Month: August 2021

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. 2338-75-2, name is 4-(Trifluoromethyl)phenylacetonitrile, A new synthetic method of this compound is introduced below., Quality Control of 4-(Trifluoromethyl)phenylacetonitrile

Step 1: Preparation of Intermediate 2-(4-Trifluoromethyl-phenyl)-ethylamine (I-16a) (4-Trifluoromethyl-phenyl)-acetonitrile (2 g, 10.81 mmol) in methanolic ammonia (50 mL) was added to Raney nickel (400 mg) in methanol taken in a parr hydrogenator. The flask was stirred at 50 PSI overnight. The reaction was monitored by TLC (10% methanol in CHCl3). The reaction mixture was filtered through celite bed and the filtrate was dried under reduced pressure to afford 2 g of the product (97.89% yield). LCMS purity: 98.73%, m/z=190.0 (M+1)

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; NOVARTIS AG; Bock, Mark Gary; Gaul, Christoph; Gummadi, Venkateshwar Rao; Moebitz, Henrik; Sengupta, Saumitra; US2014/45872; (2014); A1;,
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Related Products of 57381-51-8, 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. 57381-51-8, name is 4-Chloro-2-fluorobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows.

EXAMPLE 14 2-(4-Chloro-2-ethoxy-phenyl)-4,5-bis-(4-chloro-phenyl)-4,5-dihydro-1H-imidazole To a solution of 4-chloro-2-fluoro-benzonitrile (1 g, 6.428 mmol) in ethanol (10 mL) were added sodium ethoxide solution (4.8 mL, 12.86 mmol, 21% wt in ethanol). The reaction mixture was heated at gently reflux for 12 h. The solvent was removed and the residue was partitioned between water (10 mL) and diethyl ether (20 mL). The layers were separated and the product was extracted with diethyl ether (20 mL). The organic layers were washed with brine (5 mL) and dried over anhydrous sodium sulfate. The solid was 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 5% ethyl acetate in hexanes yielded 4-chloro-2-ethoxy-benzonitrile (670 mg, 57%). Hydrogen chloride gas was passed through a solution of 4-chloro-2-ethoxy-benzonitrile (670 mg, 3.689 mmol) in anhydrous ethanol (25 mL) cooled to 0 C. After 45 min, the hydrogen chloride gas was stopped and the reaction vessel was sealed with a Teflon stopper. It was stirred at room temperature for 5 d. The reaction vessel was cooled to 0 C. and the stopper was removed. The solvent was removed and the residue was triturated in diethyl ether to afford ethyl 4-chloro-2-ethoxy-benzimidate hydrochloride (913 mg, 94%). It was used without further purification. To a solution of meso-1,2-bis-(4-chloro-phenyl)-ethane-1,2-diamine (810 mg, 2.879 mmol) and ethyl 4-chloro-2-ethoxy-benzimidate hydrochloride (913 mg, 3.455 mmol) in ethanol (10 mL) was added triethylamine (605 muL, 4.319 mmol). The reaction mixture was heated at gentle reflux for 4 h. The solvent was evaporated to dryness and the residue was purified by flash chromatography (Biotage system, KP-Sil 32-63 mum, 60 A silica gel) eluding with 70% ethyl acetate in hexanes to afford 2-(4-chloro-2-ethoxy-phenyl)-4,5-bis-(4-chloro-phenyl)-4,5-dihydro-1H-imidazole (1.045 g, 81%). HR-MS (ES, m/z) calculated for C23H20N2OCl3 [(M+H)+]445.0636, observed 445.0644.

The chemical industry reduces the impact on the environment during synthesis 4-Chloro-2-fluorobenzonitrile. I believe this compound will play a more active role in future production and life.

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

Application of 1735-53-1, 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. 1735-53-1, name is 4-Bromo-3-(trifluoromethyl)benzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Description 21; 4-(2-methylpropyl)-3-(trifluoromethyl)benzamide (D21); To a solution of 4-bromo-3-trifluoromethylbenzonitrile (1.25 g, 5.0 mmol) and isobutylzinc bromide (25 mmol) in THF (50 ml_, 25 mmol) under argon was added1 ,1 ‘-bis(diphenylphosphino)ferrocenedichloro palladium(ll) dichloromethane complex(612 mg, 0.75 mmol) and the reaction heated at reflux for 5 h. The mixture was concentrated in vacuo and the residue partitioned between ethyl acetate (80 ml.) and water (80 ml_). A solid formed and was filtered off and discarded. The organic layer was washed with water (80 ml.) before it was dried (phase separator) and concentrated in vacuo to give the crude title compound as a black oil. This was used directly in the next step (1.35 g).

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-Bromo-3-(trifluoromethyl)benzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GLAXO GROUP LIMITED; WO2008/74820; (2008); A1;,
Nitrile – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 2182-39-0, name is 2-(Phenylamino)propanenitrile, 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 2182-39-0, Application In Synthesis of 2-(Phenylamino)propanenitrile

d) 5-[1-Ethyl-4-(2-trimethylsilanyl-ethoxymethoxy)-1H-indol-6-ylmethyl]-pyrimidine-2,4-diamine. This compound was produced from 1-ethyl-4-(2-trimethylsilanyl-ethoxymethoxy)-1H-indole-6-carbaldehyde (630 mg, 1.97 mmol), 2-anilinopropionitrile (324 mg, 2.17 mmol), and guanidine hydrochloride (634 mg, 6.60 mmol), following the procedure detailed in Example 4, step f. Yield: 425 mg (53%). Yellow solid. MS (ISP): 414.4 ([M+H]+)

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; Mattei, Patrizio; Pflieger, Philippe; US2003/119857; (2003); 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. 7357-70-2, name is 2-Cyanothioacetamide, A new synthetic method of this compound is introduced below., Safety of 2-Cyanothioacetamide

To a solution of [CC-CYANOTHIOACETAMIDE] (0.5 g, 5 mmol) in DMF (3 mL) [A-BROMOACETOPHENONE] (1 g, [5] mmol, dissolved in 3 mL of DMF) was slowly added (dropping funnel). Approximately 30min after the addition the mixture was heated to [70C] for 30min, after which the reaction was complete as judged by TLC (SiO2; hexane/AcOEt 8: 2, [RF=0.] 3) The dark solution was poured onto water (50 mL) and extracted with AcOEt (3 x 30 mL). The combined organic phases were dried over [NA2SO4] and concentrated under vacuum. The resultant oily residue was dissolved in EtOH (2 mL) and poured in water (30 mL). After 1 hour stirring at room temperature the formed solid was filtered off, washed with [H20] and dried under vacuum (2 h, [50C] ; 48 h, [25C).] Pure [4-phenylthiazol-2-yl] acetonitrile (3,0. 87 g, 87%) was obtained. Analytical data [‘H-NMR] [(DMSO-D6,] [8)] : 7.9 (bd, 2H); 7.26-7. 5 [(M,] 4H); 4.2 (s, 2H) M. P. = [60C]

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; NOVUSPHARMA S.P.A.; WO2003/105842; (2003); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 114897-91-5,Some common heterocyclic compound, 114897-91-5, name is 2-(4-Bromo-2-fluorophenyl)acetonitrile, molecular formula is C8H5BrFN, 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.

Step B: 4-Bromo-2-fluoro-phenyl-acetic acid(4-Bromo-2-fluoro-phenyl)-acetonitrile (41.4 g, 174 mmol) (21.2 g, 99.1 mmol) was suspended in 30% aq. HCI (200 ml.) and heated to reflux for 20 hours. After cooling to room temperature, the solids were collected by filtration, washed with water and allowed to dry in open air. The solids were azeotroped with toluene under reduced pressure to remove the final traces of water, yielding the title compound as a solid (21 .7 g, 89 mmol, 94%).1 H-NMR (CD3OD, 300 MHz): 3.68 (s, 2H); 7.20-7.4 (m, 3H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-(4-Bromo-2-fluorophenyl)acetonitrile, its application will become more common.

Reference:
Patent; PFIZER INC.; BROWN, Matthew Frank; MARFAT, Anthony; MELNICK, Michael Joseph; REILLY, Usa; WO2011/45703; (2011); A2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 7251-09-4,Some common heterocyclic compound, 7251-09-4, name is 4-Amino-2-methoxybenzonitrile, molecular formula is C8H8N2O, 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.

General procedure: To an ice-cold suspension of nicotinoyl chloride hydrochloride(I) (1.78 g, 10 mmol) and appropriate 4-aminobenzonitrile (IIa-g) (10 mmol, 1.0 equiv) in acetonitrile(50 ml) under nitrogen was added triethylamine (8.1 g, 11.15 ml,40 mmol, 4.0 equiv) dropwise over 30 min. The resulting suspensionwas stirred at 0 C for 1 h then at room temperatureovernight. The reaction mixture was evaporated, diluted withEtOAc, washed with 10% HCl, brine, dried over anhydrousNa2SO4 and concentrated in vacuo. The resulting solid waswashed with diethyl ether and dried to yield the desired compounds(IIIa-g) in 50-90% yield.

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

Reference:
Article; Dokla, Eman M.E.; Fang, Chun-Sheng; Abouzid, Khaled A.M.; Chen, Ching S.; European Journal of Medicinal Chemistry; vol. 182; (2019);,
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Electric Literature of 622-75-3, A common heterocyclic compound, 622-75-3, name is 2,2′-(1,4-Phenylene)diacetonitrile, molecular formula is C10H8N2, 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.

Ag(CF3SO3) (0.0231g, 0.090mmol) and p-phda (0.0281g, 0.180mmol) were dissolved in 10mL benzene. After stirring for 30min, the resultant solution were transformed to a Teflon-lined stainless steel vessel (25mL) and heated at 120C for 2h, and then cooled to room temperature naturally. The resulting colorless crystals of 2 were isolated by slow evaporation the solution in air. Yield: 69.80% (based on Ag). Anal. Calc. for C21H16AgF3N4O3S C, 44.30; N, 9.84; H, 2.83; Found: C, 44.03; N, 9.74; H, 2.70%. IR:(KBr, nu/cm-1): 2960(w), 2918(w), 2258(w), 1521(m), 1427(m), 1410(m), 1288(s), 1255(s), 1224(m), 1174(s), 1031(s), 933(m), 785(m), 761(m), 629(s), 519(m).

The synthetic route of 622-75-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Han, Jing; Yang, Jian; Yu, Zhong; Wang, Quan-jiu; Inorganica Chimica Acta; vol. 469; (2018); p. 318 – 324;,
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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. 64248-64-2, name is 2,5-Difluorobenzonitrile, A new synthetic method of this compound is introduced below., name: 2,5-Difluorobenzonitrile

A suspension of 2,5-diflurobenzonitrile (4.5 g, 32.35 mmol) and 1,2,4-triazole sodium salt (3.6 g, 40 mmol) in dimethylformamide (40 mL) was heated at 80 C. for 15 h. The reaction mixture was then cooled, diluted with CH2Cl2 (200 mL), washed with water (3×30 mL) and brine (30 mL), then dried (Na2SO4), filtered and concentrated to give a white solid which was purified by flash column chromatography (SiO2) using 1:1 to 3:1 ethyl acetate/Hexanes to afford the title compound (2.98 g, 49% yield) as a white powder. 1H NMR (500 MHz, CDCl3) ?: 8.70 (1H, s), 8.18 (1H, s), 7.76 (1H, dd, J=9.0, 4.8 Hz), 7.55 (1H, dd, J=7.3, 2.8 Hz), 7.51-7.47 (1H, m). LCMS (M+H) calcd for C9H6FN4: 189.17; found: 189.10.

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; 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,
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Reference of 98730-77-9, 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 98730-77-9 as follows.

Step 2: ( 1 -cyanocyclopropyljmethyl methane sulfonate; At r.t to a solution of l^hydroxymethyOcyclopropanecarbonitrile (0.41 g, 4.2 mmo.) in methylene chloride (10 mL) was added methanesulfonyl chloride (490 uL, 6.3 mmol), followed by triethylamine (1.5 mL, 10.0 mmol) and 4-dimethylaminopyridine (18 mg, 0.15 mmol). The mixture was stirred at r.L for 3 h. It was diluted with methylene chloride, washed with water and brine, dried over Na2SO4. After filtration the filtrate was concentrated to yield the crude product which was used in the next step reaction without further purification.

According to the analysis of related databases, 98730-77-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; INCYTE CORPORATION; ZHANG, Colin; QIAN, Ding-quan; ZHUO, Jincong; YAO, Wenqing; WO2010/75270; (2010); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts