Author: Jessica.F

Adding a certain compound to certain chemical reactions, such as: 455-18-5, name is 4-(Trifluoromethyl)benzonitrile, 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 455-18-5, Quality Control of 4-(Trifluoromethyl)benzonitrile

Take a 250 mL three-necked flask and add 100 mL of dry tert-amyl alcohol.Sodium (4.0 g, 100 mmol), 10 mg of ferric chloride, heated to 100 C,The mixture was heated and stirred under a nitrogen atmosphere for about 30 minutes, and the sodium particles were completely dissolved. Cool down to around 50 CThen, 4-trifluoromethylbenzonitrile, Compound 1-1 (11.8 g, 68.6 mmol) was added to the system, and the temperature was raised to 100 C. Diisopropyl succinate, Compound 2 (8 mL, 39.6 mmol), was diluted with 30 mL of tert-amyl alcohol, and the mixture was slowly dropped (2-3 h) into a three-necked flask using a constant pressure dropping funnel. After the addition was completed, the reaction was continued for 3 hours.After the reaction is completed, the reaction mixture is poured into a clean 500 mL beaker and naturally cooled to room temperature. Slowly add glacial acetic acid to the beaker to adjust the pH to neutrality.Out. Filter through a Buchner funnel and wash the filter cake with methanol and water until the filtrate is colorless and transparent.After drying the filter cake, a brick red solid powder, Compound 3-1, is obtained.The yield was 81%.

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

Reference:
Patent; East China University of Science and Technology; Wang Limin; Yang Qingying; Xu Jie; Li Jun; Han Jianwei; Tian He; (18 pag.)CN109897045; (2019); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Related Products of 70591-86-5, 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. 70591-86-5 name is 3-Bromobenzoylacetonitrile, 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.

A mixture of 3-(3-bromophenyl)-3-oxopropanenitrile (35 g, 156 mmol) and hydrazine hydrate (11.34 mL, 234 mmol) in ethanol (600 mL) was refluxed for 16 h. Mixture was then cooled and concentrated in vacuuo. Crude product was diluted with dichloromethane and stirred for 5 min. Solids were filtered and dried to afford 3-(3-bromophenyl)-1H-pyrazol-5-amine (30 g, 126 mmol, 81 % yield) as off-white solid. 1H NMR (400 MHz, DMSO-d6) delta 12.02 (br. s., 0.4H), 11.66 (br. s., 0.6H), 7.86 (t, J=1.6 Hz, 1H), 7.67 (d, J=7.5 Hz, 1H), 7.45 (d, J=6.8 Hz, 1H), 7.37 – 7.18 (m, 1H), 5.78 (br. s., 1H), 5.08 (br. s., 1.2H), 4.68 (br. s., 0.8H). LCMS (M+H) = 240.1.

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

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; NAIDU, B. Narasimhulu; WANG, Tao; PEESE, Kevin; YIN, Zhiwei; ZHANG, Zhongxing; KADOW, John F.; PATEL, Manoj; WO2015/126743; (2015); 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., Quality Control of 2-Cyanothioacetamide

Example 1 2-Amino-6-({[2-(4-chlorophenyl)-1,3-thiazol-4-yl]methyl}sulphanyl)-4-[4-(2-hydroxyethoxy)phenyl]pyridine-3,5-dicarbonitrile (II) 5.334 kg (24.90 mol) of 2-[4-(2-hydroxyethoxy)benzylidene]malononitrile (XI) and 1.309 kg (13.07 mol) of 2-cyanothioacetamide (XII) were suspended in 27.4 kg (34.8 l) of methanol. The suspension was warmed to 40 C., and 3.779 kg (37.35 mol) of triethylamine were metered in at at most 40 C. The mixture was stirred at 40 C. for another 3 h and cooled to room temperature. 3.147 kg (12.45 mol) of 4-(chloromethyl)-2-(4-chlorophenyl)-1,3-thiazole (XIV) were added to the dark-brown solution, and the content of the tank was stirred at room temperature overnight. The suspension now present was cooled to 5 C., isolated by filtration and washed with 11.7 kg (14.85 l) of methanol in total. The moist product was dried at 50 C. in a vacuum drying cabinet. This gave 4862 g or 75.1% of theory of 2-amino-6-({[2-(4-chlorophenyl)-1,3-thiazol-4-yl]methyl}sulphanyl)-4-[4-(2-hydroxyethoxy)phenyl]pyridine-3,5-dicarbonitrile as a beige-greenish solid (content 95.5%, ESTD).

The synthetic route of 7357-70-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; MAIS, Franz-Josef; HEILMAN, Werner; OLENIK, Britta; KEIL, Birgit; BECKER, Guido; MEIBOM, Daniel; KUHLMANN, Thomas; (42 pag.)US2018/155336; (2018); A1;,
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. 57381-34-7, name is 5-Chloro-2-fluorobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., Safety of 5-Chloro-2-fluorobenzonitrile

To a stirred [0C] solution of 1,1, 1,3, 3, [3-HEXAMETHYLDISILAZANE] (63 mL, 0.3 mmol) in dry diethyl ether was added dropwise n-Butyl lithium (2M in hexanes, 119 mL, 0.3 [MMOL).] A white suspension formed, to which was added [2-FLUORO-5-CHLOROBENZONITRILE (21.] 0 g, 0.14 mmol) over 5 min. The resultant orange mixture was allowed to warm to r. t. and stirred for 2h. The mixture was cooled to 0C and the reaction quenched by the addition [OF 3M HCI] (aq. ) (240 mL). The mixture was stirred for [0.] 5h before water (600 mL) was added. The purple organic layer was discarded and the aqueous layer basified to pH 14 with satd. NaOH (aq. ). The aqueous layer was extracted with [CHC13] [(5X100] mL) and the organic extracts dried over [NA2SO4.] Evaporation yielded the desired product as a yellow solid (16.2g, 73% yield).

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 57381-34-7.

Reference:
Patent; SCIOS INC.; WO2004/24159; (2004); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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. 628-20-6, name is 4-Chlorobutyronitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. name: 4-Chlorobutyronitrile

A solution of 4-chlorobutyronitrile (2.5 mmol) in dimethylformamide (1 mL) was added during 1.5h to a mixture of the arylamine (2.5 mmol), Cs2CO3 (2.5 mmol) and KI (5 mmol) in dimethylformamide (4 mL). The mixture was stirred at the indicated temperature and time. After completion of the reaction, as indicated by TLC, the mixture was treated with ethyl ether (50 mL) and water (10 mL). The aqueous phase was separated and extracted with ethyl ether (30 mL). The combined organic layers were dried over anhydrous sodium sulphate and filtered. The solvent was evaporated in vacuo. The crude product was purified by column chromatography (Silica gel, hexane:DCM).

The synthetic route of 628-20-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Diaz, Jimena E.; Bisceglia, Juan A.; Mollo, Ma. Cruz; Orelli, Liliana R.; Tetrahedron Letters; vol. 52; 16; (2011); p. 1895 – 1897;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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. 144649-99-0, name is 5-Bromo-2-methoxybenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 144649-99-0

Compound 64 (E)-Methyl 3-(3-(N-((3′-cyano-4′-methoxy-[l,l’-biphenyl]-4- yl)methyl)cyclohexanecarboxamido)phenyl)acrylate [00430] A mixture of Intermediate 16 (500 mg, 0.99 mmol), 5-bromo-2-methoxy-benzonitrile (316 mg, 1.49 mmol), Cs2C03 (647 mg, 1.99 mmol), Pd(PPh3)4 (230 mg, 199 mmol) in DMF (6 mL) was degassed with vacuum/nitrogen cycles (3 chi), stirred at 90 C for 12 h, and then filtered. Saturated EDTA-2Na (20 mL) was added, and the reaction mixture was stirred for 1 h and then extracted with ethyl acetate (3 x20 mL). The combined organic layers were washed with water (3 x 15 mL) and brine (2×20 mL), dried over anhydrous Na2S04, filtered and concentrated. The residue was purified by reverse-phase HPLC to give (E)-m ethyl 3-(3-(N-((3′-cyano-4′-methoxy- [l, l’-biphenyl]-4-yl)methyl)cyclohexanecarboxamido)phenyl)acrylate (110 mg, 22%) as a white solid. 1H MR (DMSO-i): delta 8.01 (d, IH), 7.96 (dd, IH), 7.58-7.70 (m, 5H), 7.42 (t, IH), 7.31 (d, IH), 7.24 (d, 2H), 7.17 (d, IH), 6.64 (d, IH), 4.89 (s., 2H), 3.95 (s, 3H), 3.71 (s, 3H), 2.19 (m, IH), 1.58-1.72 (m, 4H), 1.36-1.54 (m, 3H), 1.05-1.18 (m, IH), 0.89 (d, 2H); MS: 509.3 [M+H]+.

The synthetic route of 144649-99-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; METACRINE, INC.; SMITH, Nicholas D.; GOVEK, Steven P.; NAGASAWA, Johnny Y.; (228 pag.)WO2017/49172; (2017); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

5866-98-8, name is 2,6-Dichloro-3-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. name: 2,6-Dichloro-3-nitrobenzonitrile

Example 4 Synthesis of 2-(2,6-Dichlorophenylamino)-1,6,7-trimethyl-1,8-dihydro-imidazo[4,5-]isoquinoline-9-one A solution of 2,6-dichloro-3-nitrobenzonitrile (98.7 g, 0.455 mol) in EtOAc (910 mL) was cooled to 5 C. 40% Aqueous methylamine (79.5 mL, 1.14 mol) was added with vigorous mechanical stirring, keeping the temperature at 10-15 C. After addition was complete, stirring was continued for 3 h at the same temperature. More methylamine (16 mL, 0.23 mol) was added, and the mixture stirred for a further 1.5 h at room temperature. Water (300 mL) was added, followed by hexane (450 mL). The mixture was stirred for 15 min, filtered, and the solid washed with water and MeOH, to give 6-chloro-2-methylamino-3-nitrobenzonitrile (80.3 g, 83%), mp 167-170 C.

The synthetic route of 5866-98-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Boehringer Ingelheim Pharmaceuticals, Inc.; US6506769; (2003); B2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Reference of 29509-06-6,Some common heterocyclic compound, 29509-06-6, name is 4-Methyl-3-oxopentanenitrile, molecular formula is C6H9NO, 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 solution of 4-methyl-3-oxo-pentanenitrile (Method 30; 0.42 g, 3. 78 mmol) and hydrazine monohydrate (0.183 ml, 3.78 mmol) inEtOH (20 ml) was heated to reflux for 1 hour, cooled, and then concentrated under reduced pressure. The resulted oil was dissolved with DCM, washed with brine, dried over anhydrousNa2S04, concentrated, and purification by column chromatography (EtOAc:MeOH = 20: 1) to the title compound as an orange solid (0.26 g,56%). 1H NMR (400 MHz,CDC13) 8 1.21-1. 23 (d, J= 7.0 Hz, 6 H), 2.82-2. 89 (q, 1 H), 5.42 (s, 1 H). MS: Calcd.: 125; Found:[M+H] + 126.

The synthetic route of 29509-06-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2005/49033; (2005); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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. 610-66-2, name is 2-(2-Nitrophenyl)acetonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. name: 2-(2-Nitrophenyl)acetonitrile

Absolute ethanol (2,250 ml) and 1,500 g (9.25 moles) of o-nitrophenylacetonitrile is charged into a 22 liter flask. The suspension is cooled to 5-10 and hydrogen chloride is bubbled into the mixture for 2.5 hours. The reaction mixture is stirred at 10 under nitrogen atmosphere overnight. It is then diluted with 16,000 ml of ether and stirred for 1 hour; the solid is collected by filtration, washed with 4*1,000 ml of ether and dried (5 mm Hg/40) to give ethyl 2-(o-nitrophenyl)-acetimidate hydrochloride, m.p. 122-123 (dec).

The synthetic route of 610-66-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Ciba-Geigy Corporation; US4595535; (1986); A;,
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. 123-06-8, name is Ethoxymethylenemalononitrile, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: Ethoxymethylenemalononitrile

Triethylamine (9.7mL, 69.6mmol) was added to tert-butylhydrazine hydrochloride (8.67g, 69.6mmol) After adding absolute ethanol (460mL) and stirring at room temperature to dissolve, Ethoxymethylenemalononitrile (8.5 g, 69.6 mmol) was added in small portions, the solution was heated to reflux for 3 hours, and then the solvent was evaporated in vacuo to obtain a crude orange product. It was extracted with a mixed solution of ethyl acetate (0.5 L) and water (0.25 L), dried over anhydrous magnesium sulfate, and the organic layer was evaporated to obtain an orange solid. Continue to wash the obtained solid with a cyclohexane solution containing 10% ethyl acetate to obtain crystalline solid 5-amino-1-tert-butyl 1hydro-pyrazole-4-cyano 9.54g (yield 83% ).

According to the analysis of related databases, 123-06-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Sichuan University Huaxi Hospital; Chengdu Huaxi Jingzhun Medical Industrial Technology Institute Co., Ltd.; He Yang; Li Weimin; Zhou Xinglong; Wu Qiong; Wu Xiaoai; Chen Hai; Huang Ridong; Chai Yingying; (17 pag.)CN110642861; (2020); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts