Category: nitriles-buliding-blocks

Some common heterocyclic compound, 57381-49-4, name is 2-Bromo-4-chlorobenzonitrile, molecular formula is C7H3BrClN, 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. HPLC of Formula: C7H3BrClN

To a solution of 2-bromo-4-chlorobenzonitrile (500 mg, 2.3 mmol), in dry THF (50 mL) was added slowly borane-THF complex (1 M, 12 mL, 1 1 .5 mmol) at 0 C before refluxing for 1 h. After cooling down, 1 M HCI in MeOH (20 mL) was charged slowly with ice cooling. The solvent was removed by concentration in vacuo before water (0.61 mmol/mL to benzonitrile) was charged, then washed by Et20 (0.61 mmol/mL to benzonitrile) before basifying with 2 M NaOH solution to pH 12. Et20 (15 mL) was added and the mixture was washed with water (3 x 15 mL) and brine (1 mL). The organic phase was dried (MgS04) and concentrated in vacuo to give a yellow oil (345 mg, 68%). LCMS (EST) m/z = 220.1 [M+H]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 57381-49-4, its application will become more common.

Reference:
Patent; ASTEX THERAPEUTICS LIMITED; CANCER RESEARCH TECHNOLOGY LIMITED; CHESSARI, Gianni; HOWARD, Steven; BUCK, Ildiko Maria; CONS, Benjamin David; JOHNSON, Christopher Norbert; HOLVEY, Rhian Sara; REES, David Charles; ST. DENIS, Jeffrey David; TAMANINI, Emiliano; GOLDING, Bernard Thomas; HARDCASTLE, Ian Robert; CANO, Celine Florence; MILLER, Duncan Charles; CULLY, Sarah; NOBLE, Martin Edward Maentylae; OSBORNE, James Daniel; PEACH, Joanne; LEWIS, Arwel; HIRST, Kim Louise; WHITTAKER, Benjamin Paul; WATSON, David Wyn; MITCHELL, Dale Robert; (293 pag.)WO2017/55860; (2017); A1;,
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Electric Literature of 5414-21-1,Some common heterocyclic compound, 5414-21-1, name is 5-Bromovaleronitrile, molecular formula is C5H8BrN, 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: A solution of m-tolylmagnesium bromide 26, prepared from 416 muL of 3-bromotoluene and 83 mg of magnesium turnings in anhydrous THF (3 mL), was added dropwise under inert atmosphere to a solution of 5-bromovaleronitrile (400 muL, 3.43 mmol) in anhydrous THF (3 mL). The mixture was stirred at room temperature for 1 h, quenched with a saturated aqueous solution of NaHCO3 (3 mL) and extracted with dichloromethane (3 * 10 mL). The combined organic layers were dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure. The crude residue was purified by silica gel column chromatography (dichloromethane/methanol 95:5) to provide the compound 7 as a yellow oil (225 mg, 38% yield).

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

Reference:
Article; Matera, Carlo; Quadri, Marta; Sciaccaluga, Miriam; Pome, Diego Yuri; Fasoli, Francesca; De Amici, Marco; Fucile, Sergio; Gotti, Cecilia; Dallanoce, Clelia; Grazioso, Giovanni; European Journal of Medicinal Chemistry; vol. 108; (2016); p. 392 – 405;,
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Some common heterocyclic compound, 6393-40-4, name is 4-Amino-3-nitrobenzonitrile, molecular formula is C7H5N3O2, 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. Formula: C7H5N3O2

a) Preparation of 3,4 diamino benzonitrile 4-Amino 3-nitro-benzonitrile (5.0 g, 0.03 moles) was dissolved in ethyl acetate then treated with 2.5 g of 10% Pd/C. The reaction mixture was flushed with hydrogen and allowed to stir overnight at 23 C. The reaction was not quite complete so 0.5 g more 10% Pd/C was added. After 2 hours the reaction was complete. The solution was filtered through celite, concentrated and used without further purification (4.67 g).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6393-40-4, its application will become more common.

Reference:
Patent; SmithKline Beecham Corporation; US6133319; (2000); A;,
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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. 179897-89-3, name is 5-Bromo-2-fluorobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 5-Bromo-2-fluorobenzonitrile

Referential Example 3 5-Bromo-2-fluorobenzonitrile and piperidine were heated at 80C in DMSO in the presence of cesium carbonate to obtain 5-bromo-2-piperidin-1-ylbenzonitrile. F: 265.

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 179897-89-3.

Reference:
Patent; Astellas Pharma Inc.; EP1783116; (2007); A1;,
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These common heterocyclic compound, 2469-99-0, name is 3-Oxobutanenitrile, 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-Oxobutanenitrile

General procedure: 3-Acetyl-2-aminothiophene Derivatives; General Procedure Carbonyl compound (0.025 mol) was added to freshly prepared cya-noacetone (0.03 mol) in either MeOH or EtOH (40 mL). Sublimed sul-fur S8 (0.03 mol) and piperidine (0.03 mol) were added and the mix-ture was stirred and heated to 55-65 C for 24 h. Ice was then addedand the formed precipitate was filtered under vacuum and washedwith water. The obtained solid was crystallised from a suitable sol-vent, with the exception of 4g and 4j, which were collected directlywithout further purification.

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

Reference:
Article; Abdelwahab, Ahmed B.; Hanna, Atef G.; Kirsch, Gilbert; Synthesis; vol. 48; 17; (2016); p. 2881 – 2888;,
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Related Products of 2182-39-0, 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 2182-39-0 as follows.

EXAMPLE 5 Preparation of N-(2-Propionitrile)-N-phenylcarbamoyl chloride STR11 Phosgene, 23.0 g (0.23 mole) was absorbed in 300 ml methylene chloride. To that stirred solution, a solution of 29.2 g (0.2 mole) 2-(phenylamino)-propionitrile and 15.8 g (0.2 mole) pyridine in 50 ml methylene chloride was dropped in over 30 minutes. Stirring was continued for 5 minutes. The reaction mixture was washed twice with 100 ml ice water and once with 100 ml ice water containing 20 ml concentrated hydrochloric acid, dried over magnesium sulfate and stripped to give 41 g of a brown oil which soon solidified.

According to the analysis of related databases, 2182-39-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Chevron Research Company; US4602029; (1986); A;,
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Related Products of 33143-29-2,Some common heterocyclic compound, 33143-29-2, name is 2,2-Dimethyl-2H-chromene-6-carbonitrile, molecular formula is C12H11NO, 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: Enantioselective epoxidation reactions were performed with catalyst 1 (0.02 mmol) using styrene (STY), cis beta-methyl styrene (MSTY), indene (IND), 2,2-dimethylchromene (CHR), 6-cyano-2,2-dimethylchromene (CN-CHR), 6-methoxy-2,2-dimethylchromene (MeO-CHR), spiro[cyclohexane-1,2-[2H][1]chromene] (Cy-CHR) (1 mmol) as substrates in dichloromethane (3 mL) in the presence of PyNO (0.13 mmol) as an axial base with aqueous buffered NaOCl (12%, 2.75 mmol; pH=11.3) as an oxidant. The NaOCl was added in five equal portions at 0 C, and the reaction mass was stirred using a mechanical stirrer at 900+/-20 rpm. The course of the epoxidation reaction was monitored by GC with n-tridecane (0.1 mmol) as a GLC internal standard for product quantification. After completion of the reaction, the immobilized catalyst 1 was separated by centrifugation, washed thoroughly with dichloromethane, and dried in vacuum for subsequent catalytic runs.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2,2-Dimethyl-2H-chromene-6-carbonitrile, its application will become more common.

Reference:
Article; Roy, Tamal; Kureshy, Rukhsana I.; Khan, Noor-Ul H.; Abdi, Sayed H.R.; Sadhukhan, Arghya; Bajaj, Hari C.; Tetrahedron; vol. 68; 31; (2012); p. 6314 – 6322;,
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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 950596-58-4 as follows. SDS of cas: 950596-58-4

Example 3: Preparation of Erlotinib Trifluoro acetate2-Amino-4,5-bis(2-methoxyethoxy)benzonitrile (25 g) was charged into ethanol (350 ml) at 25C to 300C and stirred for 10 minutes to 15 minutes to get a clear solution. 3-ethynyl aniline (11.1 g) followed triethyl orthoformate (20.86g) was charged into reaction mass at 25C to 300C. Trifluoroacetic acid (3.8ml) was added slowly drop-wise into the reaction mixture at 250C to 300C and stirred for 30 minutes at 25C to 300C. Trifluoroacetic acid (3.8ml) was added slowly drop wise to reaction mixture at 250C to 300C and stirred for 30 minutes at 25C to 300C. Again, trifluoroacetic acid (3.8ml) was added slowly drop wise to reaction mixture at 250C to 300C and stirred for 30 minutes at 250C to 300C. The reaction mixture was refluxed for about 24 hours at 750C to 800C and Cooled to 25C to 300C. Ethanol (-150 ml) was recovered from the reaction mixture under vacuum at 55C to 600C. The solution obtained was Cooled to 25C to 300C and stirred for about 18 hours at 25C to 300C. The solid obtained was filtered, washed with ethanol (2x25ml) and dried under vacuum for about 18 hours at 400C to 450C to give erlotinib trifluoroacetate.Yield: 29.2 g. Purity: 97.35%

According to the analysis of related databases, 950596-58-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; RANBAXY LABORATORIES LIMITED; MURUGESAN, Balaguru; VEMPALI, Anandam; SATHYANARAYANA, Swargam; THAPER, Rajesh, Kumar; PRASAD, Mohan; WO2010/109443; (2010); A1;,
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Related Products of 134227-45-5, 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. 134227-45-5, name is 3,4,5-Trifluorobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows.

EXAMPLE 342A 3,5-difluoro-4-azepan-1-ylbenzonitrile The title compound was prepared using the procedure described in Example 325A except using 3,4,5-trifluorobenzonitrile and azepane instead of 3,4-difluorobenzonitrile and 8-aza-bicyclo[3.2.1]octane hydrochloride. 1H NMR (DMSO-d6) delta 7.62 (d, 2H), 3.39 (m, 4H), 1.73 (m, 4H), 1.61 (m, 4H); MS (ESI) m/z 237 (M+H)+.

The chemical industry reduces the impact on the environment during synthesis 3,4,5-Trifluorobenzonitrile. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Abbott Laboratories; US6933311; (2005); B2;,
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Adding a certain compound to certain chemical reactions, such as: 1194-65-6, name is 2,6-Dichlorobenzonitrile, 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 1194-65-6, Computed Properties of C7H3Cl2N

General procedure: A mixture of arylnitrile (2.0 mmol) and WR (1.07 g, 2.0 mmol) in 20 mL of dry toluene was refluxed for 8 h. Upon cooling to 90C 1.0 mL of water was added, the mixture was refluxed for another 1 h. After cooling to room temperature the reaction mixture was concentrated to ca. 5.0 mL and extracted with dichloromethane (20 mL x 3), the combined dichloromethane extracts were dried over MgSO4. The final residue was purified by silica gel chromatography (9 : 1 ethyl acetate /dichloromethane as eluent) to give the compounds 1a-1i.

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

Reference:
Article; Hua, Guoxiong; Du, Junyi; Slawin, Alexandra M. Z.; Woollins, J. Derek; Synlett; vol. 25; 15; (2014); p. 2189 – 2195;,
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