Month: June 2021

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. 874-89-5, name is 4-(Hydroxymethyl)benzonitrile, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C8H7NO

EXAMPLE 34 This example illustrates the preparation of compound 34. 4-Hydroxymethyl-benzonitrile (3.1 g, 23.3 mmoles) was combined with N,N-diisopropylethylamine (4.9 mL, 28 mmoles) in 100 mL of anhydrous THF. To this solution was added MOMCl (3.5 mL, 46.1 mmoles) and the mixture was stirred at room temperature for 16 hours. After this period a solution of NH4OH/H2O (1:1, 20 mL) was added (-MOMCl) and the solution was stirred for 15 minutes. After this period the reaction mixture was evaporated in vacuo (-THF) and the resulting mixture was extracted with DCM (3*30 mL). The combined DCM layer was dried over anhydrous Na2SO4, evaporated in vacuo, and the resulting crude product was purified using flash silica chromatography (0-20% EtOAc/Hexane) to yield 1.6 g (39% yield) of 4-Methoxymethoxymethylbenzonitrile as a colorless liquid.

According to the analysis of related databases, 874-89-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Bayne, Christopher D.; Johnson, Alan T.; Lu, Shao-Po; Mohan, Raju; Griffith, Ronald C.; US2003/181420; (2003); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 94087-40-8, name is 3-Chloro-2-fluorobenzonitrile, 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 94087-40-8, name: 3-Chloro-2-fluorobenzonitrile

To a solution of 11 (3.57 g, 16.9 mmol, 1 eq) and 3-chloro-2-fluorobenzonitrile (5.25 g, 33.74 mol, 2 eq) in dry DMSO (125 mL) was added K2CO3 (7 g, 50.6 mmol, 3.1 eq). The reaction mixture was stirred at rt for 24 h and partitioned between EtOAc and brine. The aqueous phase was extracted with EtOAc and the combined EtOAc extracts were washed with brine, dried over Na2SO4, and evaporated. Chromatography on a silica column with eluent of 20:1 CH2Cl2:Me0H afforded (R)-3-chloro-2-[2-chloro-5-(5-oxo-pyrrolidin-3-yl> phenoxy]-benzonitrile, 12. 2.4 Results[0172] Analytical data for structure 9 is provided below.2.4a (R)-3-chloro-2-[2-chloro-5-(5-oxo-pyrrolidin-3-yl)’phenoxy]-benzonit}”ile [0173] MS m/z 347.0 (M + 1).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; IRM LLC; WO2006/81554; (2006); A2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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. 179898-34-1, name is 3-Bromo-5-fluorobenzonitrile, A new synthetic method of this compound is introduced below., Formula: C7H3BrFN

[0705] A solution of 3-bromo-5-fluorobenzonitrile (CII) (44.0 g, 220.0 mmol, 1.0 eq) was dissolved in THF (30 mL). BH3-Me2S (33.43 g, 440.0 mmol, 2.0 eq) was added to the solution at 20C. Then it was stirred at 80C for 2 h, HCl (6 N, 100 mL) was added to the mixture slowly at 20C. The mixture was stirred at 80C for 1 h, then it was washed with EtOAc (300 mL). The water phase was basified with 50% aqueous NaOH and it was extracted with EtOAc (300 mL x 3). The combined organic layers were dried over anhydrous Na2S04 and concentrated in vacuo to produce (3-bromo-5-fluoro-phenyl)methanamine (CIII) (24.0 g, 117.62 mmol, 53.5% yield). NMR (CDC13, 300 MHz) delta ppm 3.86 (s, 2H), 7.01 (d, J=8Hz, IH), 7.12 (d, J=8Hz, IH), 7.28 (s, IH); ESIMS found C7H7BrFN mlz 203.9 (Br79M+H).

The synthetic route of 179898-34-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SAMUMED, LLC.; KC, Sunil Kumar; WALLACE, David Mark; CAO, Jianguo; CHIRUTA, Chandramouli; MARAKOVITS, Joseph Timothy; BOLLU, Venkataiah; HOOD, John; (293 pag.)WO2017/23988; (2017); A1;,
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Related Products of 117482-84-5, 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. 117482-84-5, name is 3-Chloro-4-fluorobenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

EXAMPLE 84B 3-chloro-4-(methylamino)benzonitrile A mixture of 3-chloro-4-fluorobenzonitrile (5.2 g, 33 mmol), THF (55 mL), and 40% methylamine in water (25 mL, 290 mmol) in a sealed tube was heated to 65 C. for 1.5 hours, cooled to room temperature. The organic phase was washed with brine, dried (Na2SO4), filtered, and concentrated. The resulting solid was dried for about 16 hours under high vacuum in the presence of P2O5 to provide 6.3 g (95%) of the desired product. MS (DCI/NH3) m/z 184, 186 (M+H+NH3)+; 1H NMR (DMSO-d6) delta 7.72 (d, 1H), 7.55 (dd, 1H), 6.70 (d, 1H), 6.52 (br q, 1H), 2.80 (d, 3H).

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-Chloro-4-fluorobenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Claiborne, Akiyo K.; Gwaltney, II, Stephen L.; Hasvold, Lisa A.; Li, Qun; Li, Tongmei; Lin, Nan-Horng; Mantei, Robert A.; Rockway, Todd W.; Sham, Hing L.; Sullivan, Gerard M.; Tong, Yunsong; Wang, Gary; Wang, Le; Wang, Xilu; Wang, Wei-Bo; US2002/115640; (2002); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 30041-95-3,Some common heterocyclic compound, 30041-95-3, name is Ethyl 2-(4-cyanophenoxy)acetate, molecular formula is C11H11NO3, 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.

EXAMPLE 8 {4-[4,5-bis-(4-Chloro-phenyl)-4,5-dihydro-1H-imidazol-2-yl]-phenoxy}-acetic Acid Ethyl Ester To a solution of 4-hydroxy-benzonitrile (1 g, 8.395 mmol) in dimethylformamide (10 mL) were added potassium carbonate (2.321 g, 16.79 mmol) and ethyl bromoacetate (1.117 mL, 10.07 mmol), respectively. The reaction mixture was stirred at room temperature for 23 h. It was taken in ethyl acetate and diethyl ether (1:1 ratio), and the solid was filtered off. The filtrate was washed with water, brine and dried over anhydrous sodium sulfate. The solid was then filtered off, and the filtrate was concentrated in vacuo to afford ethyl (4-cyano-phenoxy)-acetate. It was used without further purification. Hydrogen chloride gas was passed through a solution of ethyl (4-cyano-phenoxy)-acetate (1.48 g, 7.212 mmol) in anhydrous ethanol (160 mL) at 0 C. After 6 h, hydrogen chloride gas was stopped and the reaction vessel was sealed with a Teflon stopper. After being stirred at room temperature for 3 d, the reaction vessel was cooled to 0 C. and the stopper was removed. The solvent was evaporated in vacuo, and the residue was triturated in diethyl ether to give the product as a white solid. Ethyl (4-ethoxy-carbonimidoyl-phenoxy)-acetate hydrochloride (1.74 g, 84%) was collected by filtration and dried under vacuum. It was used without further purification. A solution of meso-1,2-bis-(4-chloro-phenyl)-ethane-1,2-diamine (500 mg, 1.778 mmol) and ethyl (4-ethoxycarbonimidoyl-phenoxy)-acetate hydrochloride (614 mg, 2.134 mmol) in ethanol (15 mL) was heated at gentle reflux for 24 h. Upon cooling to room temperature, the solvent was removed and the residue was taken in ethyl acetate. It was washed with sodium bicarbonate solution, water, brine and dried over anhydrous sodium sulfate. The solid was then filtered off, and the filtrate was concentrated in vacuo. Purification of the residue by flash chromatography (Biotage system, KP-Sil 32-63 mum, 60 A silica gel) eluding with 2-10% methanol in methylene chloride yielded {4-[4,5-bis-(4-chloro-phenyl)-4,5-dihydro-1H-imidazol-2-yl]-phenoxy}-acetic acid ethyl ester (781 mg, 94%). HR-MS (ES, m/z) calculated for C25H23N2O3Cl2 [(M+H)+] 469.1083, observed 469.1079.

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-(4-cyanophenoxy)acetate, its application will become more common.

Reference:
Patent; Hoffmann-La Roche Inc.; US6617346; (2003); B1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 53312-82-6, 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. 53312-82-6, name is 4-Amino-2-bromobenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A mixture of 4-amino-2-bromobenzonitrile (440 mg, 2.2 mmol), ferf-butyl 2-oxo-6azaspiro[3.4]octane-6-carboxylate (495 mg, 2.2 mmol) and decaborane (43 mg, 0.35 mmol) in MeOH (20 mL) was stirred at 50 C overnight under Ar. The reaction mixture was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (Petroleum ether/EtOAc = 3/1) to afford intermediate 39 (406 mg, 45% yield) as a white solid.

The synthetic route of 4-Amino-2-bromobenzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; JOHNSON & JOHNSON (CHINA) INVESTMENT LTD.; DAI, Xuedong; QUEROLLE, Olivier Alexis Georges; KROSKY, Daniel Jason; CAI, Wei; FU, Liqiang; KONG, Linglong; LIU, Yingtao; WAN, Zhao-Kui; HERKERT, Barbara; PANDE, Vineet; EDWARDS, James Patrick; PATRICK, Aaron Nathaniel; ANGIBAUD, Patrick Rene; PONCELET, Virginie Sophie; (488 pag.)WO2019/120209; (2019); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Reference of 243128-37-2, 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. 243128-37-2, name is 4-Fluoro-3-methoxybenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

4.1.1. Synthesis of the Compounds 4 from Scheme 1 (Benzonitrile Derivatives)Synthesis of 4-morpholino-3-methoxy-benzonitrile (4.3) (for Examples 10, 70)6.7 mL (75 mmol) morpholine was stirred into 50 ml dimethylsulphoxide together with 20 g (141 mmol) potassium carbonate and 10.0 g (66 mmol) 4-fluoro-3-methoxy-benzonitrile for 8 h at 100 C. 500 ml ice water was added to the reaction mixture and the precipitate formed was filtered off and dried.Yield: 11.2 g (51 mmol=78% of theory)Analysis: HPLC-MS (method D): Rt: 1.36 min, (M+H)+: 219

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-Fluoro-3-methoxybenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; US2011/201608; (2011); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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 71825-51-9 as follows. Recommanded Product: 71825-51-9

2-Methyl-2-(4-nitrophenyl)propanenitrile (Compound of step 1, 16 g, 84.1 mmol) and Raney- Ni (4.16 g) were shaken in THF-MeOH [(1:1), 160 mL] under 40 psi of hydrogen for 10 hours at RT, After completion of reaction, the catalyst was filtered-off and the solvent was evaporated to dryness. The crude product was purified by column chromatography (silica gel, ethyl acetate in hexane) to obtain the title compound as oil.Yield: 10 g (74 %); 1H NMR (DMSO-d6, 300 MHz): delta 7.091-7.119 (d, 2H, J= 8.4Hz), 6.533- 6.561 (d, 2H, J= 8.4Hz), 5.135 (s, 2H), 1.568 (s, 6H); MS: m/z 161 (M+).

According to the analysis of related databases, 71825-51-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PIRAMAL LIFE SCIENCES LIMITED; KUMAR, Sanjay; VISHWAKARMA, Ram; MUNDADA, Ramswaroop; DEORE, Vijaykumar; KUMAR, Pramod; SHARMA, Somesh; WO2011/1212; (2011); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 6575-11-7, name is 2-Amino-6-chlorobenzonitrile, 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 6575-11-7, Computed Properties of C7H5ClN2

A mixture of 2-amino-6-chlorobenzonitrile (17.72 g, 0.116 mol) and tetrahydro-2,5- dimethoxyfuran (0.116 mol) in HO Ac (100 ml) was stirred and re fluxed for 30 min. Subsequently, the mixture was cooled and evaporated. The residue was purified over silica gel on a glass filter (eluent: DCM). The product fractions were collected and the solvent was evaporated. The residue was crystallized from EtOH. Yield: 18.83 g of intermediate 3 (80 % yield).

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

Reference:
Patent; JANSSEN PHARMACEUTICA NV; MEERPOEL, Lieven; MAES, Louis, Jules, Roger, Marie; DE WIT, Kelly; AUGUSTYNS, Koen, Jan, Ludovicus; WO2012/150305; (2012); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

These common heterocyclic compound, 218632-01-0, name is 3-Fluoro-4-nitrobenzonitrile, 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. Computed Properties of C7H3FN2O2

Example 7; (5-Cvano-2-nitro-phenyl)-(5-morpholin-4-ylmethyl-pyridin-2-yl)-acetic acid ethyl ester using 3-fluoro-4-nitrobenzonitrile in tetrahydrofuran and toluene; To a solution of (5-Morpholin-4-ylmethyl-pyridin-2-yl)-acetic acid ethyl ester (51.03g, 74.5% w/w%, 143.8mmol; Example 5) in toluene (204.1ml) was added a solution of 3- fluoro-4-nitrobenzonitrile (24.5 g, 151mmol) in tetrahydrofuran (357ml) and the solution was degassed three times with nitrogen and then cooled to -200C. Lithium tert-butoxide solution in tetrahydrofuran (137.ml, 20w/w%, 302mmol) was added dropwise over lhr. After stirring for an additional lhr 20min the reaction mixture was then added to a cold aqueous solution of ammonium chloride (188ml, 4.58M, 6862.7mmol) at 00C. The biphasic mixture was warmed to 300C and Celite (76.5g) added, then filtered. The filter cake was washed twice with toluene (153ml) then the combined filtrate was separated and the organic layer washed twice with water (153ml). The organic layer was concentrated by distillation to give (5-Cyano-2-nitro-phenyl)-(5-morpholin-4-ylmethyl-pyridin-2-yl)-acetic acid ethyl ester as a toluene solution (196ml) (titration, HCIO4, assay 80.47 w/w%) .The crude product mixture is directly used in the next step.

The synthetic route of 3-Fluoro-4-nitrobenzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; WO2008/130312; (2008); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts