Month: September 2021

Adding a certain compound to certain chemical reactions, such as: 63069-50-1, name is 4-Amino-3-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 63069-50-1, Product Details of 63069-50-1

3.123. Compound 111: (lR,2R)-N-[6-(2-chloro-4-cyano-6-fluoro-N-methyl-anilino)-l-methyl- 3.123.1. Step i): 4-amino-3-chloro-5-fluoro-benzonitrile A mixture of 4-amino-3-fluorobenzonitrile (184 mmol) and NCS (276 mmol) in AcOH (300 mL) is stirred at 70C for approximately 16 h. The mixture is concentrated. H20 is added to the residue and the solid product is filtered off and washed (sat. NaHCC>3 and H20). To eliminate H20, THF is added and removed under reduced pressure to yield the desired product (Int. 21). 3.123.2. Step ii): 4-[[6-[bis[(4-methoxyphenyl)methyl]amino]-4-(methylamino)-5-nitro-2- pyridyl]amino]-3-chloro-5-fluoro-benzonitrtte

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Amino-3-fluorobenzonitrile, and friends who are interested can also refer to it.

Reference:
Patent; GALAPAGOS NV; MENET, Christel, Jeanne, Marie; MAMMOLITI, Oscar; QUINTON, Evelyne; JOANNESSE, Caroline, Martine, Andree-Marie; DE BLIECK, Ann; BLANC, Javier; (263 pag.)WO2017/12647; (2017); 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 1194-02-1 as follows. category: nitriles-buliding-blocks

To a solution of 4-fluorobenzonitrile (0.500 g, 4.13 mmol) in ethanol (3 mL) was added hydroxyl amine HCl (0.427g, 6.19 mmol) and potassium carbonate (1.14g, 8.26 mmol). The reaction mass was stirred at RT for 15-17 h. Excess of solvent was removed under vacuum. The obtained residue was diluted with water, acidified with dilute HCl and extracted with DCM. The organic layer was separated, dried over anhydrous sodium sulphate and concentrated to afford 0.450 g of desired product. 1H NMR (300 MHz, DMSO d6): delta 5.84 (br s, 2H), 7.17-7.27 (m, 2H), 7.68-7.73 (m, 2H), 9.64 (br s, 1H); MS (m/z): 155.13 (M+H)+.

According to the analysis of related databases, 1194-02-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLENMARK PHARMACEUTICALS S.A.; GHARAT, Laxmikant Atmaram; MUTHUKAMAN, Nagarajan; KHAIRATKAR-JOSHI, Neelima; KATTIGE, Vidya Ganapati; WO2013/186692; (2013); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthetic Route of 10406-24-3, 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. 10406-24-3, name is 3-(Aminomethyl)benzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example 2 m-Cyanobenzylamine (13.2 g), sodium nitrite (10.4 g), and dimethylformamide (100 ml) were mixed together, and the mixture was vigorously stirred at room temperature. Trifluoroacetic acid (22.8 g) was added dropwise to the mixture over one hour. After completion of addition, the mixture was further allowed to react at 100 C. for one hour. For the subsequent process, the procedure of Example 1 was repeated, to thereby obtain 6.9 g of m-cyanobenzyl alcohol (bp. 128-130 C./400 Pa) (yield 52%). The purity of the product was 98%.

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-(Aminomethyl)benzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Showa Denko K.K.; US6187945; (2001); B1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Related Products of 179898-34-1, These common heterocyclic compound, 179898-34-1, name is 3-Bromo-5-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.

Step 1 A solution of 3-bromo-5-fluorobenzonitrile (CIV) (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 20 C. Then it was stirred at 80 C. for 2 h, HCl (6 N, 100 mL) was added to the mixture slowly at 20 C. The mixture was stirred at 80 C. 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*3). The combined organic layers were dried over anhydrous Na2SO4 and concentrated in vacuo to produce (3-bromo-5-fluoro-phenyl)methanamine (CV) (24.0 g, 117.62 mmol, 53.5% yield). 1H NMR (CDCl3, 300 MHz) 3.86 (s, 2H), 7.01 (d, J=8 Hz, 1H), 7.12 (d, J=8 Hz, 1H), 7.28 (s, 1H); ESIMS found C7H7BrFN m/z 203.9 (Br79M+H).

Statistics shows that 3-Bromo-5-fluorobenzonitrile is playing an increasingly important role. we look forward to future research findings about 179898-34-1.

Reference:
Patent; Samumed, LLC; KC, Sunil Kumar; Wallace, David Mark; Cao, Jianguo; Chiruta, Chandramouli; Hood, John; (264 pag.)US2016/68550; (2016); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Application of 886498-08-4, The chemical industry reduces the impact on the environment during synthesis 886498-08-4, name is 2-Fluoro-5-(trifluoromethoxy)benzonitrile, I believe this compound will play a more active role in future production and life.

xxvii) 5-(Trifluoromethoxy)benzo[d]isoxazol-3-amine I63 To a solution of acetohydroxamic acid (2.2 g, 0.029 mol) in DMF (50 ml.) was added t-BuOK (3.28 g, 0.029 mol) and the mixture was stirred RT for 1 hour. 2-Fluoro-5-(trifluoromethoxy)benzonitrile (2 g, 9.75 mmol) was then added and the mixture was heated at 60 C overnight. The mixture was diluted with water and extracted with EtOAc. The organic extract was concentrated under reduced pressure to give the title compound (1.6 g, 75%) as a yellow solid. LCMS-D: Rt2.43 min; m/z 219.0 [M+H]+.

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-Fluoro-5-(trifluoromethoxy)benzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; CTXT PTY LIMITED; STUPPLE, Paul, Anthony; LAGIAKOS, Helen, Rachel; MORROW, Benjamin, Joseph; FOITZIK, Richard, Charles; HEMLEY, Catherine, Fae; CAMERINO, Michelle, Ang; BOZIKIS, Ylva, Elisabet, Bergman; WALKER, Scott, Raymond; (321 pag.)WO2019/243491; (2019); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthetic Route of 796600-15-2, A common heterocyclic compound, 796600-15-2, name is 2-Chloro-4-fluoro-3-methylbenzonitrile, molecular formula is C8H5ClFN, 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.

Examples 11 and 12Example 11 Example 12 11a to l ib(R)-2-(3 -chloro-4-cyano-2-methylphenylamino)-3 -hydroxypropanoic acidTo a stirred solution of 2-chloro-4-fluoro-3-methylbenzonitrile (1 la) (1.0 gm, 5.8 mmol) in DMSO (10 mL), D-Serine (1.4 gm, 13.3 mmol) was added followed by K2C03 (1.7 gm, 12.3 mmol) at room temperature. The resulting reaction mixture was heated to 90C for 12 h. After completion of reaction (by TLC), the reaction mixture was poured into ice-cold water (300 mL) and extracted with EtOAc (100 mL). The aqueous layer was acidified with citric acid (pH ~3) and extracted with EtOAc (2 x 100 mL). The combined organic extracts were dried over Na2S04, and concentrated under reduced pressure to afford the acid 1 lb (0.3 gm, crude) as off- white solid. The crude material was taken for the next step without purification.TLC: 10% MeOH/DCM (Rf: 0.2)1H NMR (500MHz, DMSO-c¾, delta in ppm): 8.2-10.2 (br s, 1H), 7.54 (d, J= 8.5 Hz, 1H), 6.57 (d, J= 9.0 Hz, 1H), 5.79 (d, J= 7.5 Hz, 1H), 4.20 (t, J= 3.0 Hz, 1H), 3.86-3.79 (m, 2H), 3.22 (br s, 1H), 2.25 (s, 3H).

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; RADIUS HEALTH, INC.; MILLER, Chris, P.; WO2012/47617; (2012); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthetic Route of 15760-35-7,Some common heterocyclic compound, 15760-35-7, name is 3-Methylenecyclobutanecarbonitrile, molecular formula is C6H7N, 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.

into a 500-mL 3-necked round-bottomflask, was placed a solution of 3-methylidenecyclobutane-1-carbonitrile (1.5 g, 16.11 mmol,1.00 eq.) and RuC13.H20 (360 mg, 1.60 mmol, 0.10 eq.) in DCMIACN/H20 (60/60/90 mL). This was followed by the addition of sodium periodate (5.2 g, 24.31 mmol, 1.50 eq.), in portions at 10C in 15 mm. The resulting solution was stirred for 2 hours at 25 C. The solids were filtered out. The resulting solution was extracted with dichloromethane (3×100 mL) andthe organic layers combined. The resulting mixture was washed with brine (2×200 mL), dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:1). This resulted in 1.1 g (72%) of 3- oxocyclobutane-1-carbonitrile as a yellow solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Methylenecyclobutanecarbonitrile, its application will become more common.

Reference:
Patent; BASTOS Cecilia M.; MUNOZ Benito; TAIT Bradley; WO2015/196071; A1; (2015);,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Reference of 4421-09-4, 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. 4421-09-4, name is 3,4-(Methylenedioxy)benzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Description 2: (Z)-N’ -hydroxybenzo[d][l,3]dioxole-5-carboximidamide To a solution of benzo[d][l,3]dioxole-5-carbonitrile (15 g, 102 mmol), hydroxylamine hydrochloride (14.17 g, 204 mmol) in Ethanol (500 mL) was added Na2C03 (54.0 g, 510 mmol) in one charge. The reaction mixture was stirred at 80C for 5 hr. Then the solvent was removed under reduced pressure, the residual was washed with DCM (1L><4), filtered and the combined filtrate was concentrated under reduced pressure to afford (Z)-N'-hydroxy benzo[d][l,3]dioxole-5-carboximidamide as a yellow solid (15 g, 73.5%). MS(ES+) m/z 181.1 (MH+). The synthetic route of 3,4-(Methylenedioxy)benzonitrile has been constantly updated, and we look forward to future research findings. Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; WANG, Rong; LU, Hongtao; WO2013/107336; (2013); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Application of 330792-69-3, 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. 330792-69-3, name is 2-(Methoxy(4-phenoxyphenyl)methylene)malononitrile, This compound has unique chemical properties. The synthetic route is as follows.

l,l-Dicyano-2-methoxy-2-(4-phenoxyphenyl)ethene (22.5 g) and 1 , 1 -dicyano-2-methoxy-2- (4-phenoxyphenyl)ethene oil (15 g) are treated with a solution of hydrazine hydrate (18 mL) in ethanol (25 mL) and heated on the steambath for 1 h. Ethanol (15 mL) is added followed by water (10 mL). The precipitated solid is collected and washed with ethanol: water (4:1) and then dried in air to give 3-amino-4- cyano-5-(4-phenoxyphenyl)pyrazole as a pale orange solid.

The chemical industry reduces the impact on the environment during synthesis 2-(Methoxy(4-phenoxyphenyl)methylene)malononitrile. I believe this compound will play a more active role in future production and life.

Reference:
Patent; PHARMACYCLICS, INC.; CHEN, Wei; LOURY, David, J.; MODY, Tarak, D.; WANG, Longcheng; WO2013/10136; (2013); A2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Some common heterocyclic compound, 50594-78-0, name is 5-Fluoro-2-nitrobenzonitrile, molecular formula is C7H3FN2O2, 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. HPLC of Formula: C7H3FN2O2

[0593] (a) Preparation of 5-[((2S)-1-methylpyrrolidin-2-yl)methoxy]-2-nitrobenzenecarbonitrile. To a slurry of 60% NaH (956 mg, 24 mmol) in THF (100 mL) was added (S)-(-)-1-methyl-2-pyrolidinemethanol (Aldrich) (2.8 mL, 24 mmol) resulting in gas evolution. After 30 min, 5-fluoro-2-nitrobenzonitrile (Combi Blocks) (3.3 g, 20 mmol) was added. After 3 h the reaction solvent was removed in vacuo and the residue was partitioned between CH2Cl2 and H2O. The aqueous layer was extracted with CH2Cl2 and the combined organics were dried over Na2SO4 and concentrated in vacuo to give a red oil. MS m/z: 262 (M+1). Calc’d for C13H15N3O3-261.11.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 50594-78-0, its application will become more common.

Reference:
Patent; Huang, Qi; Kaller, Matthew; Nguyen, Thomas; Norman, Mark H.; Rzasa, Robert; Wang, Hui-Ling; Zhong, Wenge; US2003/229068; (2003); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts