Month: April 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. 935-02-4, name is 3-Phenylpropiolonitrile, A new synthetic method of this compound is introduced below., Quality Control of 3-Phenylpropiolonitrile

General procedure: To a solution of cyanoacetylenes (0.4mmol) with N-tosylimines (0.2 mmol) in toluene (2 mL) was added Ph3P (0.2mmol). The mixture was then stirred at 110 C for 36 h in a reaction flask. Thenthe solvent was removed in vacuo and residue was purified by columnchromatography on silica gel to give the desired annulation product.

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:
Article; Zhang, Jinfeng; Zhang, Qi; Ji, Xin; Meng, Ling-Guo; Synlett; vol. 30; 9; (2019); p. 1095 – 1099;,
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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. 874-97-5, name is 3-Cyanobenzyl alcohol, A new synthetic method of this compound is introduced below., SDS of cas: 874-97-5

1-methyl-3-[(3-cyanophenylmethoxy)methyl]-2(1H)-pyridinone, 12a. To a 0 C suspension of sodium hydride (41 mg, 60% suspension in mineral oil, 1.01 mmol), in THF (3 mL) was added 3-cyanobenzyl alcohol (100 mg, 0.75 mmol). After the mixture was stirred for 1 h at 0 C, 3-(bromomethyl)-1-methylpyridin-2(1H)-one3 (152 mg, 0.75 mmol) in THF (3mL) was added dropwise. The reaction mixture was slowly allowed to warm to room temperature and stirred for additional 3 h before diluting with saturated aqueous ammonium chloride. After extraction with ethyl acetate, the combined organics were washed with brine, concentrated invacuo and purified by column chromatography using 5:95 MeOH/DCM to get title compound as a colorless soild (136 mg, 71 %).

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:
Article; Khatri, Buddha B.; Vrubliauskas, Darius; Sieburth, Scott McN.; Tetrahedron Letters; vol. 56; 30; (2015); p. 4520 – 4522;,
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Synthetic Route of 36282-26-5,Some common heterocyclic compound, 36282-26-5, name is 2-Bromo-4-fluorobenzonitrile, molecular formula is C7H3BrFN, 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.

Pyrrole (2, 6, 6-trimethyltetrahydroindol-4-one) (1.5 g, 8.5 mmol) and 2-bromo-4-fluorobenzonitrile (1.69 g, 8.5 mmol) were dissolved in anhydrous DMF (50 mL) . To this NaH (95%, 408 mg, 17.0 mmol) was added and stirred at 50 0C for 1 h. The reaction mixture was cooled to RT and H2O was added. Product crashed out of solution and was filtered and dried under vacuo (2.4 g, 79%). (100% clean by LCMS, product M+H = 357).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Bromo-4-fluorobenzonitrile, its application will become more common.

Reference:
Patent; SERENEX, INC.; WO2006/91963; (2006); 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. 6136-93-2, name is 2,2-Diethoxyacetonitrile, A new synthetic method of this compound is introduced below., Application In Synthesis of 2,2-Diethoxyacetonitrile

EXAMPLE II Preparation of 2-Ethylidene-6-methyl-cis-3-heptenal A solution of 5.40 g of isobutylacetylene in 50 ml of diethyl ether is treated with 30 ml of 2.2 N n-butyl-lithium in hexane at -20 C., and after several minutes the resulting solution is treated with 8.50 g of diethoxyacetonitrile and then warmed slowly to room temperature. After about 1.5 hours the dark mixture is cooled and brought to a pH of about 2 with ten percent sulfuric acid. The layers are then separated and the organic layer is washed successively with water and saturated aqueous sodium bicarbonate solution and then dried over sodium sulfate. Evaporation of the solvent provides 4.6 g of a dark oil, shown by IR and NMR to contain 1,1-diethoxy-6-methyl-3-heptyn-2-one.

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; International Flavors & Fragrances Inc.; US4045497; (1977); A;,
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Application of 327056-73-5, 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 327056-73-5 as follows.

Preparation 23: 3-Chloro-5-[2-methoxy-5-(trifluoromethoxy)phenoxylbenzonitrile To a solution of the compound of preparation 22 (270mg, 1.30mmol) in DMF (5mL) was added cesium carbonate (551 mg, 1.69mmol) at rt. The reaction mixture was stirred for 5 min and the compound from preparation 37 (1.69mmol, 263mg) was added. The mixture was then heated at 85 0C for 3h and cooled to rt. Brine was added followed by water and the aqueous phase was extracted with EtOAc. The organic extract was dried over magnesium sulfate and the solvent was concentrated in vacuo to afford the crude residue. Purification by column chromatography on silica gel using pentane:ethyl acetate (88:12) as eluent afforded the desired product, 360mg (81%). LRMS (APCI) 343 [MH”]; Preparations 2-7 To a solution of the appropriate phenol (1 eq.) in DMF (0.8 to 1.85mLmmor1) was added cesium carbonate (1-2 eq.) at rt and the solution was stirred for 10 min. The compound from preparation 37 (1.3 eq.) was then added and the reaction mixture was heated at 85 C for up to 48h (reactions monitored by tic). The solvent was removed in vacuo and the residue was partitioned between EtOAc (5OmL) and brine (5OmL). The phases were separated and the aqueous layer extracted with EtOAc (1 OmL). The organic extracts were combined, dried over magnesium sulfate and the solvent was removed in vacuo to give the crude residue. Purification by column chromatography on silica gel using pentane:ethyl acetate as eluent afforded the desired product. EPO A = 4-hydroxy-3-methoxybenzonitrile prepared as described in Synthesis 1989(6); 451-2. The product was isolated after trituration with methanol.B = potassium carbonate was used in place of cesium carbonate.

According to the analysis of related databases, 327056-73-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PFIZER LIMITED; WO2006/67587; (2006); A2;,
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Adding a certain compound to certain chemical reactions, such as: 127946-77-4, name is 1-Amino-1-cyclopropanecarbonitrile hydrochloride, 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 127946-77-4, Formula: C4H7ClN2

General procedure: Thecarboxylic acid intermediate (1 eq) was dissolved into DCM (1-3 mL/1 mmol) andcooled to 0C. HATU (2 eq) and DIPEA (4 eq) were then added and reaction wasstirred at 0C for 5-10 min. 2-aminoacetonitrile bisulfate (2-5 eq) was thenadded and reaction was allowed to warm and stir at room temperature overnight.Upon completion, the reaction was poured into a 1N HCl(aq) solutionand extracted with DCM. The combined organic layers were washed with 1N HCl(aq)solution, NaHCO3(aq) solution, and brine then dried over MgSO4,and concentrated. The crude material was purified by flash chromatography(0-100% EtOAc:Hexane gradient). 15-89%

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Amino-1-cyclopropanecarbonitrile hydrochloride, and friends who are interested can also refer to it.

Reference:
Article; Zwicker, Jeffery D.; Diaz, Nicolas A.; Guerra, Alfredo J.; Kirchhoff, Paul D.; Wen, Bo; Sun, Duxin; Carruthers, Vern B.; Larsen, Scott D.; Bioorganic and Medicinal Chemistry Letters; vol. 28; 10; (2018); p. 1972 – 1980;,
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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. 57418-97-0, name is 4-Bromo-3-chlorobenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 4-Bromo-3-chlorobenzonitrile

Step a. A mixture of 4-bromo-3-chlorobenzonitrile (150 mg, 0.69 mmol), tert-butyl 4-(4,4,5,5- tetramethyl-l,3,2-dioxaborolan-2-yl)isoindoline-2-carboxylate (Intermediate 2, 287 mg, 0.83 mmol) and K2C03 (238 mg, 1.73 mmol) in 1,4-dioxane (5.4 ml) and water (0.6 ml) was degassed by nitrogen bubbling for 5 min. Pd(PPh3)4 (79 mg, 0.069 mmol) was then added. The mixture was heated at reflux for 18 h and then cooled to rt. The mixture was filtered on a silica pad and washed with EtOAc (200 ml). The filtrate was evaporated under reduced pressure. The residue (500 mg) was dissolved in DCM and purified by flash chromatography on silica gel using hexane/EtOAc (90: 10) to give tert-butyl 4- (2-chloro-4-cyanophenyl)isoindoline-2-carboxylate (242 mg, 99%) as a bright yellow solid. LCMS: Method I, 3.66 min, MS: ES+ 355, 357; NMR (400 MHz, CDC13) delta ppm 7.80 (m, 1H), 7.63 (m, 1H), 7.33-7.41 (m, 3 H), 7.14 (m, 1H), 4.77 (m, 2 H), 4.56 (m, 2 H), 1.49 (m, 9 H).

The synthetic route of 57418-97-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MISSION THERAPEUTICS LIMITED; GIBSON, Karl Richard; JONES, Alison; KEMP, Mark Ian; MADIN, Andrew; STOCKLEY, Martin Lee; WHITLOCK, Gavin Alistair; WOODROW, Michael D; (241 pag.)WO2017/158388; (2017); 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 179897-89-3 as follows. Formula: C7H3BrFN

Add 5-bromo-2-fluoro-benzonitrile (0.5 g, 2.5 mmol), benzophenone imine (0.543 g, 3 mmol), (+-)-2,2′-bis(diphenylphosphino)-1,1′-binaphthalene (BINAP, 60 mg, 0.1 mmol), tris(dibenzylideneacetone)dipalladium [Pd2(dba)3, 50 mg, 0.05 mmol], and Cs2CO3 (1.6 g, 4.9 mmol) in 1,4-dioxane (20 mL). Stir the reaction under N2 at 110 C. for 16 hrs. Cool to room temperature, filter the solid, and concentrate the filtrate to give the crude product. Purification by chromatography (silica gel, EtOAc_PE=1:3) affords the title compound (0.78 g, 99%). MS: (M+1): 301.

According to the analysis of related databases, 179897-89-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Zhang, Deyi; Zhang, Ruihao; Zhong, Boyu; Shih, Chuan; US2015/197511; (2015); A1;,
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Adding a certain compound to certain chemical reactions, such as: 35704-19-9, name is N-(4-Cyanophenyl)acetamide, 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 35704-19-9, name: N-(4-Cyanophenyl)acetamide

STR105 To a solution of 4-acetamidobenzonitrile (9.40 g) in concentrated sulfuric acid (80 ml) was added potassium nitrate in small portions at a temperature not exceeding 10 C. The reaction mixture was stirred at 5-10 C. for 2 hours and poured into ice-water and the separated crystals were collected by suction. To the crystals was added 4N hydrochloric acid (100 ml) and the mixture was refluxed for 2 hours. After cooling to room temperature, the crystals were recovered by filtration, washed with water and dried under reduced pressure to give 7.22 g of 4-amino-3-nitrobenzonitrile. Mass spectrum (m/z): 163 (M+). NMR (DMSO-d6) delta: 7.00-7.14 (1H, m), 7.60-8.10 (3H, m), 8.40-8.60 (1H, m).

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, N-(4-Cyanophenyl)acetamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Yamanouchi Pharmaceutical Co., Ltd.; US5162318; (1992); A;,
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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. 3672-47-7, name is 3-(4-Methoxyphenyl)-3-oxopropanenitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. category: nitriles-buliding-blocks

According to the method described in Embodiment 1,Add 1d (0.5mmol, 88mg) and 2f (1.25mmol) to a 15mL pressure tube.190mg),Dichloro (pentamethylcyclopentadienyl yl)rhodium (III) dimer (0.025mmol, 15mg), copper acetate monohydrate (1mmol, 200mg),Cesium acetate (0.25mmol, 48mg) and 1,2-dichloroethane (2 mL), under an air atmosphere and the reaction tube was sealed, and then placed in an oil bath at 80 reaction was stirred 14h. The reaction was quenched with 10mL of water was added, extracted with ethyl acetate (10mL ¡Á 3), then the organic phase was washed with water and saturated brine successively, dried over anhydrous sodium sulfate. Filtration, rotary evaporation, separating silica gel column (petroleum ether / ethyl acetate = 5/1) to give a yellow solid 3df (136mg, 70%).

The synthetic route of 3672-47-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Henan Normal University; Fan Xuesen; Guo Chenhao; Zhang Beibei; Zhang Xinying; Li Bin; (17 pag.)CN108997298; (2018); A;,
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