Tag: M.W=100-200

Reference of 4640-67-9, 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. 4640-67-9, name is 3-(4-Fluorophenyl)-3-oxopropanenitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

The polyphosphoric acid 300g adding 1L the reaction bottle heating to 120 C, adding compound 3 (100g, 0.61 muM), ring octanone (161.7g, 1 . 28 muM), add 1 – ethyl -3 – methyl imidazole four fluoroborates (30g, 0.15 muM) reaction 1h, after the reaction, by adding 300 ml ice water, 1000 ml ethyl acetate, stirring 30min, then adding NaOH in and to the neutral, separating the organic layer, the organic layer dried with magnesium sulfate, filtered, the filtrate is concentrated to dry, adding isopropanol (300 ml) reflux 30min stirred and cooled to 0 C after, stirring 1h, filtered and dried to obtain white solid 4 (120g, 99.8%),

The synthetic route of 3-(4-Fluorophenyl)-3-oxopropanenitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Nanjing Yuan Shu Pharmaceutical Technology Co., Ltd; Jin, Guofan; Jin, Feng; Wang, Kai; Zheng, Bing; Fu, Yan; Jin, Zaishan; Liu, Jiongzhe; (6 pag.)CN106045909; (2016); A;,
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Related Products of 51762-67-5, 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. 51762-67-5, name is 3-Nitrophthalonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

3-nitrophthalonitrile (20 mmol) and 2,4,6-tris(dimethylaminomethyl)-phenol (20-70 mmol, preferably 60 mmol) as reactants, dimethyl sulfoxide (40) -200 mL, preferably 140 mL, is the solvent, and the reaction is stirred at room temperature ~ 60C (preferably 60C) for 24 to 72 hours in the presence of potassium carbonate (30 to 90 mmol, preferably 80 mmol) and nitrogen, and monitored by thin layer chromatography. Should be filtered to remove the reaction mixture was insoluble potassium carbonate, evaporated to dryness, adding 50 ~ 100mL of chloroform, stirred and filtered to remove insolubles, evaporated to dryness, add 50 ~ 100mL of water to the solid and 15 ~ 45mL HCl (1mol/L) stirred and filtered to remove insolubles. NaOH was added to the filtrate. The solids were precipitated and filtered. The solids were washed with water and dried in vacuo at 50C to give 3-(2,4,6-tris(dimethylamino). Methyl)-phenoxy)phthalonitrile, yield 64%.

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-Nitrophthalonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Fuzhou University; Huang Jiandong; Peng Xiaohui; Zheng Bingde; (25 pag.)CN107915740; (2018); A;,
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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. 16588-02-6, name is 2-Chloro-5-nitrobenzonitrile, A new synthetic method of this compound is introduced below., Recommanded Product: 16588-02-6

3-Cyano-4-chloroaniline. 2-Chloro-5-nitrobenzonitrile (25 g, 137 mmol) was dissolved in ethanol (275 mL). Stannous chloride dihydrate (154.5 g, 0.685 M) was added and the mixture stirred at 70 C. for 30 min. The mixture was then cooled to room temperature and poured into crushed ice. The mixture was made basic with solid sodium hydroxide. This mixture was extracted with ethyl acetate (3*100 mL). The extracts were combined, washed with brine, dried (MgSO4), concentrated and the residue dried under vacuum and recrystallized from ethanol to yield light brown needles (10.6 g, 51%).

The synthetic route of 16588-02-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chapdelaine, Marc; Davenport, Timothy; Haeberlein, Markus; Horchler, Carey; McCauley, John; Pierson, Edward; Sohn, Daniel; US2004/87575; (2004); A1;,
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Reference of 38487-86-4, These common heterocyclic compound, 38487-86-4, name is 2-Amino-4-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.

Add 2-amino-4-chlorobenzonitrile (152 mg, 1 mmol), benzyl alcohol (108 mg, 1 mmol),Fe (NO3) 3 ¡¤ 9H2O (40.4 mg, 0.10 mmol), TEMPO (15.6 mg, 0.10 mmol),t-BuOK (224mg, 2equiv) and 2mL of toluene were sequentially added to a 25mL reaction tube, and the reaction mixture was reacted under reflux for 12h and cooled to room temperature;Ethyl acetate was added to dilute the reaction solution, and then washed three times with water, and then the organic phase was separated.After drying over anhydrous magnesium sulfate, the solvent was removed by rotary evaporation under reduced pressure to obtain a crude product;The crude product was purified by column chromatography with petroleum ether / ethyl acetate, yielding 78%.

The synthetic route of 38487-86-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Nanjing University of Science and Technology; Li Bindong; Hu Yongke; (12 pag.)CN110357823; (2019); 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. 75279-53-7, name is 4-Chloro-2-fluorobenzeneacetonitrile, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C8H5ClFN

To a mixture of 3-chloro-2-fluoro-benzaldehyde (13.7 g, 86.68 mmol, 1.05 eq) and 2- (4-chloro-2-fluoro-phenyl)acetonitrile (14 g, 82.56 mmol, 1 eq) in methanol (200 mL) was added the solution of sodium methoxide (13.4 g, 247.67 mmol, 3 eq) in methanol (40 mL) dropwise at 0 C under nitrogen atmosphere. The product begins to precipitate during the addition. The suspension was stirred at 45 C for 5 hours. The solid was filtered and washed with water (200 mL) and methanol (50 mL) and then was dried in vacuum to give (Z)-3-(3-chloro-2-fluoro- phenyl)-2-(4-chloro-2-fluoro-phenyl)prop-2-enenitrile (24 g, 77.39 mmol, 93% yield) as a white solid. 1H-NMR (400MHz, CDCL) d 8.20 – 8.10 (m, 1H), 7.81 (s, 1H), 7.64 – 7.49 (m, 2H), 7.33 – 7.20 (m, 3H).

According to the analysis of related databases, 75279-53-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ARVINAS OPERATIONS, INC.; YALE UNIVERSITY; CREW, Andrew P.; HORNBERGER, Keith R.; WANG, Jing; DONG, Hanqing; BERLIN, Michael; CREWS, Craig M.; (1213 pag.)WO2019/195609; (2019); A2;,
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Some common heterocyclic compound, 60702-69-4, name is 2-Chloro-4-fluorobenzonitrile, molecular formula is C7H3ClFN, 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: C7H3ClFN

To a solution of 2-chloro-4-fluoro-benzonitrile (4 g, 25.71 mmol) in DMF (20 mL) were added Na2S (3.01 g, 38.57 mmol). The mixture was held at room temperature with stirring on for 20 h. Then the mixture was added 1 M HCl to adjust to pH 6-7. MTBE (20 ml) and water (20 ml) was added. The aqueous phase was extracted with MTBE (20 mL X 2), the combined organic phases were washed with sat. NaHCC”3 (50 mL) and brine (50 mL), dried over anhydrous sodium sulphate. Removal of solvent gave a yellow solid (3.7 g). The residue was used to next step directly. m/z calcd for [C7H4CINS]” [M-H]~: 168.0; found: 168.0.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 60702-69-4, its application will become more common.

Reference:
Patent; GALECTO BIOTECH AB; BRIMERT, Thomas; JOHNSSON, Richard; LEFFLER, Hakon; NILSSON, Ulf; ZETTERBERG, Fredrik; (284 pag.)WO2016/120403; (2016); 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. 77-57-6, name is 1-Phenylcyclopentanecarbonitrile, A new synthetic method of this compound is introduced below., Safety of 1-Phenylcyclopentanecarbonitrile

EXAMPLE 16 (R)-1-(2-((((1-Phenylcyclopent-1-yl)methylene)amino)oxy)ethyl)-3-piperidinecarboxylic acid hydrochloride To a solution of 1-phenyl-1-cyclopentanecarbonitrile (7.0 g, 41 mmol) in n-heptane (100 ml) cooled to -30 C. was dropwise added a 1M solution of diisobutylaluminium hydride in n-heptane (82 ml, 82 mmol). The mixture was stirred at -30 C. for 1 h and at 0 C. for 1 h. The mixture was diluted with diethylether (100 ml) and silica gel (60 g) was carefully added keeping the temperature below -30 C. The mixture was then allowed to warm to room temperature and then stirred for 20 h. After filtration the filtrate was washed with water (2*100 ml) and dried (MgSO4). The solvent was evaporated in vacuo to give 3.45 g of the crude 1-phenyl-1-cyclopentanecarboxaldehyde.

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; Novo Nordisk A/S; US5608069; (1997); A;,
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Synthetic Route of 69395-13-7, These common heterocyclic compound, 69395-13-7, name is 4-(2-Hydroxyethyl)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.

(ii) t-Butoxycarbonylamino-3-[2-(4-cyanophenyl)ethoxy]-2-methylbenzene Triphenylphosphine (1.31 g, 13.5 mmol) and diethylazodicarboxylate (1.7 mL) were dissolved in THF (20 mL) under nitrogen. After 15 minutes 3-t-butoxycarbonylamino-2-methylphenol (2.48 g; 11.1 mmol; from step (i) above) dissolved in THF (20 mL) and 2-(4-cyanophenyl)ethanol (1.9 g, 13 mmol) were added. After 5 days at room temperature water was added and the stirring continued for 30 minutes. The mixture was extracted with EtOAc. The organic phase was washed with water and brine, dried (MgSO4) and the solvent removed in vacuo. Purification by flash chromatography afforded 2.98 g (77%) of the sub-title compound. 1H NMR (300 MHz; CDCl3): delta7.4-7.8 (m, 5H), 7.10 (m, 1H), 6.63 (dd, 1H), 6.24 (s, 1H), 4.18 (t, 2H), 3.16 (t, 2H), 2.02 (s, 3H), 1.51 (s, 9H)

The synthetic route of 69395-13-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Astra Aktiebolag; US6221898; (2001); B1;,
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Reference of 60899-34-5, 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. 60899-34-5 name is 1-Oxo-2,3-dihydro-1H-indene-4-carbonitrile, 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.

(S)-N-[(lZ)-4-cyano-2,3-dihydro-lH-inden-l-ylidene]-2-methylpropane-2- sulfinamide: To a solution of l-oxo-2,3-dihydro-lH-indene-4-carbonitrile (5 g, 31.81 mmol, 1.00 equiv) in Toluene (60 mL) was added (S)-2-methylpropane-2-sulfinamide (4.24 g, 34.98 mmol, 1.10 equiv), Ti(OEt)4 (10.75 g, 47.15 mmol, 1.48 equiv). The resulting solution was stirred for 16 h at 60 C. The resulting solution was used directly in the next step without further purification. LC-MS: m/z = 261 [M+H]+. To a solution of l -oxo-2,3-dihydro-lH-indene-4-carbonitrile (5 g, 31.81 mmol, 1.00 equiv) in toluene (50 mL) was added (S)-2-methylpropane-2-sulfinamide (4.6 g, 37.95 mmol, 1.20 equiv), Ti(OEt)4 (1 1 g, 1.50 equiv). The resulting solution was stirred for 18 h at 60 C. The reaction progress was monitored by LCMS. The reaction was then quenched by the addition of sat. potassium sodium tartrate (30 mL). The resulting solution was extracted with ethyl acetate (3 x 50 mL) and the organic layers were combined, washed with brine (2 x 50 mL), dried over anhydrous sodium sulfate, filtered and concentrated under vacuum to afford 5.5 g (66%) of (S)-N-[(lZ)-4-cyano-2,3-dihydro-lH-inden-l -ylidene]-2- methylpropane-2-sulfinamide as a yellow green solid. LC-MS: m/z = 261 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Oxo-2,3-dihydro-1H-indene-4-carbonitrile, and friends who are interested can also refer to it.

Reference:
Patent; AUSPEX PHARMACEUTICALS, INC.; ZHANG, Chengzhi; CHAKMA, Justin; (91 pag.)WO2016/164180; (2016); 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. 67832-11-5, name is 4-Bromo-2-methylbenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 67832-11-5

30Step A: 4-bromo-2-ethylbenzonitrile A solution of 4-bromo-2-methylbenzonitrile (4.00 g, 20.4 mmol) in THF (40 mL) was addeddropwise to a solution of lithium diisopropylamide (2.0 M in THF, 16 mL, 32.0 mmol) in THF(10 mL) over a period of 20 mm at -78 C under nitrogen atmosphere. After 2 h, iodomethane(3.48 g, 24.5 mmol) was added dropwise over a period of 20 mm at the same temperature. Thereaction mixture was allowed to warm to room temperature and stirred for 3 h. The mixture wasre-cooled to 0 C and acidified with 1 M hydrochloric acid to pHi. The aqueous layer was extracted with ethyl acetate several times. The combined organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated. The residue was then purified by flash chromatography on a silica gel column using 0-10% ethyl acetate/petroleum ether as theeluting solvents to give the title compound. ?H NIVIR (400 MHz, CDC13) 7.46 (s, 1H), 7.44-7.35 (m, 2H), 2.81 (q, J 7.7 Hz, 2H), 1.26 (t, J= 7.6 Hz, 3H).

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 67832-11-5.

Reference:
Patent; MERCK SHARP & DOHME CORP.; SUZUKI, Takao; VACCA, Joseph P.; PU, Zhifa; XU, Shouning; PASTERNAK, Alexander; DAVIES, Ian; DING, Fa-Xiang; JIANG, Jinlong; DONG, Shuzhi; GU, Xin; (0 pag.)WO2016/8064; (2016); A1;,
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