Tag: M.W=200-300

Application of 79463-77-7, 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. 79463-77-7, name is Diphenyl N-cyanocarbonimidate belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

EXAMPLE 343; 1-(1-{2-[4-(Benzothiazol-2-yloxy)-phenyl]-ethyl}-piperazine-4-yl)-3-cyano-2- phenyl-isourea; The 1- {2- [4- (BENZOTHIAZOL-2-YLOXY)-PHENYL]-ETHYL}-PIPERIDIN-4-YLAMINE hydrochloride was prepared from (1- {2- [4- (BENZOTHIAZOL-2-YLOXY)-PHENYL]-ETHYL}- piperidin-4-yl)-carbamic acid tert-butyl ester EXAMPLE 337 by removal of the Boc group according to EXAMPLE 266, step B. The free base was prepared by suspending 1- {2- [4- (BENZOTHIAZOL-2-YLOXY)-PHENYL]-ETHYL}-PIPERIDIN-4-YLAMINE hydrochloride (1.3 g, 3.3 MMOL) in CH2CI2 (20 mL) and washing with a solution of saturated NaHCO3 (20 mL). The organic layer was dried over NA2SO4, filtered and concentrated under reduced pressure to give 1.0 g (83% yield) of 1- {2- [4- (BENZOTHIAZOL-2-YLOXY)-PHENYL]-ETHYL}-PIPERIDIN-4-YLAMINE free base. A solution of 1- {2- [4- (BENZOTHIAZOL-2-YLOXY)-PHENYL]-ETHYL}-PIPERIDIN-4-YL AMINE (145 mg, 0.4 MMOL) in ethanol (5 mL) was treated with diphenyl cyanocarbodiimidate (319 mg. 1.34 MMOL) and heated to 80 C for 16h. The reaction was concentrated under reduced pressure and purified on Si02 (12 g, 0-10% [2 M NH3 CH30H]/CH2CI2) to give of the title compound (173 mg, 85% yield). MS (ESI) : exact mass calculated FOR C28H27N502S1, 496.2 ; m/z found, 498.4 [M+H].. H NMR (400 MHz, CDC13) : 7.73 (d, J = 8.7, 1 H), 7.66 (dd, J = 7.9, 0.7, 1 H), 7.45-7. 36 (m, 4H), 7.31-7. 24 (m, 5H), 7.08 (d, J = 7.8, 2H), 6.36 (br d, J = 6.5, 1 H), 3. 87-3. 76 (m, 1 H), 3.02 (br d, J = 11. 2, 2H), 2.83 (dd, J = 8.4, 7.3, 2H), 2.64 (DD, J = 8. 6,5. 4, 2H), 2.21 (t, J = 11. 1, 2H), 2.07 (d, J = 11.0, 2H), 1.76 (dd, J = 20.7, 10.4, 2H)

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, Diphenyl N-cyanocarbonimidate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; JANSSEN PHARMACEUTICA N.V.; WO2005/12296; (2005); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Application of 36282-26-5, 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 36282-26-5 as follows.

A 48 mL pressure vessel containing 2-bromo-4-fluorobenzonitrile (1.00 g, 5.00 mmol), 2-pyrrolidinone (0.46 mL, 6.00 mmol), Cs2CO3 (2.28 g, 7.0 mmol) and 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (xantphos) (0.231 g, 0.40 mmol) in dioxane (6 mL) was degassed with argon for 15 min. Pd2 dba3 was introduced and the reaction mixture heated at 105 C. for 48 h. The mixture was cooled, diluted with ethyl acetate or dioxane, and then filtered through Celite. The resulting mixture was concentrated in vacuo and subjected to column chromatography on silica gel with hexanes:ethyl acetate (3:7) gradient as the eluent to afford the title compound as a white solid (0.887 g, 87% yield): 1H NMR (400 MHz, CDCl3) ? ppm: 7.69 (1H, dd, J=5.8, 8.6 Hz), 7.22 (1H, dd, J=2.5, 9.6 Hz), 7.07 (1H, ddd, J 2.5, 7.6, 8.6 Hz), 3.96 (2H, t, J=7.0 Hz), 2.62 (2H, t, J=8.1 Hz), 2.30-2.22 (2H, m); LCMS (+ESI, M+H+) m/z 205.

According to the analysis of related databases, 36282-26-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Naidu, B. Narasimhulu; Banville, Jacques; Beaulieu, Francis; Connolly, Timothy P.; Krystal, Mark R.; Matiskella, John D.; Ouellet, Carl; Plamondon, Serge; Remillard, Roger; Sorenson, Margaret E.; Ueda, Yasutsugu; Walker, Michael A.; US2005/267105; (2005); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Related Products of 134604-07-2, 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. 134604-07-2 name is 1-Cyano-2-bromo-5-nitrobenzene, 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.

To a solution of isobutylboronic acid (5.89 g), 2-bromo-5-nitrobenzo nitrile (12.5 g) and Cs2C03 (35.9 g) in toluene (150 mL) and water (5 mL) stirred under nitrogen at room temperature was added solid PdCI2(dppf)- CH2CI2 adduct (2.248 g) in one charge. The reaction mixture was stirred at 100 C for 16 h. After cooling the reacion, the solvent was removed in vacuo. The residue was purified by column chromatography to give 2-(2-methylpropyl)-5-nitrobenzonitrile (D56) (11 g) as a light yellow oil. 5H (CDCI3, 400MHz): 1.00 (6H, d), 2.06 (1 H, m), 2.86 (2H, d), 7.52 (1 H, d), 8.37 (1 H, dd), 8.51 (1 H, d).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Cyano-2-bromo-5-nitrobenzene, and friends who are interested can also refer to it.

Reference:
Patent; GLAXO GROUP LIMITED; DENG, Guanghui; LIN, Xichen; REN, Feng; ZHAO, Baowei; WO2011/134280; (2011); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 1813-33-8, These common heterocyclic compound, 1813-33-8, name is 2-Chloro-4-(trifluoromethyl)benzonitrile, 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.

2-Chloro-4-(trifluoromethyl)benzonitrile (500 mg, 2.43 mmol) was diluted with toluene (3 mL), placed under nitrogen and cooled to -78C. DIBAL-H (4865 muL, 4.86 mmol) was added dropwise and the reaction was stirred for 1 hour. The reaction was warmed to 00C and acetic acid (2 mL) was added followed by 10 mL of water. After stirring for 2 hours, the reaction was extracted twice with ethyl acetate, washed with Rochelle’s salt, dried over MgSO4, filtered and concentrated. The material was purified using a biotage 25 cartridge running a gradient, 100%hexanes to 20%DCM/hexanes to yield 2-chloro-4-(trifluoromethyl)benzaldehyde (400 mg, 1.92 mmol, 78.8 % yield) as a clear oil.

The synthetic route of 1813-33-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ARRAY BIOPHARMA INC.; WO2009/158426; (2009); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Application of 52133-67-2,Some common heterocyclic compound, 52133-67-2, name is Ethyl 2-cyano-4,4-diethoxybutyrate, molecular formula is C11H19NO4, 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.

The compound (1) (30.0 g, 0.313 mol) was added to a suspension of sodium hydride (3.77 g, 0.617 mol) in dimethylformamide (100 ml) under nitrogen atmosphere below 20° C., and the mixture was stirred at room temperature for 30 min. To the resulting mixture was added 2-(3-chloropropyl)tetrahydro-2H-pyran (25.7 g, 0.144 mol) at the same temperature, then the mixture was stirred in an oil bath at 60° C. for 16 h. The reaction mixture is evaporated under reduced pressure to remove dimethylformamide, to the residue was added water and the mixture was extracted with toluene. After the toluene layer was washed with water, dried over magnesium sulfate, and evaporated to remove toluene, the excess of 2-(3-chloropropyl)tetrahydro-2H-pyran was distilled and removed in an oil bath at 150° C. under reduced pressure to give the compound (2) (41.5 g, 85.4percent). [00174] 1H NMR (CDCl3); 1.18 (3H, t, J=6.9 Hz), 1.21 (3H, t, J=6.9 Hz), 1.33 (3H, t, J=7.2 Hz), 1.52-2.04 (12H, m), 2.40 (1H, m), 3.39-3.86 (7H, m), 4.24 (2H, m), 4.57 (1H, m), 4.77 (1H, m).

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

Reference:
Patent; Shionogi & Co., Ltd.; US6756376; (2004); B1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Application of 1735-53-1, 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. 1735-53-1 name is 4-Bromo-3-(trifluoromethyl)benzonitrile, 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.

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 lambda/,lambda/-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 gave as an off-white solid the title compound (960 mg). MS (ES): C14H9F3O2 requires 266; found 265 (M-H+).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Bromo-3-(trifluoromethyl)benzonitrile, and friends who are interested can also refer to it.

Reference:
Patent; GLAXO GROUP LIMITED; WO2008/128951; (2008); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 57381-37-0, These common heterocyclic compound, 57381-37-0, name is 2-Bromo-5-chlorobenzonitrile, 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.

GammaAlpha1 l-(2-Bromo-5-chloro-phenyl)cvclopropanamine To a stirred solution of 2-bromo-5-chlorobenzonitrile (10 g, 46 mmol) and Ti(Oi-Pr)4 (16.64 mL, 55 mmol) in THF (200 mL) at -78C was added EtMgBr (138 mL, 138 mmol) drop wise. The reaction mixture was allowed to warm up to room temperature and stirred for 2 hours. BF3-Et20 (17.2 mL) was added, and the solution was stirred for another 16 hours before it was quenched with aq. HCl solution and washed with EtOAc. The aqueous phase was adjusted to pH – 10 with aq. NaOH solution, and exacted with EtOAc three times. The combined organic layers were concentrated to give a crude product which was purified by silica gel flash chromatography to afford title compound (2 g, 17.6%). MS: 246.7 (M+H+, 1C1) as oil.

The synthetic route of 57381-37-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; AEBI, Johannes; AMREIN, Kurt E.; CHEN, Junli; HORNSPERGER, Benoit; KUHN, Bernd; LIU, Yongfu; LI, Dongbo; MAERKI, Hans Peter; MARTIN, Rainer E.; MAYWEG, Alexander; TAN, Xuefei; WU, Jun; YU, Jianhua; (109 pag.)WO2016/55394; (2016); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Application of 13544-06-4, 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 13544-06-4 as follows.

Step 1. Preparation of 2-Methyl-2-(2-nitro-4- trifluoromethyl-phenyl) -propionitrile; The title compound was synthesized according to a method described in Prasad, G. , J. Org. Chem. 1991,56, 7188-7190. To a yellow-brown solution of (2-Nitro-4-trifluoromethyl- phenyl) -acetonitrile (2.5 g, 11 mmol), 18-crown-6 (0.72 g, 2.7 mmol), and methyl iodide (1.5 mL, 24 mmol) in dry THF under nitrogen at-78 degrees C was added potassium tert- butoxide (2.7 g, 24 mmol) in one portion. The reaction immediately became a deep purple color. The reaction was allowed to stir for 2 h at-78 degrees C, and was then warmed to ambient temperature. A water-cooled reflux condenser was added and the solution heated to 70 degrees C under nitrogen. Over 40 minutes, the color changed from dark purple to cloudy gray. The mixture was allowed to cool to room temperature, and was concentrated in vacuo. The resulting material was partitioned between 1 N HCI and EtOAc. The organic layer was washed once with brine, dried over sodium sulfate, filtered, and concentrated in vacuo to give a brown oil which was judged to be primarily monoalkylated nitrile. The crude material was resubjected to the reaction conditions using 18-crown-6 (0.72 mg, 2.7 mmol), methyl iodide (0.75 mL, 12 mmol), and potassium tert- butoxide (1.4 g, 12 mmol) as before, with the following modifications: the reaction was allowed to stir only 10 min. at-78 degrees C before being warmed to room temperature, and the reaction vessel was sealed and heated to 70 degrees C for 2 h. Upon cooling to room temperature, the reaction was quenched and worked up as before. Purification by flash chromatography afforded the desired product as a light brown solid. MS (M+H) + = 259; Calc’d 258.20 for C11H9F3N2O2.

According to the analysis of related databases, 13544-06-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; AMGEN INC.; WO2005/113494; (2005); A2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Reference of 32446-66-5, The chemical industry reduces the impact on the environment during synthesis 32446-66-5, name is 4,4′-Dicyanobenzophenone, I believe this compound will play a more active role in future production and life.

EXAMPLE 2; PREPARATION OF 4,4′-(HYDROXY METHYLENE)BISBENZONITRILE OF FORMULA IV 200 ml of methanol was taken into a round bottom flask followed by charging 40 g of 4,4-dicyanobenzophenone and stirring for about 10 minutes. 3.28 g of sodium borohydride was added slowly to the above suspension at 0-5 C. followed by stirring at 25-30 C. for 30 minutes, and the formed solution was neutralized with 25 ml of glacial acetic acid to a pH of 6.33. 800 ml of water was charged to the above-neutralized suspension and stirred for 30 minutes, and the precipitate was filtered, washed with 400 ml of water and finally subjected to drying at 55-60 C. under vacuum for 4 hours to afford 40 g of title compound having a purity by HPLC of 99.36% and a water content by the Karl Fischer method of 0.27%.

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, 4,4′-Dicyanobenzophenone, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Palle, Venkata Raghavendra Acharyulu; Kalaria, Ashok Jerambhai; Shelke, Sandip Ashok; US2007/100149; (2007); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 97165-77-0, name is 3,5-Dibromobenzonitrile, 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 97165-77-0, name: 3,5-Dibromobenzonitrile

15.0 g (52.2 mmol) of (9-phenyl-9H-carbazol-3-yl)boronic acid, 27.3 g (104 mmol) of 3,5-dibromobenzonitrile, 3.02 g (2.61 mmol) of tetrakistriphenylphosphine palladium(0) (Pd(PPh3)4), and 18.1 g (131 mmol) of potassium carbonate were added to a solution of 120 ml of THF and 60 ml of water and mixed. The mixed solution was then stirred under reflux. After completion of the reaction, the resulting reaction solution was cooled to room temperature, and an extraction process was performed thereon to remove an aqueous solution layer therefrom. The obtained residue was filtered through silica gel under reduced pressure, and the filtrate was concentrated under reduced pressure. The resulting residue was then separated by silica gel column chromatography, thereby providing 11.9 g (yield: 54%) of a desired compound, Intermediate (R). LC-Mass (cald: 422.04 g/mol, found: M+1=423 g/mol).

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, 3,5-Dibromobenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SAMSUNG ELECTRONICS CO., LTD.; Samsung SDI Co., Ltd.; JUNG, Yongsik; HUH, Dalho; SON, Jhunmo; KWON, Eunsuk; KIM, Sangmo; LEE, Saeyoun; JEON, Soonok; CHUNG, Yeonsook; KIM, Jongsoo; IHN, Sooghang; (219 pag.)US2017/369439; (2017); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts