Category: 874-97-5

Application of 874-97-5, These common heterocyclic compound, 874-97-5, name is 3-Cyanobenzyl alcohol, 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.

3-[(5-Amino-2H-pyrazol-3-yl)oxymethyl]benzonitrile, used as starting material, was prepared as follows: a) 3-Amino-5-hydroxypyrazole (2 g, 20.18 mmol, 1 eq) and triphenylphosphine (6.36 g, 24.22 mmol, 1.2 eq) were stirred in DCM (20 ml) for 30 mins. After this time, DIAD (4.77 ml, 24.22 mmol, 1.2 eq) was slowly added, keeping the temp below 20 C. with a water bath, and the resulting mixture stirred for a further 45 mins. A solution of 3-cyanobenzyl alcohol (3.23 g, 24.22 mmol, 1.2 eq) in DCM (10 ml) was added slowly and the reaction left to stir at RT for 24 hours. After this time the solid was filtered off and the solution extracted with 2M HCl solution (3×30 ml). The aqueous layer was back-washed with diethyl ether (2×30 ml), then basified to pH 9 using ammonium hydroxide, cooling the mixture to avoid a strong exotherm. The solution was extracted with DCM (3×30 ml) and the organic fractions combined, dried over magnesium sulphate and concentrated to give 3-[(5-amino-2H-pyrazol-3-yl)oxymethyl]benzonitrile as a colourless gum (321 mg, 7%). MS: m/z 215 (MH+)

Statistics shows that 3-Cyanobenzyl alcohol is playing an increasingly important role. we look forward to future research findings about 874-97-5.

Reference:
Patent; ASTRAZENECA AB; US2008/4302; (2008); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 874-97-5, A common heterocyclic compound, 874-97-5, name is 3-Cyanobenzyl alcohol, molecular formula is C8H7NO, 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 tert-butyl-chloro-dimethyl-silane (11.9 g, 78.9 mmol) to a solution of 3-hydroxymethyl-benzonitrile (10.00 g, 75.10 mmol) and imidazole (6.14 g, 90.1 mmol) in dichloromethane (1 L) and stir. After 18 hours, pour reaction into 1% hydrochloric acid. Remove organic layer, dry with sodium sulfate, filter, and concentrate under EPO reduced pressure to yield the title product as a clear yellow oil (18.5 g, 99%): 1H NMR (CDCl3) delta 0.12 (s, 6H), 0.95 (s, 9H), 4.75 (s, 2H), 7.43 (t, IH), 7.53 (d, 2H), 7.63 (s, IH).

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; ELI LILLY AND COMPANY; WO2006/57860; (2006); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

These common heterocyclic compound, 874-97-5, name is 3-Cyanobenzyl alcohol, 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. Recommanded Product: 3-Cyanobenzyl alcohol

After 3-(hydroxymethyl)benzonitrile (1.33 g, 10 mmol) was dissolved in dimethylformamide (18 mL), triphenylphosphine (3.14 g, 12 mmol) and imidazole (0.82 g, 12 mmol) were added thereto, and the mixture was cooled to -20C. Iodine (2.79 g, 11 mmol) was added dividing in 5 portions thereto, and the result was stirred for 2 hours at -10C. A 5% aqueous ammonium chloride solution (60 mL) was added to the reaction solution, and the result was extracted with a diethyl ether/ethyl acetate=1/1 solution (60 mLx2). The organic layers were combined, washed with a 1% aqueous sodium thiosulfate solution to remove excess iodine, washed with salted water, dried with anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was separated and purified using silica gel column chromatography (ethyl acetate/normal-hexane=1/9) to give a target compound (1.9 g, 78%) in a white powder state. 1H-NMR (300 MHz, CDCl3) delta 4.41 (s, 2H), 7.2-7.66 (m, 4H); MS (EI, m/e)=243 (M+).

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

Reference:
Patent; Korea Research Institute of Chemical Technology; SON, Jong Chan; KIM, Bong Jin; KIM, Jae Hak; LEE, Ill Young; YUN, Chang Soo; LEE, Sang Ho; LEE, Chong Kgo; (98 pag.)EP2781519; (2014); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Related Products of 874-97-5, These common heterocyclic compound, 874-97-5, name is 3-Cyanobenzyl alcohol, 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.

The compound of Reference Example 1 3- (hydroxymethyl) benzonitrile (0.043 mL, 0.37 mmol) and sodium hydride (17 mg, 0.40 mmol) were added to a DMF (0.32 mL) solution of sodium hydride (50 mg, 0.16 mmol) And the mixture was stirred at 100 C. for 14 hours. Water (10 mL) was added to the reaction mixture at room temperature and extracted with ethyl acetate (10 mL × 2). The organic layers were combined, dried over sodium sulfate and concentrated. The resulting concentrate was purified by silica gel column chromatography (eluent: ethyl acetate / n-hexane = 30/70) to give the intermediate as a yellow oil (48 mg).To a solution of the obtained intermediate (48 mg) in 1,4-dioxane (0.32 mL) was added 4 N hydrogen chloride 1,4-dioxane solution (0.80 mL) at room temperature, and the mixture was stirred at room temperature for 2 hours. Acetonitrile (2.0 mL) was added to the reaction mixture at room temperature, diethyl ether (4.0 mL) was added dropwise at room temperature, and the mixture was stirred at room temperature for 1 hour. The solid was collected by filtration and dried under reduced pressure at room temperature to give 3 – (((6- (1,4-diazepan-1 -yl) pyrazin-2-yl) oxy) methyl) benzonitrile dihydrochloride Compound of Example 5) as a white solid (43 mg, yield 70%).

The synthetic route of 874-97-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TORAY INDUSTRIES INCORPORATED; KIKUCHI, TSUKASA; OKANO, TSUBASA; (24 pag.)JP2017/14121; (2017); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 874-97-5,Some common heterocyclic compound, 874-97-5, name is 3-Cyanobenzyl alcohol, molecular formula is C8H7NO, 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.

e 2-Chlorobenzenesulfonic acid 3-[(3-cyanophenyl)methoxy]phenyl ester Diethyl azodicarboxylate (174 mg, 1.0 mmol) was added to a solution of 2-chlorobenzenesulfonic acid 3-hydroxyphenyl ester (285 mg, 1.0 mmol), as prepared in the preceding step, 3-cyanobenzyl alcohol (133 mg, 1.0 mmol)(Yoon et al., J. Org. Chem. 38:2786-2792 (1973)), and triphenylphosphine (263 mg, 1.0 mmol) in tetrahydrofuran (10 mL) at 0 C. The mixture was stirred at 0 C. for 2 hours and at room temperature for 3 hours. The reaction mixture was quenched with water (30 mL) and extracted with ethyl acetate (3*30 mL). The organic phase was washed with saturated NaHCO3 (2*30 mL), brine (2*30 mL) and dried over Na2 SO4. The solvent was removed in vacuo the residue was purified by flash column chromatography (2:1 ethyl acetate:hexane) to give the title compound as a pale yellow oil (375 mg, 93%). 1 H-NMR (300 MHz, CDCl3) delta 5.02 (s, 2H), 6.78 (m, 2H), 6.85 (dd, 1H, J=4.2, 1.3 Hz), 7.20 (t, 1H, J=8.2 Hz), 7.38 (t, 1H, J=5.8 Hz), 7.51 (t, 1H, J=7.7 Hz), 7.59-7.68 (m, 5H) and 7.93 (dd, 1H, J=4.0, 0.7 Hz).

The synthetic route of 874-97-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; 3-Dimensional Pharmaceuticals, Inc.; US6034127; (2000); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 874-97-5, name is 3-Cyanobenzyl alcohol, 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 874-97-5, Product Details of 874-97-5

A mixture of 4 (150 mg, 1.3 mmol), hydroxymethyl-benzonitrile (212 mg, 1.6 mmol), and Triphenyl phosphine (417 mg, 1.6 mmol) dissolved in 7 ml pg THF was charged with DIAD (322 mg, 1.6 mmol) dropwise and stirred at RT for two hours. The crude mixture was then dry-loaded onto silica and purified by ISCO(0-2% MeOH in DCM) to afford 3-((4-nitro-1H-pyrazol-1-yl)methyl)benzonitrile (255 mg, 72% yield). 1H NMR (400 MHz, Chloroform-d) delta 8.14 (d, J = 9.4 Hz, 2H), 7.72 – 7.63 (m, 1H), 7.64 – 7.48 (m, 3H), 5.35 (s, 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, 3-Cyanobenzyl alcohol, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Pastor, Richard M.; Burch, Jason D.; Magnuson, Steven; Ortwine, Daniel F.; Chen, Yuan; De La Torre, Kelly; Ding, Xiao; Eigenbrot, Charles; Johnson, Adam; Liimatta, Marya; Liu, Yichin; Shia, Steven; Wang, Xiaolu; Wu, Lawren C.; Pei, Zhonghua; Bioorganic and Medicinal Chemistry Letters; vol. 24; 11; (2014); p. 2448 – 2452;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Application of 874-97-5, 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. 874-97-5, name is 3-Cyanobenzyl alcohol, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: To a well-stirred suspension of 216 mg (9.00 mmol) of sodium hydride in anhydrous THF was added (3.60 mmol) of 3-benzylalcohol in small portions over 15 min. A brown solution was formed after 30 min of stirring. A solution of 519 mg (3.00 mmol) 5-methyl-3-sulfonyl[1,2,4]triazine in anhydrous THF was added, and the resulting dark red solution was stirred for 30 additional min. After which 25 mL of saturated NaHCO3 solution was added, and the organic layers were extracted into Et2O, combined, dried over anhydrous Na2SO4, filtered, and concentrated to obtain a dark red oil. The residue was purified using column chromatography with hexane-ethyl acetate (50:50) to obtain the desired product.

The chemical industry reduces the impact on the environment during synthesis 3-Cyanobenzyl alcohol. I believe this compound will play a more active role in future production and life.

Reference:
Article; Gichinga, Moses G.; Olson, Jeremy P.; Butala, Elizabeth; Gilmour, Brian P.; Navarro, Hernan H.; Ivy Carroll; Tetrahedron Letters; vol. 52; 26; (2011); p. 3345 – 3346;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 874-97-5, 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. 874-97-5 name is 3-Cyanobenzyl alcohol, 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.

Step e 3-(4-MethoxytrityloxymethvObenzonitrile (Ie”)3-(Hydroxymethyl)benzonitrile (2 g, 15 mmol) was dissolved in dry pyridine (120 ml). 4- methoxytrityl chloride (6 g, 19.5 mmol) was added and the mixture was stirred over night at room temperature (r.t.). The reaction was quenched with ethanol (EtOH), evaporated on rotavapor and the residue partitioned between dichloromethane (DCM) and saturated aqueous sodium bicarbonate. The organic phase was dried by sodium sulphate and evaporated. Silica gel column chromatography (gradient 30%DCM / hexane – DCM) gave the title compound (5.98 g,98%).1H-NMR (400MHz, CDCl3): delta 7.70-7.25 (m, 16H), 6.85 (d, 2H), 4.23 (s, 2H), 3.81 (s, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Cyanobenzyl alcohol, and friends who are interested can also refer to it.

Reference:
Patent; MEDIVIR AB; WO2008/135488; (2008); A1;,
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. 874-97-5, name is 3-Cyanobenzyl alcohol, A new synthetic method of this compound is introduced below., Recommanded Product: 874-97-5

To a dichloromethane solution (0.2 M) of 3-cyanobenzyl alcohol (1 eq.) was added triethylamine (1.2 eq.) and then methanesulfonyl chloride (1.1 eq.) at 0 0C. The reaction mixture was stirred at 0 0C for 20 min before it was quenched with sat. aq. NaHCO3. The aqueous layer was separated and back-extracted with dichloromethane. The combined organic extracts were then dried over Na2SO4, filtered and the filtrate concentrated in vacuo to furnish the title compound as a colorless oil.

The synthetic route of 874-97-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK FROSST CANADA LTD.; CHIH-YU CHEN, Austin; LALIBERTE, Sebastien; LAROUCHE, Guillaume; HAN, Yongxin; MCKAY, Daniel; WO2011/20193; (2011); A1;,
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. 874-97-5, name is 3-Cyanobenzyl alcohol, A new synthetic method of this compound is introduced below., name: 3-Cyanobenzyl alcohol

To an ice-cold solution of 3-hydroxymethyl benzonitrile (4.95 g, 37 mmol) in CH2C12 (47 mL) was added imidazole (5.1 g, 74 mmol), DMAP (0.45 g, 3.7 mmol), and TBSC1 (6. 2 g, 41 mmol), and the reaction mixture was stirred for 12 h. The reaction mixture was diluted with water, and the aqueous layer was extracted with CH2C12 (3 x 150 mL). The combined organics were washed with brine, dried (MGS04), filtered, and concentrated under reduced pressure to provide 3- (tert-butyldimethylsilyloxymethyl)-benzonitrile (9.1 g, 99%) as a clear oil :H NMR (300 MHz, CDC13) 8 7.51 (s, 1H), 7.42 (d, J = 6 Hz, 1H), 7.35-7. 28 (m, 1H), 4.75 (s, 2H), 0.94 (s, 9H), 0.11 (s, 6H).

The synthetic route of 874-97-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PHARMACIA CORPORATION; WO2005/18557; (2005); A2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts