Tag: M.W=200-300

Reference of 1953-99-7, A common heterocyclic compound, 1953-99-7, name is 3,4,5,6-Tetrachlorobenzene-1,2-dicarbonitrile, molecular formula is C8Cl4N2, 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.

3,4,5,6- tetrachloro phthalo nitrile 0.1 mol anddiethylmalonate 0.1 mol, and potassium carbonate 0.1 mol were stirred withdimethylformamide 60 g at 60 for3~4 hours. Afterthe reaction was complete, the reaction solution was cooled down atroom temperature. The reaction solution was added to water 250 g to crystallizeitself. Thecrystals were filtered under reduce pressure and were dispersedly filtered inthe mixed solution of methanol 50g and water 50g for 1 hour. The crystals were suction filteredand vacuum dried at 60 toobtain [formulaf] compound 30g.

The synthetic route of 1953-99-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Kyung-In Synthetic Corporation; Park, Soon Hyeon; Kim, Jeong Ki; Kim, Jeong Rok; Lee, Yun Ah; Lee, Do kyeong; Lee, Min Jeong; Lee, Hui Jae; (16 pag.)KR2016/7024; (2016); A;,
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Related Products of 179898-34-1, 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. 179898-34-1, name is 3-Bromo-5-fluorobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows.

5′-(3-Cyano-5-fluorophenyl)-spiro[cyclopentane-1,3′-[3H]indol]-2′(1’H)-one: A solution of 3-cyano-5-fluoro-bromobenzene (0.5 g, 2.6 mmol), and tetrakis (triphenylphosphine)palladium(0) (0.2 g) in ethylene glycol dimethyl ether (20 cm3) was stirred under N2 for 20 minutes. To this mixture was then (spiro[cyclopentane-1,3′-[3H]indol]-2′(1’H)-one-5-yl) boronic acid (0.9 g, 3.9 mmol) and sodium carbonate (0.8 g, 7.8 mmol) in water (5 cm3). The solution was brought to reflux for 18 hours and then cooled to room temperature, poured into 2N NaOH and extracted with EtOAc (×3). The combined extracts were washed with water, brine, dried (MgSO4), and evaporated. The residue was purified by column chromatography (SiO2, EtOAc, hexane) to afford the subtitled compound (0.35 g, 44%) as white needles. mp: 235-237 C.; 1H NMR (DMSO-d6) delta 10.5 (s, 1H), 8.1 (s, 1H), 8.0 (dt, 1H, J=1.7, 2.0, 7.0 Hz), 7.8-7.7 (m, 2H), 7.6 (dd, 1H, J=1.8, 6.4 Hz), 6.9 (d, 1H, J=8.1 Hz), 2.0-1.9 (m, 8H); MS (EI) M+ m/z 306.

The chemical industry reduces the impact on the environment during synthesis 3-Bromo-5-fluorobenzonitrile. I believe this compound will play a more active role in future production and life.

Reference:
Patent; American Home Products Corporation; Ligand Pharmaceuticals, Inc.; US6355648; (2002); B1;,
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Application of 179897-89-3, 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. 179897-89-3 name is 5-Bromo-2-fluorobenzonitrile, 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.

a 2-Hydroxyl-4-bromobenzonitrile A mixture of 2-fluoro-5-bromobenzonitrile (30 g, 152.3 mmole), potassium acetate (222.4 g, 228.5 mmole), and 18-crown-6 ether (60.4 g, 288.5 mmole) in MeCN (400 mL) was heated at reflux in 36 h. The mixture was cooled, added 2.5 N NaOH (200 mL), stirred at RT overnight. The mixture was extracted with ether (discarded). The aqueous layer was acidified with 6N HCl, extracted with EtOAc, dried over MgSO4, concentrated, purified by flash column chromatography (40% EtOAc/Hex) to give a light yellow foam (24.45 g, 81%). 1H-NMR (300 MHz, DMSO-d6): delta7.13 (dd, J=1.7, 8.3 Hz, 1H), 7.17 (d, J=1.7 Hz, 1H), 7.61 (d, J=8.3 Hz, 1H).

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

Reference:
Patent; SmithKline Beecham Corporation; US6417215; (2002); B1;,
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Adding a certain compound to certain chemical reactions, such as: 52133-67-2, name is Ethyl 2-cyano-4,4-diethoxybutyrate, 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 52133-67-2, Application In Synthesis of Ethyl 2-cyano-4,4-diethoxybutyrate

3-Dihydroxybenzamidine hydrochloride as obtained above (89.2 g) was dissolved in absolute ethanol (3080 mL) and a part of the ethanol (2200 mL) was subsequently distilled off again. More absolute ethanol (2200 mL) was added to this receiving solution, together with DBU (175 g), 2-cyano-4,4-diethoxy-butyric acid ethyl ester (237.0 g) and triethyl amine (1 1 1 g). The resulting mixture was heated until reflux and further refluxed for 22 hrs. Most of the solvent (2950 mL) was then distilled off while the remainder was allowed to cool to 50 0C. An aqueous solution of hydrochloric acid (2.3 M, 1360 mL) was added slowly, the reaction mixture was allowed to cool to ambient temperature and stirring was continued for 1 hr. The resulting precipitate was filtered off, washed with water (3 x 100 mL) and dried in vacuo at 40 0C for 2 days to yield 82.8 g 2-(3-hydroxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-ol.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Ethyl 2-cyano-4,4-diethoxybutyrate, and friends who are interested can also refer to it.

Reference:
Patent; SOLVAY PHARMACEUTICALS GMBH; WO2009/153261; (2009); 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. 154607-01-9, name is 4-Bromo-2-chlorobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., Formula: C7H3BrClN

Reference Example 14; 2-chloro-4-(1H-pyrazol-4-yl)benzonitrile tert-Butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole-1-carboxylate (1.53 g), 4-bromo-2-chlorobenzonitrile (1.43 g) and triethylamine (1.45 mL) were dissolved in THF-water (6:1, 11.7 mL), and 1,1′-bis(diphenylphosphino)ferrocene palladium (II) dichloride dichloromethane complex (1:1) (127.4 mg) was added under a nitrogen atmosphere. The reaction mixture was stirred with heating under reflux for 3 hr, and the mixture was cooled to room temperature and TFA (20 mL) was added. The reaction mixture was stirred at room temperature for 1.5 hr, and concentrated. 1 mol/L Aqueous sodium hydroxide solution was added to the obtained residue, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated. The obtained residue was purified by column chromatography (hexane-ethyl acetate) to give the title compound (808.6 mg) as pale-orange crystals.1H-NMR (CDCl3) delta: 7.80 (1H, dd), 7.93 (1H, d), 8.05 (1H, d), 8.22 (1H, brs), 8.44 (1H, brs), 13.27 (1H, brs).

According to the analysis of related databases, 154607-01-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; US2009/270359; (2009); 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. 5866-98-8, name is 2,6-Dichloro-3-nitrobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 2,6-Dichloro-3-nitrobenzonitrile

Example 4 Synthesis of 2-(2,6-Dichlorophenylamino)-1,6,7-trimethyl-1,8-dihydro-imidazo[4,5-h]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.

According to the analysis of related databases, 5866-98-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Snow, Roger John; Cardozo, Mario; Goldberg, Daniel; Hammach, Abdelhakim; Morwick, Tina; Moss, Neil; Patel, Usha R.; Prokopowicz III, Anthony S.; Takahashi, Hidenori; Tschantz, Matt Aaron; Wang, Xiao-Jun; US2002/16460; (2002); A1;,
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1953-99-7, name is 3,4,5,6-Tetrachlorobenzene-1,2-dicarbonitrile, 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. Computed Properties of C8Cl4N2

In a 100 ml flask, 3,4,5,6-tetrachlorophthalonitrile (5 g), 2,4-dimethylphenol (2.75 g), K2CO3 (3.9 g), N, N-dimethylformamide (N, N-dimethylformamide) (25 ml) And the mixture was stirred while heating to 70 ° C. After completion of the reaction, the reaction mixture is extracted with EA (ethyl acetate). After extraction and concentration, a solid can be obtained. The resulting solid was dissolved in a small amount of dichloromethane, Washed several times with hexane, After filtration and vacuum drying, 3,4,6-Trichloro-5- (2,4-dimethylphenoxy) phthalonitrile is obtained.

The synthetic route of 1953-99-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Samsung SDI Co., Ltd; Shin Myeong-yeop; Seo Hye-won; Jeong Ui-su; Han Gyu-seok; (41 pag.)KR2019/27185; (2019); A;,
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Application of 17216-62-5, The chemical industry reduces the impact on the environment during synthesis 17216-62-5, name is Diethyl 2-(2-cyanoethyl)malonate, I believe this compound will play a more active role in future production and life.

(a) 2-(2-Cyanoethyl)malonic acid diethylester (40 g) was reacted with sodium hydride (4.4 gm) in tetrahydrofuran at 20 C. 2-Chloro-5-methyl-3-nitro-pyridine (35 g) was added and the internal temperature was raised to 100 C. (some tetrahydrofuran distilled off) over 4.25 hrs. The reaction mixture was partitioned between chloroform and water and treated with charcoal. Vacuum distillation of the chloroform extract and then chromatography (CHCl3, silica column) of the distillation residues gave 4-(5-methyl-3-nitropyrid-2-yl)-4,4-bis (carbethoxy)-butyronitrile (24.5 g) as a yellow solid m.p. 48-49 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, Diethyl 2-(2-cyanoethyl)malonate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Smith Kline & French Laboratories Limited; US4444772; (1984); A;,
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Related Products of 236750-65-5, These common heterocyclic compound, 236750-65-5, name is 4,5-Bis(2-methoxyethoxy)-2-nitrobenzonitrile, 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.

A 4 ml 5-neck flask was charged with 2.96 g (10 mmol) of 4,5-bis(2-methoxyethoxy)-2-nitrobenzonitrile, 38.4 mg (0.3 mmol) of molybdenum dioxide, and 0.12 g of activated carbon. 30 ml of absolute ethanol was added dropwise to a solution of hydrazine hydrate (80%) at a temperature of 1.88 g (30 mmol). After the reaction was completed at room temperature for 7 h, TLC monitoring showed that the reaction was completed, filtered, and the filtrate was concentrated, then ethyl acetate (20 mL) and water (10 ml) were added and extracted. The organic phase was washed with water and concentrated to near dryness, slurried with petroleum ether to give 2.4g desired product as a pale yellow solid, yield 90.2%, HPLC purity 99%.

The synthetic route of 236750-65-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Puji Bio-technology (Taizhou) Co., Ltd.; Jia Qiang; Ma Chi; Ma Tianhua; Yang Zhengwei; (11 pag.)CN109574853; (2019); A;,
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Related Products of 120315-65-3, A common heterocyclic compound, 120315-65-3, name is 4-Bromo-3-methoxybenzonitrile, molecular formula is C8H6BrNO, 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.

A mixture of 4-bromo-3-methoxy~benzonitrile (400mg, 1.88mmol), 5-(4,4,5,5-tetramethyl- p ,3.2Jdioxaborotan-2-yl)«py?dine-3-carbaldehyde (440 mg, 1.88 mmol), PdCl2(PPh3)Z (108mg, 0.15mmol) and Na2CO3 (2M in water, 1.88mL, 3.77mmol) in 1,4-dioxanbeta (8 mL) was heated at 100C for 1.5h. After concentration in vacuo, the resulting residue was purified by flash column to give the title compound (449 mg, 100%) as white solid; ESI- MS mlr. 239 IM+1)*.

The synthetic route of 120315-65-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; CHAMOIN, Sylvie; HU, Qi-Ying; PAPILLON, Julien; WO2010/130796; (2010); A1;,
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