Tag: M.W=200-300

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 1953-99-7 as follows. Quality Control of 3,4,5,6-Tetrachlorobenzene-1,2-dicarbonitrile

General procedure: To a 250 mL flask was added 4-dodecathio-3,5,6-Trichlorophthalonitrile (4.3 g), 3,4,5,6-Tetrachlorophthalonitrile (8.0 g), Diazabicycloundec-7-ene (4.5 g),1-Pentanol (80 mL) was added and the solid was dissolved by heating,Zinc acetate (1.8g) And reflux while heating.After completion of the reaction,Removed, Purify by column chromatography.Dichloromethane was appropriately added to the obtained solid to dissolve the solid, followed by addition of methanol to crystallize the solid. The obtained solid was filtered and dried under vacuum to obtain a compound represented by the following Chemical Formula 4-1. To a 250 mL flask was added 4-dodecathio-3,5,6-Trichlorophthalonitrile (4.3 g)3,4,5,6-Tetrachlorophthalonitrile (8.0 g) Instead, 4-dodecathio-3,5,6-Trichlorophthalonitrile (8.6 g)3,4,5,6-Tetrachlorophthalonitrile (5.3 g)Was obtained in the same manner as in Synthesis Example 1, except thatTo obtain the indicated compound.

According to the analysis of related databases, 1953-99-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Samsung SD I Co., Ltd.; Park, In Kul; Kim, Hyung Mook; Park, Chae Won; Sin, Myung Yeop; Lee, Young Gi; Jung, Uii Soo; (31 pag.)KR2016/47824; (2016); A;,
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5866-98-8, name is 2,6-Dichloro-3-nitrobenzonitrile, 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. category: nitriles-buliding-blocks

Example 4 Synthesis of 2-(2,6-Dichlorophenylamino)-1,6,7-trimethyl-1,8-dihydro-imidazo[4,5-]isoquinoline-9-one A solution of 2,6-dichloro-3-nitrobenzonitrile (98.7 g, 0.455 mol) in EtOAc (910 mL) was cooled to 5 C. 40% Aqueous methylamine (79.5 mL, 1.14 mol) was added with vigorous mechanical stirring, keeping the temperature at 10-15 C. After addition was complete, stirring was continued for 3 h at the same temperature. More methylamine (16 mL, 0.23 mol) was added, and the mixture stirred for a further 1.5 h at room temperature. Water (300 mL) was added, followed by hexane (450 mL). The mixture was stirred for 15 min, filtered, and the solid washed with water and MeOH, to give 6-chloro-2-methylamino-3-nitrobenzonitrile (80.3 g, 83%), mp 167-170 C.

The synthetic route of 5866-98-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Boehringer Ingelheim Pharmaceuticals, Inc.; US6506769; (2003); B2;,
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These common heterocyclic compound, 1953-99-7, name is 3,4,5,6-Tetrachlorobenzene-1,2-dicarbonitrile, 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. COA of Formula: C8Cl4N2

A reaction was performed at 270¡ã C. for 16 hours by following the procedure of Example 1 while using 80.0 g (0.301 mol) of 3,4,5,6-tetrachlorophthalonitrile in the place of pentachlorobenzonitrile and 0.1 g of sodium hydroxide in the place of potassium hydroxide. After the reaction was completed, the reaction solution was cooled to room temperature and then filtered to remove the suspended potassium chloride and the unaltered potassium fluoride. When the benzonitrile solution as the mother liquor was analyzed by gas chromatography, it was found to contain 55.4 g of 3,4,5,6-tetrafluorophthalonitrile and 0.018 g of benzoic acid fluoride (325 ppm based on the amount of 3,4,5,6-tetrafluorophthalonitrile). The stainless steel reaction vessel showed no discernible sign of corrosion.

The synthetic route of 3,4,5,6-Tetrachlorobenzene-1,2-dicarbonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Nippon Shokubai Co., Ltd.; US6392084; (2002); B1;,
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Related Products of 1735-53-1, 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. 1735-53-1, name is 4-Bromo-3-(trifluoromethyl)benzonitrile, This compound has unique chemical properties. The synthetic route is as follows.

Description for D29 2-(Trifluoromethyl)-4-biphenylcarboxylic acid (D29)The reaction was split into 4, using a quarter of the reagents in each: to a mixture of 4-bromo-3-(trifluoromethyl)benzonitrile (4 g, 16.00 mmol), phenylboronic acid (3.90 g, 32.0 mmol) and potassium carbonate (6.63 g, 48.0 mmol) in N,N-dimethylformamide (DMF) (64 ml) was added palladium tetrakistriphenylphosphine(O) (1.849 g, 1.600 mmol). Each reaction was heated in the microwave at 150 0C for 30 min. The combined reaction mixtures were filtered through celite, washed with ethyl acetate and the solvent removed in vacuo. The residue was partitioned between ethyl acetate (100 ml.) and water (100 ml.) and the organic phase washed with sodium bicarbonate solution (100 ml_). The organic phase was dried (MgSO4), filtered and the solvent removed in vacuo. The brown oil was triturated with dichloromethane and filtered to give a pale yellow solid, 2-(trifluoromethyl)-4-biphenylcarboxamide (2.47 g) which was used without further purification. To 2-(trifluoromethyl)-4- biphenylcarboxamide (2 g, 7.54 mmol) in ethanol (80 ml) was added potassium hydroxide (4.23 g, 75 mmol) and water and the mixture heated to 90 0C for 18 h. The reaction mixture was concentrated in vacuo and the residue partitioned between dichloromethane (100 ml.) and 2M HCI (100 ml_). The organic phase was isolated and dried (phase separator) and the solvent removed in vacuo to give the crude product. Purification using the Biotage Horizon, reverse phase cartridge, eluting 5- 100 % MeCN in water to give an off-white solid the title compound (960 mg) (N2123- 46-A5). MS (ES): C14H9F3O2 requires 266; found 265 (M-H+).

The chemical industry reduces the impact on the environment during synthesis 4-Bromo-3-(trifluoromethyl)benzonitrile. I believe this compound will play a more active role in future production and life.

Reference:
Patent; GLAXO GROUP LIMITED; WO2008/74821; (2008); A1;,
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Synthetic Route of 77668-42-9, 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. 77668-42-9 name is 2,3-Dichlorobenzoyl cyanide, 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.

6. Synthesis of lamotrigine via the tetrafluoroborate salt as a one-pot reactionThe condensation step was performed as described in example 5, with the exception that the isolation of the tetrafluoroborate intermediate was omitted. After the condensation step the solvents were removed on a rotary evaporator, then an equal volume of acetonitrile was added and the subsequent cyclization step was performed as described in example 2.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2,3-Dichlorobenzoyl cyanide, and friends who are interested can also refer to it.

Reference:
Patent; LONZA AG; WO2008/19798; (2008); 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. 328-87-0, name is 2-Chloro-5-trifluoromethylbenzonitrile, A new synthetic method of this compound is introduced below., name: 2-Chloro-5-trifluoromethylbenzonitrile

Preparation of 2-cyano-alpha,alpha,alpha-trifluoro-p-tolyl-4-nitro phenyl ether A solution of potassium hydroxide (3.2 g. 0.05 mole of 89.3% purity) and p-nitrophenol (7.0 g. 0.05 mole) in methanol (25 ml.) is stripped under reduced pressure. The residue is dissolved in sulfolane, 4-chloro-3-cyano alpha,alpha,alpha-trifluorotoluene (10.3 g. 0.05 mole) added, and the resulting solution heated at 150 C for 5 hours. After cooling, the solution is diluted with benzene (350 ml.) washed with water (6 * 250 ml.), dried, and the solvent removed. The residue (12.5 g.) is recrystallized from isopropanol to give 2-cyano-alpha,alpha,alpha-trifluoro-p-tolyl-4-nitrophenyl ether (7.6 g., 49%) m.p. 93-98 C.

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; Rohm and Haas Company; US4076741; (1978); A;,
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Synthetic Route of 92616-49-4, 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. 92616-49-4, name is 4-Bromo-1-naphthonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A mixture of 4-bromo-1-naphthonitrile (230 mg, 0.991 mmol), bis(pinacolato)diboron (277 mg,1.090 mmol), potassium acetate (292 mg, 2.97 mmol) in DMSO (2 ml) was degassed and treatedwith PdC12(dppf) (21.75 mg, 0.030 mmol). The mixture was then capped and heated to 80 Covernight. The reaction mixture was then washed with water and exctracted with ethyl acetate. Theorganics were collected, dried, filtered, and concentrated. The mixture was purified by silica gel chromatography (24 G, 0-50% EtOAc-hexanes) to provide 4-(4,4,5,5-tetramethyl-1,3,2- dioxaborolan-2-yl)-1-naphthonitrile as a white solid (118 mg, 43%). 1H NMR (400 MHz, Chloroform-d) 8.86-8.80 (m, 1H), 8.30-8.24 (m, 1H), 8.08 (d, J= 7.1 Hz, 1H), 7.89 (d, J 7.1Hz, 1H), 7.71 – 7.62 (m, 2H), 1.44 (s, 12H).

The synthetic route of 4-Bromo-1-naphthonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THE BRIGHAM AND WOMEN’S HOSPITAL, INC.; THE UNITED STATES OF AMERICA, AS REPRESENTED BY THE SECRETARY, DEPARTMENT OF HEALTH AND HUMAN SERVICES; LEE, Arthur; MCKEW, John, C.; PATEL, Paresma, R.; YU, Paul, B.; MOHEDAS, Agustin, H.; SANDERSON, Philip, E.; ZHENG, Wei; HUANG, Xiuli; UNIVERSITY OF HOUSTON SYSTEM; CUNY, Gregory, D.; (304 pag.)WO2016/11019; (2016); A1;,
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Some common heterocyclic compound, 1953-99-7, name is 3,4,5,6-Tetrachlorobenzene-1,2-dicarbonitrile, molecular formula is C8Cl4N2, 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. category: nitriles-buliding-blocks

0.60g (0.015 mol) of sodium hydroxide was added to a solution of 1.22g(0.0075 mol) of 3,5-dichloropyridin-4-amine in 40 mL of DMF, followed by addition of 2g (0.0075 mol) of 3,4,5,6-tetrachlorophthalonitrile under stirring, themixture was stirred for 5 h after addition at room temperature. After the reaction was over by Thin-Layer Chromatographymonitoring, the reaction mixture was poured into water and extracted with ethyl acetate, the organic phase was washedwith water and saturated brine, dried over anhydrous magnesium sulfate, filtered and then concentrated under reducedpressure. The residue was purified through silica column (ethyl acetate/petroleum ether (boiling point range 60-90¡ãC)= 1:4, as an eluent) to give 2.6 g of compound A-87 as yellow solid, m.p. 214-216¡ãC.[0070] 1H-NMR (300MHz, internal standard TMS, solvent DMSO), 8.26(s, 2H, Py-2,6-2H), 11.0(br, 1H, NH).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1953-99-7, its application will become more common.

Reference:
Patent; Sinochem Corporation; Shenyang Research Institute of Chemical Industry Co., Ltd.; LIU, Changling; HUANG, Guang; LAN, Jie; HAO, Shulin; LI, Zhinian; LI, Huichao; GUAN, Aiying; JIANG, Airu; XU, Ying; EP2757092; (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. 52864-54-7, name is 2-(2-Bromo-4-chlorophenyl)acetonitrile, A new synthetic method of this compound is introduced below., Formula: C8H5BrClN

To a stirred suspension of NH4Cl (9.241 g, 169.565 mmol) in dry toluene (120 mL) was added tri-methyl aluminum (2 M) (45.23 mL, 90.435 mmol) at 5 C. the reaction mixture was warmed to room temperature and the reaction mixture was stirred for 2 h. A solution of (2-bromo-4-chlorophenyl)-acetonitrile (374) (13 g, 56.522 mmol) in toluene (30 mL) was added to the above reaction mixture and the reaction mixture was stirred for 14 h at 80 C. while silica thin layer chromatography was performed (10% methanol in dichloromethane; Rf=0.2). After completion of the reaction, the reaction mixture was quenched with a suspension of silica gel (20 g) in chloroform (200 mL) and the reaction mixture was stirred for half an hour at room temperature and filtered. The silica gel was washed with methanol (100 mL) and the combined filtrate was concentrated under reduced pressure to get 2-(2-bromo-4-chlorophenyl)-acetamidine hydrochloride (375) (14.0 g, 87.68%) as a white solid. [1341] LC-MS: 248.8 (M+H)

The synthetic route of 52864-54-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Wolkerstorfer, Andrea; Szolar, Oliver; Handler, Norbert; Buschmann, Helmut; Cusack, Stephen; Smith, Mark; So, Sung-Sau; Hawley, Ronald Charles; Sidduri, Achyutharao; Zhang, Zhuming; US2014/194431; (2014); 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 57381-49-4 as follows. Quality Control of 2-Bromo-4-chlorobenzonitrile

2-bromo-4-chlorobenzonitrile 1 g (1.18 g, 5.48 mmol) and 1f (1.3 g, 5.48 mmol) were added to 20 mL of 1,4-dioxane, followed by[1,1′- (Diphenylphosphino)ferrocene]dichloropalladium (240 mg, 0.33 mmol) and potassium carbonate(2.3 g, 16.4 mmol) were added. The reaction mixture was heated to 100-110C and the reaction was stirred for 16 hours.The reaction solution was allowed to cool to roomtemperature and 50 mL of water was added to the reaction mixture. The mixture was extracted with ethyl acetate (50 mL ¡Á 3). The organic phases were combined and the organic phase was washed with water(50 mL) and saturated sodium chloride solution (50 mL). After drying over anhydrous sodium sulfate, the desiccant was removed by filtration and the filtrate was concentrated under reduced pressure.The resulting residue was purifiedwith aCombiFlash flash reader using eluent system B to give the title product 1h (570 mg, colorless oil), yield: 31.6%.

According to the analysis of related databases, 57381-49-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Jiangsu Hengrui Pharmaceutical Co., Ltd.; Shanghai Hengrui Pharmaceutical Co., Ltd.; Yang Fanglong; Chi Jiangtao; He Feng; Tao Weikang; (33 pag.)CN107793396; (2018); A;,
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