Tag: M.W=100-200

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 3598-13-8 as follows. Formula: C8H6ClNO

Starting Material 7: (6-Nitro-2-phenyl-benzoxazole-7-yl)-acetonitrile STR24 To a stirred suspension of potassium tert-butoxide (701 mg, 6.25 mmol) in DMF (6 mL) was added a solution of 6-nitro-2-phenyl-benzoxazole (500 mg, 2.08 mmol)(Starting Material 3) and 4-chlorophenoxyacetonitrile (366 mg, 2.19 mmol) (Aldrich) in DMF (20 mL) at -30 C. The mixture was then stirred at this temperature for 3 h and neutralized with aqueous 1N hydrochloric acid solution at 0 C. The aqueous layer was extracted with ethyl acetate. The combined extracts were dried over anhydrous magnesium sulfate and concentrated in vacuo to give a yellow solid. The crude product was purified by silica gel chromatography. (Yield 520 mg, 90%).

According to the analysis of related databases, 3598-13-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Hoffmann-La Roche Inc.; US6153634; (2000); A;,
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Synthetic Route of 6621-59-6, 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. 6621-59-6, name is 6-Bromohexanenitrile, This compound has unique chemical properties. The synthetic route is as follows.

Step a: A 3% solution of the respective iminoalditol in dry DMF was stirred with omega-bromohexanoic nitrile (2 equiv.) in the presence OfNa2CO3 (1.3 equiv.) at 40 0C for 72 h. Removal of the solvent and chromatographic purification (CHClj/MeOH 1 :1) gave the respective reaction products in yields ranging between 45 and 90 %.

The chemical industry reduces the impact on the environment during synthesis 6-Bromohexanenitrile. I believe this compound will play a more active role in future production and life.

Reference:
Patent; TECHNISCHE UNIVERSITAeT GRAZ; WO2006/100586; (2006); A1;,
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Application of 57381-34-7, 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. 57381-34-7, name is 5-Chloro-2-fluorobenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a stirred 00C solution of 1,1,1,3,3,3-Hexamethyldisilazane (63 mL, 0.3 mol) in dry diethyl ether was added dropwise n-Butyl lithium (2M in hexanes, 150 mL, 0.3 mol). A white suspension formed, to which was added 2-Fluoro-5-chlorobenzonitrile (21.0 g, 0.14 mol) over 5 min. The resultant orange mixture was allowed to warm to r.t. and stirred for 2h. The mixture was cooled to 00C and the reaction quenched by the addition of 3M HCl (aq.) (240 mL). The mixture was stirred for 0.5h before water (600 mL) was added. The purple organic layer was discarded and the aqueous layer basified to pH 14 with satd. NaOH (aq.). The aqueous layer was extracted with CHCI3 (5×100 mL) and the organic extracts dried over Na2SO4. Evaporation yielded the desired product as a yellow solid (16.2g, 73% yield).

The synthetic route of 5-Chloro-2-fluorobenzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TIBOTEC PHARMACEUTICALS LTD.; WO2008/40778; (2008); A2;,
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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. 29509-06-6, name is 4-Methyl-3-oxopentanenitrile, This compound has unique chemical properties. The synthetic route is as follows., name: 4-Methyl-3-oxopentanenitrile

General procedure: A mixture of 4-methyl-3-oxopentanenitrile 10i or 10ii (1.5eq), aldehyde 6(a-m) (1.0 eq), urea (1.5 eq) and CuCl (0.01eq) in MeOH containing concentrated H2SO4 (0.62 eq) wasstirred at reflux temperature for 3-5 days. After the reactionwas deemed complete by TLC, methanol was removed byconcentration in vacuo. The precipitated solid was extractedin dichloromethane. The dichloromethane layer was washedwithwater twice so as to removewater soluble impurities. Theorganic layerwas concentrated again to dryness in vacuo. Thecrude residue was purified by silica gel column chromatographyusing ethyl acetate: hexanes to give pyrimidine compound11(a-m).

According to the analysis of related databases, 29509-06-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Pachore, Sharad S; Ambhaikar, Narendra B; Siddaiah, Vidavalur; Khobare, Sandip R; Kumar, Sarvesh; Dahanukar, Vilas H; Kumar, U K Syam; Journal of Chemical Sciences; vol. 130; 6; (2018);,
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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. 64248-62-0, name is 3,4-Difluorobenzonitrile, A new synthetic method of this compound is introduced below., Application In Synthesis of 3,4-Difluorobenzonitrile

In N, N-dimethylformamide (DMF, 40 mL)(R) -2- (4-hydroxyphenoxy) propionic acid (3.03 g, 0.02 mol) was added,Potassium carbonate (5.52 g, 0.04 mol) was added in portions,Heating to 70 C to 80 C,Continuous stirring 1h,(2.38 g, 0.02 mol) of 3,4-difluorobenzonitrile was added in portions,Continue to stir the reaction 6 ~ 7h.Cooled to room temperature,Poured into ice water (250 mL)Slowly add dilute hydrochloric acid,Adjusted to pH 4 to 5,Filter,Washed,(R) -2- [4- (4-cyano-2-fluorophenoxy) phenoxy] propionic acid as a gray solid in (R) -2- [4- (4-cyanide) Yl-2-fluorophenoxy) phenoxy] propionic acid3.26g,Yield 65.7%.

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; China Three Gorges University; Liu, Qixing; Zhou, Haifeng; Zhu, Rui; Chen, Lei; (9 pag.)CN106632007; (2017); A;,
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Synthetic Route of 34667-88-4, 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. 34667-88-4 name is 2-Fluoro-4-nitrobenzonitrile, 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.

Example 69; Synthesis of 2-(pyridin-2-ylamino)-lH-benzimidazole-5-carboxylic acid (3 -amino- IH- indazol-6-yl)-amideTo a solution of 2-fluoro-4-nitrobenzonitrile (10 mmol) in isopropanol (30 mL) was added aqueous hydrazine (4 mL). The resulting solution was heated at 800C for 12 h. The reaction mixture was then concentrated, water (30 mL) was added, and the solution was extracted with ethyl acetate (2×25 mL). The combined organics were washed with water (30 mL) and brine (30 mL) and dried over anhydrous sodium sulfate. The volatiles were removed in vacuo yielding 3-amino-6-nitroindazole as an orange solid, which was utilized for further transformation without further purification.The nitro compound from above was hydrogenated, following general procedure F, to yield 3,6-diaminoindazole.2-Isothiocyanatopyridine (4 mmol), prepared from 2-aminopyridine employing general procedure A, was reacted with methyl 3,4-diaminobenzoate as described in general procedure B to afford 2-(pyridin-2-ylamino)-lH-benzirnidazole-S-carboxylic acid methyl ester. This ester was hydrolyzed, following general procedure C, to obtain 2-(pyridin-2- ylamino)-lH-benzimidazole-5-carboxylic acid.The cafboxylic acid (0.5 mmol) from above was coupled with aforementioned 3,6- diaminoindazole (0.5 mmol) using HBTU as described in general procedure D to afford 2- (pyridin-2-ylamino)-lH-benzimidazole-5-carboxylic acid (3-amino-lH-indazol-6-yl)-amide. MS: m/z 385 (M+H)+.

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

Reference:
Patent; TRANSTECH PHARMA, INC.; WO2007/95124; (2007); A2;,
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Related Products of 5653-62-3, The chemical industry reduces the impact on the environment during synthesis 5653-62-3, name is 2,3-Dimethoxybenzonitrile, I believe this compound will play a more active role in future production and life.

Preparation of 2, 3-dihydroxy benzoic acid form 2, 3-dimethoxy benzoic acid To a stirred solution of 2, 3-dimethoxy benzoic acid (lOOg; 0.549 mol) in dichloromethane (500 mL) and catalytic amount of DMF (~2 mL) at a temperature about 30-35C, thionyl chloride (130.6g ; 1.102 mol) was added and stirred for a period of two hours. Reaction was monitored by TLC for completion of the starting material (NMT- 5%).If reaction not completed added thionyl chloride (9.8 g; 0.823 mol). Upon completion of reaction, the reaction mass was quenched in to the -5C chilled aqueous ammonia (580 mL) solution at a temperature below 15C under stirring. The reaction mass was stirred at temperature 30-35C over a period of 30 min. The separated organic fraction was concentrated under atmospheric distillation at below 50C, charged toluene (100 ml) and co-distilled until the reaction mass moisture content become less than 0.5 %. The obtained benzamide compound was dissolved in toluene (500 mL) at temperature about 30-35C.To the reaction mass was added POCl3 (126.3 g; 0.824 mol).The temperature of the reaction mass was raised to 80-85C and maintained over a period of 1 -2 hours for the completion of the reaction (Progress of the reaction was monitored by HPLC until the benzamide NMT 1.0 %). If the reaction was not completed, added second lot of POCl3 (lO.lg; 0.06 mol) at 30-35C. The reaction mass was cooled to a temperature about 30-35C upon completion of the reaction. The reaction mixture was added to cold water (1000 mL) at 0-5C.The organic fraction was separated and washed with 8% sodium bicarbonate solution. The organic fraction was separated and azeotropic distilled at 110-115C (until moisture content NMT 0.2 %), after reaching moisture content to normal limit cooled the reaction mass temperature to 40C and distilled reaction mass volume becomes ~3 volumes under vacuum at a temperature 40-50C.After distillation cooled the reaction mass temperature to 30-35C. In another RB flask charged toluene (160 ml), triethyl amine (199.7 g; 1.977 mol) at 30-35C and stirred for 10 min. charged aluminum chloride (52.7 g 5; 1.977 mol) in five lots with the gap of 10 min between each lot addition (addition of aluminum chloride may raise the temperature to 45-50C). The reaction mass temperature was raised to about 70-75 C and added above reaction mass (methoxy compound) for 30 min. maintained the reaction mass at 70-75C for 8 hr. Progress of the reaction was monitored by HPLC (until the 2,3-dimethoxybenzonitrile content 0.25 % and 3-methoxy-2-hydroxybenzonitrile content 0.2 %). If reaction was not completed added second lot of triethyl amine (27.7 g; 0.27 mol) and aluminum chloride (36.6 g; 0.27 mol).Upon completion of the reaction, the reaction mixture was cooled to 30-35C and quenched with chilled aqueous HC1 (prepared by addition of water (500 ml) and Cone. HC1 (500 ml)) at 15C. Stirred reaction mass at 25-30C for about 30 min, filtered the obtained solids and separated aqueous and organic layers. Charged MIBK (320 ml) to the solids and charged above aqueous layer, filtered through celite and separated aqueous and organic layers. To the aqueous layer given MIBK (320+160 ml) extractions. To the combined organic layer given 20% sodium chloride solution washing, organic layer was azeotropic distilled at 110C to remove the water (moisture content NMT 0.2 %).Cooled the reaction mass temperature to 30C and filtered through 0.45 micron / 1 micron filter. To the filterate charged 1% EDTA (400 ml), stirred for 30 min and filtered through 10 micron cloth. The organic fraction was separated and distilled off to obtain the residue. The residue was treated with dichloromethane (400 ml) and the solid obtained was filtered and dried under vacuum over 6 hr at 60-65C to obtain the title compound 2, 3-dihydroxy benzonitrile. (56g, yield 75.4%) Purity by HPLC 99.81 %; Impurity A: 0.05% Impurity B: 0.07 %

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, 2,3-Dimethoxybenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; LAURUS LABS PRIVATE LIMITED; MUDDULURU, Hari Krishna; MADHAVARAM, Shankar; WO2014/13512; (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. 628-20-6, name is 4-Chlorobutyronitrile, A new synthetic method of this compound is introduced below., SDS of cas: 628-20-6

To a solution of 2-bromo-4-nitrophenol (100 g, 0.46 mol) and potassium carbonate (190 g, 1.37 mol) in DMF (1.20 L) was added 4-chlorobutanenitrile (52.1 mL, 550 mmol) and heated at 65 C for 2 h. Ice water was added and the mixture was extracted with ethyl acetate. The organic layer was separated and washed with water and brine, dried over anhydrous sodium sulphate, concentrated and purified by columnchromatography (silica gel, 1:1 ethyl acetate in petroleum ether) to obtain the title compound. Yield: 101 g (77 %); 1H NMR (300 MHz, DMSO-d6): O 2.06-2.17 (m, 2H, -CH2), 2.69 (t, J = 6.0 Hz, 2H, CH2), 4.28 (t, J = 6.0 Hz, 2H, -OCH2), 7.35 (d, J = 9.3 Hz, 1H, Ar), 8.26 (dd, J = 2.7 Hz, 9.3 Hz, 1 H, Ar), 8.43 (d, J = 2.7 Hz, 1 H, Ar); MS: mlz 285.0 (M).

The synthetic route of 628-20-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PIRAMAL ENTERPRISES LIMITED; SHARMA, Rajiv; KULKARNI, Sarang; KULKARNI, Mahesh; MUKHERJEE, Sumit; YADAV, Rajesh, Kumar; AGARWAL, Madhavi; BURUDKAR, Sandeep; SATHE, Santosh; WO2015/49629; (2015); A1;,
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3215-64-3, name is 2-(2,6-Dichlorophenyl)acetonitrile, 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. Recommanded Product: 3215-64-3

EXAMPLE 1 2,7-Diamino-6-(2,6-dichlorophenyl)-pyrido[2,3-d]pyrimidine (Prepared by the method of U.S. Pat. No. 3,534,039). To a solution of sodium 2-ethoxyethoxide prepared from 0.14 g of sodium and 60 mL of 2-ethoxyethanol was added 2.07 g of 2,4-diamino-5-pyrimidinecarboxaldehyde and 2.79 g of 2,6-dichlorophenylacetonitrile. The mixture is heated at reflux for 4 hours, cooled, and the insoluble product washed with diethylether to give 2,7-diamino-6-(2,6-dichlorophenyl)-pyrido[2,3-d]pyrimidine, mp 325-332 C. (MS).

The synthetic route of 3215-64-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Blankley; Clifton John; Doherty; Annette Marian; Hamby; James Marino; Panek; Robert Lee; Schroeder; Mel Conrad; Showalter; Howard Daniel Hollis; Connolly; Cleo; US5733913; (1998); A;,
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Application of 622-75-3, A common heterocyclic compound, 622-75-3, name is 2,2′-(1,4-Phenylene)diacetonitrile, molecular formula is C10H8N2, 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.

Scheme I, step A: Into a 250 ML single neck flask was placed sodium hydride 60% (5.4 g, 134.5 mmol) in DMF (100 ML) at -15 C. 1,4-Phenyldiacetonitrile (5 g, 32 mmol) was added to the solution slowly and the mixture was stirred for 1/2 hour.The reaction mixture was treated with methyl iodide (8.4 ML, 134.5 mmol).The mixture was warmed up to RT while stirring for 12 hours.The reaction mixture was poured into ice water (600 ML) until product was precipitated out.The precipitate was filtered off and washed with cold water to provide the intermediate title compound, 2-[4-(1-cyano-isopropyl)phenyl]-2-methylpropanenitrile, (6.8 g, 100%) as a white solid.Electron spray M.S. 230 (M*+H2O).

The synthetic route of 622-75-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Knobelsdorf, James Allen; Shepherd, Timothy Alan; Tromiczak, Eric George; Zarrinmayeh, Hamideh; Zimmerman, Dennis Michael; US2003/229102; (2003); A1;,
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