Tag: M.W=100-200

Reference of 134450-56-9, The chemical industry reduces the impact on the environment during synthesis 134450-56-9, name is 4,5-Difluorophthalonitrile, I believe this compound will play a more active role in future production and life.

A solution of 5a (67 mg, 0.61 mmols) in DMF (10 mL) was treated NaH (60 %, 48mg, 1.2 mmols), allowed to stir for half a minute at room temperature followed by addition of phthalonitrile 6 (100 mg, 0.61 mmols). A deep blue coloration developed in the reaction flask and TLC monitoring in 10 minutes showed complete consumption of both starting materials 5a and 6 and appearance of a new spot more non-polar to both starting materials, which was very strongly UV-active. The reaction was quenched in cold water (100 mL), extracted into ethyl acetate (20 mL), organic layer repeatedly washed with brine solution (5 × 15 mL) and dried over sodium sulfate. Evaporation of the majority of ethyl acetate followed by re-crystallization in an ice-bath yielded 7a (single spot by TLC control, 30% Ethyl acetate/Petroleum ether) as buff-colored crystals. Yield (62 mg, 43%). 1H NMR (300 MHz, d6-DMSO): delta 7.82 (s, 2H), 7.05 (s, 4H); 13C NMR (150 MHz, d6-DMSO): delta 145.57, 140.06, 125.67, 121.99, 116.76, 115.27, 110.81; UV-vis (DMSO) lambdamax (log epsilon) 261 (4.53), 324 (3.48); HRMS (ESI+) calcd. for C14H6N2O2Na 257.0327, observed for C14H6N2O2Na 257.0293. Melting point: 311 C.

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, 4,5-Difluorophthalonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Banerjee, Subhadeep; Chattopadhyay, Anjan; Banerjee, Arnab; Haridas, Meera; Saini, Praveen; Das, Moitreyi; Majik, Mahesh S.; Maurya, Yogesh Kr.; Bioorganic and Medicinal Chemistry Letters; vol. 25; 4; (2015); p. 753 – 757;,
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Related Products of 4640-66-8,Some common heterocyclic compound, 4640-66-8, name is 4-Chlorophenacylcyanide, molecular formula is C9H6ClNO, 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: General procedure: The substrate 1 (1.0 mmol) and thiourea 2(2.0 mmol) were added to solvent (5 mL methanol) at room tem-perature. To the reaction mixture, TBHP (3.0 mmol) and AIBN(0.2 mmol) were added respectively. The reaction mixture wasstirred at room temperature (for substrates 1a-f) or reux tem-perature (for substrates 1g-r) until TLC indicated the total consumption of 1 (for substrates 1p-q, the reaction time is 24 h).The residue was treated with saturated aqueous NaHCO3 (50 mL)and then extracted with EA (30 mL 3). The organic phase waswashed with brine (50 mL 1), dried over anhydrous Na2SO4. Thesolvent was removed and the residue was puried by ash columnchromatography on silica gel (EA/PE) to afford the desired compound 3.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Chlorophenacylcyanide, its application will become more common.

Reference:
Article; Sun, Jiyun; Ge, Huaibin; Zhen, Xiaohua; An, Xuechan; Zhang, Guangtao; Zhang-Negrerie, Daisy; Du, Yunfei; Zhao, Kang; Tetrahedron; vol. 74; 17; (2018); p. 2107 – 2114;,
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Electric Literature of 16932-49-3, 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. 16932-49-3 name is 2,6-Dimethoxybenzonitrile, 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.

General procedure: :2,6-dimethoxybenzonitrile (501 mg, 3.07 mmol) and4-amino-7-chloroquinoline (548 mg, 3.07 mmol) were dissolved together in 20 mLof anhydrous tetrahydrofuran. The vesselwas swept with nitrogen and chilled in an ice-water bath. Ethereal 3.0 M ethyl magnesium bromide (2.05 mL,6.14 mmol) was added dropwise over 3 min.After briefly forming an off-white solid suspended in a yellow solution,within minutes the mixture became a dark amber homogenous solution with someoff-white solid material remaining. Thevessel was placed in a 75 C oil bath for 21 h before diluting with 60 mL ofwater. The pH was decreased to ca. 14 byaddition of 4 pellets of NaOH. Themixture was then extracted with 60 mL of ethyl acetate, using solid NaCl tofacilitate partitioning. The organicswere dried over MgSO4 and concentrated to 1.27 g of a crude brownoily paste containing mostly unreacted starting materials. Flash chromatography (150 mL silica gel, 50%ethyl acetate / hexane, then neat ethyl acetate, then 10% methanol in ethylacetate) returned 100 mg (9.6%) ofN-(7-chloroquinolin-4-yl)-2,6-dimethoxybenzimidamide (G).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2,6-Dimethoxybenzonitrile, and friends who are interested can also refer to it.

Reference:
Article; Hershberger, Paul M.; Hedrick, Michael P.; Peddibhotla, Satyamaheshwar; Mangravita-Novo, Arianna; Gosalia, Palak; Li, Yujie; Gray, Wilson; Vicchiarelli, Michael; Smith, Layton H.; Chung, Thomas D.Y.; Thomas, James B.; Caron, Marc G.; Pinkerton, Anthony B.; Barak, Lawrence S.; Roth, Gregory P.; Bioorganic and Medicinal Chemistry Letters; vol. 24; 1; (2014); p. 262 – 267;,
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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 21524-39-0 as follows. HPLC of Formula: C7H3F2N

H) 3-fluoro-2-(4-methoxy-3-(4-(morpholin-4-yl)phenyl)-1H-pyrazolo[4,3-c]pyridin-1-yl)benzonitrile [1038] A solution of 4-methoxy-3-(4-(morpholin-4-yl)phenyl)-1H-pyrazolo[4,3-c]pyridine (355 mg), 2,3-difluorobenzonitrile (180 mg) and potassium carbonate in DMF (5 mL) was stirred at 100C for 2.5 hr. The reaction mixture was added to water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting solid was washed with petroleum ether to give the title compound (380 mg). MS(ESI+): [M+H]+ 430.2. MS(ESI+), found: 430.2.

According to the analysis of related databases, 21524-39-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Takeda Pharmaceutical Company Limited; NARA, Hiroshi; DAINI, Masaki; KAIEDA, Akira; KAMEI, Taku; IMAEDA, Toshihiro; KIKUCHI, Fumiaki; EP2857400; (2015); A1;,
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These common heterocyclic compound, 77326-36-4, name is 2-Amino-6-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. Product Details of 77326-36-4

Example 24d 2-amino-6-(2-amino-2-methylpropoxy)benzonitrile To a solution of 2-amino-2-methylpropan-1-ol (14.4 g, 161 mmol) in anhydrous THF (150 mL) was added NaH (6.8 g, 161 mmol, 60% in mineral oil) in small portions at 0 C. under nitrogen. The mixture was stirred at 0 C. for 30 minutes and then stirred at room temperature for another 30 minutes. The solution was cooled down to 0 C. again, and to this solution was added dropwise a solution of 2-amino-6-fluorobenzonitrile (20.0 g, 147 mmol) in anhydrous THF (50 mL). The reaction mixture was then refluxed overnight under nitrogen. The reaction mixture was cooled down to room temperature and carefully quenched with aqueous NH4Cl solution and extracted with ethyl acetate (3*). The combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated. The crude mixture was purified by chromatography on silica gel eluting with 10% MeOH in DCM to give the title compound as yellow solid (23.4 g 71%). 1H NMR (400 MHz, DMSO-d6) delta 1.08 (s, 6H), 3.15 (s, 2H), 3.64 (s, 2H), 5.98 (s, 2H), 6.13 (d, J=8.0 Hz, 1H), 6.31 (d, J=8.4 Hz, 1H), 7.15 (t, J=8.4 Hz, 1H). MS 236 (MH+).

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

Reference:
Patent; SENOMYS, INC.; US2011/245353; (2011); 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. 149793-69-1, name is 3-Fluoro-5-(trifluoromethyl)benzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. HPLC of Formula: C8H3F4N

Synthesis of 3-(methylthio)-5-(trifluor e:[00376] In a 500-mL, 3 -neck round-bottomed flask equipped with an 100-mL pressure- equalizing addition funnel fitted with an nitrogen inlet, and a rubber septum, 3-fluoro-5- (trifluoromethyl)benzonitrile (8.0 g, 1.0 eq.), in acetone (40 mL). Sodiumthiomethoxide (3.42 g, 1.15 eq) was dissolved in water to make 21% aqueous solution and was added dropwise in 30 min at 5C temperature. The temperature of the reaction was slowly raised to RT and stirred for 3 h. Then temperature was raised to 50-60C and maintained for further 4-6 h. The progress of the reaction was followed by TLC analysis on silica gel with 10% MeOH – dichloromethane as mobile phase and visualization with UV, SM Rf =0.40 and Product Rf = 0.25. Reaction was stirred for 3 hr at 25C and 4-6 hrs at 50-60C and reaction mixture was transparent. The reaction mass was quench by water and extracted by ethyl acetate (3×100 mL). The combined organic layer was washed with brine 50 mL and dried over sodium sulphate and evaporated on buchi rotaevaporator. The resulting crude compound (8 g) was subjected to further stage Yield (80.9 %); Mass: (ES+) 235.94 (M+l).

The synthetic route of 149793-69-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KARYOPHARM THERAPEUTICS, INC.; SANDANAYAKA, Vincent, P.; SHACHAM, Sharon; SHECHTER, Sharon; MCCAULEY, Dilara; WO2012/99807; (2012); 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 42872-74-2 as follows. SDS of cas: 42872-74-2

A mixture of ((R)-tetrahydrofuran-2-yl)(1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-6-azaspiro[2.5]octan-6-yl)methanone (826 mg, 2.01 mmol), 3-bromo-4-methylbenzonitrile (394 mg, 2.09 mmol), bis (di-tert-butyl(4- dimethylaminophenyl) phosphine)dichloropalladium (142 mg, 0.20 mmol), potassium phosphate (852 mg, 4.02 mmol) and water (2 mL) in dioxane (10 mL) was stirred for 2 h at 90 C under nitrogen atmosphere. The mixture was cooled to room temperature and concentrated under vacuum. The residue was purified by silica gel column chromatography, eluted with petroleum ether /ethyl acetate (1:1) to afford 6-methyl-4′-(6-((R)-tetrahydrofuran-2-carbonyl)-6-azaspiro[2.5]octan-1-yl)-[1,1′-biphenyl]-3-carbonitrile (636 mg, 80%) as a yellow solid. LCMS (ES, m/z): 401 [M+H]+.

According to the analysis of related databases, 42872-74-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Forma Therapeutics, Inc.; Martin, Matthew W.; Zablocki, Mary-Margaret; Mente, Scot; Dinsmore, Christopher; Wang, Zhongguo; Zheng, Xiaozhang; (382 pag.)EP3636637; (2020); 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. 654-70-6, name is 4-Cyano-3-trifluoromethylaniline belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Product Details of 654-70-6

To a nitrogen flushed, 30-L kettle was charged aniline E (4.0 kg, 21.49 mol) followed by w-heptane (9 L, 2.25 vol) and H20 (10 L, 2.5 vol). The mixture was then agitated for 8 min, cooled to 5-10 C and thiophosgene (1.81 L, 2.72 kg, 23.64 mol, 1.1 equiv) was charged over 12 min, maintaining the batch temperature at 10-16 C, followed by an w-heptane (1 L, 0.25 vol) rinse. The resulting orange slurry was then warmed to 30-40 C over 1.5 h and a slight exotherm to a maximum temperature of 46.4 C was observed. After stirring for 15 h, the orange solution was sampled (>99% conversion). The batch was then heated to 36 C and the phases were allowed to separate. A rag layer was observed and most of it was purged with the bottom aqueous layer. In two portions, w-heptane (18 L, 4.5 vol) was next charged to the orange heptane layer and the solution was distilled to 1.5 vol (45-46 C, 160 mbar). The solution was diluted once more with w-heptane (8 L, 2 vol) and the batch was distilled to 1.5 vol (45-46 C, 160 mbar). The solution was then diluted with w-heptane (10 L, 2.5 vol), cooled to 30-31 C (heptane:product F, 5.3:1) and seeded with product F (10 g). Crystallization was visible within 2-3 min after seeding and the slurry was further cooled to 0-10 C over 3 h and held at 0-10 C for 2 h. The batch was then filtered, rinsed with filtrate and cold w-heptane (4 L, 1 vol) and dried at 20-25 C, under vacuum, for 13 h to yield product F (4.51 kg, 92%), with an HPLC purity of >99%, and a moisture level of 0.04%.

The synthetic route of 654-70-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MEDIVATION PROSTATE THERAPEUTICS, INC.; JAIN, Rajendra, Parasmal; ANGELAUD, Remy; THOMPSON, Andrew; LAMBERSON, Carol; GREENFIELD, Scott; WO2011/106570; (2011); A1;,
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Electric Literature of 1194-02-1, 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. 1194-02-1, name is 4-Fluorobenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A 40% methylamine methanol solution (7.5 mL) was added to a methanol (2.5 mL) solution of 4-fluorobenzonitrile (2.00 g) and the mixture was heated under reflux for fifteen hours under nitrogen atmosphere. After the solvent was removed under reduced pressure, to the residue obtained was added water (15 mL) and the mixture was extracted with ethyl acetate. The organic layer was washed with water and brine successively, and dried over anhydrous sodium sulfate. The oil obtained by removal of the solvent under reduced pressure was purified by silica gel column chromatography (eluent; hexane : ethyl acetate = 2 : 1) to obtain the titled compound (0.48 g) as crystals.

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-Fluorobenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MOCHIDA PHARMACEUTICAL CO., LTD.; EP1391452; (2004); 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. 874-97-5, name is 3-Cyanobenzyl alcohol, A new synthetic method of this compound is introduced below., name: 3-Cyanobenzyl alcohol

To an ice-cold solution of 3-hydroxymethyl benzonitrile (4.95 g, 37 mmol) in CH2C12 (47 mL) was added imidazole (5.1 g, 74 mmol), DMAP (0.45 g, 3.7 mmol), and TBSC1 (6. 2 g, 41 mmol), and the reaction mixture was stirred for 12 h. The reaction mixture was diluted with water, and the aqueous layer was extracted with CH2C12 (3 x 150 mL). The combined organics were washed with brine, dried (MGS04), filtered, and concentrated under reduced pressure to provide 3- (tert-butyldimethylsilyloxymethyl)-benzonitrile (9.1 g, 99%) as a clear oil :H NMR (300 MHz, CDC13) 8 7.51 (s, 1H), 7.42 (d, J = 6 Hz, 1H), 7.35-7. 28 (m, 1H), 4.75 (s, 2H), 0.94 (s, 9H), 0.11 (s, 6H).

The synthetic route of 874-97-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PHARMACIA CORPORATION; WO2005/18557; (2005); A2;,
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