Month: October 2020

Adding a certain compound to certain chemical reactions, such as: 19472-74-3, name is 2-Bromophenylacetonitrile, 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 19472-74-3, 19472-74-3

A/ Preparation of 2-(2′-bromophenyl)-2-methylpropionitrile: A solution of 2-(2′-bromophenyl)-acetonitrile (7.5 g; 38 mmole) and iodomethane (16.2 g; 114 mmole) in THF (30 ml) was slowly added (60 minutes) to a suspension of NaH (4.0 g; 100 mmole) in THF (100 ml) which had been refluxed in an inert atmosphere. The reaction was exothermic. Refluxing was continued for 2.5 h. The reaction mixture was then stirred at room temperature for 15 h. The solvent was evaporated off under reduced pressure; the residue was taken up in 100 ml of water and extracted with 2*100 ml of tertiobutylmethylether. The organic phases were combined, washed with 3*100 ml of a saturated NaCl solution; dried over MgSO4 then filtered. The solvent was evaporated off under reduced pressure. The desired product was obtained as a colorless oil after distillation under reduced pressure (T=125-140 C.; p=0.1 mbar). Yield=79%. This substance was also made using the procedure described by W. E. Parham and L. D. Jones (see J. Org. Chem., (1976), 41, pp 1187-1191) with a yield of 90%. Physical characteristics: 1 H NMR (CDCl3) 1.90 ppm (s; 6H); 7.19 ppm (m; 1H; J=7.5 Hz); 7.35 ppm (t; 1H; J=7.5 Hz); 7.49 ppm (m; 1H; J=7.5 Hz); 7.67 ppm (d; 1H; J=7.5 Hz). 13 C NMR: (CDCl3) 27.13 ppm; 37.64 ppm; 123.08 ppm; 123.92 ppm; 127.76 ppm; 128.49 ppm; 130.15 ppm; 136.18 ppm; 138.77 ppm. MS (IE; 70 eV) 225/223 (M+; 80%); 210/208 (100%); 183/181 (75%); 102 (20%).

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

Reference:
Patent; Oxis Isle of Man, Limited; US5968920; (1999); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

40497-11-8, Adding some certain compound to certain chemical reactions, such as: 40497-11-8, name is Ethyl 2,3-dicyanopropanoate, 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 40497-11-8.

Sodium nitrite (224 mg, 3.25 mmol) was added carefully to sulphuric acid (concentrated, 1 ml), ensuring that the temperature did not rise above 30 C. After stirring at 15 C. for 1 h, acetic acid (2 ml) was added, followed by Preparation 36 (850 mg, 3.24 mmol) in acetic acid (3 ml). The reaction mixture was then heated at 50 C. for 1 h and cooled to room temperature. To a solution of Preparation 24 (500 mg, 3.29 mmol) in acetic acid (5 ml) was added ice water (5 ml), followed by the solution of the diazonium salt, added dropwise at 0 C. After complete addition, ammonium hydroxide (6 ml) was added and the reaction mixture was stirred overnight at room temperature. The reaction mixture was filtered through Arbocel and the filtrate was concentrated in vacuo. The residue was partitioned between dichloromethane and water and the organic phase was separated, dried (Na2SO4) and concentrated in vacuo to give Preparation 70 (1.0 g). MS (ES): M/Z [MH+] 353.0; expected mass for C11H5Cl2F3N4S+H is 353.0 1H-NMR (CDCl3): 6.01-6.03 (1H), 7.75-7.78 (2H)

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 40497-11-8.

Reference:
Patent; Billen, Denis; Chubb, Nathan Anthony Logan; Gethin, David Morris; Hall, Kim Thomas; Roberts, Lee Richard; Walshe, Nigel Derek Arthur; US2005/148649; (2005); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

78473-00-4, These common heterocyclic compound, 78473-00-4, name is 4-Amino-3,5-dichlorobenzonitrile, 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.

Intermediate 13: 3,5-Dichloro-4-isothiocyanato-benzonitrile To a solution of 4-amino-3,5-dichloro-benzonitrile (2.1 g, 11 mmol) and DMF (0.3 mL, 3.2 mmol) in 1,2-dichlorobenzene (15 mL) was added thiophosgene (2.6 g, 23 mmol). The resulting solution was heated to 160 C. and held at that temperature for 10 min then cooled to rt. The room temperature solution was purified by a plug of silica (220 g) using 10% EtOAc-hexanes (750 mL) to afford the title compound as a colorless solid (2.4 g, 95%). MS (ESI): mass calcd. for C8H2Cl2N2S, 227.9; m/z found, 229.0 [M+H]+. 1H NMR (CDCl3): delta 7.63 (s, 2H). 13C NMR (CDCl3): 6143.7, 133.5, 133.6, 131.5, 115.8, 111.0.

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 78473-00-4.

Reference:
Patent; Branstetter, Bryan James; Breitenbucher, James Guy; Lebsack, Alec D.; Xiao, Wei; US2008/4253; (2008); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

A common compound: 25808-30-4, name is 2-(Methylamino)acetonitrile hydrochloride, belongs to nitriles-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 25808-30-4

tert-butyl (4-chloro-2-formylphenyl)carbamate (3.00 g, 11.7 mmol, 1 eq.), 2-(methylamino)-acetonitrile hydrochloride (3.74 g, 35.1 mmol, 3 eq.), and DIPEA (6.16 g, 35.1 mmol, 3 eq.) were mixed in DCE (76 mL) and stirred for 15 min at 25 C. Acetic acid (2.1 mL, 35.1 mmol, 3 eq.)) and MgSO4 (4.32 g, 35.1 mmol, 3 eq.) were added, and the suspension was stirred for 2 h at 60 C. After the reaction mixture was cooled to 25 C, sodium triacetoxyborohydride (6.21 g, 29.3 mmol, 2.5 eq.) was added in two portions, and the reaction was stirred for 18 h at 25 C. The reaction was quenched with methanol and sodium bicarbonate (sat. aq.) to pH 8, and the aqueous layer was extracted with ethyl acetate twice. The organic layers were combined, dried over MgSO4, and evaporated under reduced pressure. The residue was purified by column chromatography (SiO2, 0-30percent EtOAc/Hex) to give tert-butyl (4-chloro-2- (((cyanomethyl)(methyl)amino)methyl)phenyl)carbamate (1.33 g, 37percent yield) as a white solid. LCMS (ESI): m/z 310 (M+H); Retention time: 3.36 min (50-100 percent ACN/H2O, method 3).

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, 25808-30-4, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BLACKTHORN THERAPEUTICS, INC.; JONES, Robert, M.; URBANO, Mariangela; BRANDT, Gary; HARDICK, David; KNIGHT, Chris; (337 pag.)WO2018/226769; (2018); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

26391-06-0, The chemical industry reduces the impact on the environment during synthesis 26391-06-0, name is 2-Cyano-N,N-diethylacetamide, I believe this compound will play a more active role in future production and life.

EXAMPLE-.Preparation of N,N-DIETHYL-2-CYANO-3-(3-lambdalambdaETHOXY-4-HYDROXY-S-NITROPHENYL)ACRYL AMIDE. ; STEP-I; 3-Methoxy-4-hydroxy-5-nitrobenzaldehyde of the formula (6) 150.0 gm (0.761 mole), N,N-diethyl cyanoacetamide of the formula (4) 135.3 gm (0.96 mole), glycine 10.5 gm (0.13 mole) and acetic acid 25.12 gm (0.41 mole) were charged sequentially to 1500.0 ml toluene. The resulting reaction mixture was heated to reflux and maintained with removal of water by azeotropically for 12-15 hrs. After the completion of reaction the solvent is concentrated and quenched into a cooled solution of isopropy. alcohol, aqueous HBr and water (2400.0 ml) and stirred for 3 hrs. The precipitated solid is filtered and dried to get 229.0 gm (94.2%) of title product of trhe formula (7) as crystalline solid. This product is used for next stage with out purification.

The chemical industry reduces the impact on the environment during synthesis 2-Cyano-N,N-diethylacetamide. I believe this compound will play a more active role in future production and life.

Reference:
Patent; SUVEN LIFE SCIENCES LTD.,; WO2007/94007; (2007); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

3939-09-1, 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. 3939-09-1, name is 2,4-Difluorobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows.

To a stirred solution of 2,4-difluorobenzonitrile (AI, 2.0 g, 28.7 mmol) in dry diethyl ether (250 mL), EtMgBr (10.5 mL, 3M solution in THF, 63.3 mmol) and Ti(0-iPr)4 (4.5 g, 31.5 mmol) were added at -78C. BF3.Et20 (10.7 mL, 57.4 mmol) was added and the reaction mixture was allowed to stirred at RT for 12 h. The progress of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was quenched with NH4C1 solution and extracted with EtOAc. The combined organic layer was washed with brine, dried over anhydrous Na2S04 and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography using 30% EtOAc/hexane to afford compound AJ (1.0 g, 20 %) as a pale yellow oil. LC-MS: m/z 170 [M+l]+.

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; VPS-3, INC.; YATES, Christopher, M.; (397 pag.)WO2018/165520; (2018); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding some certain compound to certain chemical reactions, such as: 63089-50-9, name is 4-Methylphthalonitrile, 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 63089-50-9. 63089-50-9

General procedure: A mixture of desired phthalonitrile (4a-i, 200mg) and corresponding metal salts (0.25 equivalents) were stirred at 100C with functional ionic liquid 2c (1 equivalent) for the appropriate time (Table 1, 2 and 3). The progress of the reaction was monitored by TLC and UV-Visible spectroscopic analysis. When reaction was completed, the mixture was cooled to room temperature, and distilled water (50 mL) was added to dissolve the functional ionic liquid. The blue-green solid mass was filtered and the aqueous filtrate was evaporated using reduced pressure to recover the pure ionic liquid for further use. The solid mass was further washed thoroughly with H2O-MeOH (1:1, 100 mL) to remove the colorless impurities and metallophthalocyanines are obtained in pure form. All of the phthalocyanines are known compounds and their purities were confirmed by UV-Visible spectroscopic analysis and further comparison with literature.

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 4-Methylphthalonitrile.

Reference:
Article; Yadav, Kumar Karitkey; Poonam; Chauhan, Shive M. S.; Synthetic Communications; vol. 44; 19; (2014); p. 2797 – 2807;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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. 139152-08-2 name is 4,5-Dichlorophthalonitrile, 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. 139152-08-2

4,5-Dichlorophthalonitrile (1.0g, 5.3mmol) and 13 5-hydroxy-2-methylpyridine (1.4g, 12.4mmol) were dissolved in 15mL of dry 14 N,N-dimethylformamide at 80C under N2. 15 Potassium carbonate (4.5g, 32.6mmol) was added to the reaction solution in 5 portions every 5min. The reaction mixture was heated for 3h at 80C, then cooled to room temperature, and poured into 100mL of 16 ice-water. The title compound was extracted for the reaction liquid using 50mL of 17 CHCl3 at 3 times. After filtration under vacuum, the 18 title compound was obtained as a white powder. Yield, 1.8g (97% (based on 4,5-Dichlorophthalonitrile)). Anal. Calc. for C20H14N4O2: C; 70.17, H; 4.12, N; 16.37. Found: C; 69.93, H; 4.21, N; 16.08%. HR-MS (ESI-TOF): Found 343.1190m/z. [M+H]+ (calcd. for C20H14N4O2 343.1191). 1H NMR (CD2Cl2): delta=8.31 (s, 2H, Ar-H), 7.34 (d, 2H, J=8.4Hz, Ar-H), 7.26 (d, 2H, J=8.4Hz, Ar-H), 7.23 (s, 2H, Ar-H), and 2.57ppm (s, 6H, CH3).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4,5-Dichlorophthalonitrile, and friends who are interested can also refer to it.

Reference:
Article; Fujishiro, Rei; Sonoyama, Hayato; Ide, Yuki; Fujimura, Takuya; Sasai, Ryo; Nagai, Atsushi; Mori, Shigeki; Kaufman, Nichole E.M.; Zhou, Zehua; Vicente, M. Graca H.; Ikeue, Takahisa; Journal of Inorganic Biochemistry; vol. 192; (2019); p. 7 – 16;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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. 25808-30-4, name is 2-(Methylamino)acetonitrile hydrochloride, This compound has unique chemical properties. The synthetic route is as follows., 25808-30-4

Example 122-Cyclopropyl-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid [(R)-1-(cyanomethylmethyl-carbamoyl)-ethyl]-amide2-Cyclopropyl-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid [(R)-1-(cyanomethylmethyl-carbamoyl)-ethyl]-amide.Prepared according to the procedure outlined in Example 11 substituting Boc-D-alanine for Boc-D-leucine monohydrate and methylaminoacetonitrile hydrochloride for dimethylamine hydrochloride. MS: (M+H)+=327.

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; Hendricks, Robert Than; Hermann, Johannes; Kondru, Rama; Lou, Yan; Lynch, Stephen M.; Owens, Timothy D.; Soth, Michael; US2011/230414; (2011); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

218632-01-0, 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 218632-01-0 as follows.

4-Cyano-2-fluoro-1 -nitrobenzene (300 mg, 0.0018 mol, 1 eq), 1-(tetrahydro-2H-pyran-4- yl)-4~piperidinamine (D9, 330 mg, 0.0018 mol, 1 eq), diisopropylethylamine (350 mg, 0.0027 mol, 1.5 eq), and dimethylformamide (5ml) were combined, heated to 2000C and held for 1 min in a microwave reactor. 100 ml of water was then added and the reaction extracted with 2 x 75 ml dichloromethane. The dichloromethane layers were combined, dried with sodium sulfate, and evaporated to yield the title compound which was used without further purification in the next step. MS (ESI): 331 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 218632-01-0, and friends who are interested can also refer to it.

Reference:
Patent; GLAXO GROUP LIMITED; WO2007/36711; (2007); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts