Month: March 2021

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. 68119-31-3, name is 2-(2,2-Difluorobenzo[d][1,3]dioxol-5-yl)acetonitrile, A new synthetic method of this compound is introduced below., Quality Control of 2-(2,2-Difluorobenzo[d][1,3]dioxol-5-yl)acetonitrile

[00308] A mixture of (2,2-difluoro-l ,3-benzodioxol-5-yl)-acetonitrile (1.0 eq), 50 wt % aqueous KOH (5.0 eq) 1 -bromo-2-chloroethane (1.5 eq), and Oct4NBr (0.02 eq) was heated at 70 C for 1 h. The reaction mixture was cooled, then worked up with MTBE and water. The organic phase was washed with water and brine. The solvent was removed to afford (2,2-difluoro-l ,3- benzodioxol-5-yl)-cyclopropanecarbonitrile.

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; VERTEX PHARMACEUTICALS INCORPORATED; SWINNEY, Kelly, Ann; HURTER, Patricia, Nell; NADIG, David, E.; SMITH, David; THOMAS, Vance, Hayden; WARMAN, Martin, Paul; WO2015/73231; (2015); A1;,
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Related Products of 73629-43-3,Some common heterocyclic compound, 73629-43-3, name is 2,3-Diaminobenzonitrile, molecular formula is C7H7N3, 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.

2,3-Diaminobenzonitrile (80 mg; may be prepared as described in intermediate 164) was taken up in ethanol (10 ml). Ethyl 3-bromo-2-oxopropanoate (0.076 ml; Aldrich) was added and left to stir at room temperature overnight. The reaction mixture was filtered, leaving a light orange solid as the residue (15mg). The filtrate was concentrated under vacuum. It was then diluted with DCM and purified, along with the residue, using silica chromatography (10 – 70% EtOAc / isohexane) to give the title compound (70 mg) as an orange solid, m/z [M+H]+: 264.0 / 266.0. Retention time 0.72 min (LC/MS method 3).

The synthetic route of 73629-43-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; BLUNT, Richard; EATHERTON, Andrew John; GARZYA, Vincenzo; HEALY, Mark Patrick; MYATT, James; PORTER, Roderick Alan; WO2011/12622; (2011); A1;,
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These common heterocyclic compound, 630-18-2, name is Pivalonitrile, 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. Application In Synthesis of Pivalonitrile

General procedure: To a solution of anisole 3A (3.0 mmol, 324.4 mg) in THF (3.0 mL) was added n-BuLi (4.5 mmol,1.55 M in hexane, 2.87 mL) at 0 C. The mixture was stirred for 2 h at 0 C under an argon atmosphere. Then, pivalonitrile (9.0 mmol, 748.2 mg) in THF (2.0 mL) was added to the mixture at 0 C and the obtained mixture was stirred for 30 min in the temperature range of 0 C to room temperature. MeOH (2.0 mL) was added to the mixture. Then, I2 (12.0 mmol, 3045.6 mg) and K2CO3 (12.0 mmol, 1658.4 mg) were added to the mixture at room temperature, and the obtained mixture was stirred for 6 h at 70 C. 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. After filtration and removal of the solvent, the residue was purified by silica-gel column chromatography (chloroform: n-hexane 1:1) to give 2-methoxybenzonitrile 2A (315.6 mg, 79%).

The synthetic route of Pivalonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Article; Uchida, Ko; Togo, Hideo; Tetrahedron; vol. 75; 39; (2019);,
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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. 20099-89-2, name is 4-(2-Bromoacetyl)benzonitrile, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 20099-89-2

Step-I: 4-(2-amino-4-hydroxy-7H-pyrrolo[2,3-d]pyrimidin-6-yl)benzonitrile (XI-10-I) A mixture of 2,6-diaminopyrimidin-4-ol (1 g, 7.93 mmol) and NaOAc (0.846 g, 10.31 mmol) in water (180 mL) was heated to 100 C. for 20 minutes. To this was added a suspension of 4-(2-bromoacetyl)benzonitrile (2.2 gm, 8.73 mmol) [prepared according to procedure mentioned in J. Med. Chem., 2011, 54(12), 4042-4056] in MeOH (25 mL) and heated overnight at 100 C. After completion of reaction, the reaction mixture was cooled to 0 C. Resultant solid product was filtered off and dried under reduced pressure to provide title compound XI-10-I (1.2 g, 100%). LCMS: m/z 252 (M+1)+.

According to the analysis of related databases, 20099-89-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Thakkar, Mahesh; Koul, Summon; Bhuniya, Debnath; Mookhtiar, Kasim; Kurhade, Santosh; Munot, Yogesh; Mengawade, Tanaji; Kulkarni, Bheemashankar A.; US2015/64196; (2015); A1;,
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Application of 1080-74-6, 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. 1080-74-6, name is 2-(3-Oxo-2,3-dihydro-1H-inden-1-ylidene)malononitrile, This compound has unique chemical properties. The synthetic route is as follows.

Add 4,4-((([2,1,3] -benzoseladiazole-4,7-substituent bis (4-dodecylthiophene-5,2-substituent)) di (4, 1-phenylene)) bis (aniline) dibenzaldehyde (737mg, 0.599mmol) and 3- (dicyanomethylene) indone (348.7mg, 1.797mol) were added to a 100ml round bottom flask,Add 80 ml of trichloromethane and 10 ml of pyridine. After reacting at room temperature for 6 hours, pour the reaction solution into ethanol to precipitate a large amount of blue-black solids at this time, filter, dissolve the solid with dichloromethane, and purify by column chromatography. Methane: petroleum ether = 3: 1 was used as an eluent to separate the crude product, and then recrystallized from dichloromethane and ethanol to obtain a blue-black powdery solid (345 mg, 36.5%). The blue-black powdery solid is IND-TPA-Th-BSe, and its NMR experimental data is as follows:

The chemical industry reduces the impact on the environment during synthesis 2-(3-Oxo-2,3-dihydro-1H-inden-1-ylidene)malononitrile. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Jiangxi Normal University; Liang Aihui; Zhou Wenjing; Zhang Jiayu; Hu Sifan; Xie Qi; Liu Zhiqian; (13 pag.)CN110229148; (2019); A;,
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Reference of 21803-75-8, 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. 21803-75-8, name is 4-Amino-3-chlorobenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To 4-amino-3-chlorobenzonitrile (52 mg, 0.34 mmol), CS2CO3 (130 mg, 0.4 mmol) were added to tert-butyl 5-chloro-3-formyl-6-methylpyrazolo[l,5-a]pyrimidin-7- yl(cyclopropyl)carbamate (100 mg, 0.29 mmol) dissolved in 1,4-dioxane (1.1 mL). Racemic BINAP (11 mg, 0.017 mmol) and palladium(II) acetate (8 mg, 0.011 mmol) were then added. The mixture was sealed and irradiated at 110 C for 60 min in the microwave. Et20 (3 mL) was added and the solution was filtered. The filtrate was concentrated in vacuo. The crude residue was dissolved in dichloromethane (1.5 mL) and trifluoroacetic acid (1.5 mL). After stirring at room temperature for 1 hour, the solution was concentrated under a stream of air. The crude material was purified by silica gel chromatography (3% acetone/dichloromethane) to yield the product, 3-chloro-4-(7-(cyclopropylamino)-3-formyl-6-methylpyrazolo[l,5- a]pyrimidin-5-ylamino)benzonitrile (34 mg, 33% yield). LCMS (M+l=367)

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-Amino-3-chlorobenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; CYLENE PHARMACEUTICALS INC.; HADDACH, Mustapha; RYCKMAN, David; RAFFAELE, Nicholas; WO2011/31979; (2011); 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. 10406-25-4, name is 4-(Aminomethyl)benzonitrile, A new synthetic method of this compound is introduced below., Product Details of 10406-25-4

4-(Aminomethyl)benzonitrile (25.09 g, 0.149 mol) and L-cysteine (18.1 g, 0.149 mol) were suspended in 500 mL MeOH and pH 6.4 buffer solutions (1 : 1) and stirred for 3 days at RT. Triethylamine (30 mL) was added to the mixture and Boc20 (68 g, 0.31mol) was added to this mixture and stirred for 2 h. The solvents were removed and filtered to yield white solid (R)-2-(4-((?ri-butoxycarbonylamino)methyl)phenyl)-4,5-dihydrothiazole-4- carboxylic acid (38.4 g, 76.8%). Compound 67a was obtained from this acid following the same method as used for 38d. Yield: 84.4 %. 1H NMR (500 MHz, CDC13) delta 7.75 – 7.77 (d, 2 H, J = 7.5 Hz), 7.27 – 7.26 (d, 2 H, J = 7.5 Hz), 7.23 (s, 1 H), 5.62 (br, 1 H), 4.87 (br, 1 H), 4.30 (br, 2 H), 3.86 (s, 3 H), 3.78 (t, J = 10.0 Hz, 1 H), 3.48 – 3.4 (m, 1 H), 3.25 (s, 3 H), 1.42 (s, 9 H). MS (ESI) m/z 402.1(M + Na)+, 378.0 (M – H)-.

The synthetic route of 10406-25-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GTX, INC.; UNIVERSITY OF TENNESSEE RESEARCH FOUNDATION; DALTON, James, T.; MILLER, Duane, D.; AHN, Sunjoo; CHEN, Jianjun; DUKE, Charles; LI, Chien-ming; LI, Wei; LU, Yan; WANG, Zhao; WO2011/109059; (2011); A1;,
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Related Products of 2469-99-0, A common heterocyclic compound, 2469-99-0, name is 3-Oxobutanenitrile, molecular formula is C4H5NO, 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-Aminobenzenesulfonic acid (1.73 g,10 mmol)was dissolved in50 mL water, and 0.40 g (10 mmol) of NaOH was added. The solution was cooled in an ice bath to 0 C and 0.69 g (10 mmol) ofNaNO2 was added; 2.00 mL HCl was then added in 0.5 mL portionsfor 1 h. The temperature of the mixture should not exceed 5 C.3-Oxobutanenitrile (0.83 mL, 10 mmol) was added to 30 mLwater-ethanol (5/25, v/v) solution of sodium hydroxide (0.4 g,10 mmol) and sodium acetate (0.82 g, 10 mmol). The resulting solutionwas stirred and cooled to ca. 0 C, and a suspension of thediazonium salt (see above) was added in three portions undervigorous stirring for 1 h. A yellow precipitate of the title compoundwas formed in ca. 1 h, filtered off, dried in air and recrystallizedfrom methanol.NaHL. Yield: 86% (based on 3-oxobutanenitrile), yellow powdersoluble in water, methanol, ethanol, acetone and insoluble inchloroform. Anal. Calcd for C10H8N3NaO4S (Mr 289.24): C, 41.53;H, 2.79; N, 14.53; found: C, 41.46; H, 2.61; N, 14.47%. ESI-MS: m/z:266.02 [Mr-Na]-. IR (KBr): 3459 upsilon(NH), 2206 n(C^N), 1645 n(C]O),1606 and 1534 n(C]N) cm-1. 1H NMRof a mixture of isomeric EandZ-hydrazone forms (300.130 MHz) in DMSO-d6, internal TMS,delta (ppm): E-Hydrazone, 2.43 (s, 3H, CH3), 6.93e7.93 (4H, AreH),12.60 (s, 1H, NeH). Z-Hydrazone, 2.40 (s, 3H, CH3), 6.93e7.93 (4H,AreH), 15.04 (s, 1H, NeH). 13C{1H} NMR (75.468 MHz, DMSO-d6). EHydrazone,delta: 24.65 (CH3), 110.34 (C^N), 115.77 (AreH), 118.00(C]N),124.43 (AreH),127.68 (AreH),130.88 (AreH),134.11 (Are-SO3Na), 136.77 (AreNHN]), 192.51 (C]O). Z-Hydrazone, delta: 28.08(CH3), 112.74 (C^N), 115.39 (AreH), 118.00 (C]N), 125.26 (AreH),127.52 (AreH), 130.62 (AreH), 135.50 (AreSO3Na), 137.62(AreNHN]), 191.42 (C]O).

The synthetic route of 2469-99-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Gurbanov, Atash V.; Mahmudov, Kamran T.; Kopylovich, Maximilian N.; Guedes da Silva, Fatima M.; Sutradhar, Manas; Guseinov, Firudin I.; Zubkov, Fedor I.; Maharramov, Abel M.; Pombeiro, Armando J.L.; Dyes and Pigments; vol. 138; (2017); p. 107 – 111;,
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Adding a certain compound to certain chemical reactions, such as: 1835-49-0, name is Tetrafluoroterephthalonitrile, 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 1835-49-0, Product Details of 1835-49-0

Dry tetrafluoroterephthalonitrile 51.02 g (98% pure, 50.0 g in terms of tetrafluoroterephthalonitrile), dry 5% Pd/C 1.0 G, Zeolite 4A powder 37. 5 g (Molecular Sieve 4A produced by Union Showa K. K. ), and toluene 200.0 g were introduced into a 500 ml stainless steel autoclave (NU-4 model produced by Nitto Koatu Co., Ltd. ), and the autoclave was purged with nitrogen. Thereafter the contents were heated to 160C under stirring, and hydrogen pressurized at a pressure higher than that in the autoclave at the above temperature by 0.1 MPa was supplied to initiate hydrogenolysis. The rate of hydrogen absorption lowered in 2 hours after the hydrogen supply was initiated, so that the pressure in the autoclave was raised by 0. 05 MPa with hydrogen.The supply of hydrogen was terminated when the hydrogen absorption was achieved at 125 mol% (based on the mol of tetrafluoroterephthalonitrile under standard conditions). The above reaction was completed in 8 hours. Cooled to room temperature, the reaction slurry was filtered, and the filtrate was analyzed with the gas chromatography analyzer. The analysis gave a conversion of 98. 0% and a reaction yield of 78. 0% (product: 2,3, 5,6-tetrafluorobenzonitrile). The solvent of the above reaction solution was removed by means of an evaporator, and the residue was distilled under reduced pressure to obtain 2,3, 5, 6-tetrafluorobenzonitrile as a fraction under 50 mmHg at 88C.

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

Reference:
Patent; SHOWA DENKO K.K.; WO2004/9535; (2004); 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. 1080-74-6, name is 2-(3-Oxo-2,3-dihydro-1H-inden-1-ylidene)malononitrile, This compound has unique chemical properties. The synthetic route is as follows., Formula: C12H6N2O

7.1. Under argon (Ar) protection, add 0.43 mmol (486 mg) of intermediate M1 to a 100 mL three-necked bottle.1.73 mmol (336 mg) of 2-(3-oxo-2,3-dihydro-1H-inden-1-ylidene)malononitrile and 30 mL of chloroform.7.2. Add 1 mL of pyridine to the flask and react at 65 C for 24 hours.The reaction was stopped, the solvent was spun off, the mixture was taken up in methanol and filtered to give a crude product.7.3. The crude product is separated and purified by column chromatography. The eluent is a mixed solution of dichloromethane and petroleum ether in a volume ratio of 1..1.A black solid of 450 mg was obtained in a yield: 70%. That is, the small molecule LS1.

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 1080-74-6.

Reference:
Patent; Xiangtan University; Shen Ping; Liang Jingtang; Yin Pan; Zheng Tao; Zeng Xiaoying; (32 pag.)CN110283184; (2019); A;,
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