Month: November 2020

63069-50-1, These common heterocyclic compound, 63069-50-1, name is 4-Amino-3-fluorobenzonitrile, 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.

A mixture containing 6-bromo-1 -methyl-benzimidazole (2.38 mmol), 4-amino-3-fluoro-benzonitrile (3.57 mmol),XPhos (0.95 mmol), Cs2CO3 (7.14 mmol) and Pd(OAc)2 (0.71 mmol) in dry toluene (8 mE) was stirred at 1100 C. forapproximately 16 h. The mixture was diluted (EtOAc), washed (H20), dried (Na2SO4) and concentrated to yield thedesired product 3-fluoro-4-[(3-methylbenzimidazol-5-yl)amino]benzonitrile.

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 63069-50-1.

Reference:
Patent; GALAPAGOS NV; Menet, Christel Jeanne Marie; Mammoliti, Oscar; Blanc, Javier; Orsulic, Mislav; Roscic, Maja; (81 pag.)US9440929; (2016); B2;,
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117482-84-5, Adding a certain compound to certain chemical reactions, such as: 117482-84-5, name is 3-Chloro-4-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 117482-84-5.

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) delta7.72 (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; US2003/87940; (2003); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

3218-50-6, Adding a certain compound to certain chemical reactions, such as: 3218-50-6, name is 2,5-Dichlorobenzyl cyanide, 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 3218-50-6.

EXAMPLE 3 Preparation of 2-[1l-[(2,5-dichlorophenyl)acetyl]-4-piperidinyl]-N-methyl-N-[(1R)-1-phenylpropyl]-4-thiazolecarboxamide (Compound 110) Step A: Preparation of 2,5-dichlorobenzeneacetic acid. A mixture of 2,5-dichlorobenzyl bromide (5.4 g, 22.5 mmol) in 16 mL of ethanol and potassium cyanide (1.63 g, 25 mmol) in 4 mL of water was heated at 80 0C overnight, then cooled, and the solids were filtered and washed with ethanol to give 3.5 g of 2,5- dichlorophenylacetonitrile as a white powder melting at 89-91 C. The nitrile was suspended in 20 mL of ethanol, and 20 mL of a 25 % aqueous NaOH solution was added. The mixture was heated in a CEM Explore microwave reactor at 140 0C for 30 minutes, then cooled, poured into ice water and acidified to pH 1 with concentrated HCl to give a precipitate. The precipitate was filtered, washed with water and dried in a vacuum oven at 90 0C for 5 h to give the title compound as a white powder. 1H NMR (CDCl3) delta 3.79 (s, 2H), 7.2-7.4 (m, 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, 2,5-Dichlorobenzyl cyanide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; E. I. DU PONT DE NEMOURS AND COMPANY; WO2007/14290; (2007); A2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

170572-49-3, A common compound: 170572-49-3, name is 3-Fluoro-4-methylbenzonitrile, 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.

Intermediate 54 2- [4- (5-cyano-2-methylphenoxy)-2-methylphenoxy]-2-methylpropionic acid ethyl ester Step A . 3-fluoro-4-methyl-5-nitrobenzonitrile; Add potassium nitrate (4.51 g, 44.54 mmol) in three or four portions to 3-fluoro-4- methylbenzonitrile (6.02 g, 44.54 mmol) in concentrated H2SO4 (50 ml) at 0C and stir. Stir the deep orange solution for 2 hours at 0C and then for 1 hour at rt. Add the mixture over 800 ml of ice and extract with 150 ml of AcOEt. Allow the mixture to warm at rt and separate the organic layer. Extract again the aqueous layer with 100 ml of AcOEt. Combine the organic extracts and washed with water (50 ml) and brine (50 ml). Dry the organic layer over magnesium sulfate, filter, and concentrate under reduced pressure to give the crude product (7.64 g, 93% yield). Although the product can be used without further purification, flash chromatogapy can be performed in silica using hexane: ethyl acetate (10: 1) as eluent.

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-Fluoro-4-methylbenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ELI LILLY AND COMPANY; WO2005/54176; (2005); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

623-00-7, Adding a certain compound to certain chemical reactions, such as: 623-00-7, name is 4-Bromobenzonitrile, 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 623-00-7.

General procedure: after standard cycles of evacuation and back-filling with dry and pure nitrogen, an oven-dried Schlenk tube equipped with a magnetic stirring bar was charged with Pd source (see Table 1, Table 2, Table 3 and Table 4), ligand (see Table 1, Table 2, Table 3 and Table 4), N,N-dimethylpyridin-4-amine (DMAP, see Table 1, Table 2, Table 3 and Table 4), and ethyl potassium malonate (see Table 1, Table 2, Table 3 and Table 4). The tube was evacuated and backfilled with argon (this procedure was repeated three times). Under a counter flow of argon, aryl halide (see Table 1, Table 2, Table 3 and Table 4) and solvent (see Table 1, Table 2, Table 3 and Table 4) were added by syringe. The tube was sealed and stirred at room temperature for 10 min. Then the tube was connected to the Schlenk line, which was full of argon, stirred in a preheated oil bath (140-150 C) for the appointed time (20-25 h). Upon completion of the reaction, the mixture was cooled to room temperature and diluted with diethyl ether, and the yields were determined by gas chromatography using 1,3-dimethoxybenzene as the internal standard.

According to the analysis of related databases, 623-00-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Feng, Yi-Si; Wu, Wei; Xu, Zhong-Qiu; Li, Yan; Li, Ming; Xu, Hua-Jian; Tetrahedron; vol. 68; 9; (2012); p. 2113 – 2120;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

2973-50-4, 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. 2973-50-4 name is 2-(2-Aminophenyl)acetonitrile, 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.

To a suitable amount of an organic solvent (a mixture of 1-cyanopropyl-3-methylimidazolium tetrafluoroborate and ethylene glycol at a mass ratio of 1: 4)The compound of formula (I) above 100mmo 1 is added,100mmo 1 The compound of formula (II)15 mmo 1 catalyst (3.75 mmol1-diphenylphosphino-1 ‘_ (di-tert-butylphosphino) ferrocene11.25 mmol Tin iodide mixture),150 mmol of base 1,5,7-triazabicyclo [4.4.0] dec-5-ene (TBD) with16 mmol Promoter Cerium triflate (Ce(OTf) 3), then warmed to 80 C, and the reaction was stirred at this temperature for 12 hours;[0036] After completion of the reaction, deionized water was added to the reaction system and thoroughly shaken, washed, and then extracted with chloroform 2-3 times,The combined organic phases were washed again with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was passed over 300-400 meshSilica gel column chromatography eluting with a mixture of acetone and petroleum ether in a volume ratio of 1: 2 to give a compound of the above formula (III)The yield of the compound was 95.7%.

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

Reference:
Patent; Gong Xiaoqian; Bu Gonggaofamingren; (9 pag.)CN105949109; (2016); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

218632-01-0, name is 3-Fluoro-4-nitrobenzonitrile, belongs to nitriles-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. 218632-01-0

3-Fluoro-4-nitrobenzonitrile (3.50 mmol, 581 mg) in CH2Cl2 (12 mL) was added Et3N (3.85 mmol, 0.54 mL) at -15 C. The reaction solution was stirred at -15 C. for 30 min. To the reaction solution was added 3-methoxypropan-1-amine (3.50 mmole, 0.36 mL) and stirred at -15 C. for 30 min. The cooling bath was removed to let the reaction solution warm to rt and kept stirring at rt for 30 min. The reaction solution containing 3-(3-methoxypropylamino)-4-nitrobenzonitrile (41A) was concentrated in vacuo and carried directly on to the next step without further purification. ESI-MS: m/z 236.3 (M+H)+.

Statistics shows that 218632-01-0 is playing an increasingly important role. we look forward to future research findings about 3-Fluoro-4-nitrobenzonitrile.

Reference:
Patent; Takeda Pharmaceutical Company Limited; US8138168; (2012); B1;,
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. 3939-09-1, name is 2,4-Difluorobenzonitrile, A new synthetic method of this compound is introduced below., 3939-09-1

Potassium nitrate (16.4 g, 147.4 mmol) was added to concentrated H2SO4 (85 ml, 1582 mmol) at 0 C, followed by slow addition of 2,4-difluorobenzonitrile (11.0 g, 79.1 mmol).The suspension was stirred at this temperature for an additional 4 hrs and quenched ice / water (800 ml). The resulting solid was collected by filtration and dried to give the title compound (13.8 g, 95%) as a white solid. NMR (400 MHz, CDCl3) 8.48 (m, IH), 7.24 (m, 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; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2006/87530; (2006); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

939-79-7, These common heterocyclic compound, 939-79-7, name is 4-Methyl-3-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.

Synthesis of 3-(4-Methyl-3-nitro-phenyl)-4H-[1,2,4]triazole Hydrogen chloride was bubbled through a solution of 3-nitro-p-tolunitrile (0.49 g, 3 mmol) in 40 mL of ethanol at room temp for 10 min. The solution was continued stirring at room temp for 60 min and the solvent was then evaporated under vacuum to dryness to give a white solid. The intermediate so obtained was dissolved in 20 mL of ethanol, neutralized with sodium ethoxide solution and the resulting precipitate was removed by filtration. To the filtrate was added at room temp formic hydrazide (0.2 g, 3 mmol) and the solution was continued stirring at room temp for 2 h. After removal of volatiles in vacuo, the residue was dissolved in 30 mL of m-xylene and refluxed at 150 C. for 16 h. Removal of volatiles in vacuo and purification using flash chromatography afforded 0.26 g of the final productproduct. (Yield: 43%). MS (m/z) calcd for C9H8N4O2 (MH+) 205.2, found, 205.1.

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 939-79-7.

Reference:
Patent; Bristol-Myers Squibb Company; Pharmaceopeia, Inc.; US6906067; (2005); B2;,
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.

(i) Preparation of N-trifluoroacetyl-4-cyano-2,6-dichloroaniline Twenty-five grams (0.1337 mole) of 4-cyano-2,6-dichloroaniline was dissolved in 250 ml of methylene chloride, and 30.9 g (20.8 ml, 0.1471 mole) of trifluoroacetic anhydride was added slowly with stirring. The solution was allowed to stand overnight and then was neutralized by the addition of 5% aqueous sodium carbonate, precipitating a white crystalline solid which was filtered and dried to give 28.0 g (74% yield) of N-trifluoroacetyl-4-cyano-2,6-dichloroaniline, m.p.: 134-136 C.

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; SmithKline Beckman Corporation; US4719223; (1988); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts