) containing 1g of Pd-C catalyst was used. To avoid an overpressure of the system in the event of blockage, the upper pressure cut-off limit on the Knauer pump was set to 25bar. With the injection loop disconnected from the flow line, the loop was opened and filled manually (using a syringe) with 3.6mL of a 0.076M solution of starting material in ethanol (excess starting material solution exiting the loop was recovered for reuse). The injection loop was then closed off and switched into the flow stream. The outlet from the system (downstream of the back-pressure regulator) was collected for 120min. The solvent was removed under reduced pressure (using a rotary evaporator followed by a 2-stage rotary vane pump) to afford the product.

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:
Article; Dimitriou, Eleni; Jones, Richard H.; Pritchard, Robin G.; Miller, Gavin J.; O’Brien, Matthew; Tetrahedron; vol. 74; 47; (2018); p. 6795 – 6803;,
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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. 874-97-5, name is 3-Cyanobenzyl alcohol, A new synthetic method of this compound is introduced below., Application In Synthesis of 3-Cyanobenzyl alcohol

NaH (28.8 mg, 60%, 0.72 mmol) was added to a solution of 7-chloro-1-methyl-2,3-dihydroimidazo[1,2-c]pyrimidin-5(1H)-one (44 mg, 0.24 mmol) and 5-(hydroxymethyl)-2-(3-(trifluoromethyl)phenoxy)benzonitrile (71 mg, 0.242 mmol) in DMF (1.8 mL). The reaction mixture was stirred at rt for 30 min. Aqueous HCl solution was added to adjust pH to 7. Purification by Mass Directed AutoPrep (MDAP) afforded the title compound as a white solid (60 mg, 56% yield).

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; Wan, Zehong; Long, Kai; Sang, Yingxia; Su, Xiaobo; US2014/179715; (2014); A1;,
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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., Application In Synthesis of 2-Cyanothioacetamide

[00288] 2-(((butylthio)methyl)thio)-4-(l,2-dimethyl-lH-imidazol-5-yl)-6-(thiazol-2- yl)nicotinonitrile. To a suspension of 3-(l,2-dimethyl-lH-imidazol-5-yl)-l-(thiazol-2- yl)prop-2-en-l-one (0.31 mmol, 72 mg) and 2-cyanothioacetamide (0.93 mmol, 93 mg, 3.0 equiv.) in EtOH (1.5 mL), a few drops of piperidine were added. After being stirred at 80C for 2 h, EtOH was evaporated and crude product was redissolved in CH3CN. Butyl(chloromethyl)sulfane (0.62 mmol, 85.5 mg) and Et3N (0.93 mmol, 94.1 mg, 130 mu,) were then added and the reaction mixture was stirred at 80C for 20 min. Once complete, the reaction was diluted with EtOAc and water. The organic phase was separated and aqueous layer was extracted twice with EtOAc. The combined extractions were washed with saturated NaCl solution, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography to give 99 mg of designed product (77%). FontWeight=”Bold” FontSize=”10″ H NMR (400 MHz, CDC13) delta 7.96 (d, / = 3.1 Hz, 1H), 7.85 (s, 1H), 7.56 (d, J = 3.1 Hz, 1H), 7.37 (s, 1H), 4.49 (s, 2H), 3.60 (s, 3H), 2.72 (t, / = 7.4 Hz, 2H), 2.48 (s, 3H), 1.62 (p, / = 7.3 Hz, 2H), 1.40 (h, / = 7.3 Hz, 2H), 0.90 (t, / = 7.3 Hz, 3H). ESI- MS (m/z): 416.6 [M+H]+.

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

Reference:
Patent; CASE WESTERN RESERVE UNIVERSITY; BOARD OF REGENTS OF THE UNIVERSITY OF TEXAS SYSTEM; MARKOWITZ, Sanford D.; READY, Joseph; ZHANG, Yongyou; ANTCZAK, Monika; WILLSON, James K.V.; POSNER, Bruce A.; GREENLEE, William; (254 pag.)WO2016/168472; (2016); A1;,
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Related Products of 5414-21-1, A common heterocyclic compound, 5414-21-1, name is 5-Bromovaleronitrile, molecular formula is C5H8BrN, 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 solution of the tetrabutylammonium salt of 10-methylthio-7,8-dicarba-nido-caborane [1] (0.40 g, 0.95 mmol) in ethanol (10ml) chloroacetonitrile (0.06 ml, 0.95 mmol) was added. After stirring for 15 min, r.t., the mixture was heated under reflux for about 15 h and the solvent was evaporated under reduced pressure. The column chromatography on silica gel was used for the purification of the substance with CH2Cl2 as an eluent. Finally the solvent was removed in a vacuum to yield white solid (0.14 g, 68% yield).

The synthetic route of 5414-21-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Erokhina, Svetlana A.; Stogniy, Marina Yu.; Suponitsky, Kyrill Yu.; Kosenko, Irina D.; Sivaev, Igor B.; Bregadze, Vladimir I.; Polyhedron; vol. 153; (2018); p. 145 – 151;,
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Synthetic Route of 118431-88-2, The chemical industry reduces the impact on the environment during synthesis 118431-88-2, name is 3-Cyclopropyl-3-oxopropanenitrile, I believe this compound will play a more active role in future production and life.

3-Cyclopropyl-3-oxopropanenitrile (2.61 g, 24 mmol) and 4-hydrazinylbenzoic acid (3.0 g, 20 mmol) were dissolved in ethanol and the solution was heated at reflux for 12 h. The reaction mixture was concentrated and re-dissolved in methanol (30 mL) followed by addition of CF3CO2H (15 mL). The reaction mixture was stirred at room temperature for 12 h and the volatile components were removed on a rotary evaporator. The remaining residues were washed with ethyl acetate and 4-(5-amino-3-cyclopropyl- 1H-pyrazol-1-yl)benzoic acid was collected by filtration as a solid (6.44 g). ?H NMR (400 MHz, DMSO-d6): 8.02 (d, I = 8.70 Hz, 2H), 7.74 (d, I = 8.70 Hz, 2H), 5.30 (s, 1H), 1.85-1.75 (m, 1H), 0.95-0.85 (m, 2H), 0.73-0.65 (m, 2H). ESI-MS calculated for C,3H,4N302[M+Hj+ = 244.11; Observed: 244.1.

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-Cyclopropyl-3-oxopropanenitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; THE REGENTS OF THE UNIVERSITY OF MICHIGAN; WANG, Shaomeng; ZHAO, Yujun; ZHOU, Bing; AGUILAR, Angelo; (114 pag.)WO2016/138332; (2016); A1;,
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